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| vanillin |
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| CHEBI:18346 |
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| A member of the class of benzaldehydes carrying methoxy and hydroxy substituents at positions 3 and 4 respectively. |
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This entity has been manually annotated by the ChEBI Team.
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CHEBI:1842, CHEBI:48387, CHEBI:15302, CHEBI:20380
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| No supplier information found for this compound. |
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Molfile
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SDF
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more structures >>
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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__1736243591850224__ initializing getValue debug = null getValue logLevel = null getValue allowjavascript = null AppletRegistry.checkIn(jmolApplet0_object__1736243591850224__) 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:1842","platform":"J.awtjs2d.Platform","fullName":"jmolApplet0_object__1736243591850224__","display":"jmolApplet0_canvas2d","signedApplet":"true","appletReadyCallback":"Jmol._readyCallback","statusListener":"[J.appletjs.Jmol.MyStatusListener object]","codeBase":"https://www.ebi.ac.uk/chebi/javascripts/jsmol/","syncId":"1736243591850224","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__1736243591850224__ 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 V55 - Ideal conformer Mrv1927 07012111543D starting HoverWatcher_5 Time for openFile( V55 - Ideal conformer Mrv1927 07012111543D 19 19 0 0 0 0 999 V2000 -1.3510 -0.1750 0.0020 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1590 -0.9100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0540 -0.2500 0.0080 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0900 1.1440 0.0180 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0920 1.8740 0.0200 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6760 -0.2320 -0.0110 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3060 1.2240 0.0060 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6450 -0.8700 -0.0080 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0280 -2.3780 -0.0020 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2140 -0.9610 0.0070 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2840 1.7900 0.0260 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1880 -1.9890 -0.0070 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6770 -1.9500 -0.0110 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2240 1.7940 0.0020 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0590 2.9530 0.0270 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6320 1.9830 -0.8550 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9990 -2.8710 -0.0020 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4680 -2.6770 0.8840 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4740 -2.6650 -0.8960 H 0 0 0 0 0 0 0 0 0 0 0 0 3 2 1 0 0 0 0 3 4 2 0 0 0 0 3 10 1 0 0 0 0 2 1 2 0 0 0 0 1 8 1 0 0 0 0 1 7 1 0 0 0 0 8 6 2 0 0 0 0 5 4 1 0 0 0 0 5 7 2 0 0 0 0 4 11 1 0 0 0 0 9 10 1 0 0 0 0 2 12 1 0 0 0 0 8 13 1 0 0 0 0 7 14 1 0 0 0 0 5 15 1 0 0 0 0 11 16 1 0 0 0 0 9 17 1 0 0 0 0 9 18 1 0 0 0 0 9 19 1 0 0 0 0 M END): 17 ms reading 19 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 19 atoms created ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation Script completed Jmol script terminated
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| Vanillin is an organic compound with the molecular formula C8H8O3. It is a phenolic aldehyde. Its functional groups include aldehyde, hydroxyl, and ether. It is the primary component of the ethanolic extract of the vanilla bean. Synthetic vanillin is now used more often than natural vanilla extract as a flavoring in foods, beverages, and pharmaceuticals.
Vanillin and ethylvanillin are used by the food industry; ethylvanillin is more expensive, but has a stronger note. It differs from vanillin by having an ethoxy group (−O−CH2CH3) instead of a methoxy group (−O−CH3).
Natural vanilla extract is a mixture of several hundred different compounds in addition to vanillin. Artificial vanilla flavoring is often a solution of pure vanillin, usually of synthetic origin. Because of the scarcity and expense of natural vanilla extract, synthetic preparation of its predominant component has long been of interest. The first commercial synthesis of vanillin began with the more readily available natural compound eugenol (4-allyl-2-methoxyphenol). Today, artificial vanillin is made either from guaiacol or lignin.
Lignin-based artificial vanilla flavoring is alleged to have a richer flavor profile than that from guaiacol-based artificial vanilla; the difference is due to the presence of acetovanillone, a minor component in the lignin-derived product that is not found in vanillin synthesized from guaiacol. |
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Read full article at Wikipedia
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| InChI=1S/C8H8O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-5,10H,1H3 |
| MWOOGOJBHIARFG-UHFFFAOYSA-N |
| [H]C(=O)C1=CC(OC)=C(O)C=C1 |
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Beilschmiedia tsangii
(IPNI:462970-1)
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Found in
root
(BTO:0001188).
