Microbial transformation of cycloastragenol

被引:23
作者
Kuban, Melis [1 ]
Ongen, Gaye [1 ]
Khan, Ikhlas A. [2 ]
Bedir, Erdal [1 ]
机构
[1] Ege Univ, Fac Engn, Dept Bioengn, TR-35100 Izmir, Turkey
[2] Univ Mississippi, Sch Pharm, Dept Pharmacognosy, University, MS 38677 USA
关键词
Astragalus; Cycloastragenol; Biotransformation; Cunninghamella blakesleeana NRRL 1369; Glomerella fusarioides ATCC 9552; Mycobacterium sp NRRL 3805; BIOTRANSFORMATION; ACID; TRITERPENES; GLYCOSIDES; CLEAVAGE; RING;
D O I
10.1016/j.phytochem.2012.12.007
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The microbial transformation of cycloastragenol by the fungi Cunninghamella blakesleeana NRRL 1369 and Glomerella fusarioides ATCC 9552, and the bacterium Mycobacterium sp. NRRL 3805 were investigated. Both fungi mainly provided hydroxylated metabolites together with products formed by cyclization, dehydrogenation and Baeyer-Villiger oxidation resulting in a ring cleavage. The bacteria yielded only a single oxidation product, namely, 3-oxo-cycloastragenol. Structures of the metabolites were elucidated by 1-D (H-1,C-13), 2-D NMR (COSY, HMBC, HMQC) and HRMS analyses. (C) 2013 Elsevier Ltd. All rights regerved.
引用
收藏
页码:99 / 104
页数:6
相关论文
共 30 条
[1]  
Abourashed EA, 2000, CHEM PHARM BULL, V48, P1996, DOI 10.1248/cpb.48.1996
[2]  
Agzamova M.A., 1995, CHEM NAT COMPD, V31, P589
[3]   Biotransformation of cycloartane-type triterpenes by the fungus Glomerella fusarioides [J].
Akihisa, T ;
Watanabe, K ;
Yoneima, R ;
Suzuki, T ;
Kimura, Y .
JOURNAL OF NATURAL PRODUCTS, 2006, 69 (04) :604-607
[4]   Microbial transformations of two lupane-type triterpenes and anti-tumor-promoting effects of the transformation products [J].
Akihisa, T ;
Takamine, Y ;
Yoshizumi, K ;
Tokuda, H ;
Kimura, Y ;
Ukiya, M ;
Nakahara, T ;
Yokochi, T ;
Ichiishi, E ;
Nishino, H .
JOURNAL OF NATURAL PRODUCTS, 2002, 65 (03) :278-282
[5]   Podocarpaside, a triterpenoid possessing a new backbone from Actaea podocarpa [J].
Ali, Zulfiqar ;
Khan, Shabana I. ;
Ferreira, Daneel ;
Khan, Ikhlas A. .
ORGANIC LETTERS, 2006, 8 (24) :5529-5532
[6]  
Bedir E, 2000, CHEM PHARM BULL, V48, P1081
[7]   The telomerase activator TA-65 elongates short telomeres and increases health span of adult/old mice without increasing cancer incidence [J].
Bernardes de Jesus, Bruno ;
Schneeberger, Kerstin ;
Vera, Elsa ;
Tejera, Agueda ;
Harley, Calvin B. ;
Blasco, Maria A. .
AGING CELL, 2011, 10 (04) :604-621
[8]   Biotransformation enzymes in Cunninghamella blakesleeana (NCIM-687) [J].
Bhosale, Sanjyot ;
Saratale, Ganesh ;
Govindwar, Sanjay .
JOURNAL OF BASIC MICROBIOLOGY, 2006, 46 (06) :444-448
[9]   Cycloartane glycosides from Astragalus campylosema Boiss. ssp campylosema [J].
Calis, Ihsan ;
Donmez, Ali A. ;
Perrone, Angela ;
Pizza, Cosimo ;
Piacente, Sonia .
PHYTOCHEMISTRY, 2008, 69 (14) :2634-2638
[10]   Maintenance of steroid 11-hydroxylation activity in immobilized Cunninghamella elegans protoplasts [J].
Dlugonski, J ;
Paraszkiewicz, K ;
Sedlaczek, L .
WORLD JOURNAL OF MICROBIOLOGY & BIOTECHNOLOGY, 1997, 13 (04) :469-473