TRITIUM TRANSFER DURING BIOSYNTHESIS OF CADALENE STRESS COMPOUNDS IN COTTON

被引:6
作者
DAVIS, GD [1 ]
EISENBRAUN, EJ [1 ]
ESSENBERG, M [1 ]
机构
[1] OKLAHOMA STATE UNIV,DEPT CHEM,STILLWATER,OK 74078
关键词
GOSSYPIUM-HIRSUTUM; MALVACEAE; UPLAND COTTON; BIOSYNTHESIS; SESQUITERPENES; PHYTOALEXINS; 2,7-DIHYDROXYCADALENE; 2-HYDROXY-7-METHOXYCADALENE;
D O I
10.1016/0031-9422(91)84123-A
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
Chemical degradation of 2,7-dihydroxycadalene and 2-hydroxy-7-methoxycadalene biosynthesized in cotton cotyledons from a mixture of ]2-C-14[mevalonolactone and ]5-H-3[mevalonolactone has revealed that formation of each of these cadalene sesquiterpenoids involves a hydrogen transfer to the methine carbon of the isopropyl side chain. The transfer may occur as a 1,3-hydride shift following cyclization of the farnesyl precursor to a 10-membered ring cation.
引用
收藏
页码:197 / 199
页数:3
相关论文
共 12 条
[1]   STEREOCHEMICAL ASPECTS OF SESQUITERPENE BIOSYNTHESIS [J].
ARIGONI, D .
PURE AND APPLIED CHEMISTRY, 1975, 41 (1-2) :219-245
[2]   ELECTRON-TRANSFER OXIDATION OF ORGANIC-COMPOUNDS .5. OXIDATION OF CYCLOHEXANONE BY THE TRIS-2,2'-BIPYRIDYLRUTHENIUM(III) CATION [J].
AUDSLEY, AJ ;
QUICK, GR ;
LITTLER, JS .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1980, (03) :557-560
[3]   A HIGHLY EFFECTIVE LIGAND-BOUND RUTHENIUM CATALYST FOR CHEMOSELECTIVE DEGRADATION OF AROMATIC RINGS TO CARBOXYLIC-ACIDS [J].
CHAKRABORTI, AK ;
GHATAK, UR .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (12) :2605-2609
[4]   THE BIOSYNTHESIS OF 2,7-DIHYDROXYCADALENE IN INFECTED COTTON COTYLEDONS - THE FOLDING PATTERN OF THE FARNESOL PRECURSOR AND POSSIBLE IMPLICATIONS FOR GOSSYPOL BIOSYNTHESIS [J].
ESSENBERG, M ;
STOESSL, A ;
STOTHERS, JB .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (09) :556-557
[5]  
ESSENBERG M, 1982, PHYTOPATHOLOGY, V72, P1349, DOI 10.1094/Phyto-72-1349
[6]   ACCUMULATION OF ANTIBACTERIAL SESQUITERPENOIDS IN BACTERIALLY INOCULATED GOSSYPIUM LEAVES AND COTYLEDONS [J].
ESSENBERG, M ;
GROVER, PB ;
COVER, EC .
PHYTOCHEMISTRY, 1990, 29 (10) :3107-3113
[7]   A REVISED SCHEME FOR THE BIOSYNTHESIS OF GOSSYPOL [J].
MASCIADRI, R ;
ANGST, W ;
ARIGONI, D .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (22) :1573-1574
[8]  
MEYER VR, 1988, PRACTICAL HIGH PERFO, P104
[9]   POTASSIUM FLUORIDE ASSISTED DERIVATIZATION OF CARBOXYLIC-ACIDS TO PHENACYL ESTERS FOR DETERMINATION BY HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY [J].
MILLER, JM ;
BRINDLE, ID ;
CATER, SR ;
SO, KH ;
CLARK, JH .
ANALYTICAL CHEMISTRY, 1980, 52 (14) :2430-2432