pyrroloquinoline quinone (CHEBI:18315)

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CHEBI:18315 - pyrroloquinoline quinone

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ChEBI Name	pyrroloquinoline quinone

ChEBI ID	CHEBI:18315

Definition	A pyrroloquinoline having oxo groups at the 4- and 5-positions and carboxy groups at the 2-, 7- and 9-positions.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:45251, CHEBI:49082, CHEBI:7881, CHEBI:14986, CHEBI:26460

Supplier Information	ChemicalBook:CB6140290, eMolecules:526745, ZINC000001532545

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-0.0420 -1.7672 -0.2868 C 0 0 0 0 0 0 0 0 0 0 0 0

1.2466 -2.2571 -0.5701 C 0 0 0 0 0 0 0 0 0 0 0 0

2.3258 -1.4103 -0.6270 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.2899 -0.3735 -0.0969 C 0 0 0 0 0 0 0 0 0 0 0 0

0.8667 0.4623 -0.1329 C 0 0 0 0 0 0 0 0 0 0 0 0

2.1435 -0.0534 -0.3868 C 0 0 0 0 0 0 0 0 0 0 0 0

1.0145 1.7801 0.0641 N 0 0 0 0 0 0 0 0 0 0 0 0

2.2972 2.1625 -0.0284 C 0 0 0 0 0 0 0 0 0 0 0 0

3.0369 1.0165 -0.3267 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.0886 -2.6284 -0.1849 N 0 0 0 0 0 0 0 0 0 0 0 0

-2.3796 -2.2826 0.0577 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.6601 -0.9049 0.1699 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.6321 0.0642 0.0994 C 0 0 0 0 0 0 0 0 0 0 0 0

2.7161 3.4610 0.1589 C 0 0 0 0 0 0 0 0 0 0 0 0

3.8872 3.7930 0.0435 O 0 0 0 0 0 0 0 0 0 0 0 0

1.9203 4.3403 0.4570 O 0 0 0 0 0 0 0 0 0 0 0 0

-3.3452 -3.2678 0.1931 C 0 0 0 0 0 0 0 0 0 0 0 0

-4.5164 -3.0205 0.4459 O 0 0 0 0 0 0 0 0 0 0 0 0

-3.0804 -4.4586 0.0839 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.0322 1.3839 0.2391 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.8818 1.8702 -0.4948 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.6042 2.1030 1.1304 O 0 0 0 0 0 0 0 0 0 0 0 0

3.4523 -1.8194 -0.8836 O 0 0 0 0 0 0 0 0 0 0 0 0

1.4061 -3.4536 -0.7794 O 0 0 0 0 0 0 0 0 0 0 0 0

0.2954 2.3948 0.2598 H 0 0 0 0 0 0 0 0 0 0 0 0

4.0488 0.9673 -0.4669 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.6315 -0.6112 0.3216 H 0 0 0 0 0 0 0 0 0 0 0 0

4.1207 4.6336 0.1706 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.7155 -5.0620 0.1773 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.8784 2.9379 1.1934 H 0 0 0 0 0 0 0 0 0 0 0 0

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2 1 1 0 0 0 0

24 2 2 0 0 0 0

3 2 1 0 0 0 0

23 3 2 0 0 0 0

4 1 4 0 0 0 0

13 4 4 0 0 0 0

5 4 1 0 0 0 0

7 5 4 0 0 0 0

6 5 4 0 0 0 0

3 6 1 0 0 0 0

9 6 4 0 0 0 0

8 7 4 0 0 0 0

9 8 4 0 0 0 0

14 8 1 0 0 0 0

11 10 4 0 0 0 0

12 11 4 0 0 0 0

17 11 1 0 0 0 0

12 13 4 0 0 0 0

20 13 1 0 0 0 0

15 14 1 0 0 0 0

16 14 2 0 0 0 0

18 17 2 0 0 0 0

19 17 1 0 0 0 0

21 20 2 0 0 0 0

22 20 1 0 0 0 0

7 25 1 0 0 0 0

9 26 1 0 0 0 0

12 27 1 0 0 0 0

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Wikipedia	License
Pyrroloquinoline quinone (PQQ), also called methoxatin, is a redox cofactor and antioxidant. Quinoprotein glucose dehydrogenase is used as a glucose sensor in bacteria. PQQ stimulates growth in bacteria.
Read full article at Wikipedia

Formula

C14H6N2O8

Net Charge

Average Mass

330.20612

Monoisotopic Mass

330.01242

InChI

InChI=1S/C14H6N2O8/c17-10-4-2-6(14(23)24)15-8(4)7-3(12(19)20)1-5(13(21)22)16-9(7)11(10)18/h1-2,15H,(H,19,20)(H,21,22)(H,23,24)

InChIKey

MMXZSJMASHPLLR-UHFFFAOYSA-N

SMILES

OC(=O)c1cc(C(O)=O)c-2c(n1)C(=O)C(=O)c1cc([nH]c-21)C(O)=O

Roles Classification
Chemical Role(s):	antioxidant A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	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). (via pyrroloquinoline cofactor ) water-soluble vitamin (role) Any vitamin that dissolves in water and readily absorbed into tissues for immediate use. Unlike the fat-soluble vitamins, they are not stored in the body and need to be replenished regularly in the diet and will rarely accumulate to toxic levels since they are quickly excreted from the body via urine.

