Hydroxylation of oleanolic acid to queretaroic acid by cytochrome P450 from Nonomuraea recticatena

Bioscience, Biotechnology and Biochemistry

Volumn 70, Issue 9, 2006, Pages 2299-2302

  Fujii, Yoshikazu ^a   Hirosue, Shinji ^a   Fujii, Tadashi ^a   Matsumoto, Naoki ^a   Agematu, Hitosi ^a   Arisawa, Akira ^a  

^a MERCIAN CORPORATION   (Japan)

Author keywords

Cytochrome P450; Hydroxylation; Oleanolic acid; Queretaroic acid

Indexed keywords

CYTOCHROME P450; NONOMURAEA RECTICATENA; OLEANOLIC ACID; QUERETAROIC ACID;

CELLS; CYTOLOGY; ESCHERICHIA COLI; GENES; HYDROXYLATION;

ORGANIC ACIDS;

CYTOCHROME P450; OLEANOLIC ACID; RECOMBINANT PROTEIN;

ACTINOBACTERIA; ARTICLE; CELL FREE SYSTEM; CHEMICAL STRUCTURE; ELECTROSPRAY MASS SPECTROMETRY; ENZYMOLOGY; ESCHERICHIA COLI; GENETICS; HYDROXYLATION; METABOLISM; METHODOLOGY; MICROBIOLOGY; NUCLEAR MAGNETIC RESONANCE;

ACTINOBACTERIA; CELL-FREE SYSTEM; CYTOCHROME P-450 ENZYME SYSTEM; ESCHERICHIA COLI; HYDROXYLATION; INDUSTRIAL MICROBIOLOGY; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; OLEANOLIC ACID; RECOMBINANT PROTEINS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

ESCHERICHIA COLI; NONOMURAEA RECTICATENA;

EID: 33749018513     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.60126     Document Type: Article

References (22)

1. Arisawa, A., and Kumeda, A., Patent WO2003/087381 (Oct. 23, 2003).
2. Peterson, J. A., Lorence, M. C., and Amarneh, B., Putidaredoxin reductase and putidaredoxin: cloning, sequence determination, and heterologous expression of the proteins. J. Biol. Chem., 265, 6066-6073 (1990).
3. Agematu, H., Matsumoto, N., Fujii, Y., Kabumoto, H., Doi, S., Machida, K., Ishikawa, J., and Arisawa, A., Hydroxylation of testosterone by bacterial cytochromes P450 using the Escherichia coli expression system. Biosci. Biotechnol. Biochem., 70, 307-311 (2006).
4. Kinoshita, K., Yang, Y., Koyama, K., Takahashi, K., and Nishino, H., Inhibitory effect of some triterpenes from cacti on 32Pi-incorporation into phospholipids of HeLa cells promoted by 12-O-tetradecanoylphorbol-13-acetate. Phytomedicine, 6, 73-77 (1999).
5. Tang, H. Q., Hu, J., Yang, L., and Tan, R. X., Terpenoids and flavonoids from Artemisia species. Planta Med., 66, 391-393 (2000).
6. Marquina, S., Maldonado, N., Garduno-Ramirez, M. L., Aranda, E., Villarreal, M. L., Navarro, V., Bye, R., Delgado, G., and Alvarez, L., Bioactive oleanolic acid saponins and other constituents from the roots of Viguiera decurrens. Phytochemistry, 56, 93-97 (2001).
7. Kashiwada, Y., Nagao, T., Hashimoto, A., Ikeshiro, Y., Okabe, H., Cosentino, L. M., and Lee, K. H., Anti-AIDS agents 38: anti-HIV activity of 3-O-acyl ursolic acid derivatives. J. Nat. Prod., 63, 1619-1622 (2000).
8. Ma, C., Nakamura, N., Hattori, M., Kakuda, H., Qiao, J., and Yu, H., Inhibitory effects on HIV-1 protease of constituents from the wood of Xanthoceras sorifolia. J. Nat. Prod., 63, 238-242 (2000).
9. Alvarez, M. E., Maria, A. O., and Saad, J. R., Diuretic activity of Fabiana patagonica in rats. Phytother. Res., 16, 71-73 (2002).
10. Assefa, H., Nimrod, A., Walker, L., and Sindelar, R., Enantioselective synthesis and complement inhibitory assay of A/B-ring partial analogues of oleanolic acid. Bioorg. Med. Chem. Lett., 11, 1619-1623 (2001).
11. Yoshikawa, M., and Matsuda, H., Antidiabetogenic activity of oleanolic acid glycosides from medicinal foodstuffs. Biofactors, 13, 231-237 (2000).
12. Yim, T. K., Wu, W. K., Pak, W. F., and Ko, K. M., Hepatoprotective action of an oleanolic acid-enriched extract of Ligustrum lucidum fruits is mediated through an enhancement on hepatic glutathione regeneration capacity in mice. Phytother. Res., 15, 589-592 (2001).
13. Ismaili, H., Tortora, S., Sosa, S., Fkih-Tetouani, S., Ilidrissi, A., Della, L. R., Tubaro, A., and Aquino, R., Topical anti-inflammatory activity of Thymus willdenowii. J. Pharm. Pharmacol., 53, 1645-1652 (2001).
14. Giner-Larza, E. M., Manez, S., Recio, M. C., Giner, R. M., Prieto, J. M., Cerda-Nicolas, M., and Rios, J. L., Oleanolic acid, a 3-oxotriterpene from Pistacia, inhibits leukotriene synthesis and has anti-inflammatory activity. Eur. J. Pharmacol., 428, 137-143 (2001).
15. Fujii, T., Hirosue, S., Narita, T., Kobayashi, Y., Jodo, O., and Ishiki, K., Japan Kokai Tokkyo Koho, P2002-247984A (Feb. 23, 2001).
16. GenBank accession no. AB180844.
17. Watanabe, I., Nara, F., and Serizawa, N., Cloning, characterization and expression of the gene encoding cytochrome P-450sca-2 from Streptomyces carbophilus involved in production of pravastatin, a specific HMG-CoA reductase inhibitor. Gene, 163, 81-85 (1995).
18. Kusano, K., Waterman, M. R., Sakaguchi, M., Omura, T., and Kagawa, N., Protein synthesis inhibitors and ethanol selectively enhance heterologous expression of P450s and related proteins in Escherichia coli. Arch. Biochem. Biophys., 367, 129-136 (1999).
19. Kagawa, N., and Cao, Q., Osmotic stress induced by carbohydrates enhances expression of foreign proteins in Escherichia coli. Arch. Biochem. Biophys., 393, 290-296 (2001).
20. Omura, T., and Sato, R., The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature. J. Biol. Chem., 239, 2370-2378 (1964).
21. Shao, C., Kasai, R., Xu, J., and Tanaka, O., Saponins from leaves of Acanthopanax senticosus Harms., Ciwujia. II. Structures of Ciwujianosides A1, A2, A3, A4, and D3. Chem. Pharm. Bull., 37, 42-45 (1989).
22. Yang, Y., Kinoshita, K., Koyama, K., Takahashi, K., Kondo, N., and Yuasa, H., New triterpenes from Machaerocereus eruca. J. Nat. Prod., 61, 456-460 (1998).