Cold MeOH extract of dry and sliced roots
See:
PubMed
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Pisonia aculeata
(NCBI:txid363212)
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Found in
stem
(BTO:0001300).
Cold methanolic extract of dried stems and roots
See:
PubMed
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Pisonia aculeata
(NCBI:txid363212)
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Found in
root
(BTO:0001188).
Cold methanolic extract of dried stems and roots
See:
PubMed
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Panax japonicus var. major
(NCBI:txid45211)
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Found in
root
(BTO:0001188).
Ethanolic extract of dried and pulverized roots
See:
PubMed
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antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
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plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
flavouring agent
A food additive that is used to added improve the taste or odour of a food.
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anti-inflammatory agent
Any compound that has anti-inflammatory effects.
anticonvulsant
A drug used to prevent seizures or reduce their severity.
flavouring agent
A food additive that is used to added improve the taste or odour of a food.
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View more via ChEBI Ontology
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4-hydroxy-3-methoxybenzaldehyde
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3-methoxy-4-hydroxybenzaldehyde
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UM-BBD
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4-formyl-2-methoxyphenol
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ChemIDplus
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4-Hydroxy-3-methoxy-benzaldehyde
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KEGG COMPOUND
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4-hydroxy-3-methoxybenzaldehyde
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ChemIDplus
|
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4-Hydroxy-3-methoxybenzaldehyde
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KEGG COMPOUND
|
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4-hydroxy-m-anisaldehyde
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NIST Chemistry WebBook
|
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methylprotocatechuic aldehyde
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ChemIDplus
|
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p-hydroxy-m-methoxybenzaldehyde
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NIST Chemistry WebBook
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p-vanillin
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NIST Chemistry WebBook
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vaniline
|
ChEBI
|
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vanillaldehyde
|
ChemIDplus
|
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Vanillaldehyde
|
KEGG COMPOUND
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vanillic aldehyde
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ChemIDplus
|
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Vanillin
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KEGG COMPOUND
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vanillin
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UniProt
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121-33-5
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CAS Registry Number
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NIST Chemistry WebBook
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121-33-5
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CAS Registry Number
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ChemIDplus
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3596
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Gmelin Registry Number
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Gmelin
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472792
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Beilstein Registry Number
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Beilstein
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Arya S, Rookes J, Cahill D, Lenka S (2021)
Vanillin: a review on the therapeutic prospects of a popular flavouring molecule
Advances in Traditional Medicine 21, 1-17 [PubMed Central:PMC7790484] | Qu B, Jiang J, Mao X, Dong G, Liu Y, Li L, Zhao H (2021)
Simultaneous determination of vanillin, ethyl vanillin and methyl vanillin in Chinese infant food and other dairy products by LC-MS/MS.
Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment 38, 1096-1104 [PubMed:33938405]
[show Abstract]
An efficient and simple method for determining vanillin, methyl vanillin and ethyl vanillin in milk and dairy products was developed using a liquid-liquid extraction (LLE) procedure coupled to high-performance liquid chromatography-tandem mass spectrometry (LC-MS/MS). Different extraction procedures were tested and optimised by spiking three vanillin compounds into a blank matrix in which none of any food additives were detected, and the extraction with acetonitrile solution and n-hexane as cleaning sorbent allowed an efficient recovery of 87.6-101.7% with RSDs less than 5%. The limit of detection (LOD) ranged from 6.2 to 20.1 μg/kg. High sensitivity, accuracy and selectivity were found for the in-house validated method, which can eliminate the interferences from complicated matrices effectively, and fulfil the quality criteria for routine laboratory application for real samples. The developed method was then finally applied to screen the three analytes in 65 milk and dairy products including infant formula milk powders from local markets to check for compliance with Chinese Regulation. Concentrations of the total vanillin and ethyl vanillin ranged from 0.0323 to 246.3 mg/kg, which is within the limits of Chinese regulations. | Hansen CA (2021)
Vanillin biosynthesis from sucrose ex-sugarcane: authentication of an alternative vanillin source through stable isotope data analysis.