Application(s):	anti-inflammatory agent Any compound that has anti-inflammatory effects.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	pyrroloquinoline quinone (CHEBI:18315) has role anti-inflammatory agent (CHEBI:67079) pyrroloquinoline quinone (CHEBI:18315) has role antioxidant (CHEBI:22586) pyrroloquinoline quinone (CHEBI:18315) has role cofactor (CHEBI:23357) pyrroloquinoline quinone (CHEBI:18315) has role water-soluble vitamin (role) (CHEBI:27314) pyrroloquinoline quinone (CHEBI:18315) is a orthoquinones (CHEBI:25622) pyrroloquinoline quinone (CHEBI:18315) is a pyrroloquinoline cofactor (CHEBI:26461) pyrroloquinoline quinone (CHEBI:18315) is a tricarboxylic acid (CHEBI:27093) pyrroloquinoline quinone (CHEBI:18315) is conjugate acid of pyrroloquinoline quinone(3−) (CHEBI:58442)

Incoming	pyrroloquinoline quinone(3−) (CHEBI:58442) is conjugate base of pyrroloquinoline quinone (CHEBI:18315)

IUPAC Name

4,5-dioxo-4,5-dihydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid

Synonyms	Sources
2,4,6-tricarboxylic-pyrrolo[2,3-5,6]quinoline 8,9-quinone	RESID
2,7,9-tricarboxy-1H-pyrrolo(2,3-f)quinoline-4,5-dione	ChemIDplus
4,5-dihydro-4,5-dioxo-1H-pyrrolo[2,3-5,6]quinoline-2,7,9-tricarboxylic acid	RESID
4,5-Dioxo-4,5-dihydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate	KEGG COMPOUND
coenzyme PQQ	ChemIDplus
Methoxatin	KEGG COMPOUND
methoxatin	ChemIDplus
PQQ	KEGG COMPOUND
Pyrrolo-quinoline quinone	KEGG COMPOUND
Pyrroloquinoline quinone	KEGG COMPOUND
PYRROLOQUINOLINE QUINONE	PDBeChem
Pyrroloquinoline-quinone	KEGG COMPOUND

Manual Xrefs	Databases
997	ChemSpider
AA0283	RESID
C00053736	KNApSAcK
C00113	KEGG COMPOUND
DB03205	DrugBank
FDB012848	FooDB
HMDB0013636	HMDB
MOL000073	COMe
PQQ	PDBeChem
Pyrroloquinoline_quinone	Wikipedia
View more database links

Registry Numbers	Types	Sources
3596812	Beilstein Registry Number	Beilstein
56633	Gmelin Registry Number	Gmelin
72909-34-3	CAS Registry Number	ChemIDplus

Citations

Wu Y, Zhao M, Lin Z (2021)
Pyrroloquinoline quinone (PQQ) alleviated sepsis-induced acute liver injury, inflammation, oxidative stress and cell apoptosis by downregulating CUL3 expression.
Bioengineered 12, 2459-2468 [PubMed:34227919]
[show Abstract]

Huang C, Fan Z, Han D, Johnston LJ, Ma X, Wang F (2021)
Pyrroloquinoline quinone regulates the redox status in vitro and in vivo of weaned pigs via the Nrf2/HO-1 pathway.
Journal of animal science and biotechnology 12, 77 [PubMed:34140030]
[show Abstract]

Background

Oxidative stress is a main cause of piglet gut damage and diarrhea. Pyrroloquinoline quinone (PQQ), is a novel redox cofactor with antioxidant properties. However, the effect and mechanism that PQQ supplementation decreases oxidative injury in weaned pigs is not understood. Therefore, the aim of this study is to confirm the effect of PQQ on regulating redox status in weaned pigs and the mechanism for antioxidant function by porcine intestinal epithelial cell line (IPEC-J2) challenged with H₂O₂.

