3-OXOTEASTERONE AND THE EPIMERIZATION OF TEASTERONE - IDENTIFICATION IN LILY ANTHERS AND DISTYLIUM-RACEMOSUM LEAVES AND ITS BIOTRANSFORMATION INTO TYPHASTEROL

被引:37
作者
ABE, H
HONJO, C
KYOKAWA, Y
ASAKAWA, S
NATSUME, M
NARUSHIMA, M
机构
[1] Department of Applied Biological Sciences, Tokyo University of Agriculture and Technology, Fuchu
关键词
D O I
10.1271/bbb.58.986
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
3-Oxo TE has been assumed to be involved as a biosynthetic intermediate in the epimerization of the C-3 hydroxyl group of teasterone to typhasterol. We have isolated and identified it in lily anthers by using normal-phase HPLC. Mass spectral analysis, chemical synthesis, and identification of the biotransformation product by lily cell cultures confirmed it to be 3-oxo TE. Reduction of this compound stereoselectively transformed it into typhasterol in cell cultures. It is suggested that 3-oxo TE is distributed widely in the plant kingdom as a biosynthetic intermediate from TE to TY.
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收藏
页码:986 / 989
页数:4
相关论文
共 13 条
[1]  
ABE H, 1991, ACS SYM SER, V474, P18
[2]  
ABE H, 1991, ACS SYM SER, V474, P200
[3]   A NEW BRASSINOLIDE-RELATED STEROID IN THE LEAVES OF THEA-SINENSIS [J].
ABE, H ;
MORISHITA, T ;
UCHIYAMA, M ;
TAKATSUTO, S ;
IKEKAWA, N .
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1984, 48 (08) :2171-2172
[4]   SYNTHESIS OF BRASSINOLIDE .4. FACILE SYNTHESES OF BRASSINOSTEROIDS - BRASSINOLIDE, CASTASTERONE, TEASTERONE AND TYPHASTEROL [J].
ABURATANI, M ;
TAKEUCHI, T ;
MORI, K .
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1987, 51 (07) :1909-1913
[5]   C-13 NMR ASSIGNMENTS OF BRASSINOSTEROIDS BY 2-DIMENSIONAL TECHNIQUES [J].
ANDO, T ;
ABURATANI, M ;
KOSEKI, N ;
ASAKAWA, S ;
MOURI, T ;
ABE, H .
MAGNETIC RESONANCE IN CHEMISTRY, 1993, 31 (01) :94-99
[6]   TEASTERONE 3-MYRISTATE - A NEW-TYPE OF BRASSINOSTEROID DERIVATIVE IN LILIUM-LONGIFLORUM ANTHERS [J].
ASAKAWA, S ;
ABE, H ;
KYOKAWA, Y ;
NAKAMURA, S ;
NATSUME, M .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1994, 58 (01) :219-220
[7]   ANALYSIS OF NATURAL BRASSINOSTEROIDS BY GAS-CHROMATOGRAPHY AND GAS-CHROMATOGRAPHY MASS-SPECTROMETRY [J].
IKEKAWA, N ;
TAKATSUTO, S ;
KITSUWA, T ;
SAITO, H ;
MORISHITA, T ;
ABE, H .
JOURNAL OF CHROMATOGRAPHY, 1984, 290 (MAY) :289-302
[8]   STUDIES ON PLANT-TISSUE CULTURES .58. BIOTRANSFORMATION OF DIGITOXIGENIN BY CELL-SUSPENSION CULTURES OF STROPHANTHUS-INTERMEDIUS [J].
KAWAGUCHI, K ;
HIROTANI, M ;
FURUYA, T .
PHYTOCHEMISTRY, 1989, 28 (04) :1093-1097
[9]   ECDYSONE OXIDASE - REACTION AND SPECIFICITY [J].
KOOLMAN, J ;
KARLSON, P .
EUROPEAN JOURNAL OF BIOCHEMISTRY, 1978, 89 (02) :453-460
[10]   BIOTRANSFORMATION OF AROMATIC KETONES WITH CELL-CULTURES OF CARROT, TOBACCO AND GARDENIA [J].
NAOSHIMA, Y ;
AKAKABE, Y .
PHYTOCHEMISTRY, 1991, 30 (11) :3595-3597