|
|
| β-carotene |
|
| CHEBI:17579 |
|
| beta-carotene |
|
| A cyclic carotene obtained by dimerisation of all-trans-retinol. A strongly-coloured red-orange pigment abundant in plants and fruit and the most active and important provitamin A carotenoid. |
|
This entity has been manually annotated by the ChEBI Team.
|
|
|
CHEBI:40987, CHEBI:10355, CHEBI:12392, CHEBI:22834
|
|
| ZINC000100067275 |
|
|
Molfile
XML
SDF
|
|
|
more structures >>
|
|
call loadScript javascripts\jsmol\core\package.js call loadScript javascripts\jsmol\core\core.z.js -- required by ClazzNode call loadScript javascripts\jsmol\J\awtjs2d\WebOutputChannel.js Jmol JavaScript applet jmolApplet0_object__590499358805133__ initializing getValue debug = null getValue logLevel = null getValue allowjavascript = null AppletRegistry.checkIn(jmolApplet0_object__590499358805133__) call loadScript javascripts\jsmol\core\corestate.z.js viewerOptions: { "name":"jmolApplet0_object","applet":true,"documentBase":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:17579","platform":"J.awtjs2d.Platform","fullName":"jmolApplet0_object__590499358805133__","display":"jmolApplet0_canvas2d","signedApplet":"true","appletReadyCallback":"Jmol._readyCallback","statusListener":"[J.appletjs.Jmol.MyStatusListener object]","codeBase":"https://www.ebi.ac.uk/chebi/javascripts/jsmol/","syncId":"590499358805133","bgcolor":"#000" } (C) 2012 Jmol Development Jmol Version: 13.2.7 $Date: 2013-10-01 11:35:15 -0500 (Tue, 01 Oct 2013) $ java.vendor: j2s java.version: 0.0 os.name: j2s Access: ALL memory: 0.0/0.0 processors available: 1 useCommandThread: false appletId:jmolApplet0_object (signed) starting HoverWatcher_1 getValue emulate = null defaults = "Jmol" getValue boxbgcolor = null getValue bgcolor = #000 backgroundColor = "#000" getValue ANIMFRAMECallback = null getValue APPLETREADYCallback = Jmol._readyCallback APPLETREADYCallback = "Jmol._readyCallback" getValue ATOMMOVEDCallback = null getValue CLICKCallback = null getValue ECHOCallback = null getValue ERRORCallback = null getValue EVALCallback = null getValue HOVERCallback = null getValue LOADSTRUCTCallback = null getValue MEASURECallback = null getValue MESSAGECallback = null getValue MINIMIZATIONCallback = null getValue PICKCallback = null getValue RESIZECallback = null getValue SCRIPTCallback = null getValue SYNCCallback = null getValue STRUCTUREMODIFIEDCallback = null getValue doTranslate = null language=en_US getValue popupMenu = null getValue script = null Jmol applet jmolApplet0_object__590499358805133__ ready call loadScript javascripts\jsmol\core\corescript.z.js call loadScript javascripts\jsmol\J\script\FileLoadThread.js starting QueueThread0_2 script 1 started starting HoverWatcher_3 starting HoverWatcher_4 The Resolver thinks Mol Marvin 02070614483D starting HoverWatcher_5 Time for openFile( Marvin 02070614483D 96 97 0 0 0 0 999 V2000 9.4731 -5.5451 3.8925 C 0 0 2 0 0 0 0 0 0 0 0 0 10.9476 -6.0010 4.2086 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0045 -7.4257 4.7950 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3027 -8.3971 3.8241 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0987 -7.9178 3.1319 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7315 -6.5975 3.1145 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6416 -6.2679 2.3326 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5336 -5.5806 2.6596 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4192 -5.4496 1.8807 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9253 -4.2186 1.6115 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7899 -3.9331 0.9099 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3669 -8.9982 2.4392 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6233 -4.1837 3.1246 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7712 -5.2353 5.2634 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7561 -6.6839 1.4456 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0718 -2.7956 0.9947 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8717 -2.4765 0.3747 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4395 -1.1885 0.3911 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2982 -0.6386 -0.1314 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0724 0.6531 -0.0233 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2317 1.2023 -0.5088 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7042 2.4713 -0.4010 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9184 2.8051 -0.9906 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4434 4.0286 -1.2212 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6756 4.3127 -1.7519 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3356 5.5008 -1.8398 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6058 5.5509 -2.4148 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3601 6.5960 -2.8253 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6596 6.7362 -3.3434 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2455 7.9827 -3.3553 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5862 8.2354 -3.9221 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.5426 7.0354 -3.9994 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.7614 5.8849 -4.6455 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4126 5.5379 -3.8880 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0818 -3.5295 -0.2815 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9451 3.4951 0.3339 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7301 6.7316 -1.3088 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6973 9.2702 -2.8667 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5898 4.7711 -4.9872 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8299 4.5479 -2.7368 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5564 -6.0024 3.2979 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4538 -5.3242 4.9041 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0412 -7.7340 4.9556 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5151 -7.4593 5.7714 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0997 -9.3051 4.4009 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0240 -8.6700 3.0468 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6569 -6.6213 1.4000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4665 -5.1587 3.5494 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4187 -3.4288 1.9725 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4617 -4.6391 0.2973 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6963 -10.0152 2.6669 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4600 -8.8868 1.3574 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3086 -8.9732 2.7072 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1179 -4.3204 2.1603 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6625 -3.7055 2.9281 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2103 -3.4564 3.6927 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3940 -4.6105 5.9081 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8443 -4.6758 5.1688 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5348 -6.1435 5.8198 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2397 -7.6079 1.7728 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6945 -6.7324 0.3573 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7457 -6.7177 1.8596 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4666 -2.1088 1.6022 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0240 -0.5244 0.8540 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3226 -1.2303 -0.6295 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5613 1.2461 0.4568 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7976 0.5521 -1.0124 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4977 2.0489 -1.2877 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8773 4.8009 -0.9797 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1411 3.5081 -2.1143 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0226 4.6719 -2.5371 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8370 7.4218 -2.7442 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4426 8.6340 -4.9325 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1611 8.9959 -3.3806 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.4155 7.2917 -4.6088 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.9030 6.7606 -3.0050 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.4426 5.0319 -4.7346 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5857 6.1948 -5.6824 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0038 -3.3927 -0.2014 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3526 -3.5786 -1.3381 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2165 -4.5196 0.1561 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2491 3.9873 -0.3481 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3857 3.1140 1.1879 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5753 4.2548 0.7980 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4602 7.4566 -0.9465 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1246 7.2029 -2.0854 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1064 6.5786 -0.4275 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6225 9.9850 -3.6912 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3492 9.7038 -2.1037 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7224 9.2879 -2.3907 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6971 4.2706 -4.6238 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2626 5.4574 -5.7730 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1752 3.9811 -5.4661 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0161 4.0061 -2.2682 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4808 3.7442 -3.0887 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3544 5.0684 -1.9337 H 0 0 0 0 0 0 0 0 0 0 0 0 34 40 1 0 0 0 0 34 39 1 0 0 0 0 33 34 1 0 0 0 0 32 33 1 0 0 0 0 31 32 1 0 0 0 0 30 38 1 0 0 0 0 30 31 1 0 0 0 0 29 34 1 0 0 0 0 29 30 2 0 0 0 0 28 29 1 0 0 0 0 27 28 2 0 0 0 0 26 37 1 0 0 0 0 26 27 1 0 0 0 0 25 26 2 0 0 0 0 24 25 1 0 0 0 0 23 24 2 0 0 0 0 22 36 1 0 0 0 0 22 23 1 0 0 0 0 21 22 2 0 0 0 0 20 21 1 0 0 0 0 19 20 2 0 0 0 0 18 19 1 0 0 0 0 17 35 1 0 0 0 0 17 18 2 0 0 0 0 16 17 1 0 0 0 0 11 16 2 0 0 0 0 10 11 1 0 0 0 0 9 15 1 0 0 0 0 9 10 2 0 0 0 0 8 9 1 0 0 0 0 7 8 2 0 0 0 0 6 7 1 0 0 0 0 5 12 1 0 0 0 0 5 6 2 0 0 0 0 4 5 1 0 0 0 0 3 4 1 0 0 0 0 2 3 1 0 0 0 0 1 14 1 0 0 0 0 1 13 1 0 0 0 0 1 6 1 0 0 0 0 1 2 1 0 0 0 0 41 2 1 0 0 0 0 42 2 1 0 0 0 0 43 3 1 0 0 0 0 44 3 1 0 0 0 0 45 4 1 0 0 0 0 46 4 1 0 0 0 0 47 7 1 0 0 0 0 48 8 1 0 0 0 0 49 10 1 0 0 0 0 50 11 1 0 0 0 0 51 12 1 0 0 0 0 52 12 1 0 0 0 0 53 12 1 0 0 0 0 54 13 1 0 0 0 0 55 13 1 0 0 0 0 56 13 1 0 0 0 0 57 14 1 0 0 0 0 58 14 1 0 0 0 0 59 14 1 0 0 0 0 60 15 1 0 0 0 0 61 15 1 0 0 0 0 62 15 1 0 0 0 0 63 16 1 0 0 0 0 64 18 1 0 0 0 0 65 19 1 0 0 0 0 66 20 1 0 0 0 0 67 21 1 0 0 0 0 68 23 1 0 0 0 0 69 24 1 0 0 0 0 70 25 1 0 0 0 0 71 27 1 0 0 0 0 72 28 1 0 0 0 0 73 31 1 0 0 0 0 74 31 1 0 0 0 0 75 32 1 0 0 0 0 76 32 1 0 0 0 0 77 33 1 0 0 0 0 78 33 1 0 0 0 0 79 35 1 0 0 0 0 80 35 1 0 0 0 0 81 35 1 0 0 0 0 82 36 1 0 0 0 0 83 36 1 0 0 0 0 84 36 1 0 0 0 0 85 37 1 0 0 0 0 86 37 1 0 0 0 0 87 37 1 0 0 0 0 88 38 1 0 0 0 0 89 38 1 0 0 0 0 90 38 1 0 0 0 0 91 39 1 0 0 0 0 92 39 1 0 0 0 0 93 39 1 0 0 0 0 94 40 1 0 0 0 0 95 40 1 0 0 0 0 96 40 1 0 0 0 0 M END): 29 ms reading 96 atoms ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false 1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them. Default Van der Waals type for model set to Babel 96 atoms created ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation Script completed Jmol script terminated
|
| β-Carotene (beta-carotene) is an organic, strongly colored red-orange pigment abundant in fungi, plants, and fruits. It is a member of the carotenes, which are terpenoids (isoprenoids), synthesized biochemically from eight isoprene units and thus having 40 carbons.
Dietary β-carotene is a provitamin A compound, converting in the body to retinol (vitamin A). In foods, it has rich content in carrots, pumpkin, spinach, and sweet potato. It is used as a dietary supplement and may be prescribed to treat erythropoietic protoporphyria, an inherited condition of sunlight sensitivity.
β-carotene is the most common carotenoid in plants. When used as a food coloring, it has the E number E160a.: 119 The structure was deduced in 1930.