Heliyon 7, e06970 [PubMed:34013088]
[show Abstract]
As one of the largest volume flavor ingredients, vanillin remains an attractive target for development of a cost-effective and sustainable process to manufacture. Presented here is newly available data on the production of vanillin via fermentation in an engineered strain of Saccharomyces cerevisiae grown on sucrose ex-sugarcane. The use of the C4 plant source of carbohydrate resulted in a δ13C mean stable isotope ratio of -14.43 ‰ (SD = 0.24) relative to the V-PDB standard and a δ2H mean stable isotope ratio of -122.8 ‰ (SD = 2.9) relative to the SMOW standard by IRMS. The abundance of 14C in the fermentation derived vanillin averaged 14.01 dpm/gC (SD = 0.09) by AMS measurement. These data are compared to historical data collected on vanillin derived from a number of sources to provide a more holistic view on vanillin bulk isotope data based on its method of manufacture. | Costantini E, Sinjari B, Falasca K, Reale M, Caputi S, Jagarlapodii S, Murmura G (2021)
Assessment of the Vanillin Anti-Inflammatory and Regenerative Potentials in Inflamed Primary Human Gingival Fibroblast.
Mediators of inflammation 2021, 5562340 [PubMed:34035660]
[show Abstract]
BackgroundInflammatory responses have been associated with delayed oral mucosal wound healing and the pathogenesis of the periodontal disease. The invasion of microbes into the tissues and the establishment of a chronic infection may be due to impaired healing. The protracted inflammatory phase may delay wound healing and probably support tissue fibrosis and reduce tissue regeneration. Vanillin is a well-known natural compound with potential anti-inflammatory capacity. Hence, we hypothesized that Vanillin could accelerate wound healing reducing inflammation and especially cytokine production making the oral tissue repair process easier.MethodsOur hypothesis was tested using primary human gingival fibroblast (HGF) cell pretreated with Vanillin and primed with IL-1β, as inductor of proinflammatory environment. After 24 hours of treatments, the gene expression and production of IL-6, TNF-α, IL-8, COX-2, iNOS, and nitric oxide (NO) generation and the wound healing rate were determined.ResultsIn IL-1β-primed cells, preincubation with Vanillin reduced IL-6, IL-8, COX-2, and iNOS expression and NO release, compared to IL-1β-primed cells. Moreover, Vanillin determines the increased gene expression of nAChRα7, leading us to hypothesize a role of Vanillin in the activation of the cholinergic anti-inflammatory pathway. Furthermore, in presence of mechanical injury, the Vanillin preincubation, wound closure may be reducing the expression and release of IL-6 and TNF-α and upregulation of COX-2 and IL-8.ConclusionTogether, the results of this study highlight the anti-inflammatory and tissue repair ability of Vanillin in IL-1β-primed HGF. Therefore, Vanillin shows a potential therapeutic interest as an inflammatory modulator molecule with novel application in periodontal regeneration and oral health. | Zhao X, Zhang Y, Cheng Y, Sun H, Bai S, Li C (2021)
Identifying environmental hotspots and improvement strategies of vanillin production with life cycle assessment.
The Science of the total environment 769, 144771 [PubMed:33477040]
[show Abstract]
Vanillin, an important aroma chemical, can be synthesized through industrial oxidation processes and biotechnological processes. Studying the environmental impacts of synthetic vanillin production processes is fundamental to making these processes feasible and sustainable; however, few studies have focused on such analyses. This study involved performing a life cycle assessment (LCA) to evaluate multiple industrial synthesis and biosynthesis processes for producing synthetic vanillin. The results indicated that human toxicity potential (HTP) appeared to be the most affected indicator among all the impact categories considered. The dominant drivers of the HTP of the vanillin synthesis process were electricity consumption and ultrapure water consumption. Improvement strategies were then proposed to investigate the possibility of reducing the environmental burdens created by vanillin synthesis. Natural gas power generation was determined to be the best choice for replacing traditional coal-fired power generation, thus reducing the negative impacts of these processes on the environment. The best ways to reduce chemical consumption were to recover organic solvents and to replace ultrapure water with industrial or distilled water. All these improvement strategies were demonstrated to be able to effectively reduce the HTP. In addition, suggestions for evaluating scaled-up vanillin production, increasing the LCA coverage to include technological advancements in biosynthesis techniques, and introducing cost-benefit analysis into the LCA were discussed. | Cozza G, Zonta F, Dalle Vedove A, Venerando A, Dall'Acqua S, Battistutta R, Ruzzene M, Lolli G (2020)
Biochemical and cellular mechanism of protein kinase CK2 inhibition by deceptive curcumin.
