RING-D EXPANSION AND AROMATIZATION IN THE BIOSYNTHESIS OF NIC-1, AN ANTIFEEDANT STEROID FROM NICANDRA-PHYSALOIDES

被引:16
作者
GILL, HK [1 ]
SMITH, RW [1 ]
WHITING, DA [1 ]
机构
[1] UNIV NOTTINGHAM,DEPT CHEM,NOTTINGHAM NG7 2RD,ENGLAND
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1990年 / 11期
关键词
D O I
10.1039/p19900002989
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Isotope administration experiments with Nicandra physaloides plants using [3'-C2H3]- and [3'-14C3]mevalonic acid, analysed by 2H NMR and by degradation, respectively, show that the aromatic ring-D of Nic-1 2 is formed by ring-D expansion in a steroid precursor with oxidative inclusion of the C/D angular methyl.
引用
收藏
页码:2989 / 2993
页数:5
相关论文
共 15 条
[1]   STUDIES ON A SYNTHESIS OF (RS)-MEVALONIC ACID LACTONE [J].
BARDSHIRI, E ;
SIMPSON, TJ ;
SCOTT, AI ;
SHISHIDO, K .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (08) :1765-1767
[2]   STRUCTURES OF 3 OXYGENATED 24-METHYL-STEROIDS (NIC-3, NIC-7, AND NIC-11) FROM INSECT REPELLANT PLANT NICANDRA-PHYSALOIDES (SOLANACEAE) - X-RAY ANALYSIS OF NIC-3 ACETATE AND NIC-11 ETHYL ETHER [J].
BEGLEY, MJ ;
CROMBIE, L ;
HAM, PJ ;
WHITING, DA .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (03) :296-304
[3]   NEW CLASS OF NATURAL STEROIDS, WITH RING-D AROMATIC, FROM NICANDRA-PHYSALOIDES (SOLANACEAE) - X-RAY ANALYSIS OF NIC-10, AND STRUCTURES OF NIC-1 (NICANDRENONE), NIC-12, AND NIC-17 [J].
BEGLEY, MJ ;
CROMBIE, L ;
HAM, PJ ;
WHITING, DA .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (03) :304-308
[5]   5 NEW STEROIDAL ALKALOIDS FROM BUXUS-PAPILOSA - SOME RELATIONSHIPS BETWEEN STRUCTURES AND SPECIFIC ROTATIONS [J].
CHOUDHARY, MI ;
ATTAURRAHMAN ;
FREYER, AJ ;
SHAMMA, M .
TETRAHEDRON, 1986, 42 (20) :5747-5752
[6]  
FRAENKEL G, 1960, 11 P INT C ENT, V3, P122
[7]   BIOSYNTHESIS OF THE INSECT ANTIFEEDANT STEROID NIC-1 - ORIGINS OF THE AROMATIC RING-D [J].
GILL, HK ;
SMITH, RW ;
WHITING, DA .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (18) :1457-1458
[8]  
Glotter E., 1978, BIOORG CHEM, V2, P57
[9]  
GOODWIN TW, 1971, RODDS CHEM CARBON E, V2, P101
[10]   RECENT DEVELOPMENTS IN NATURALLY-OCCURRING ERGOSTANE-TYPE STEROIDS - A REVIEW [J].
KIRSON, I ;
GLOTTER, E .
JOURNAL OF NATURAL PRODUCTS, 1981, 44 (06) :633-647