CATHARANTHUS-ROSEUS ENZYME MEDIATED SYNTHESIS OF 3-HYDROXYVOAFRINE-A AND 3-HYDROXYVOAFRINE-B - A SIMPLE ROUTE TO THE VOAFRINES

被引:10
作者
FAHN, W [1 ]
KAISER, V [1 ]
SCHUBEL, H [1 ]
STOCKIGT, J [1 ]
DANIELI, B [1 ]
机构
[1] UNIV MILAN,FAC SCI,DIPARTIMENTO CHIM ORGAN & IND,CNR,CTR STUDIO SOSTANZE ORGAN NAT,I-20133 MILAN,ITALY
关键词
3-hydroxyvoafrine; Apocynaceae; Catharanthus roseus; dimeric indole alkaloids; enzyme mediated synthesis; tabersonine; voafrine;
D O I
10.1016/0031-9422(90)89025-5
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
Dimerization of tabersonine by a crude enzyme preparation from Catharanthus roseus led to the novel 3-hydroxyvoafrines A and B which were reduced enzymatically or chemically to the voafrines A and B, recently isolated in trace amounts from cell cultures of Voacanga africana. © 1990.
引用
收藏
页码:127 / 133
页数:7
相关论文
共 12 条
[1]  
BRADFORD MM, 1976, ANAL BIOCHEM, V72, P248, DOI 10.1016/0003-2697(76)90527-3
[2]  
BROWN RT, 1977, TETRAHEDRON LETT, P4251
[3]   MICROBIAL TRANSFORMATIONS OF NATURAL ANTI-TUMOR AGENTS .18. CONVERSIONS OF VINDOLINE WITH COPPER OXIDASES [J].
ECKENRODE, F ;
PECZYNSKACZOCH, W ;
ROSAZZA, JP .
JOURNAL OF PHARMACEUTICAL SCIENCES, 1982, 71 (11) :1246-1250
[4]  
HESSE M, 1979, PROGR MASS SPECTROME, V1, P32
[5]   STEREOCHEMICAL CONTROL IN BIOMIMETIC CONVERSION OF HETERO-YOHIMBINE ALKALOID PRECURSORS - ISOLATION OF A NOVEL KEY INTERMEDIATE [J].
KANFAN, C ;
HUSSON, HP .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (14) :618-619
[6]  
LOUNASMAA M, 1988, ACTA CHEM SCAND B, V34, P379
[7]  
NAOBIH T, 1978, J CHEM SOC P1, P757
[8]  
PAWELKA KH, 1985, THESIS MUNICH
[9]   PHOTOCHEMICAL OXIDATION OF TERTIARY-AMINES AND ALKALOIDS .8. PHOTOCHEMICAL OXIDATION OF INDOLINO-INDOLIZIDINE ALKALOIDS, VINCADIFFORMINE, TABERSONINE, N(A)-ACETYL-2, 16-DIHYDROVINCADIFFORMINE AND N(A)-ACETYL-2, 16-DIHYDROTABERSONINE [J].
SANTAMARIA, J ;
HERLEM, D ;
KHUONGHUU, F .
TETRAHEDRON, 1977, 33 (18) :2389-2392
[10]   ONE-ELECTRON OXIDATION OF VINDOLINE AND 16-O-ACETYLVINDOLINE CATALYZED BY PEROXIDASE [J].
SARIASLANI, FS ;
DUFFEL, MW ;
ROSAZZA, JP .
JOURNAL OF MEDICINAL CHEMISTRY, 1985, 28 (05) :629-633