BIOTRANSFORMATION OF HIGHLY SUBSTITUTED ENT-KAUR-16-ENES BY RHIZOPUS-NIGRICANS

被引:11
作者
GARCIAGRANADOS, A
MARTINEZ, A
ONORATO, ME
RUIZ, ML
SANCHEZ, JM
ARIAS, JM
机构
[1] UNIV GRANADA, SERV TECN, E-18071 GRANADA, SPAIN
[2] UNIV GRANADA, FAC CIENCIAS, DEPT MICROBIOL, E-18071 GRANADA, SPAIN
关键词
biotransformation; fungus; metabolites; Rhizopus nigricans; structural determination; tetrasubstituted ent-kaur-16-enes;
D O I
10.1016/0031-9422(90)89024-4
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 behaviour of Rhizopus nigricans in the biotransformation of 3,7,15,18-tetrasubstituted ent-kaur-16-enes has been studied. Incubation of ent-18-acetoxy-3β-hydroxy-7α,15β-isopropylidenedioxykaur -16-ene by R. nigricans for 48 hr yielded mainly a 13-hydroxyl derivative. Incubation for eight days produced ent-16β,17-epoxidation, hydroxylation at C-12 and C-13, and ent-16α,1 7-dihydroxylation. Occasionally R. nigricans deacetylated and hydrolysed the isopropilidene group. The structure of the metabolites were determined by both spectroscopic (mainly by monodimensional and bidimensional NMR) and chemical means. © 1990.
引用
收藏
页码:121 / 126
页数:6
相关论文
共 25 条
[1]   HOMONUCLEAR BROAD-BAND DECOUPLING AND 2-DIMENSIONAL J-RESOLVED NMR-SPECTROSCOPY [J].
AUE, WP ;
KARHAN, J ;
ERNST, RR .
JOURNAL OF CHEMICAL PHYSICS, 1976, 64 (10) :4226-4227
[3]  
BEILBY JP, 1973, TETRAHEDRON LETT, P2589
[4]   NATURAL TERPENE DERIVATIVES .257. NEW ENT-ATISIRENIC ACID AND ENT-KAURENIC ACID-DERIVATIVES FROM HELIANTHUS SPECIES [J].
BOHLMANN, F ;
JAKUPOVIC, J ;
KING, RM ;
ROBINSON, H .
PHYTOCHEMISTRY, 1980, 19 (05) :863-868
[5]   TERPENIC COMPONENTS OF SPANISH LABIATAE .16. DITERPENOIDS FROM SIDERITIS-HIRSUTA SUBSP NIVALIS [J].
CABRERA, E ;
GARCIAGRANADOS, A ;
DEBURUAGA, AS ;
DEBURUAGA, JMS .
PHYTOCHEMISTRY, 1983, 22 (12) :2779-2781
[6]  
CARRASCAL MI, 1978, AN QUIM, V74, P1547
[7]   OSMIUM TETROXIDE-CATALYZED HYDROXYLATION OF FURAN-MALEIC ANHYDRIDE ADDUCTS [J].
DANIELS, R ;
FISCHER, JL .
JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (02) :320-&
[8]  
DEQUESADA TG, 1973, AN QUIM-INT, V69, P757
[9]   MICROBIOLOGICAL HYDROXYLATION OF 3BETA,7BETA-DIHYDROXYKAURENOLIDE [J].
ELLAMES, G ;
HANSON, JR .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (15) :1666-1668
[10]   MICROBIAL TRANSFORMATION OF TETRACYCLIC DITERPENES - CONVERSION OF ENT-KAURENONES BY ASPERGILLUS-NIGER [J].
GARCIAGRANADOS, A ;
MARTINEZ, A ;
ONORATO, ME ;
ARIAS, JM .
JOURNAL OF NATURAL PRODUCTS, 1986, 49 (01) :126-132