Microbial metabolism of methyl protodioscin by Aspergillus niger culture-A new androstenedione producing way from steroid

Journal of Steroid Biochemistry and Molecular Biology

Volumn 100, Issue 1-3, 2006, Pages 87-94

  He, Xiangjiu ^a,b   Liu, Bo ^c   Wang, Guanghui ^d   Wang, Xinluan ^d   Su, Lina ^d   Qu, Gexia ^d   Yao, Xinsheng ^a,d  

^a JINAN UNIVERSITY   (China)

^b Cornell University ^*  (United States)

^c UNIVERSITY OF EXETER   (United Kingdom)

^d SHENYANG PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

Anticancer activities; Aspergillus niger; Methyl protodioscin; Microbial transformation

Indexed keywords

26 O BETA DEXTRO GLUCOPYRANNOSYLFURAN 5 ENE 3BETA,22ALPHA,26 TRIHYDROXY 3 O ALPHA LEVO RHAMNOPYRANOSYL (1-2) BETA DEXTRO GLUCOPYRANOSIDE; 26 O BETA DEXTRO GLUCOPYRANNOSYLFURAN 5,20(22) DIENE 3BETA,26 DIHYDROXY 3 O [ALPHA LEVO RHAMNOPYRANOSYL (1-2)] BETA DEXTRO GLUCOPYRANOSIDE; 26 O BETA DEXTRO GLUCOPYRANNOSYLFURAN 5,20(22) DIENE 3BETA,26 DIHYDROXY 3 O ALPHA LEVO RHAMNOPYRANOSYL(1-2) [ALPHA LEVO RHAMNOPYRANOSYL (1-4)] BETA DEXTRO GLUCOPYRANOSIDE; ANDROSTENEDIONE; DIOSGENIN; HYPOGLAUCIN G; METHYL PROTODIOSCIN; PREGNA 5,16 DIEN 3BETA OL 20 ONE O ALPHA LEVO RHAMNOPYRANOSYL (1-2) [ALPHA LEVO RHAMNOPYRANOSYL (1-4)] BETA DEXTRO GLUCOPYRANOSIDE; PYRANOSIDE; STEROID; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; ASPERGILLUS NIGER; BIOSYNTHESIS; BIOTECHNOLOGY; BIOTRANSFORMATION; CHEMICAL MODIFICATION; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOTOXICITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; NONHUMAN;

ADENOCARCINOMA; ANDROSTENEDIONE; ASPERGILLUS NIGER; BIOTRANSFORMATION; BREAST NEOPLASMS; CARCINOMA; CARCINOMA, HEPATOCELLULAR; CARCINOMA, NON-SMALL-CELL LUNG; CELL LINE, TUMOR; DIOSGENIN; DOSE-RESPONSE RELATIONSHIP, DRUG; FEMALE; HELA CELLS; HUMANS; INHIBITORY CONCENTRATION 50; LIVER NEOPLASMS; LUNG NEOPLASMS; MOLECULAR STRUCTURE; SAPONINS; STEROIDS; UTERINE CERVICAL NEOPLASMS;

ASPERGILLUS NIGER;

EID: 33745976498     PISSN: 09600760     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jsbmb.2006.03.007     Document Type: Article

References (17)

1. Hu K., Dong A.J., Yao X.S., Kobayashi H., and Iwasaki S. Antineoplastic agents; I. Three spirostanol glycosides from rhizomes of Dioscorea collettii var. hypoglauca. Planta Med. 62 6 (1996) 573-575
2. Hu K., and Yao X.S. The cytotoxicity of methyl protoneodioscin (NSC-698791) against human cancer cell lines in vitro. Anticancer Res. 22 2A (2002) 1001-1005
3. Hu K., Yao X.S., Dong A.J., Kobayashi H., Iwasaki S., and Jing Y.K. A new pregnane glycoside from Dioscorea collettii var. hypoglauca. J. Nat. Prod. 62 2 (1999) 299-301
4. Hu K., and Yao X.S. The cytotoxicity of methyl protodioscin against human cancer cell lines in vitro. Cancer Invest. 21 3 (2003) 389-393
5. Ju Y., and Jia Z.J. Steroidal saponins from the rhizomes of Smilax menispermoidea. Phytochemistry 31 4 (1992) 1349-1351
6. Ju Y., Jia Z.J., and Sun X.J. Steroidal saponins from Smilax menispermoidea and S. Lebrunii. Phytochemistry 37 5 (1994) 1433-1436
7. Shao Y., Poobrasert O., Kennelly E.J., Chin C.K., Ho C.T., Huang M.T., Garrison S.A., and Cordell G.A. Steroidal saponins from Asparagus officinalis and their cytotoxic activity. Planta Med. 63 3 (1997) 258-262
8. Singh S.B., and Thakur R.S. Saponins from the seeds of Costus speciosus. J. Nat. Prod. 45 6 (1982) 667-671
9. Cheng M.S., Wang Q.L., Tian Q., Song H.Y., Liu Y.X., Li Q., Xu X., Miao H.D., Yao X.S., and Yang Z. Total synthesis of methyl protodioscin: a potent agent with antitumor activity. J. Org. Chem. 68 9 (2003) 3658-3662
10. Rosazza J.P.N., and Duffel M.W. Metabolic transformation of alkaloids. In: Brossi X. (Ed). Alkaloids: Chemistry and Pharmacology (1986), Academic Press, New York 391-392
11. Fernandes P., Cruz A., Angelova B., Pinheiro H.M., and Cabral J.M.S. Microbial conversion of steroid compounds: recent developments. Enzyme Microb. Technol. 32 6 (2003) 688-705
12. Teshima S., Kajimoto T., Nakano K., Tomimatsu T., Yamasaki M., and Nohara T. Conversion of furostanol glycosides into steroidal alkaloid glycoside. I. From methyl protodioscin to kryptogenin 3-O-β-chacotrioside. Chem. Pharm. Bull. 34 9 (1986) 3925-3927
13. Agrawal P., Jain D.C., Gupta P.K., and Thakur R.S. Carbon-13 NMR spectroscopy of steroidal sapogenins and steroidal saponins. Phytochemistry 24 11 (1985) 2479-2496
14. Agrawal P.K. NMR Spectroscopy in the structural elucidation of oligosaccharides and glycosides. Phytochemistry 31 10 (1992) 3307-3330
15. Ju Y., Peng H.N., Jia Z.J., and Sun X.J. The research on the steroidal saponins of Smilax menispermoidea. Lanzhou Daxue Xuebao 30 1 (1994) 64-67
16. Dong M., Feng X.Z., Wang B.X., Wu L.J., and Ikejima T. Two novel furostanol saponins from the rhizomes of Dioscorea panthaica Prain et Burkill and their cytotoxic activity. Tetrahedron 57 3 (2001) 501-506
17. Pauli G.F. The cardenolides of Speirantha convallarioides. Planta Med. 61 2 (1995) 162-166