| Name | cytochrome P450 (protein family or complex) |
|---|---|
| Synonyms | cytochrome P450; cytochrome P 450; CYP450; CYP 450 |
| Name | anthraquinone |
|---|---|
| CAS | 9,10-anthracenedione |
| PubMed | Abstract | RScore(About this table) | |
|---|---|---|---|
| 9616189 | Mueller SO, Stopper H, Dekant W: Biotransformation of the anthraquinones emodin and chrysophanol by cytochrome P450 enzymes. Drug Metab Dispos. 1998 Jun;26(6):540-6. The anthraquinone chrysophanol (1,8-dihydroxy-3-methylanthraquinone) is transformed, in a cytochrome P450-dependent oxidation, to aloe-emodin (1, 8-dihydroxy-3-hydroxymethylanthraquinone) as the major product formed. |
35(0,1,1,5) | Details |
| 8611554 | Anzenbacher P, Niwa T, Tolbert LM, Sirimanne SR, Guengerich FP: Oxidation of 9-alkylanthracenes by cytochrome P450 2B1, horseradish peroxidase, and iron tetraphenylporphine/iodosylbenzene systems: anaerobic and aerobic mechanisms. Biochemistry. 1996 Feb 27;35(8):2512-20. Variously substituted alkylanthracenes were studied as models for polycyclic hydrocarbon oxidations. 9-Methylanthracene was oxidized to 9-(hydroxymethyl) anthracene, 10-methyl-10--9-anthrone, and anthraquinone in several systems, including (i) - and O2-fortified rat liver microsomes, (ii) cytochrome P450 (P450) 2B1 Supported by either iodosylbenzene (PhIO) or a mixture of -P450 reductase, and O2, (iii) horseradish peroxidase and either H2O2 or ethyl hydroperoxide, and (iv) a mixture of iron tetraphenylporphine (FeTPP) and PhIO (in anhydrous CH2Cl2/MeOH). |
32(0,1,1,2) | Details |
| 10760564 | Cary JW, Montalbano BG, Ehrlich KC: Promoter elements involved in the expression of the Aspergillus parasiticus aflatoxin biosynthesis pathway gene avnA. Biochim Biophys Acta. 2000 Apr 25;1491(1-3):7-12. One of the early genes in aflatoxin biosynthesis, avnA, encodes a pathway-specific cytochrome P-450 monooxygenase that catalyzes the hydroxylation of the polyketide anthraquinone, averantin. |
31(0,1,1,1) | Details |
| 19067753 | Bhadauria M, Nirala SK, Shrivastava S, Sharma A, Johri S, Chandan BK, Singh B, Saxena AK, Shukla S: Emodin reverses CCl induced hepatic cytochrome P450 (CYP) enzymatic and ultrastructural changes: The in vivo evidence. Hepatol Res. 2009 Mar;39(3):290-300. Epub 2008 Dec 2. Aim: The curative effect of emodin (1,3,8-trihydroxy-6-methyl anthraquinone), an active compound of the plant species Ventilago maderaspatana Gaertn, was evaluated against carbon tetrachloride (CCl (4)) induced hepatic cytochrome P450 (CYP) enzymatic and ultrastructural alterations in rats. |
7(0,0,1,2) | Details |
| 12744663 | Marczylo T, Sugiyama C, Hayatsu H: Protection against Trp-P-2 DNA adduct formation in C57bl6 mice by purpurin is accompanied by induction of cytochrome P450. J Agric Food Chem. 2003 May 21;51(11):3334-7. Purpurin, an anthraquinone constituent from madder root, has previously been reported as antimutagenic in the Ames Salmonella bacterial mutagenicity assay and as antigenotoxic in Drosophila melanogaster, against a range of environmental carcinogens. |
3(0,0,0,3) | Details |
| 9654063 | Dorovska-Taran V, Posthumus MA, Boeren S, Boersma MG, Teunis CJ, Rietjens IM, Veeger C: exchange with water in heme-oxo intermediates during H2O2-driven incorporation in aromatic hydrocarbons catalyzed by microperoxidase-8. Eur J Biochem. 1998 May 1;253(3):659-68. The present paper describes the incorporation into naphthalene and anthracene by H2O2-driven microperoxidase-8, forming alpha-naphthol and anthraquinone, respectively. Additional experiments were performed to investigate whether the reaction mechanism involved is like that of peroxidase and/or cytochrome P-450. |
3(0,0,0,3) | Details |
| 6435683 | Ruettinger RT, Kim BH, Fulco AJ: Acylureas: a new class of barbiturate-like bacterial cytochrome P-450 inducers. Biochim Biophys Acta. 1984 Oct 16;801(3):372-80. |