Isolation of β-carotene from fruits abundant in carotenoids is commonly done using column chromatography. It is industrially extracted from richer sources such as the algae Dunaliella salina. The separation of β-carotene from the mixture of other carotenoids is based on the polarity of a compound. β-Carotene is a non-polar compound, so it is separated with a non-polar solvent such as hexane. Being highly conjugated, it is deeply colored, and as a hydrocarbon lacking functional groups, it is lipophilic. |
|
Read full article at Wikipedia
|
InChI=1S/C40H56/c1- 31(19-13-21-33(3)25-27-37-35(5)23-15-29-39(37,7)8)17-11-12-18-32(2)20-14-22-34(4)26-28-38-36(6)24-16-30-40(38,9)10/h11-14,17-22,25-28H,15-16,23-24,29-30H2,1-10H3/b12-11+,19-13+,20-14+,27-25+,28-26+,31-17+,32-18+,33-21+,34-22+ |
| OENHQHLEOONYIE-JLTXGRSLSA-N |
| CC(\C=C\C=C(C)\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C |
|
|
Mus musculus
(NCBI:txid10090)
|
Source: BioModels - MODEL1507180067
See:
PubMed
|
|
Homo sapiens
(NCBI:txid9606)
|
See:
DOI
|
|
antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
|
|
|
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
cofactor
An organic molecule or ion (usually a metal ion) that is required by an enzyme for its activity. It may be attached either loosely (coenzyme) or tightly (prosthetic group).
biological pigment
An endogenous molecular entity that results in a colour of an organism as the consequence of the selective absorption of light.
provitamin A
A provitamin that can be converted into vitamin A by enzymes from animal tissues.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
ferroptosis inhibitor
Any substance that inhibits the process of ferroptosis (a type of programmed cell death dependent on iron and characterized by the accumulation of lipid peroxides) in organisms.
|
|
View more via ChEBI Ontology
|
1,1'-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaene-1,18-diyl]bis(2,6,6-trimethylcyclohexene)
|
ChEBI
|
|
all-trans-β-carotene
|
UniProt
|
|
all-trans-β-carotene
|
NIST Chemistry WebBook
|
|
beta-Carotene
|
KEGG COMPOUND
|
|
BETA-CAROTENE
|
PDBeChem
|
|
β-Karotin
|
ChEBI
|
|
1917416
|
Reaxys Registry Number
|
Reaxys
|
|
7235-40-7
|
CAS Registry Number
|
KEGG COMPOUND
|
|
7235-40-7
|
CAS Registry Number
|
ChemIDplus
|
|
7235-40-7
|
CAS Registry Number
|
NIST Chemistry WebBook
|
Sliwa A, Góralska J, Czech U, Gruca A, Polus A, Zapała B, Dembińska-Kieć A (2012)
Modulation of the human preadipocyte mitochondrial activity by beta-carotene.
Acta biochimica Polonica 59, 39-41 [PubMed:22428124]
[show Abstract]
Increased ROS generation by the overload by metabolic substrates mitochondria paralleled by decrease of antioxidant activity are typical events found in metabolic syndrome and diabetes type 2. Metabolites of beta-carotene (BC) such as retinoic acid (RA), as well as low concentration of reactive oxygen species (ROS) modify the mitochondrial bioenergetic function. The aim of the study was to investigate the effect of beta-carotene on mitochondrial activity in human preadipocytes. BC used in concentrations, 10 or 30 µM, decreased mitochondrial membrane potential, inhibited mitochondrial respiration and decreased cellular ATP content. We conclude, that BC, the known antioxidant may decrease oxidative phosphorylation capacity of mitochondria. | Araya-Garay JM, Ageitos JM, Vallejo JA, Veiga-Crespo P, Sánchez-Pérez A, Villa TG (2012)
Construction of a novel Pichia pastoris strain for production of xanthophylls.
AMB Express 2, 24 [PubMed:22534340]
[show Abstract]
In this study, we used the yeast carotenogenic producer Pichia pastoris Pp-EBIL strain, which has been metabolically engineered, by heterologously expressing β-carotene-pathway enzymes to produce β-carotene, as a vessel for recombinant astaxanthin expression. For this purpose, we designed new P. pastoris recombinant-strains harboring astaxanthin-encoding genes from carotenogenic microorganism, and thus capable of producing xanthophyllic compounds. We designed and constructed a plasmid (pGAPZA-WZ) containing both the β-carotene ketolase (crtW) and β-carotene hydroxylase (crtZ) genes from Agrobacterium aurantiacum, under the control of the GAP promoter and containing an AOX-1 terminator. The plasmid was then integrated into the P. pastoris Pp-EBIL strain genomic DNA, producing clone Pp-EBILWZ. The recombinant P. pastoris (Pp-EBILWZ) cells exhibited a strong reddish carotenoid coloration and were confirmed, by HPLC, to produce not only the previous described carotenoids lycopene and β-carotene, but also de novo synthesized astaxanthin. | Roswall N, Olsen A, Christensen J, Hansen L, Dragsted LO, Overvad K, Tjønneland A (2012)
Micronutrient intake in relation to all-cause mortality in a prospective Danish cohort.
Food & nutrition research 56, [PubMed:22489215]
[show Abstract]
BackgroundFew studies have considered source-specific micronutrient intake in relation to mortality under the consideration that dietary and supplemental intake could exhibit different effects.ObjectiveTo evaluate the association between intake of vitamin C, E, folate, beta-carotene from diet and supplements, and overall mortality. Furthermore, to examine effect modification by smoking, alcohol intake, and BMI and to investigate if the effect of supplement use differs with dietary micronutrient intake.Methods and materialIn a prospective cohort study of 55,453 middle-aged Danes, information regarding diet, supplement use, and lifestyle was collected through questionnaires. During follow-up, 6,767 deaths were identified and incidence rate ratios (IRRs) of mortality related to micronutrient intake were calculated using Cox proportional hazards models.ResultsThe present study found no effect of dietary vitamin C, E, folate, or beta-carotene in relation to mortality. In contrast, supplemental folic acid was associated with a significantly increased mortality, whereas no other micronutrient supplement was associated with mortality. Effect modification by smoking and alcohol intake, but not BMI, was suggested in relation to some dietary micronutrients. The effect of supplements did not differ in groups defined by dietary micronutrient intake.ConclusionThis study suggests no effect of dietary micronutrients in relation to overall mortality. Supplemental folic acid was found to be associated with increased mortality, but further studies are required. No other supplemental micronutrient was associated with mortality. | Hao H, Ma L, Cong H, Li Q, Yu X (2012)
Isolation and characterization of a muskmelon cDNA encoding Lycopene Beta-cyclase.
Gene 503, 147-151 [PubMed:22575730]
[show Abstract]
Lycopene Beta-cyclase (LCY-B) is thought to play a critical role in Beta-carotene synthesis in fruit. A full-length cDNA clone encoding Lycopene Beta-cyclase was isolated from muskmelon (Cucumis melo L.) by RT-PCR and RACE. The clone, designated CmLcyb1, contains 1871 nucleotides, with an open reading frame of 1512 nucleotides. The deduced 504-amino-acid sequence showed high identities with other plant Lycopene Beta-cyclases. Real time quantitative RT-PCR analysis indicated that CmLcyb1 was expressed in all tissues and organs of muskmelon inbred M01-3 with white mesocarp and, 'Homoka', an orange mesocarp cultivar. The expression levels of CmLcyb1 in roots, stems, leaves and flowers in the two genotypes differed little. The expression level was highest in mature fruit of 'Homoka' and was much higher than that in mature fruit of M01-3. Moreover, the mRNA level of CmLcyb1 was very low in fruits before fruit-size fixation and increased dramatically in the size-fixed fruits of these two genotypes. The mRNA levels of CmLcyb1 during fruit development of 'Homoka' were all higher than those of M01-3. Interestingly, Beta-carotene content showed almost the same change trend as mRNA levels during fruit development in these two genotypes, suggesting that Beta-carotene accumulation may be linked to the CmLcyb1 transcript level in muskmelon fruit. | Margalit DN, Kasperzyk JL, Martin NE, Sesso HD, Gaziano JM, Ma J, Stampfer MJ, Mucci LA (2012)
Beta-carotene antioxidant use during radiation therapy and prostate cancer outcome in the Physicians' Health Study.
International journal of radiation oncology, biology, physics 83, 28-32 [PubMed:22079732]
[show Abstract]
PurposeThe safety of antioxidant supplementation during radiation therapy (RT) for cancer is controversial. Antioxidants could potentially counteract the pro-oxidant effects of RT and compromise therapeutic efficacy. We performed a prospective study nested within the Physicians' Health Study (PHS) randomized trial to determine if supplemental antioxidant use during RT for prostate cancer is associated with an increased risk of prostate cancer death or metastases.Methods and materialsPHS participants (383) received RT for prostate cancer while randomized to receive beta-carotene (50 mg on alternate days) or placebo. The primary endpoint was time from RT to lethal prostate cancer, defined as prostate cancer death or bone metastases. The Kaplan-Meier method was used to estimate survival probabilities and the log-rank test to compare groups. Cox proportional hazards regression was used to estimate the effect of beta-carotene compared with that of placebo during RT.ResultsWith a median follow-up of 10.5 years, there was no significant difference between risk of lethal prostate cancer with the use of beta-carotene during RT compared with that of placebo (hazard ratio = 0.72; 95% confidence interval [CI], 0.42-1.24; p = 0.24). After we adjusted for age at RT, prostate-specific antigen serum level, Gleason score, and clinical stage, the difference remained nonsignificant. The 10-year freedom from lethal prostate cancer was 92% (95% CI, 87-95%) in the beta-carotene group and 89% (95% CI, 84-93%) in the placebo group.ConclusionThe use of supplemental antioxidant beta-carotene during RT was not associated with an increased risk of prostate cancer death or metastases. This study suggests a lack of harm from supplemental beta-carotene during RT for prostate cancer. | Hezaveh H, Muhamad II, Noshadi I, Shu Fen L, Ngadi N (2012)
Swelling behaviour and controlled drug release from cross-linked κ-carrageenan/NaCMC hydrogel by diffusion mechanism.
Journal of microencapsulation 29, 368-379 [PubMed:22309480]
[show Abstract]
We studied a model system of controlled drug release using beta-carotene and κ-carrageenan/NaCMC hydrogel as a drug and a device, respectively. Different concentrations of genipin were added to crosslink the beta-carotene loaded beads by using the dripping method. Results have shown that the cross-linked beads possess lower swelling ability in all pH conditions (pH 1.2 and 7.4), and swelling ratio decreases with increasing genipin concentration. Microstructure study shows that cross-linking has enhanced the stability and structure of the beads network. Determination of diffusion coefficient for the release of encapsulated beta-carotene indicates less diffusivity when beads are cross-linked. Swelling models using adaptive neuro fuzzy show that using genipin as a cross-linker in the kC/NaCMC hydrogels affects the transport mechanism. The model shows very good agreement with the experimental data that indicates that applying ANFIS modelling is an accurate, rapid and simple way to model in such a case for controlled release applications. | Karppi J, Nurmi T, Kurl S, Rissanen TH, Nyyssönen K (2010)
Lycopene, lutein and beta-carotene as determinants of LDL conjugated dienes in serum.
Atherosclerosis 209, 565-572 [PubMed:19896667]
[show Abstract]
Oxidative modification of low-density lipoprotein (LDL) in the vascular endothelium is considered to be important in the development of early atherosclerosis. The aim of this study was to investigate the main determinants of serum LDL conjugated dienes in women (n=124) and men (n=225). We focused on the influence of fat-soluble vitamins and carotenoids on the concentration of conjugated dienes in LDL. In multivariate linear regression models, including age, body mass index, diastolic blood pressure, symptomatic ischaemic heart disease (IHD) or IHD history, statin medication, leukocytes and serum triglycerides as covariates, plasma lycopene (standardized beta=-0.33; P=0.002) and lutein (standardized beta=-0.22; P=0.027) concentrations were the strongest determinants of serum LDL conjugated dienes in women, whereas plasma beta-carotene (standardized beta=-0.23; P=0.002) was the most important factor in men. Furthermore, statin medication, diastolic blood pressure, age and serum triglycerides were significant determinants of LDL conjugated dienes. The regression model with lycopene contributed to 29% in women and 15% in men with beta-carotene of the variation of serum LDL conjugated dienes. Results of the present study suggest that plasma lycopene, lutein and beta-carotene are the most powerful antioxidants for explaining the content of in vivo oxidatively modified LDL in serum. | Lemmens L, De Vleeschouwer K, Moelants KR, Colle IJ, Van Loey AM, Hendrickx ME (2010)
Beta-carotene isomerization kinetics during thermal treatments of carrot puree.
