CIS-STEREOISOMERS OF BETA-CAROTENE AND ITS CONGENERS IN THE ALGA DUNALIELLA-BARDAWIL, AND THEIR BIOGENETIC INTERRELATIONSHIPS

被引:5
作者
EBENEZER, WJ [1 ]
PATTENDEN, G [1 ]
机构
[1] UNIV NOTTINGHAM,DEPT CHEM,NOTTINGHAM NG7 2RD,ENGLAND
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1993年 / 16期
关键词
D O I
10.1039/p19930001869
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The acyclic carotenoids phytoene and phytofluene, which are precursors of 9-cis-beta-carotene produced by the alga Dunaliella bardawil, have been separated and characterised. Spectroscopic data, and comparison with synthetic model compounds and corresponding carotenoids found in the fruits of the Tangerine tomato Lycopersicon esculentum var., establish that the pigments have the stereochemistries 15-cis-6 and 9-cis-11 respectively. The data suggest that phytoene 6 is the clear branch point for the formation of 9-cis-beta-carotene 2 in D. bardawil. In addition, spectroscopic data for beta-carotene isolated from D. bardawil showed that it was isomerically pure 9-cis-beta-carotene 2.
引用
收藏
页码:1869 / 1873
页数:5
相关论文
共 19 条
[1]  
Avron M., 1992, DUNALIELLA PHYSL BIO
[2]   SYNTHESIS OF POLY-Z-ISOMERS OF 2,6,11,15-TETRAMETHYLHEXADECA-2,6,8,10,14-PENTAENE, A C-20 ANALOG OF PHYTOENE - RE-EXAMINATION OF STEREOCHEMISTRY OF A NEW ISOMER OF PHYTOENE FROM RHODOSPIRILLUM-RUBRUM [J].
BARLOW, L ;
PATTENDEN, G .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (09) :1029-1034
[3]   ACCUMULATION OF BETA-CAROTENE IN HALOTOLERANT ALGAE - PURIFICATION AND CHARACTERIZATION OF BETA-CAROTENE-RICH GLOBULES FROM DUNALIELLA-BARDAWIL (CHLOROPHYCEAE) [J].
BENAMOTZ, A ;
KATZ, A ;
AVRON, M .
JOURNAL OF PHYCOLOGY, 1982, 18 (04) :529-537
[4]   STEREOISOMERS OF BETA-CAROTENE AND PHYTOENE IN THE ALGA DUNALIELLA-BARDAWIL [J].
BENAMOTZ, A ;
LERS, A ;
AVRON, M .
PLANT PHYSIOLOGY, 1988, 86 (04) :1286-1291
[5]   ON THE FACTORS WHICH DETERMINE MASSIVE BETA-CAROTENE ACCUMULATION IN THE HALOTOLERANT ALGA DUNALIELLA-BARDAWIL [J].
BENAMOTZ, A ;
AVRON, M .
PLANT PHYSIOLOGY, 1983, 72 (03) :593-597
[6]   APPLICATION OF NUCLEAR MAGNETIC-RESONANCE SPECTROSCOPY IN THE STEREOCHEMICAL ASSIGNMENT OF POLY-Z-ISOMERIC CONJUGATED POLYENE ISOPRENOIDS [J].
CAREY, L ;
CLOUGH, JM ;
PATTENDEN, G .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (12) :3005-3009
[7]  
CLOUGH JM, 1978, TETRAHEDRON LETT, P4159
[8]   NATURALLY OCCURRING POLY-CIS CAROTENOIDS - STEREOCHEMISTRY OF POLY-CIS LYCOPENE AND ITS CONGENERS IN TANGERINE TOMATO FRUITS [J].
CLOUGH, JM ;
PATTENDEN, G .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1979, (14) :616-619
[9]   STEREOCONTROLLED SYNTHESIS OF CONJUGATED POLYENE ISOPRENOIDS USING PHOSPHINE OXIDE ANION INTERMEDIATES [J].
CLOUGH, JM ;
PATTENDEN, G .
TETRAHEDRON, 1981, 37 (23) :3911-3920
[10]   STEREOCHEMICAL ASSIGNMENT OF PROLYCOPENE AND OTHER POLY-Z-ISOMERIC CAROTENOIDS IN FRUITS OF THE TANGERINE TOMATO LYCOPERSICON-ESCULENTUM VAR TANGELLA [J].
CLOUGH, JM ;
PATTENDEN, G .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (12) :3011-3018