2(0,0,0,2) | Details |
| 10792014 | Marczylo T, Arimoto-Kobayashi S, Hayatsu H: Protection against Trp-P-2 mutagenicity by purpurin: mechanism of in vitro antimutagenesis. Mutagenesis. 2000 May;15(3):223-8. Purpurin (1,2,4-trihydroxy-9,10-anthraquinone) is a natural pigment isolated from madder root (Rubia tinctorum) which inhibits the mutagenicity of a number of heterocyclic amines in the Ames mutagenicity test. Cytochrome P450-dependent O-dealkylation of methoxy-, ethoxy- and pentoxyresorufin by these microsomes was also significantly inhibited by purpurin. |
2(0,0,0,2) | Details |
| 15771506 | Henry KM, Townsend CA: Ordering the reductive and cytochrome P450 oxidative steps in demethylsterigmatocystin formation yields general insights into the biosynthesis of aflatoxin and related fungal metabolites. J Am Chem Soc. 2005 Mar 23;127(11):3724-33. Mechanistic and stereoelectronic principles that underlie this proposal are described and may prove general as illustrated in biogenetic hypotheses for four other fungal anthraquinone --> xanthone transformations. |
2(0,0,0,2) | Details |
| 8221649 | Mewes K, Blanz J, Ehninger G, Gebhardt R, Zeller KP: Cytochrome P-450-induced cytotoxicity of mitoxantrone by formation of electrophilic intermediates. Cancer Res. 1993 Nov 1;53(21):5135-42. Recent studies of our group have shown that the oxidation of the substituted anthraquinone skeleton is involved in the biotransformation of mitoxantrone. |
2(0,0,0,2) | Details |
| 14562683 | Mikhailova ON, Filipenko ML, Timofeeva OA, Kaledin VI, Guliaeva LF, Liakhovich VV: [mRNA level and cytochrome P450 1A activity in the liver of C57BL mice induced by various xenobiotics]. Biomed Khim. 2003 Jul-Aug;49(4):388-93. |
2(0,0,0,2) | Details |
| 1880787 | Das M, Garg K, Joshi A, Singh GB, Khanna SK: Interaction of benzanthrone with cytochrome P450: altered patterns of hepatic xenobiotic metabolism in rats. J Biochem Toxicol. 1991 Spring;6(1):37-44. Benzanthrone, an anthraquinone dye intermediate, is commonly used for the synthesis of a number of polycyclic vat and disperse dyes. |
2(0,0,0,2) | Details |
| 9488113 | Chat M, Bayol-Denizot C, Suleman G, Roux F, Minn A: Drug metabolizing enzyme activities and formation in primary and immortalized rat brain endothelial cells. Life Sci. 1998;62(2):151-63. The activities of several enzymes involved in drug metabolism, NADPH-cytochrome P450 reductase, cytochrome P450 isoforms CYP1A and CYP2B, and glucuronosyltransferase (UGT) have been measured in primary cultures of rat cerebrovascular endothelial cells and in the immortalized rat brain endothelial cell line RBE4. The production observed during NADPH-cytochrome P450 reductase-dependent monoelectronic reduction of four xenobiotics, anthraquinone, nitrofurazone and diquat, was also investigated in these cultured cells at confluence. |
1(0,0,0,1) | Details |
| 11996570 | Udwary DW, Casillas LK, Townsend CA: Synthesis of 11- O-methylsterigmatocystin and the role of a cytochrome P-450 in the final step of aflatoxin biosynthesis. J Am Chem Soc. 2002 May 15;124(19):5294-303. The major skeletal rearrangements (anthraquinone --> xanthone --> that occur in the complex biosynthesis of aflatoxin B (1) are mediated by cytochromes P-450. |
1(0,0,0,1) | Details |
| 2850767 | Vile GF, Winterbourn CC: Microsomal reduction of low-molecular-weight Fe3+ chelates and ferritin: enhancement by adriamycin, paraquat, and anthraquinone 2-sulfonate and inhibition by Arch Biochem Biophys. 1988 Dec;267(2):606-13. This implies that, except for Fe3+ (EDTA), cytochrome P450 was involved in reduction of the complexes. |
1(0,0,0,1) | Details |