Journal of agricultural and food chemistry 58, 6816-6824 [PubMed:20515074]
[show Abstract]
The effect of thermal processing on the stability of beta-carotene in carrot puree was investigated in a broad temperature range (80-150 degrees C). Heat induced changes in the stability of beta-carotene resulting in the conversion into its cis-isomers until an equilibrium state was reached after prolonged heating. By using nonlinear one-step regression analysis, the overall isomerization of all-trans-beta-carotene and the formation of individual cis-isomers could be modeled with a fractional conversion model. The Arrhenius equation was used to describe the temperature dependence of the reaction rate constants. As indicated by the low activation energies for all compounds (11 kJ mol(-1)), the isomerization rate constants showed little sensitivity toward the treatment temperature. The temperature dependence of the equilibrium concentration values after prolonged heating (C(f)) varied for the different compounds, but in all cases, a linear relation between the C(f) values and the treatment temperature could be noted. Although isomerization was observed as a result of thermal processing, it could be concluded that during industrially relevant heating processes, the retention of all-trans-beta-carotene in plain carrot puree was relatively high, which is most likely due to the presence of the protecting food matrix. | Sun Y, Ma G, Ye X, Kakuda Y, Meng R (2010)
Stability of all-trans-beta-carotene under ultrasound treatment in a model system: effects of different factors, kinetics and newly formed compounds.
Ultrasonics sonochemistry 17, 654-661 [PubMed:20074992]
[show Abstract]
The effects of factors and kinetics of all-trans-beta-carotene degradation under ultrasound treatment in a model system were investigated. The compounds of degradation were also tentatively identified by HPLC-DAD, Raman and FT-IR spectroscopy. The type of solvents and temperature were important factors in determining the degradation reaction. Liquid height, ultrasonic intensity and duty cycle of ultrasound exposure only affected the rate of degradation but did not change the nature of degradation. Degradation rate of beta-carotene in dichloromethane was the highest. Degradation rate of beta-carotene decreased with increasing of temperature. Degradation kinetics of all-trans-beta-carotene under ultrasound fitted first-order reaction at -5 to 15 degrees C, and fitted second-order reaction at 25 degrees C. Degradation products included isomers: 15-cis-beta-carotene, di-cis-beta-carotene and other compounds with function group of C-O. | Acosta O, Pérez AM, Vaillant F (2009)
Chemical characterization, antioxidant properties, and volatile constituents of naranjilla (Solanum quitoense Lam.) cultivated in Costa Rica.
Archivos latinoamericanos de nutricion 59, 88-94 [PubMed:19480350]
[show Abstract]
Naranjilla (Solanum quitoense Lam.) is a native fruit of the Andes, cultivated and consumed mainly in Ecuador, Colombia, and Central America. Because of its pleasant aroma and attractive color, it has high potential as an ingredient of products such as juices, nectars, and jams. The main characteristics of mature naranjilla fruits cultivated in Costa Rica were assessed, including sugar content, total titratable acidity, total soluble solids, oxygen radical absorbance capacity (H-ORAC), and total polyphenolic and ascorbic acid content. Carotenoid and volatile compound identification was also done. The samples showed sucrose, glucose, and fructose content of 1.6 +/- 0.3, 0.68 +/- 0.05, and 0.7 +/- 0.1 g/100 g, respectively. Total titratable acidity was 2.63 +/- 0.07 g citric acid equivalent / 100 g and total soluble solids amounted to 9.1 +/- 0.5 degrees Brix. H-ORAC value was 17 +/- 1 micromol Trolox equivalent /g, total polyphenolic content was 48 +/- 3 mg gallic acid equivalent /100 g and ascorbic acid content was 12.5 +/- 0.0 mg/100 g. Carotenoid content of the whole fruit and pulp was 33.3 +/- 0.6 and 7.2 +/- 0.3 microg/g, respectively. The predominant carotenoid among the compounds identified in the whole fruit was beta-carotene. Ten volatile compounds were identified in naranjillapulp, the predominant being methyl butanoate. The chemical composition of naranjilla cultivated in Costa Rica does not seem to differ from that previously reported in studies at different locations. | Riccioni G (2009)
Carotenoids and cardiovascular disease.
Current atherosclerosis reports 11, 434-439 [PubMed:19852884]
[show Abstract]
Carotenoids are a class of natural fat-soluble pigments found principally in plants. They have potential antioxidant biological properties due to their chemical structure and interaction with biological membranes. The most abundant carotenoids in the diet are beta-carotene, lycopene, lutein, beta-cryptoxanthin, zeaxanthin, and astaxanthin. Numerous epidemiologic studies have supported the hypothesis that antioxidants could be used as an inexpensive means of prevention, and possibly treatment, of cardiovascular diseases, even though findings from interventional trials have been mixed, with some positive findings, many null findings, and some suggestion of harm in certain high-risk populations. Recent smaller interventional studies with carefully chosen populations, such as those under high levels of oxidative stress, have yielded largely positive results. This suggests that we need more hypothesis-driven and rigorous clinical trial designs. The aim of this review is to examine the published studies about the use of carotenoids, especially lycopene and astaxanthin, in the treatment of cardiovascular diseases. | Takaichi S, Maoka T, Mochimaru M (2009)
Unique carotenoids in the terrestrial cyanobacterium Nostoc commune NIES-24: 2-hydroxymyxol 2'-fucoside, nostoxanthin and canthaxanthin.
Current microbiology 59, 413-419 [PubMed:19669835]
[show Abstract]
Cyanobacteria produce some carotenoids. We identified the molecular structures, including the stereochemistry, of all the carotenoids in the terrestrial cyanobacterium, Nostoc commune NIES-24 (IAM M-13). The major carotenoid was beta-carotene. Its hydroxyl derivatives were (3R)-beta-cryptoxanthin, (3R,3'R)-zeaxanthin, (2R,3R,3'R)-caloxanthin, and (2R,3R,2'R,3'R)-nostoxanthin, and its keto derivatives were echinenone and canthaxanthin. The unique myxol glycosides were (3R,2'S)-myxol 2'-fucoside and (2R,3R,2'S)-2-hydroxymyxol 2'-fucoside. This is only the second species found to contain 2-hydroxymyxol. We propose possible carotenogenesis pathways based on our identification of the carotenoids: the hydroxyl pathway produced nostoxanthin via zeaxanthin from beta-carotene, the keto pathway produced canthaxanthin from beta-carotene, and the myxol pathway produced 2-hydroxymyxol 2'-fucoside via myxol 2'-fucoside. This cyanobacterium was found to contain many kinds of carotenoids and also displayed many carotenogenesis pathways, while other cyanobacteria lack some carotenoids and a part of carotenogenesis pathways compared with this cyanobacterium. | Slimani N, Deharveng G, Southgate DA, Biessy C, Chajès V, van Bakel MM, Boutron-Ruault MC, McTaggart A, Grioni S, Verkaik-Kloosterman J, Huybrechts I, Amiano P, Jenab M, Vignat J, Bouckaert K, Casagrande C, Ferrari P, Zourna P, Trichopoulou A, Wirfält E, Johansson G, Rohrmann S, Illner AK, Barricarte A, Rodríguez L, Touvier M, Niravong M, Mulligan A, Crowe F, Ocké MC, van der Schouw YT, Bendinelli B, Lauria C, Brustad M, Hjartåker A, Tjønneland A, Jensen AM, Riboli E, Bingham S (2009)
Contribution of highly industrially processed foods to the nutrient intakes and patterns of middle-aged populations in the European Prospective Investigation into Cancer and Nutrition study.
European journal of clinical nutrition 63 Suppl 4, S206-25 [PubMed:19888275]
[show Abstract]
ObjectivesTo describe the contribution of highly processed foods to total diet, nutrient intakes and patterns among 27 redefined centres in the 10 countries participating in the European Prospective Investigation into Cancer and Nutrition (EPIC).MethodsSingle 24-hour dietary recalls were collected from 36,034 individuals (aged 35-74 years) using a standardized computerized interview programme (EPIC-SOFT). Centre-specific mean food intakes (g/day) were computed according to their degree of food processing (that is, highly, moderately and non-processed foods) using a specifically designed classification system. The contribution (%) of highly processed foods to the centre mean intakes of diet and 26 nutrients (including energy) was estimated using a standardized nutrient database (ENDB). The effect of different possible confounders was also investigated.ResultsHighly processed foods were an important source of the nutrients considered, contributing between 61% (Spain) and 78-79% (the Netherlands and Germany) of mean energy intakes. Only two nutrients, beta-carotene (34-46%) and vitamin C (28-36%), had a contribution from highly processed foods below 50% in Nordic countries, in Germany, the Netherlands and the United Kingdom, whereas for the other nutrients, the contribution varied from 50 to 91% (excluding alcohol). In southern countries (Greece, Spain, Italy and France), the overall contribution of highly processed foods to nutrient intakes was lower and consisted largely of staple or basic foods (for example, bread, pasta/rice, milk, vegetable oils), whereas highly processed foods such as crisp bread, breakfast cereals, margarine and other commercial foods contributed more in Nordic and central European centres.ConclusionsHighly industrially processed foods dominate diets and nutrient patterns in Nordic and central European countries. The greater variations observed within southern countries may reflect both a larger contribution of non/moderately processed staple foods along with a move from traditional to more industrialized dietary patterns. | Dias CD, Araújo BC, Dutra ES, Nepomuceno JC (2009)
Protective effects of beta-carotene against the genotoxicity of doxorubicin in somatic cells of Drosophila melanogaster.
Genetics and molecular research : GMR 8, 1367-1375 [PubMed:19937581]
[show Abstract]
beta-carotene (BC), pro-vitamin A, is an efficient antioxidant, effective in the neutralization of oxygen reactive species, which cause serious damage to DNA. Various studies have been conducted on the effectiveness of BC for chemoprevention of cancer and heart disease. Doxorubicin is a chemotherapeutic agent used for cancer treatment that generates free radicals. We examined the effects of BC (1, 2 and 4 mg/mL) on the genotoxicity of doxorubicin (0.125 mg/mL), using the wing spot test in Drosophila melanogaster (somatic mutation and recombination test). The BC alone had no significant effect on the frequency of mutant spots. However, it significantly reduced the number of spots caused by doxorubicin. We concluded that BC is not genotoxic and that it exerts protective effects against the genotoxic action of the chemotherapeutic free-radical generator doxorubicin. | Linden GJ, McClean KM, Woodside JV, Patterson CC, Evans A, Young IS, Kee F (2009)
Antioxidants and periodontitis in 60-70-year-old men.