Results

Experiment 1, 144 Duroc × Landrace × Yorkshire pigs (weaned at 28 d) were allocated to four groups: received a basal diet (control) and diets supplemented with 0.15%, 0.30% and 0.45% PQQ, respectively. On d 28, growth performance, diarrhea incidence and redox factors were measured. Experiment 2, IPEC-J2 were treated with or without PQQ in the presence or absence of H₂O₂ for indicated time points. Experiment 3, IPEC-J2 were transfected with or without Nrf2 siRNA, then treated according to Experiment 2. The cell viability, redox factors, protein of tight junctions and Nrf2 pathway were determined. In vivo, PQQ supplementation demonstrated dose-related improvements in average daily gain, and gain to feed ratio (Linear P < 0.05). During d 0-28, compared to controls, 0.45% PQQ supplementation for pigs decreased diarrhea incidence and MDA content in liver and jejunum, and increased concentration of SOD in liver; 0.3% PQQ supplementation decreased ileal and liver MDA concentration; and 0.15% PQQ supplementation decreased ileal MDA concentration (P < 0.05). In vitro, compared to cells cultured with H₂O₂, pre-treatment with PQQ increased cell viability, tight junction proteins expression including ZO-1, ZO-2, Occludin and Claudin-1; and decreased ROS concentration and level of Caspase-3 (P < 0.05); as well as upregulated the ratio of Bcl-2 to Bax and protein expression of nuclear Nrf2, HO-1. Notably, Nrf2 knockdown by transfection with Nrf2 siRNA largely abrogated the positive effects of PQQ pretreatment on H₂O₂-induced intracellular changes.

Conclusions

PQQ administration attenuated oxidative stress in weaned pigs which is associated with activation of Nrf2/HO-1 pathway.

Xu X, Chen C, Lu WJ, Su YL, Shi JY, Liu YC, Wang L, Xiao CX, Wu X, Lu Q (2020)
Pyrroloquinoline quinone can prevent chronic heart failure by regulating mitochondrial function.
Cardiovascular diagnosis and therapy 10, 453-469 [PubMed:32695625]
[show Abstract]

Background

Myocardial mitochondrial dysfunction is the leading cause of chronic heart failure (CHF). Increased reactive oxygen species (ROS) levels, disruption of mitochondrial biogenesis and mitochondrial Ca²⁺([Ca²⁺]m) homeostasis and reduction of the mitochondrial membrane potential (ΔΨm) cause myocardial mitochondrial dysfunction. Therefore, treating CHF by targeting mitochondrial function is a focus of current research. For the first time, this study investigated the effects of the strong antioxidant pyrroloquinoline quinone (PQQ) on mitochondrial function in a cardiac pressure overload model, and the mechanism by which PQQ regulates [Ca²⁺]m homeostasis was explored in depth.

Methods

After transaortic constriction (TAC), normal saline and PQQ (0.4, 2 and 10 mg/kg) were administered intragastrically to Sprague Dawley (SD) rats for 12 weeks. In vitro, neonatal rat left ventricle myocytes (NRVMs) were pretreated with 200 nm angiotensin II (Ang II) with or without PQQ (1, 10 and 100 μM). Rat heart remodelling was verified by assessment of atrial natriuretic peptide (ANP) and brain natriuretic peptide (BNP) levels (qRT-PCR), cell surface area (wheat germ agglutinin (WGA) staining in vivo and α-actin in vitro) and echocardiography. Myocardial mitochondrial morphology was assessed by transmission electron microscopy. Western blotting was used to assess mitochondrial biogenesis [peroxisome proliferator-activated receptor gamma coactivator 1-alpha (PGC-1α) and transcription factor A, mitochondrial (TFAM)]. The ΔΨm was determined by tetraethyl benzimidazolyl carbocyanine iodide (JC-1) staining and flow cytometry, and ROS levels were measured by dichloro-dihydro-fluorescein diacetate (DCFH-DA) and MitoSOX Red staining. [Ca²⁺]m was measured by isolating rat mitochondria, and mitochondrial Ca²⁺ channel proteins [the mitochondrial Na⁺/Ca²⁺ exchanger (NCLX) and mitochondrial Ca²⁺ uniporter (MCU)] were detected by Western blot.

Results

In vivo and in vitro, PQQ pretreatment improved pressure overload-induced cardiac remodelling and cell hypertrophy, thus preventing the occurrence of CHF. PQQ also prevented mitochondrial morphology damage and reduced the PGC-1α and TFAM downregulation caused by TAC or Ang II. In addition, in NRVMs treated with Ang II + PQQ, PQQ regulated ROS levels and increased the ΔΨm. PQQ also regulated [Ca²⁺]m homeostasis and prohibited [Ca²⁺]m overloading by increasing NCLX expression.

Conclusions

These results show that PQQ can prevent [Ca²⁺]m overload by increasing NCLX expression and thereby reducing ROS production and protecting the ΔΨm. At the same time, PQQ can increase PGC-1α and TFAM expression to regulate mitochondrial biogenesis. These factors can prevent mitochondrial dysfunction, thereby reducing cardiac damage caused by pressure overload and preventing the occurrence of CHF.

Last Modified

04 August 2021

CHEBI:18315 - pyrroloquinoline quinone

Background

Results

Conclusions

Background

Methods

Results

Conclusions

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