The FEBS journal 287, 1850-1864 [PubMed:31661600]
[show Abstract]
Protein kinase CK2 is an antiapoptotic cancer-sustaining protein. Curcumin, reported previously as a CK2 inhibitor, is too bulky to be accommodated in the CK2 active site and rapidly degrades in solution generating various ATP-mimetic inhibitors; with a detailed comparative analysis, by means of both protein crystallography and enzymatic inhibition, ferulic acid was identified as the principal curcumin degradation product responsible for CK2 inhibition. The other curcumin derivatives vanillin, feruloylmethane and coniferyl aldehyde are weaker CK2 inhibitors. The high instability of curcumin in standard buffered solutions flags this compound, which is included in many commercial libraries, as a possible source of misleading interpretations, as was the case for CK2. Ferulic acid does not show any cytotoxicity and any inhibition of cellular CK2, due to its poor cellular permeability. However, curcumin acts as a prodrug in the cellular context, by generating its degradation products inside the treated cells, thus rescuing CK2 inhibition and consequently inducing cell death. Through the intracellular release of its degradation products, curcumin is expected to affect various target families; here, we identify the first bromodomain of BRD4 as a new target for those compounds. DATABASE: Structural data are available in the PDB database under the accession numbers 6HOP (CK2α/curcumin), 6HOQ (CK2α/ferulic acid), 6HOR (CK2α/feruloylmethane), 6HOT (CK2α/ferulic aldehyde), 6HOU (CK2α/vanillin) and 6HOV (BRD4/ferulic acid). | Mallinson SJB, Machovina MM, Silveira RL, Garcia-Borràs M, Gallup N, Johnson CW, Allen MD, Skaf MS, Crowley MF, Neidle EL, Houk KN, Beckham GT, DuBois JL, McGeehan JE (2018)
A promiscuous cytochrome P450 aromatic O-demethylase for lignin bioconversion.
Nature communications 9, 2487 [PubMed:29950589]
[show Abstract]
Microbial aromatic catabolism offers a promising approach to convert lignin, a vast source of renewable carbon, into useful products. Aryl-O-demethylation is an essential biochemical reaction to ultimately catabolize coniferyl and sinapyl lignin-derived aromatic compounds, and is often a key bottleneck for both native and engineered bioconversion pathways. Here, we report the comprehensive characterization of a promiscuous P450 aryl-O-demethylase, consisting of a cytochrome P450 protein from the family CYP255A (GcoA) and a three-domain reductase (GcoB) that together represent a new two-component P450 class. Though originally described as converting guaiacol to catechol, we show that this system efficiently demethylates both guaiacol and an unexpectedly wide variety of lignin-relevant monomers. Structural, biochemical, and computational studies of this novel two-component system elucidate the mechanism of its broad substrate specificity, presenting it as a new tool for a critical step in biological lignin conversion. | Dallmann R, Viola AU, Tarokh L, Cajochen C, Brown SA (2012)
The human circadian metabolome.
Proceedings of the National Academy of Sciences of the United States of America 109, 2625-2629 [PubMed:22308371]
[show Abstract]
The circadian clock orchestrates many aspects of human physiology, and disruption of this clock has been implicated in various pathologies, ranging from cancer to metabolic syndrome and diabetes. Although there is evidence that metabolism and the circadian clockwork are intimately linked on a transcriptional level, whether these effects are directly under clock control or are mediated by the rest-activity cycle and the timing of food intake is unclear. To answer this question, we conducted an unbiased screen in human subjects of the metabolome of blood plasma and saliva at different times of day. To minimize indirect effects, subjects were kept in a 40-h constant routine of enforced posture, constant dim light, hourly isocaloric meals, and sleep deprivation. Under these conditions, we found that ~15% of all identified metabolites in plasma and saliva were under circadian control, most notably fatty acids in plasma and amino acids in saliva. Our data suggest that there is a strong direct effect of the endogenous circadian clock on multiple human metabolic pathways that is independent of sleep or feeding. In addition, they identify multiple potential small-molecule biomarkers of human circadian phase and sleep pressure. | Chan HH, Hwang TL, Reddy MV, Li DT, Qian K, Bastow KF, Lee KH, Wu TS (2011)
Bioactive constituents from the roots of Panax japonicus var. major and development of a LC-MS/MS method for distinguishing between natural and artifactual compounds.