Journal of clinical periodontology 36, 843-849 [PubMed:19703237]
[show Abstract]
ObjectiveThe aim was to investigate the association between periodontal health and the serum levels of various antioxidants including carotenoids, retinol and vitamin E in a homogenous group of Western European men.Materials and methodsA representative sample of 1258 men aged 60-70 years, drawn from the population of Northern Ireland, was examined between 2001 and 2003. Each participant had six or more teeth, completed a questionnaire and underwent a clinical periodontal examination. Serum lipid-soluble antioxidant levels were measured by high-performance liquid chromatography with diode array detection. Multivariable analysis was carried out using logistic regression with adjustment for possible confounders. Models were constructed using two measures of periodontal status (low- and high-threshold periodontitis) as dependent variables and the fifths of each antioxidant as a predictor variable.ResultsThe levels of alpha- and beta-carotene, beta-cryptoxanthin and zeaxanthin were highly significantly lower in the men with low-threshold periodontitis (p<0.001). These carotenoids were also significantly lower in high-threshold periodontitis. There were no significant differences in the levels of lutein, lycopene, alpha- and gamma-tocopherol or retinol in relation to periodontitis. In fully adjusted models, there was an inverse relationship between a number of carotenoids (alpha- and beta-carotene and beta-cryptoxanthin) and low-threshold periodontitis. beta-Carotene and beta-cryptoxanthin were the only antioxidants that were associated with an increased risk of high-threshold severe periodontitis. The adjusted odds ratio for high-threshold periodontitis in the lowest fifth relative to the highest fifth of beta-cryptoxanthin was 4.02 (p=0.003).ConclusionIt is concluded that low serum levels of a number of carotenoids, in particular beta-cryptoxanthin and beta-carotene, were associated with an increased prevalence of periodontitis in this homogenous group of 60-70-year-old Western European men. | Ampomah-Dwamena C, McGhie T, Wibisono R, Montefiori M, Hellens RP, Allan AC (2009)
The kiwifruit lycopene beta-cyclase plays a significant role in carotenoid accumulation in fruit.
Journal of experimental botany 60, 3765-3779 [PubMed:19574250]
[show Abstract]
The composition of carotenoids, along with anthocyanins and chlorophyll, accounts for the distinctive range of colour found in the Actinidia (kiwifruit) species. Lutein and beta-carotene are the most abundant carotenoids found during fruit development, with beta-carotene concentration increasing rapidly during fruit maturation and ripening. In addition, the accumulation of beta-carotene and lutein is influenced by the temperature at which harvested fruit are stored. Expression analysis of carotenoid biosynthetic genes among different genotypes and fruit developmental stages identified Actinidia lycopene beta-cyclase (LCY-beta) as the gene whose expression pattern appeared to be associated with both total carotenoid and beta-carotene accumulation. Phytoene desaturase (PDS) expression was the least variable among the different genotypes, while zeta carotene desaturase (ZDS), beta-carotene hydroxylase (CRH-beta), and epsilon carotene hydroxylase (CRH-epsilon) showed some variation in gene expression. The LCY-beta gene was functionally tested in bacteria and shown to convert lycopene and delta-carotene to beta-carotene and alpha-carotene respectively. This indicates that the accumulation of beta-carotene, the major carotenoid in these kiwifruit species, appears to be controlled by the level of expression of LCY-beta gene. | Tanvetyanon T, Bepler G (2008)
Beta-carotene in multivitamins and the possible risk of lung cancer among smokers versus former smokers: a meta-analysis and evaluation of national brands.
Cancer 113, 150-157 [PubMed:18429004]
[show Abstract]
BackgroundSome studies have suggested that beta-carotene supplementation may increase the risk of lung cancer, particularly among smokers or former smokers. Beta-carotene, a provitamin A, is available in multivitamins. In the current study, the authors investigated the risk of lung cancer associated with beta-carotene in smokers or former smokers and surveyed the beta-carotene content in national brand multivitamins.MethodsThe authors systemically reviewed the published literature using a search of the MEDLINE database and performed a meta-analysis of large randomized trials that reported on the effect of beta-carotene supplementation on the incidence of lung cancer among smokers or former smokers. A sample of multivitamins was evaluated for their beta-carotene content and the suggested daily dosage.ResultsFour studies contributing 109,394 subjects were available for analysis. The average daily beta-carotene dosage in these trials ranged from 20 to 30 mg daily. Among current smokers, beta-carotene supplementation was found to be significantly associated with an increased risk of lung cancer (odds ratio [OR], 1.24; 95% confidence interval [95% CI], 1.10-1.39). Among former smokers, there was no significant increase noted (OR, 1.10; 95% CI, 0.84-1.45). In a sample of 47 common multivitamins, beta-carotene was present in 70% of the identified formulas. The median dosage of beta-carotene was 0.3 mg (range, 0-17.2 mg) daily. The beta-carotene content was found to be significantly higher among multivitamins sold to improve visual health than among other multivitamins, with a median daily dosage of 3 mg (range, 0-24 mg).ConclusionsHigh-dose beta-carotene supplementation appears to increase the risk of lung cancer among current smokers. Although beta-carotene was prevalent in multivitamins, high-dose beta-carotene was observed among multivitamin formulas sold to promote visual health. | Hughes JL, Rutherford AW, Sugiura M, Krausz E (2008)
Quantum efficiency distributions of photo-induced side-pathway donor oxidation at cryogenic temperature in photosystem II.
Photosynthesis research 98, 199-206 [PubMed:18766464]
[show Abstract]
We monitored illuminated-minus-dark absorption difference spectra in the range of 450-1100 nm induced by continuous illumination at 8 K of photosystem II (PSII) core complexes from Thermosynechococcus elongatus. The photo-induced oxidation of the side-path donors Cytb(559), beta-carotene and chlorophyll Z, as well as the concomitant stable (t(1/2) > 1 s) reduction of the first plastoquinone electron acceptor, Q(A) (monitored by the well-known 'C550' shift), were quantified as a function of the absorbed photons per PSII. The Q(A) photo-induced reduction data can be described by three distinct quantum efficiency distributions: (i) a very high efficiency of approximately 0.5-1, (ii) a middle efficiency with a very large range of approximately 0.014-0.2, and (iii) a low efficiency of approximately 0.002. Each of the observed side-path donors exhibited similar quantum efficiency distributions, which supports a branched pathway model for side-path oxidation where beta-carotene is the immediate electron donor to the photo-oxidized chlorophyll (P680(+)). The yields of the observed side-path donors account quantitatively for the wide middle efficiency range of photo-induced Q(A) reduction, but not for the PSII fractions that exhibit the highest and lowest efficiencies. The high-efficiency component may be due to Tyr(Z) oxidation. A donor that does not exhibit an identified absorption in the visible-near-IR region is mainly responsible for the lowest efficiency component. | Iwai M, Maoka T, Ikeuchi M, Takaichi S (2008)
2,2'-beta-hydroxylase (CrtG) is involved in carotenogenesis of both nostoxanthin and 2-hydroxymyxol 2'-fucoside in Thermosynechococcus elongatus strain BP-1.
Plant & cell physiology 49, 1678-1687 [PubMed:18794175]
[show Abstract]
We identified the molecular structures, including the stereochemistry, of all carotenoids in Thermosynechococcus elongatus strain BP-1. The major carotenoid was beta-carotene, and its hydroxyl derivatives of (3R)-beta-cryptoxanthin, (3R,3'R)-zeaxanthin, (2R,3R,3'R)-caloxanthin and (2R,3R,2'R,3'R)-nostoxanthin were also identified. The myxol glycosides were identified as (3R,2'S)-myxol 2'-fucoside and (2R,3R,2'S)-2-hydroxymyxol 2'-fucoside. 2-Hydroxymyxol 2'-fucoside is a novel carotenoid, and similar carotenoids of 4-hydroxymyxol glycosides were previously named aphanizophyll. Ketocarotenoids, such as echinenone and 4-ketomyxol, which are unique carotenoids in cyanobacteria, were absent, and genes coding for both beta-carotene ketolases, crtO and crtW, were absent in the genome. From a homology search, the Tlr1917 amino acid sequence was found to be 41% identical to 2,2'- beta-hydroxylase (CrtG) from Brevundimonas sp. SD212, which produces nostoxanthin from zeaxanthin. In the crtG disruptant mutant, 2-hydroxymyxol 2'-fucoside, caloxanthin and nostoxanthin were absent, and the levels of both myxol 2'-fucoside and zeaxanthin were higher. Therefore, the gene has a CrtG function for both myxol to 2-hydroxymyxol and zeaxanthin to nostoxanthin. This is the first functional identification of CrtG in cyanobacteria. We also investigated the distribution of crtG-like genes, and 2-hydroxymyxol and/or nostoxanthin, in cyanobacteria. Based on the identification of the carotenoids and the completion of the entire nucleotide sequence of the genome in T. elongatus, we propose a biosynthetic pathway of the carotenoids and the corresponding genes and enzymes. | Yu B, Lydiate DJ, Young LW, Schäfer UA, Hannoufa A (2008)
Enhancing the carotenoid content of Brassica napus seeds by downregulating lycopene epsilon cyclase.
Transgenic research 17, 573-585 [PubMed:17851775]
[show Abstract]
The accumulation of carotenoids in higher plants is regulated by the environment, tissue type and developmental stage. In Brassica napus leaves, beta-carotene and lutein were the main carotenoids present while petals primarily accumulated lutein and violaxanthin. Carotenoid accumulation in seeds was developmentally regulated with the highest levels detected at 35-40 days post anthesis. The carotenoid biosynthesis pathway branches after the formation of lycopene. One branch forms carotenoids with two beta rings such as beta-carotene, zeaxanthin and violaxanthin, while the other introduces both beta- and epsilon-rings in lycopene to form alpha-carotene and lutein. By reducing the expression of lycopene epsilon-cyclase (epsilon-CYC) using RNAi, we investigated altering carotenoid accumulation in seeds of B. napus. Transgenic seeds expressing this construct had increased levels of beta-carotene, zeaxanthin, violaxanthin and, unexpectedly, lutein. The higher total carotenoid content resulting from reduction of epsilon-CYC expression in seeds suggests that this gene is a rate-limiting step in the carotenoid biosynthesis pathway. epsilon-CYC activity and carotenoid production may also be related to fatty acid biosynthesis in seeds as transgenic seeds showed an overall decrease in total fatty acid content and minor changes in the proportions of various fatty acids. | Zadorozhnyĭ Pa, borisovets EE, Iakush EV, Davidiuk TS (2008)
[Change of carotenoid composition in crabs during embryogenesis].
Zhurnal evoliutsionnoi biokhimii i fiziologii 44, 381-390 [PubMed:18767554]
[show Abstract]
Changes of the qualitative and quantitative compositions of carotenoids are studied at various development stages of the external egg, determined based on color differences, for the species C. opilio, P. camtschaticus, and P. platypus. It has been established that the main carotenoids of the new egg are astaxanthin and beta-carotene. Intermediate products of transformation of beta-carotene into astaxanthin are identified: echinenon, cantaxanthin, and phoenicoxanthin. The carotenoid content per embryo for the new egg of C. opilio (the orange egg) amounted to 22.7 ng, of P. camtschaticus and P. platypus (the violet egg)--to 49.2 and 23.3 ng, respectively. In the egg at the later development stage (the brown egg) the carotenoid content was decreased to 13.1 ng in C. opilio and to 20.1 ng in P. camtschaticus. Development of embryos is accompanied by accumulation of esterified carotenoids and a decrease of beta-carotene and astaxanthin concentrations in all studied species. | Ornelas-Paz Jde J, Yahia EM, Gardea-Bejar A (2007)
Identification and quantification of xanthophyll esters, carotenes, and tocopherols in the fruit of seven Mexican mango cultivars by liquid chromatography-atmospheric pressure chemical ionization-time-of-flight mass spectrometry [LC-(APcI(+))-MS].