| 10685079 | Wiltshire M, Patterson LH, Smith PJ: A novel deep red/low infrared fluorescent flow cytometric probe, DRAQ5NO, for the discrimination of intact nucleated cells in apoptotic cell populations. Cytometry. 2000 Mar 1;39(3):217-23. We describe a new probe for cellular integrity, based upon a structure which has the additional potential to act as a substrate for cytochrome P450-dependent bioreductive metabolism. DRAQ5NO is an N-oxide modified anthraquinone with optimal fluorescence excitation maxima compatible with He-Ne (633 nm) and Kr-Ar (647 nm) lasers. |
1(0,0,0,1) | Details |
| 11502733 | Wang HW, Chen TL, Yang PC, Ueng TH: Induction of cytochromes P450 1A1 and 1B1 by emodin in human lung adenocarcinoma cell line CL5. Drug Metab Dispos. 2001 Sep;29(9):1229-35. Treatment of the lung cells with 100 microM emodin or purpurin (1,2,4-trihydroxyanthraquinone) for 24 h produced greater induction of P450s 1A1 and 1B1 mRNA than did anthraflavic acid (2,6-dihydroxyanthraquinone) or anthraquinone. The present study aimed to determine the effects of emodin on cytochrome P450 (P450)-dependent monooxygenases of human lung adenocarcinoma CL5 cells. |
1(0,0,0,1) | Details |
| 15755146 | Henry KM, Townsend CA: Synthesis and fate of o-carboxybenzophenones in the biosynthesis of aflatoxin. J Am Chem Soc. 2005 Mar 16;127(10):3300-9. o-Carboxybenzophenones have long been postulated to be intermediates in the oxidative rearrangement of anthraquinone natural products to xanthones in vivo. Many of these Baeyer-Villiger-like cleavages are believed to be carried out by cytochrome P450 enzymes. |
1(0,0,0,1) | Details |
| 15638760 | Kubin A, Wierrani F, Burner U, Alth G, Grunberger W: Hypericin--the facts about a controversial agent. Curr Pharm Des. 2005;11(2):233-53. John's Wort (Hypericum species) and can also be synthesized from the anthraquinone derivative emodin. In other contemporary studies, screening hypericin for inhibitory effects on various pharmaceutically important enzymes such as MAO (monoaminoxidase), PKC (protein kinase C), dopamine-beta-hydroxylase, reverse transcriptase, telomerase and CYP (cytochrome P450), has yielded results supporting therapeutic potential. |
1(0,0,0,1) | Details |
| 16535361 | Bezalel L, Hadar Y, Fu PP, Freeman JP, Cerniglia CE: Initial Oxidation Products in the Metabolism of Pyrene, Anthracene, Fluorene, and Dibenzothiophene by the White Rot Fungus Pleurotus ostreatus. Appl Environ Microbiol. 1996 Jul;62(7):2554-2559. The identity of the dihydrodiol metabolites implicates a cytochrome P-450 monooxygenase mechanism. Anthracene was metabolized predominantly to anthracene trans-1,2-dihydrodiol and 9,10-anthraquinone. |
1(0,0,0,1) | Details |
| 12379470 | Takahashi E, Fujita K, Kamataki T, Arimoto-Kobayashi S, Okamoto K, Negishi T: Inhibition of human cytochrome P450 1B1, 1A1 and 1A2 by antigenotoxic compounds, purpurin and alizarin. Mutat Res. 2002 Oct 31;508(1-2):147-56. Recently we have shown that anthraquinone food pigments such as purpurin and alizarin suppress the genotoxic activities of several mutagens including heterocyclic amines and polycyclic aromatic hydrocarbons in the Drosophila DNA repair test and in the Ames test. The activities of eight human recombinant cytochrome P450 (CYP) isozymes were measured in the presence of purpurin, alizarin or carminic acid. |
1(0,0,0,1) | Details |
| 3309636 | Murakami H, Kobayashi J, Masuda T, Morooka N, Ueno Y: omega-Hydroxyemodin, a major hepatic metabolite of emodin in various animals and its mutagenic activity. Mutat Res. 1987 Oct;180(2):147-53. The hepatic microsomes derived from various animal species transformed emodin (1,3,8-trihydroxy-6-methylanthraquinone), an anthraquinoid pigment present in fungal metabolites and a constituent of plant medicines, into an unidentified anthraquinone h, along with 2--, 4-- and 7-hydroxyemodins. |
0(0,0,0,0) | Details |