Journal of natural products 74, 796-802 [PubMed:21417387]
[show Abstract]
Two new saponins, panajaponol (1) and pseudoginsenoside RT1 butyl ester (2), together with 35 known compounds (3-37), were isolated from the roots of Panax japonicus var. major. The structures of 1 and 2 were elucidated on the basis of spectroscopic analysis and chemical methods. Furthermore, a LC-MS/MS method was developed for confirming 2, 3, and 8 as natural compounds containing a butyl ester group. This method should be useful for distinguishing between minor natural and artifactual compounds in Panax species. Moreover, compounds 3, 6, 8, 9, 11, 13, and 15 exhibited strong inhibition of superoxide anion generation and elastase release by human neutrophils in response to formyl-l-methionyl-l-leucyl-l-phenylalanine/cytochalasin B (fMLP/CB), with IC(50) values ranging from 0.78 to 43.6 μM. In addition, 1 showed greater than 2- to 3-fold selective cytotoxic activity against KB and DU145 cancer cell lines. | Wu MC, Peng CF, Chen IS, Tsai IL (2011)
Antitubercular chromones and flavonoids from Pisonia aculeata.
Journal of natural products 74, 976-982 [PubMed:21542597]
[show Abstract]
Three new chromones, pisonins A (1), B (2), and D (4), two new flavonoids, pisonivanone [(2S)-5,7,2'-trihydroxy-8-methylflavanone] (7) and pisonivanol [(2R,3R)-3,7-dihydroxy-5,6-dimethoxyflavanone] (8), one new isoflavonoid, pisonianone (5,7,2'-trihydroxy-6-methoxy-8-methylisoflavone) (9), and five compounds first isolated from nature, namely, pisonins C (3), E (5), and F (6), pisoniamide (10), and pisonolic acid (11), together with 18 known compounds have been isolated from the methanol extract of the combined stem and root of Pisonia aculeata. Among these isolates, 2, 7, 14, 16, and 19 exhibited antitubercular activities (MICs≤50.0 μg/mL) against Mycobacterium tuberculosis H37Rv in vitro. | Huang YT, Chang HS, Wang GJ, Cheng MJ, Chen CH, Yang YJ, Chen IS (2011)
Anti-inflammatory endiandric acid analogues from the roots of Beilschmiedia tsangii.
Journal of natural products 74, 1875-1880 [PubMed:21846089]
[show Abstract]
Bioassay-guided fractionation of roots of Beilschmiedia tsangii led to the isolation of six new endiandric acid analogues: tsangibeilin A (1), tsangibeilin B (2), endiandramide A (3), endiandric acid K (4), endiandric acid L (5), and endiandramide B (6). Also isolated were two new lignans, beilschminol A (7) and tsangin C (8), and six known compounds. The structures of 1-8 were determined by spectroscopic techniques. Compounds 3 and 6 exhibited potent iNOS inhibitory activity, with IC(50) values of 9.59 and 16.40 μM, respectively. | Loke WM, Jenner AM, Proudfoot JM, McKinley AJ, Hodgson JM, Halliwell B, Croft KD (2009)
A metabolite profiling approach to identify biomarkers of flavonoid intake in humans.