Journal of agricultural and food chemistry 55, 6628-6635 [PubMed:17625873]
[show Abstract]
A liquid chromatography-mass spectrometry (LC-MS) method was developed to simultaneously identify and quantify carotenoids and tocopherols in the fruit of seven mango cultivars grown in Mexico. Fruit maturity was characterized objectively, and carotenoids and tocopherols were isolated by solvent extraction and analyzed by HPLC coupled to a C30 stationary phase and diode array, fluorescence, and mass (time-of-flight) detectors. All cultivars had a similar carotenoid pattern, in which all-trans-beta-carotene and dibutyrates of all-trans-violaxanthin and 9-cis-violaxanthin were the most abundant. The content of all-trans-beta-carotene ranged between 0.4 and 2.8 mg/100 g, and 'Haden' and 'Ataulfo' mangoes had the highest amount. The amounts of all-trans-violaxanthin and 9-cis-violaxanthin (as dibutyrates) ranged between 0.5 and 2.8 mg/100g and between 0.4 and 2.0 mg/100 g, respectively. The content of alpha-tocopherol was low (200-500 microg/100 g). The results of this study indicate that all-trans-beta-carotene, all-trans-violaxanthin, and 9-cis-violaxanthin are the most abundant carotenoids in mango grown in Mexico. | Zhou CH, Xu CJ, Sun CD, Li X, Chen KS (2007)
Carotenoids in white- and red-fleshed loquat fruits.
Journal of agricultural and food chemistry 55, 7822-7830 [PubMed:17708644]
[show Abstract]
Fruits of 23 loquat ( Eriobotrya japonica Lindl.) cultivars, of which 11 were white-fleshed and 12 red-fleshed, were analyzed for color, carotenoid content, and vitamin A values. Color differences between two loquat groups were observed in the peel as well as in the flesh. beta-Carotene and lutein were the major carotenoids in the peel, which accounted for about 60% of the total colored carotenoids in both red- and white-fleshed cultivars. beta-Cryptoxanthin and, in some red-fleshed cultivars, beta-carotene were the most abundant carotenoids in the flesh, and in total, they accounted for over half of the colored carotenoids. Neoxanthin, violaxanthin, luteoxanthin, 9- cis-violaxanthin, phytoene, phytofluene, and zeta-carotene were also identified, while zeaxanthin, alpha-carotene, and lycopene were undetectable. Xanthophylls were highly esterified. On average, 1.3- and 10.8-fold higher levels of colored carotenoids were observed in the peel and flesh tissue of red-fleshed cultivars, respectively. The percentage of beta-carotene among colored carotenoids was higher in both the peel and the flesh of red-fleshed cultivars. Correlations between the levels of total colored carotenoids and the color indices were analyzed. The a* and the ratio of a*/ b* were positively correlated with the total content of colored carotenoids, while L*, b*, and H degrees correlated negatively. Vitamin A values, as retinol equivalents (RE), of loquat flesh were 0.49 and 8.77 microg/g DW (8.46 and 136.41 microg/100 g FW) on average for white- and red-fleshed cultivars, respectively. The RE values for the red-fleshed fruits were higher than fruits such as mango, red watermelon, papaya, and orange as reported in the literature, suggesting that loquat is an excellent source of provitamin A. | Ibdah M, Azulay Y, Portnoy V, Wasserman B, Bar E, Meir A, Burger Y, Hirschberg J, Schaffer AA, Katzir N, Tadmor Y, Lewinsohn E (2006)
Functional characterization of CmCCD1, a carotenoid cleavage dioxygenase from melon.
Phytochemistry 67, 1579-1589 [PubMed:16563447]
[show Abstract]
Carotenoids are nutritionally important tetraterpenoid pigments that upon oxidative cleavage give rise to apocarotenoid (norisoprene) aroma volatiles. beta-Carotene is the predominant pigment in orange-fleshed melon (Cucumis melo L.) varieties, reaching levels of up to 50 microg/gFW. Pale green and white cultivars have much lower levels (0-10 microg/gFW). In parallel, beta-ionone, the 9,10 cleavage product of beta-carotene, is present (12-33ng/gFW) in orange-fleshed melon varieties that accumulate beta-carotene, and in much lower levels (0-5 ng/gFW) in pale green and white fleshed varieties. A search for a gene putatively responsible for the cleavage of beta-carotene into beta-ionone was carried out in annotated melon fruit EST databases yielding a sequence (CmCCD1) highly similar (84%) to other plant carotenoid cleavage dioxygenase genes. To test its function, the clone was overexpressed in Escherichia coli strains previously engineered to produce different carotenoids. We show here that the CmCCD1 gene product cleaves carotenoids at positions 9,10 and 9',10', generating geranylacetone from phytoene; pseudoionone from lycopene; beta-ionone from beta-carotene, as well as alpha-ionone and pseudoionone from delta-carotene. CmCCD1 gene expression is upregulated upon fruit development both in orange, pale-green and white melon varieties, despite the lack of apocarotenoid volatiles in the later. Thus, the accumulation of beta-ionone in melon fruit is probably limited by the availability of carotenoid substrate. | Takaichi S, Mochimaru M, Maoka T (2006)
Presence of free myxol and 4-hydroxymyxol and absence of myxol glycosides in Anabaena variabilis ATCC 29413, and proposal of a biosynthetic pathway of carotenoids.
Plant & cell physiology 47, 211-216 [PubMed:16338959]
[show Abstract]
We identified the molecular structures of all carotenoids in Anabaena variabilis ATCC 29413 (= IAM M-204). The major carotenoids were beta-carotene, echinenone and canthaxanthin. Myxol glycosides were absent, while free forms of myxol and 4-hydroxymyxol were present. The 4-hydroxyl group of the latter was a mixture of (4R) and (4S) configurations, which is a rare mixture in carotenoids. Thus, this strain was the first cyanobacterium found to have free myxol and not myxol glycosides, and seemed to lack the gene for or activity of glycosyl transferase. In another strain of A. variabilis IAM M-3 (= PCC 7118), we recently identified (3R,2'S)-myxol 2'-fucoside and (3S,2'S)-4-ketomyxol 2'-fucoside, and hence the strain ATCC 29413 might be useful for investigating the characteristics of myxol glycosides in cyanobacteria. Based on the identification of the carotenoids and the completion of the entire nucleotide sequence of the genome in A. variabilis ATCC 29413, we proposed a biosynthetic pathway of the carotenoids and the corresponding genes and enzymes. The homologous genes were searched by sequence homology only from the functionally confirmed genes. | Chen Z, Lee C, Lenzer T, Oum K (2006)
Solvent effects on the S0(1(1)Ag-) --> S2(1(1)Bu+) transition of beta-carotene, echinenone, canthaxanthin, and astaxanthin in supercritical CO2 and CF3H.
The journal of physical chemistry. A 110, 11291-11297 [PubMed:17004738]
[show Abstract]
Solvent-induced spectral shifts of the four C40 carotenoids, beta-carotene, echinenone, canthaxantin, and astaxanthin, have been studied in supercritical CO2 and CF3H. In situ absorption spectroscopic analysis was used to determine the maximum peak position of the electronic transitions from the ground state (1(1)Ag-) to the S2 state (1(1)Bu+) of the carotenoids. The medium polarizability function, R(n) = (n2 - 1)/(n2 + 2) of the refractive index of the solvent was varied over the range R(n) = 0.08-0.14, by changing the pressure of CO2 or CF3H between 90 and 300 bar at the temperature 308 K. For all the carotenoids studied here, a significant hypsochromic shift of ca. 20-30 nm was observed in supercritical fluids as compared to that in nonpolar liquids. The spectral shifts in supercritical fluids were compared with those in liquids and showed a clear linear dependence on the medium polarizability. The temperature-dependent shift of the absorption maxima was less significant. Interestingly, there was almost no difference in the energetic position of the absorption maxima in supercritical CO2 and CF3H at a given R(n) value. This is in contrast to previous extrapolations from studies in liquids at larger R(n) values, which yielded different slopes of the R(n)-dependent spectral shifts for polar and nonpolar solvents toward the gas-phase limit of R(n) = 0. The current experimental results in the gas-to-liquid range show that the polarity of the solvent has only a minor influence on the 1(1)Ag- --> 1(1)Bu+ transition energy in the region of low R(n). We also obtain more reliable extrapolations of this 0-0 transition energy to the gas-phase limit nu(0-0)(gas-phase) approximately (23,000 +/- 120) cm(-1) for beta-carotene. | Keijer J, Bunschoten A, Palou A, Franssen-van Hal NL (2005)
Beta-carotene and the application of transcriptomics in risk-benefit evaluation of natural dietary components.
Biochimica et biophysica acta 1740, 139-146 [PubMed:15949680]
[show Abstract]
Beta-carotene is a natural food component that is present in fruits and vegetables and is also used as a food colorant and a supplement. Beta-carotene is an anti-oxidant and a source of vitamin A. It is endowed with health beneficial properties, but a number of studies showed that with high intakes it may increase the risk for lung cancer in at risk individuals (heavy smokers, asbestos workers and alcohol users). To establish the window of benefit, it is necessary to identify early markers of effect and to obtain insight in the mechanism of action of beta-carotene, in the absence and presence of environmental risk factors. Genomics technologies are well suited to dissect the mechanisms of action and identify the markers of effect. Human cell lines can be used to analyse the effects of beta-carotene, but exposure studies with beta-carotene show that cell lines display a widely variant behaviour, which hampers translation to the in vivo situation in humans. Alternatively, animal studies can be used. Especially the ferret seems to be a good model, but little sequence information of this species is available. However, heterologous hybridization on human cDNA seems possible and provides and a new tool for molecular analysis of health effects of beta-carotene. | Rühl R (2005)
Induction of PXR-mediated metabolism by beta-carotene.
Biochimica et biophysica acta 1740, 162-169 [PubMed:15949683]
[show Abstract]
beta-carotene is the major carotenoid occurring in the human diet and in the human organism. Besides its function as pro-vitamin A, beta-carotene has been shown to be an activator of the human pregnan X receptor (PXR). PXR is mainly expressed in the liver/intestine and an inducer of enzymes involved in phase I, II and III metabolism. This review is focused on the evaluation of physiological and nutritional relevance of beta-carotene as an inducer of phase I enzymes in the human organism via PXR-mediated mechanisms. Beneficial and detrimental effects of beta-carotene on xenobiotica metabolism and metabolism of various other derivatives will be discussed. | Lele S (2005)
Although leukoplakia responds to some treatments relapses and adverse effects are common.
Evidence-based dentistry 6, 15-16 [PubMed:15789045]
[show Abstract]
Data sourcesThe Cochrane Oral Health Group's Trials Register, Cochrane Central Trials Register, Medline and Embase were searched, as well as the following journals: Cancer, Community Dentistry and Oral Epidemiology, European Journal of Oral Sciences, Journal of Dental Research, Oral Oncology, Oral Surgery, Oral Medicine, Oral Pathology, Oral Radiology and Endodontics. The reference lists of included studies and reviews were checked, and oral medicine experts were contacted through a European mailing list (EURORALMED).Study selectionRandomised controlled trials (RCT) were included if they had enrolled patients who had a diagnosis of oral leukoplakia and who were undergoing any surgical or medical (topical and systemic) treatment. The primary outcome considered was malignant transformation of leukoplakia demonstrated by histopathological examination. Other outcomes considered were clinical resolution, histological modification and frequency of adverse effects.Data extraction and synthesisData were collected using a specific extraction form. The validity of studies included was assessed by two reviewers, on the basis of the method of allocation concealment, blindness of the study and loss of participants. Data were analysed by calculating relative risk (RR). When valid and relevant data were collected, a meta-analysis of the data was undertaken.ResultsThe possible effectiveness of surgical interventions, including laser therapy and cryotherapy, has never been studied by means of an RCT. Nineteen RCT of nonsurgical interventions were identified: seven were included. Vitamin A and retinoids were tested in five RCT (245 patients); the other drugs tested were bleomycin (one study), mixed tea (one study) and beta-carotene (one study). Malignant transformation was recorded in just two studies. None of the treatments tested showed a benefit compared with placebo. Treatment with beta-carotene and vitamin A or retinoids was associated with significant rates of clinical resolution, compared with placebo or absence of treatment. Whenever reported, a high rate of relapse was a common finding. Side effects of variable severity were often described but interventions were well accepted by patients, since dropout rates were similar between treatment and control.ConclusionsTo date there is no evidence of effective treatment in preventing malignant transformation of leukoplakia. Treatments may be effective in the resolution of lesions, but relapses and adverse effects are common. | Vulcain E, Goupy P, Caris-Veyrat C, Dangles O (2005)
Inhibition of the metmyoglobin-induced peroxidation of linoleic acid by dietary antioxidants: Action in the aqueous vs. lipid phase.
