STUDIES ON PLANT-TISSUE CULTURES .66. BIOTRANSFORMATION OF DIGITOXIGENIN BY GINSENG HAIRY ROOT CULTURES

被引:31
作者
KAWAGUCHI, K [1 ]
HIROTANI, M [1 ]
YOSHIKAWA, T [1 ]
FURUYA, T [1 ]
机构
[1] KITASATO UNIV,SCH PHARMACEUT SCI,MINATO KU,TOKYO 108,JAPAN
关键词
Araliaceae; biotransformation; cardenolides; digitoxigenin; digitoxigenin palmitate; β-D-sophoroside; esterification; glycosylation; hairy root cultures; Panax ginseng;
D O I
10.1016/0031-9422(90)80029-G
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
Five new compounds (three esters and two glycosides) and seven previously reported compounds were isolated as biotransformation products of digitoxigenin by ginseng hairy root cultures. The new esters and glycosides were elucidated as digitoxigenin stearate, digitoxigenin palmitate, digitoxigenin myristate, 3-epidigitoxigenin β-D- gentiobioside and digitoxigenin β-D-sophoroside using 1H and 13C NMR and FAB mass spectral data. Biotransformations involving esterification (of stearic acid, palmitic acid, myristic acid and lauric acid) and glycosylation (of gentiobiose and sophorose) of digitoxigenin have been demonstrated for the first time in the plant cell and tissue cultures. The hairy roots showed high glycosylation ability to the digitoxigenin molecule. © 1990.
引用
收藏
页码:837 / 843
页数:7
相关论文
共 21 条
[1]   CARDENOLIDE ANALOGS .12. C-13 NMR OF SEMI-SYNTHETIC GLYCOSIDES AND SIDE-CHAIN MODIFIED GENINS [J].
CHEUNG, HTA ;
BROWN, L ;
BOUTAGY, J ;
THOMAS, R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (06) :1773-1778
[2]   STUDIES ON PLANT TISSUE CULTURES .3. BIOTRANSFORMATION OF PROGESTERONE AND PREGNENOLONE BY PLANT SUSPENSION CULTURES [J].
FURUYA, T ;
HIROTANI, M ;
KAWAGUCHI, K .
PHYTOCHEMISTRY, 1971, 10 (05) :1013-+
[3]   STUDIES ON PLANT-TISSUE CULTURE .50. GLYCOSYLATION OF 2-PHENYLPROPIONIC ACID AND ITS ETHYL-ESTER IN SUSPENSION-CULTURES OF NICOTIANA-TABACUM DIOSCOREOPHYLLUM-CUMMINSII AND ACONITUM-JAPONICUM [J].
FURUYA, T ;
USHIYAMA, M ;
ASADA, Y ;
YOSHIKAWA, T .
PHYTOCHEMISTRY, 1987, 26 (11) :2983-2989
[4]   STUDIES ON PLANT-TISSUE CULTURE .61. BIOTRANSFORMATION OF (-)-MENTHOL BY EUCALYPTUS-PERRINIANA CULTURED-CELLS [J].
FURUYA, T ;
ORIHARA, Y ;
MIYATAKE, H .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (10) :1711-1719
[5]   STUDIES ON PLANT-TISSUE CULTURES .55. BIOTRANSFORMATION OF DIGITOXIGENIN BY CELL-SUSPENSION CULTURES OF STROPHANTHUS-GRATUS [J].
FURUYA, T ;
KAWAGUCHI, K ;
HIROTANI, M .
PHYTOCHEMISTRY, 1988, 27 (07) :2129-2133
[6]   STUDIES ON PLANT-TISSUE CULTURE .51. BIOTRANSFORMATION OF PHENYLACETIC ACID AND 2-PHENYL-PROPIONIC ACID IN SUSPENSION-CULTURE OF COFFEA-ARABICA [J].
FURUYA, T ;
USHIYAMA, M ;
ASADA, Y ;
YOSHIKAWA, T ;
ORIHARA, Y .
PHYTOCHEMISTRY, 1988, 27 (03) :803-807
[7]   STUDIES ON PLANT-TISSUE CULTURE .59. BIOTRANSFORMATION OF 2-PHENYLPROPIONIC ACID IN ROOT CULTURE OF PANAX-GINSENG [J].
FURUYA, T ;
USHIYAMA, M ;
ASADA, Y ;
YOSHIKAWA, T .
PHYTOCHEMISTRY, 1989, 28 (02) :483-487
[8]   STUDIES ON PLANT-TISSUE CULTURES .22. BIOTRANSFORMATION OF TESTOSTERONE AND OTHER ANDROGENS BY SUSPENSION CULTURES OF NICOTIANA-TABACUM BRIGHT YELLOW [J].
HIROTANI, M ;
FURUYA, T .
PHYTOCHEMISTRY, 1974, 13 (10) :2135-2142
[9]   STUDIES ON PLANT-TISSUE CULTURES .32. BIOTRANSFORMATION OF DIGITOXIGENIN BY CELL-SUSPENSION CULTURES OF DIGITALIS-PURPUREA [J].
HIROTANI, M ;
FURUYA, T .
PHYTOCHEMISTRY, 1980, 19 (04) :531-534
[10]  
JONES A, 1978, LLOYDIA, V41, P476