The Journal of nutrition 139, 2309-2314 [PubMed:19812218]
[show Abstract]
Flavonoids are phytochemicals that are widespread in the human diet. Despite limitations in their bioavailability, experimental and epidemiological data suggest health benefits of flavonoid consumption. Valid biomarkers of flavonoid intake may be useful for estimating exposure in a range of settings. However, to date, few useful flavonoid biomarkers have been identified. In this study, we used a metabolite profiling approach to examine the aromatic and phenolic profile of plasma and urine of healthy men after oral consumption of 200 mg of the pure flavonoids, quercetin, (-)-epicatechin, and epigallocatechin gallate, which represent major flavonoid constituents in the diet. Following enzymatic hydrolysis, 71 aromatic compounds were quantified in plasma and urine at 2 and 5 h, respectively, after flavonoid ingestion. Plasma concentrations of different aromatic compounds ranged widely, from 0.01 to 10 micromol/L, with variation among volunteers. None of the aromatic compounds was significantly elevated in plasma 2 h after consumption of either flavonoid compared with water placebo. This indicates that flavonoid-derived aromatic compounds are not responsible for the acute physiological effects reported within 2 h in previous human intervention studies involving flavonoids or flavonoid-rich food consumption. These effects are more likely due to absorption of the intact flavonoid. Our urine analysis suggested that urinary 4-ethylphenol, benzoic acid, and 4-ethylbenzoic acid may be potential biomarkers of quercetin intake and 1,3,5-trimethoxybenzene, 4-O-methylgallic acid, 3-O-methylgallic acid, and gallic acid may be potential markers of epigallocatechin gallate intake. Potential biomarkers of (-)-epicatechin were not identified. These urinary biomarkers may provide an accurate indication of flavonoid exposure. | Bennett JP, Bertin L, Moulton B, Fairlamb IJ, Brzozowski AM, Walton NJ, Grogan G (2008)
A ternary complex of hydroxycinnamoyl-CoA hydratase-lyase (HCHL) with acetyl-CoA and vanillin gives insights into substrate specificity and mechanism.
The Biochemical journal 414, 281-289 [PubMed:18479250]
[show Abstract]
HCHL (hydroxycinnamoyl-CoA hydratase-lyase) catalyses the biotransformation of feruloyl-CoA to acetyl-CoA and the important flavour-fragrance compound vanillin (4-hydroxy-3-methoxybenzaldehyde) and is exploited in whole-cell systems for the bioconversion of ferulic acid into natural equivalent vanillin. The reaction catalysed by HCHL has been thought to proceed by a two-step process involving first the hydration of the double bond of feruloyl-CoA and then the cleavage of the resultant beta-hydroxy thioester by retro-aldol reaction to yield the products. Kinetic analysis of active-site residues identified using the crystal structure of HCHL revealed that while Glu-143 was essential for activity, Ser-123 played no major role in catalysis. However, mutation of Tyr-239 to Phe greatly increased the K(M) for the substrate ferulic acid, fulfilling its anticipated role as a factor in substrate binding. Structures of WT (wild-type) HCHL and of the S123A mutant, each of which had been co-crystallized with feruloyl-CoA, reveal a subtle helix movement upon ligand binding, the consequence of which is to bring the phenolic hydroxyl of Tyr-239 into close proximity to Tyr-75 from a neighbouring subunit in order to bind the phenolic hydroxyl of the product vanillin, for which electron density was observed. The active-site residues of ligand-bound HCHL display a remarkable three-dimensional overlap with those of a structurally unrelated enzyme, vanillyl alcohol oxidase, that also recognizes p-hydroxylated aromatic substrates related to vanillin. The data both explain the observed substrate specificity of HCHL for p-hydroxylated cinnamate derivatives and illustrate a remarkable convergence of the molecular determinants of ligand recognition between the two otherwise unrelated enzymes. | Chen SL, Zhou BL, Wang RH, Fu YW (2008)
[Regulation effects of grafting on cinnamic acid and vanillin in eggplant root exudates].
Ying yong sheng tai xue bao = The journal of applied ecology 19, 2394-2399 [PubMed:19238838]
[show Abstract]
Cinnamic acid and vanillin are the allelochemicals commonly existed in eggplant root exudates. With pot culture experiment, the regulation effects of grafting on the cinnamic acid and vanillin in eggplant root exudates were studied, and the results showed that grafting decreased the amount of the two substances, especially of vanillin, in eggplants root system. The maximum reduction amount of cinnamic acid reached 68.96%, and that of vanillin reached 100%. Under the stress of exotic cinnamic acid and vanillin, especially of exotic cinnamic acid, grafting relieved the autotoxicity of the two substances on eggplants. Compared with own-rooted eggplant, grafted eggplant had a higher plant height and a larger stem diameter, its leaf chlorophyll content increased by 5.26%-13.12%, root electric conductivity and MDA content decreased, and root SOD activity enhanced. |
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