Free radical research 39, 547-563 [PubMed:16036331]
[show Abstract]
The gastric digestion of food containing oxidizable lipids and iron catalysts for peroxide decomposition such as (met)myoglobin from muscle meat can be accompanied by an extensive formation of potentially toxic lipid hydroperoxides. An early protective action by dietary antioxidants in the gastro-intestinal tract is plausible, especially for poorly bioavailable antioxidants such as polyphenols. Hence, the ability of antioxidants to inhibit lipid peroxidation initiated by dietary iron in mildly acidic emulsions is a valuable and general model. In this work, the ability of some ubiquitous dietary antioxidants representative of the main antioxidant classes (alpha-tocopherol, the flavonol quercetin, beta-carotene) to inhibit the metmyoglobin-induced peroxidation of linoleic acid is investigated by UV-visible spectroscopy and HPLC in mildly acidic emulsions. The phenolic antioxidants quercetin and alpha-tocopherol come up as the most efficient peroxidation inhibitors. Inhibition by quercetin essentially proceeds in the aqueous phase via a fast reduction of an unidentified activated iron species (with a partially degraded heme) produced by reaction of metmyoglobin with the lipid hydroperoxides. This reaction is faster by, at least, a factor 40 than the reduction of ferrylmyoglobin (independently prepared by reacting metmyoglobin with hydrogen peroxide) by quercetin. By contrast, alpha-tocopherol mainly acts in the lipid phase by reducing the propagating lipid peroxyl radicals. The poorer inhibition afforded by beta-carotene may be related to both its slower reaction with the lipid peroxyl radicals and its competitive degradation by autoxidation and/or photo-oxidation. | Apak R, Güçlü K, Ozyürek M, Karademir SE, Altun M (2005)
Total antioxidant capacity assay of human serum using copper(II)-neocuproine as chromogenic oxidant: the CUPRAC method.
Free radical research 39, 949-961 [PubMed:16087476]
[show Abstract]
BackgroundTests measuring the combined antioxidant effect of the nonenzymatic defenses in biological fluids may be useful in providing an index of the organism's capability to counteract reactive species known as prooxidants, resist oxidative damage and combat oxidative stress-related diseases. The selected chromogenic redox reagent for the assay of human serum should be easily accessible, stable, selective, respond to all types of biologically important antioxidants such as ascorbic acid, alpha-tocopherol, beta-carotene, reduced glutathione (GSH), uric acid and bilirubin, regardless of chemical type or hydrophilicity. Currently, there is no rapid method for total antioxidant assay of human serum meeting the above criteria.MethodsOur recently developed cupric reducing antioxidant capacity (CUPRAC) spectrophotometric method for a number of polyphenols and flavonoids using the copper(II)-neocuproine reagent in ammonium acetate buffer was now applied to a complete series of plasma antioxidants for the assay of total antioxidant capacity (TAC) of serum, and the resulting absorbance at 450 nm was recorded either directly (e.g. for ascorbic acid, alpha-tocopherol and glutathione) or after incubation at 50 degrees C for 20 min (e.g. for uric acid, bilirubin and albumin), quantitation being made by means of a calibration curve. The lipophilic antioxidants, alpha-tocopherol and beta-carotene, were assayed in dichloromethane (DCM). Lipophilic antioxidants of serum were extracted with n-hexane from an ethanolic solution of serum subjected to centrifugation. Hydrophilic antioxidants of serum were assayed after perchloric acid precipitation of proteins in the centrifugate.ResultsThe molar absorptivities, linear ranges and trolox equivalent antioxidant capacity (TEAC) coefficients of the serum antioxidants were established with respect to the CUPRAC spectrophotometric method, and the results (TEAC, or TEAC coefficients) were evaluated in comparison to the findings of the ABTS/TEAC reference method using persulfate as oxidant. As for hydrophilic phase, a linear correlation existed between the CUPRAC and ABTS findings (r=0.58), contrary to current literature reporting that either serum ORAC or serum ferric reducing antioxidant potency (FRAP) does not correlate at all with serum TEAC. The analytical responses of serum antioxidants were shown to be additive, enabling a TAC assay. The intra- and inter-assay CVs were 0.7 and 1.5%, respectively, for serum.ConclusionsThe CUPRAC assay proved to be efficient for glutathione and thiol-type antioxidants, for which the FRAP test was nonresponsive. The findings of CUPRAC completely agreed with those of ABTS-persulfate for lipophilic phase. The additivity of absorbances of all the tested antioxidants confirmed that antioxidants in the CUPRAC test did not chemically interact among each other so as to cause an intensification or quenching of the theoretically expected absorbance. As a distinct advantage over other electron-transfer based assays (e.g. Folin, FRAP, ABTS, DPPH), CUPRAC is superior in regard to its realistic pH close to the physiological pH, favourable redox potential, accessibility and stability of reagents and applicability to lipophilic antioxidants as well as hydrophilic ones. | Seo JS, Burri BJ, Quan Z, Neidlinger TR (2005)
Extraction and chromatography of carotenoids from pumpkin.
Journal of chromatography. A 1073, 371-375 [PubMed:15909543]
[show Abstract]
Vitamin A deficiency is a health problem in Southeast Asia that can be corrected by feeding orange fruits and vegetables such as mango. Pumpkin is a traditional Korean food that is easy to store and is already believed to have health benefits. We extracted carotenoids from pumpkin by liquid-liquid extraction and by supercritical fluid extraction. We measured carotenoids by reversed-phase chromatography with diode array detection. The major carotenoid in pumpkin (> 80%) is beta-carotene, with lesser amounts of lutein, lycopene, alpha-carotene and cis-beta-carotene. Pumpkin is a rich source of beta-carotene and might be useful for preventing Vitamin A deficiency. | Takaichi S, Mochimaru M, Maoka T, Katoh H (2005)
Myxol and 4-ketomyxol 2'-fucosides, not rhamnosides, from Anabaena sp. PCC 7120 and Nostoc punctiforme PCC 73102, and proposal for the biosynthetic pathway of carotenoids.
Plant & cell physiology 46, 497-504 [PubMed:15695449]
[show Abstract]
We identified the molecular structures of carotenoids in some Anabaena and Nostoc species. The myxoxanthophyll and ketomyxoxanthophyll in Anabaena (also known as Nostoc) sp. PCC 7120, Anabaena variabilis IAM M-3, Nostoc punctiforme PCC 73102 and Nostoc sp. HK-01 were (3R,2'S)-myxol 2'-fucoside and (3S,2'S)-4-ketomyxol 2'-fucoside, respectively. The glycoside moiety of the pigments was fucose, not rhamnose. The major carotenoids were beta-carotene and echinenone, and the minor ones were beta-cryptoxanthin, zeaxanthin, canthaxanthin and 3'-hydroxyechinenone. Based on the identification of the carotenoids and the completion of the entire nucleotide sequence of the genome in Anabaena sp. PCC 7120 and N. punctiforme PCC 73102, we proposed a biosynthetic pathway for the carotenoids and the corresponding genes and enzymes. Since only zeta-carotene desaturase (CrtQ) from Anabaena sp. PCC 7120 and beta-carotene ketolase (CrtW) from N. punctiforme PCC 73102 have been functionally identified, the other genes were searched by sequence homology only from the functionally confirmed genes. Finally, we investigated the phylogenetic relationships among some Anabaena and Nostoc species, including some newly isolated species. | Simova ED, Frengova GI, Beshkova DM (2004)
Synthesis of carotenoids by Rhodotorula rubra GED8 co-cultured with yogurt starter cultures in whey ultrafiltrate.
Journal of industrial microbiology & biotechnology 31, 115-121 [PubMed:14997360]
[show Abstract]
Two cultures, a yeast ( Rhodorula rubra GED8) and a yogurt starter ( Lactobacillus bulgaricus 2-11+ Streptococcus thermophilus 15HA), were selected for associated growth in whey ultrafiltrate (WU) and active synthesis of carotenoids. In associated cultivation with the yogurt culture L bulgaricus 2-11+S. thermophilus 15HA under intensive aeration (1.3 l(-1)min(-1) air-flow rate) in WU (45 g lactose l(-1)), initial pH 5.5, 30 degrees C, the lactose-negative strain R. rubra GED8 synthesized large amounts of carotenoids (13.09 mg l(-1 )culture fluid). The carotenoid yield was approximately two-fold higher in association with a mixed yogurt culture than in association with pure yogurt bacteria. The major carotenoid pigments comprising the total carotenoids were beta-carotene (50%), torulene (12.3%) and torularhodin (35.2%). Carotenoids with a high beta-carotene content were produced by the microbial association 36 h earlier than by Rhodotorula yeast species. No significant differences were notd in the ratio between the pigments synthesized by R. rubra GED8+ L. bulgaricus 2-11, R. rubra GED8+ S. thermophilus 15HA, and R.rubra GED8+yogurt culture, despite the fact that the total carotenoid concentrations were lower in the mixed cultures with pure yogurt bacteria. | Gumpricht E, Dahl R, Devereaux MW, Sokol RJ (2004)
Beta-carotene prevents bile acid-induced cytotoxicity in the rat hepatocyte: Evidence for an antioxidant and anti-apoptotic role of beta-carotene in vitro.
Pediatric research 55, 814-821 [PubMed:14764912]
[show Abstract]
Hydrophobic bile acids are implicated in the pathogenesis of cholestatic liver disorders through mechanisms involving oxidative stress and mitochondrial dysfunction. Antioxidants ameliorate bile acid-induced cytotoxicity in rat hepatocyte suspensions. The purpose of the current study was to evaluate the potential protective role of beta-carotene (betaC), a putative fat-soluble antioxidant that is reduced in patients with cholestasis, against bile acid-induced hepatotoxicity. In freshly isolated rat hepatocyte suspensions that were exposed to the toxic hydrophobic bile acid glycochenodeoxycholic acid (100 or 500 microM), betaC (100 microM) decreased generation of reactive oxygen species by >50%, similar to the inhibition afforded by alpha-tocopherol. Commensurate with this antioxidant effect, 100 microM betaC also protected hepatocytes against both glycochenodeoxycholic acid-induced cellular necrosis and apoptosis, which was associated with reduction in caspase 3 activation, inhibition of mitochondrial cytochrome c release in rat hepatocytes, and prevention of the mitochondrial permeability transition in both liver mitochondria and rat hepatocytes. A lower concentration of betaC (50 microM) produced similar antioxidant and anti-apoptotic protection but with less inhibition against cell necrosis, suggesting that the higher concentration of betaC may have conferred additional cytoprotection not directly related to its antioxidant function. These results demonstrate that the antioxidant effects of betaC may provide hepatoprotection against cholestatic liver injury by preventing bile acid-induced oxidative stress and mitochondrial perturbations. | Fujisawa S, Ishihara M, Kadoma Y (2004)
Kinetics of the radical scavenging activity of beta-carotene-related compounds.
SAR and QSAR in environmental research 15, 33-41 [PubMed:15113067]
[show Abstract]
To clarify the non-enzymatic radical-scavenging activity of beta-carotene-related compounds and other polyenes, we used differential scanning calorimetry to study the kinetics of radical polymerization of methyl methacrylate (MMA) by 2,2'-azobisisobutyronitrile (AIBN) or benzoyl peroxide (BPO) in the absence or presence of polyenes under nearly anaerobic conditions at 70 degrees C, and analyzed the results with an SAR approach. The polyenes studied were all-trans retinol, retinol palmitate, calciferol, beta-carotene and lycopene. Polyenes produced a small induction period. The stoichiometric factor (n) (i.e. the number of radicals trapped by each inhibitor molecule) of polyenes was close to 0. Tetraterpenes (beta-carotene, lycopene) suppressed significantly more of the initial rate of polymerization (R(inh)) than did diterpenes (retinol, retinol palmitate). The inhibition rate constants (k(inh)) for the reaction of beta-carotene with AIBN- or BPO-derived radicals were determined to be 1.2-1.6x10(5) l/mol s, similar to published values. A linear relationship between (k(inh)) and the kinetic chain length (KCL) for polyenes was observed; as (k(inh)) increased, KCL decreased. KCL also decreased significantly as the number of conjugated double bonds in the polyenes increased. Polyenes, particularly beta-carotene and lycopene, acted as interceptors of growing poly-MMA radicals. | Sayo T, Sakai S, Inoue S (2004)
Synergistic effect of N-acetylglucosamine and retinoids on hyaluronan production in human keratinocytes.
Skin pharmacology and physiology 17, 77-83 [PubMed:14976384]
[show Abstract]
Hyaluronan (HA) is well known to reside in the extracellular matrix as a water-sorbed macromolecule. The aims of this study were twofold: to investigate the regulation of HA synthesis in keratinocytes, and to develop a method to modulate this regulatory process. We found that N-acetylglucosamine (NAG) increased the production of HA by cultured keratinocytes dose dependently, but had no effect on the production by skin fibroblasts. The effect of NAG in keratinocytes was found to be specific for HA production, as there was no change in sulfated glycosaminoglycan formation. The copresence of NAG with either of two retinoids, retinoic acid (RA) or retinol, exerted a synergistic effect on HA production. To investigate whether human HA synthase (HAS) genes were regulated by NAG or retinoids, total RNA extracted from cells treated with these agents was subjected to Northern blot analysis. We observed that RA and retinol markedly induced the expression of HA synthase-3 (HAS3) mRNA. Moreover, beta-carotene, a provitamin A, influenced HA production and HAS3 gene expression in a manner similar to the retinoids. Conversely, NAG had no effect on the expression of HAS3 transcripts. Pretreatment of cells with RA stimulated the activity of membrane-associated HAS, whereas pretreatment with NAG did not. These results suggest that HA production is regulated by at least two pathways: one involving the regulation of HAS gene expression, and the other independent of such a regulatory effect. Taken together, our findings suggest that NAG is a new modulator of HA synthesis. | Gireesh T, Nair PP, Sudhakaran PR (2004)
Studies on the bioavailability of the provitamin A carotenoid, beta-carotene, using human exfoliated colonic epithelial cells.
The British journal of nutrition 92, 241-245 [PubMed:15333155]
[show Abstract]
The possibility of using exfoliated colonic epithelial cells for assessing the bioavailability of beta-carotene was examined. Analysis of exfoliated colonic epithelial cells showed the presence of beta-carotene and vitamin A. The beta-carotene content was significantly lower in cells from stool samples of subjects on a beta-carotene-poor diet than those receiving a single dose of a beta-carotene supplement. Colonic epithelial cells isolated from stool samples collected daily during a wash-out period while the subjects were on a beta-carotene-poor diet showed a steady decrease in beta-carotene content, reaching the lowest value on day 7. Kinetic analysis showed that a single dose of a beta-carotene supplement in the form of spirulina (Spirulina platensis) or agathi (Sesbania grandiflora) after the wash-out period caused an increase in the beta-carotene content after a lag period of 5-7 d, but the vitamin A levels during these periods were not significantly affected. Analysis of plasma beta-carotene concentration also showed similar changes, which correlated with those of exfoliated colonic cells. A relationship between the beta-carotene content of the diet and that of the colonic epithelial cells suggests that analysis of the beta-carotene content in exfoliated human colonic epithelial cells is a useful non-invasive method to assess the bioavailability of provitamin A beta-carotene. | Vuong LT, King JC (2003)
A method of preserving and testing the acceptability of gac fruit oil, a good source of beta-carotene and essential fatty acids.
Food and nutrition bulletin 24, 224-230 [PubMed:12891827]
[show Abstract]
Gac fruit (Momordica cochinchinensis Spreng) is indigenous to Vietnam and other countries in Southeast Asia. Its seed pulp contains high concentrations of carotenoids, especially the provitamin A, beta-carotene. In northern Vietnam, gac fruits are seasonal and are mainly used in making a rice dish called xoi gac. The purpose of this study was to develop a method to collect and preserve gac fruit oil, to evaluate the nutritional composition of the oil, and to assess the acceptability of the gac oil by typical Vietnamese homemakers. One hundred women participated in training to learn how to prepare the fruits and operate the oil press. The women also participated in a survey of gac fruit use and their habitual use of animal fat and vegetable oil. Among all the participants in the training and surveys, 35 women actually produced oil from gac fruits grown in the village, using manual oil presses and locally available materials. The total carotene concentration in gac fruit oil was 5,700 micrograms/ml. The concentration of beta-carotene was 2,710 micrograms/ml. Sixty-nine percent of total fat was unsaturated, and 35% of that was polyunsaturated. The average daily consumption of gac fruit oil was estimated at 2 ml per person. The daily beta-carotene intake (from gac fruit oil) averaged approximately 5 mg per person. It was found that gac oil can be produced locally by village women using manual presses and locally available materials. The oil is a rich source of beta-carotene, vitamin E, and essential fatty acids. Although the beta-carotene concentration declines with time without a preservative or proper storage, it was still high after three months. The oil was readily accepted by the women and their children, and consumption of the oil increased the intake of beta-carotene and reduced the intake of lard. | Massimino S, Kearns RJ, Loos KM, Burr J, Park JS, Chew B, Adams S, Hayek MG (2003)
Effects of age and dietary beta-carotene on immunological variables in dogs.
Journal of veterinary internal medicine 17, 835-842 [PubMed:14658721]
[show Abstract]
beta-Carotene is a naturally occurring carotenoid reported to have health-promoting effects in several species. Advancing age is known to have a negative impact on various immune variables in several species. This study was conducted in order to assess the effect of age on immune response in dogs and to determine whether beta-carotene is able to reverse this age-associated decline. To test this hypothesis, young and old dogs (n = 36) were fed either a control diet or experimental diets containing supplemental beta-carotene for 2-month periods. Age significantly (P < .05) lowered CD4+ T cell populations (47.2% versus 33.7%; young-control versus old-control, respectively) and beta-carotene restored percent distributions in old dogs to nonsignificance versus younger controls (41.0%). T cell proliferation was lower in old dogs (30,254 +/- 2,248 versus 14,811 +/- 2,497 cCPM; young-control versus old-control, respectively; P < .05), and beta-carotene supplementation significantly improved responses in this age group (21,329 +/- 2,275 cCPM). Although B cell proliferation was depressed with age (17,967 +/- 1,384 versus 7,535 +/- 1,469 cCPM; young-control versus old-control, respectively; P < .05), beta-carotene supplementation improved B cell proliferation in young dogs (23,500 +/- 1,339 cCPM). Old dogs displayed lower delayed-type hypersensitivity test (DTH) responses versus younger controls to both phytohemagglutinin-P (PHA; 11.1 +/- 0.95 versus 7.57 +/- 1.15 mm; young-control versus old-control, respectively; P < .05) and sheep red blood cell (RBC; 9.12 +/- 0.62 versus 8.08 +/- 0.75 mm; young-control versus old-control, respectively; P < .10). beta-Carotene improved these responses, mostly within the first 24-48 hours after injection. In summary, older dogs have lower immunological responses compared with younger controls. beta-Carotene supplementation significantly restored immune responses in older dogs when compared with their age-matched controls and younger counterparts. | Sackett CS, Schenning S (2002)
The age-related eye disease study: the results of the clinical trial.
Insight (American Society of Ophthalmic Registered Nurses) 27, 5-7 [PubMed:11962062]
[show Abstract]
The Age-Related Eye Disease Study (AREDS) is a multi-center study sponsored by the National Eye Institute to determine the natural history and risk factors associated with both cataract and age-related macular degeneration (AMD). AREDS incorporated a clinical trial to determine what role micro nutrients may play in the development and progression of cataracts and AMD. The micro nutrients studied were the antioxidants vitamins E,C, beta-carotene and zinc with copper. Participants were randomized to either antioxidants, mineral, a combination of antioxidants and minerals or placebo. The participants were categorized, by the presence of drusen and diagnosis of AMD into one of four groups: no AMD, early AMD, intermediate AMD or advanced AMD. They were followed for an average of 6.3 years. There was no statistically significant difference in the cataract trial between treatment and placebo. In the AMD trial groups, those at high risk of developing advanced AMD lowered their risk by about 25% when treated with the mega dosages of the combination of antioxidants and minerals. | Gossage CP, Deyhim M, Yamini S, Douglass LW, Moser-Veillon PB (2002)
Carotenoid composition of human milk during the first month postpartum and the response to beta-carotene supplementation.
The American journal of clinical nutrition 76, 193-197 [PubMed:12081834]
[show Abstract]
BackgroundInformation is lacking regarding normal changes in milk carotenoid concentrations in healthy, well-nourished women during the first month of lactation.ObjectivesThis study investigated milk carotenoid concentrations during days 4-32 postpartum and assessed the effects of maternal beta-carotene supplementation.DesignSubjects (n = 21; aged 19-39 y) were randomly assigned to receive beta-carotene (30 mg/d) or placebo from days 4 to 32 postpartum. Each subject provided 8 diet records and 8 milk samples during the study. Diet records were analyzed for energy, macronutrients, vitamins A and E, and carotenoids. Milk samples were analyzed with HPLC for concentrations of carotenoids, retinol, and alpha-tocopherol. Data were analyzed by using repeated-measures analysis and orthogonal contrasts.ResultsNo significant differences in average dietary intakes, body mass index, age, or parity were found between groups at baseline or after supplementation. Milk carotenoid concentrations decreased over time (P < 0.01), as did retinol and alpha-tocopherol concentrations (P < 0.003). Concentrations of most carotenoids decreased to those reported for mature milk by day 32 postpartum. Milk lutein concentrations remained elevated throughout the study compared with values reported for mature milk, whereas plasma lutein concentrations decreased significantly over time. beta-carotene supplementation did not significantly change the milk concentrations of beta-carotene, the other carotenoids, retinol, or alpha-tocopherol.ConclusionsThe lack of increase in milk beta-carotene despite supplementation suggests that transitional milk may be already nearly saturated with beta-carotene. The elevated milk lutein concentration and simultaneous decrease in plasma lutein suggest that lutein metabolism may be altered during early lactation. | Sidransky H, Verney E (2001)
Effects of vitamins on hepatic nuclear binding of L-tryptophan.
Amino acids 20, 123-134 [PubMed:11332447]
[show Abstract]
This study investigated the in vitro effects of selected vitamins on nuclear L-tryptophan receptor binding of rat liver. Our results revealed that some fat-soluble vitamins, beta-carotene, retinyl acetate, calciferol, alpha-tocopherol, and Trolox, as well as some water-soluble vitamins, thiamine and riboflavin, acted to inhibit in vitro 3H-tryptophan binding to hepatic nuclei. On the other hand, pyridoxine had little or no effect. The addition of dithiothreitol, a protective agent for sulfhydryl groups, along with each vitamin decreased the vitamin's inhibitory effect on in vitro 3H-tryptophan binding to nuclei, with the exception of riboflavin and calciferol. The addition of L-leucine, which alone had no inhibitory effect on in vitro 3H-tryptophan binding to hepatic nuclei but when added with unlabeled L-tryptophan negated the effect of unlabeled L-tryptophan, caused a markedly diminished inhibitory binding effect due to each of the following vitamins, thiamine, beta-carotene, retinyl acetate, and alpha-tocopherol and Trolox, but no effect on riboflavin and calciferol. | Aldini G, Yeum KJ, Russell RM, Krinsky NI (2001)
A method to measure the oxidizability of both the aqueous and lipid compartments of plasma.
Free radical biology & medicine 31, 1043-1050 [PubMed:11677037]
[show Abstract]
The lipophilic radical initiator (MeO-AMVN) and the fluorescent probe C11BODIPY581/591 (BODIPY) were used to measure the lipid compartment oxidizability of human plasma. Aqueous plasma oxidizability was initiated by the aqueous peroxyl radical generator, AAPH, and 2',7'-dichlorodihydrofluorescein (DCFH) was employed as the marker of the oxidative reaction. The distribution in aqueous and lipid compartments of the two radical initiators was determined by measuring the rate of consumption of the plasma hydrophilic and lipophilic endogenous antioxidants. In the presence of AAPH (20 mM), the order of consumption was: ascorbic acid > alpha-tocopherol > uric acid > beta-carotene, indicating a gradient of peroxyl radicals from the aqueous to the lipid phase. When MeO-AMVN was used (2mM), beta-carotene was consumed earlier than uric acid and almost at the same time as alpha-tocopherol, reflecting the diffusion and activation of MeO-AMVN in the lipophilic phase. The rate of BODIPY oxidation (increase in green fluorescence) significantly increased after the depletion of endogenous alpha-tocopherol and beta-carotene, whereas it was delayed for 180 min when AAPH was used instead of MeO-AMVN. The measurement of lipid oxidation in plasma was validated by adding to plasma the two lipophilic antioxidants, alpha-tocopherol and beta-carotene, whose inhibitory effects on BODIPY oxidation were dependent on the duration of the preincubation period and hence to their lipid diffusion. DCFH oxidation induced by AAPH only began after uric acid, the main hydrophilic plasma antioxidant, was consumed. In contrast, when MeO-AMVN was used, DCFH oxidation was delayed for 120 min, indicating its localization in the aqueous domain. In summary, the selective fluorescence method reported here is capable of distinguishing the lipophilic and hydrophilic components of the total antioxidant capacity of plasma. | Georgiou CD, Zervoudakis G, Tairis N, Kornaros M (2001)
beta-Carotene production and its role in sclerotial differentiation of Sclerotium rolfsii.
Fungal genetics and biology : FG & B 34, 11-20 [PubMed:11567548]
[show Abstract]
The fungus Sclerotium rolfsii produces beta-carotene, the main detected carotenoid, in levels dependent upon oxidative growth conditions and upon differentiation. beta-Carotene accumulation is 5-, 6.5-, and 6.7-fold higher in undifferentiated mycelia, sclerotia, and differentiated mycelia, respectively, at high than at low oxidative stress. It accumulates more in older than in younger mycelia and is 2-fold higher in differentiated than in undifferentiated mycelia. We propose that beta-carotene is formed possibly to help the fungus reduce oxidative stress that develops during growth. This is supported by the finding that exogenous beta-carotene at non-growth-inhibiting concentrations causes a concentration-dependent reduction of oxidative stress (lipid peroxidation) of undifferentiated mycelia, which results in an equally proportional reduction of sclerotial differentiation. The data of this study support our hypothesis that sclerotial differentiation is induced by oxidative stress. | Guedes De Pinho P, Silva Ferreira AC, Mendes Pinto M, Benitez JG, Hogg TA (2001)
Determination of carotenoid profiles in grapes, musts, and fortified wines from Douro varieties of Vitis vinifera.
Journal of agricultural and food chemistry 49, 5484-5488 [PubMed:11714348]
[show Abstract]
beta-Carotene and six xanthophylls (lutein, neoxanthin, violaxanthin, luteoxanthin, cryptoxanthin, and echinenone) have been identified and semiquantitatively or quantitatively determined in musts and port wines for the first time. An HPLC method was developed and compared with that of one based on thin layer cromatography with scanning densitometry. The most abundant carotenoids present in red grape varieties are beta-carotene and lutein. In wines, significant quantities of violaxanthin, luteoxanthin, and neoxanthin were found. This study was done with berries (skin and pulp), musts, and fortified wines. Some experiments were performed to follow carotenoid content from grapes to wines. Although the levels of beta-carotene and lutein found in fortified wines were lower than those found in musts, other xanthophylls, such as neoxanthin, violaxanthin, and luteoxanthin, exist in appreciable amounts in young ports. | Polle JE, Niyogi KK, Melis A (2001)
Absence of lutein, violaxanthin and neoxanthin affects the functional chlorophyll antenna size of photosystem-II but not that of photosystem-I in the green alga Chlamydomonas reinhardtii.
Plant & cell physiology 42, 482-491 [PubMed:11382814]
[show Abstract]
Chlamydomonas reinhardtii double mutant npq2 lor1 lacks the beta, epsilon-carotenoids lutein and loroxanthin as well as all beta,beta-epoxycarotenoids derived from zeaxanthin (e.g. violaxanthin and neoxanthin). Thus, the only carotenoids present in the thylakoid membranes of the npq2 lor1 cells are beta-carotene and zeaxanthin. The effect of these mutations on the photochemical apparatus assembly and function was investigated. In cells of the mutant strain, the content of photosystem-II (PSII) and photosystem-I (PSI) was similar to that of the wild type, but npq2 lor1 had a significantly smaller PSII light-harvesting Chl antenna size. In contrast, the Chl antenna size of PSI was not truncated in the mutant. SDS-PAGE and Western blot analysis qualitatively revealed the presence of all LHCII and LHCI apoproteins in the thylakoid membrane of the mutant. The results showed that some of the LHCII and most of the LHCI were assembled and functionally connected with PSII and PSI, respectively. Photon conversion efficiency measurements, based on the initial slope of the light-saturation curve of photosynthesis and on the yield of Chl a fluorescence in vivo, showed similar efficiencies. However, a significantly greater light intensity was required for the saturation of photosynthesis in the mutant than in the wild type. It is concluded that zeaxanthin can successfully replace lutein and violaxanthin in most of the functional light-harvesting antenna of the npq2 lor1 mutant. | Burczynski JM, Hayes JR, Voigt JM, Longhurst PA, Colby HD (2001)
Suppression of lipid peroxidation in adrenal microsomes following ACTH administration to guinea pigs.
The Journal of endocrinology 168, 333-338 [PubMed:11182771]
[show Abstract]
Previous studies demonstrated high levels of lipid peroxidation (LP) in the guinea pig adrenal cortex. The present studies were done to determine if adrenal LP activity was influenced by ACTH, the major hormonal regulator of the gland. Guinea pigs were treated with ACTH for 1, 3 or 7 days. In addition, some guinea pigs received ACTH for 7 days and were killed 3 or 7 days later. After treatment, adrenal microsomal fractions were prepared and incubated in vitro with 1 mM ferrous sulfate to initiate LP. ACTH treatment caused a progressive decrease in adrenal LP; activity was almost totally inhibited within 3 days. The inhibitory effects of ACTH on LP were dose-dependent. Following cessation of ACTH treatment, adrenal LP gradually returned toward control levels. Microsomal concentrations of linoleic acid, a major substrate for adrenal LP, were increased by ACTH administration and then also returned to control levels after cessation of treatment. There were no significant changes in adrenal alpha-tocopherol or beta-carotene concentrations resulting from ACTH treatment. The results indicate that ACTH has a role in the regulation of adrenal LP. The actions of ACTH cannot be attributed to an increase in adrenal content of the antioxidants, alpha-tocopherol and beta-carotene, or to a decrease in LP substrate. The actions of ACTH to inhibit LP may contribute to an increase in adrenal hormone production by protecting steroidogenic enzymes from peroxidative degradation. | Li L, Paolillo DJ, Parthasarathy MV, Dimuzio EM, Garvin DF (2001)
A novel gene mutation that confers abnormal patterns of beta-carotene accumulation in cauliflower (Brassica oleracea var. botrytis).
The Plant journal : for cell and molecular biology 26, 59-67 [PubMed:11359610]
[show Abstract]
The Or gene of cauliflower (Brassica oleracea var. botrytis) causes many tissues of the plant to accumulate carotenoids and turn orange, which is suggestive of a perturbation of the normal regulation of carotenogenesis. A series of experiments to explore the cellular basis of the carotenoid accumulation induced by the Or gene was completed. The Or gene causes obvious carotenoid accumulation in weakly or unpigmented tissues such as the curd, pith, leaf bases and shoot meristems, and cryptically in some cells of other organs, including the roots and developing fruits. The dominant carotenoid accumulated is beta-carotene, which can reach levels that are several hundred-fold higher than those in comparable wild-type tissues. The beta-carotene accumulates in plastids mainly as a component of massive, highly ordered sheets. The Or gene does not affect carotenoid composition of leaves, nor does it alter color and chromoplast appearance in flower petals. Interestingly, mRNA from carotenogenic and other isoprenoid biosynthetic genes upstream of the carotenoid pathway was detected both in orange tissues of the mutant, and in comparable unpigmented wild-type tissues. Thus the unpigmented wild-type tissues are likely to be competent to synthesize carotenoids, but this process is suppressed by an unidentified mechanism. Our results suggest that the Or gene may induce carotenoid accumulation by initiating the synthesis of a carotenoid deposition sink in the form of the large carotenoid-sequestering sheets. | Biacs PA, Daood HG (2000)
Lipoxygenase-catalysed degradation of carotenoids from tomato in the presence of antioxidant vitamins.
Biochemical Society transactions 28, 839-845 [PubMed:11171227]
[show Abstract]
Carotenoid extract from ripe tomato fruit was subjected to a lipoxygenase-catalysed co-oxidation in the presence of vitamin C and vitamin E at different concentrations. Relative retention (%) of major carotenoids by the experimental mixture was used as an index of their degradation and interaction with the antioxidants. Oxidation-prevention activity of each antioxidant against pigment co-oxidation as impacted by their molar concentration was studied. beta-Carotene was found to be the most sensitive pigment, followed by lycoxanthin and lycopene. Ascorbic acid when added in the range of 0-1.8 mM interacted with the different carotenoids by different modes. Evidence was given on regeneration, by ascorbic acid, of lycopene during the course of co-oxidation. The concentration required for alpha-tocopherol acetate to exhibit antioxidative effect was 10 times higher than that of ascorbic acid. beta-Carotene was prevented, by alpha-tocopherol acetate, faster than lycoxanthin and lycopene. The latter carotenoids differed substantially in their interaction with the lipophilic antioxidant at only the lowest concentration (0.3 mM). It was established that under the given conditions there is no synergism between vitamin C and vitamin E that improves their oxidation prevention against co-oxidation of carotenoids. Moreover, the combined use of antioxidants caused more oxidative degradation of beta-carotene. |
|
