BIOTRANSFORMATION OF CARYOPHYLLENE BY DIPLODIA-GOSSYPINA

被引：23
作者：
ABRAHAM, WR [1 ]
ERNST, L [1 ]
STUMPF, B [1 ]
机构：
[1] TECH UNIV BRUNSWICK,INST CHEM,NUCL MAGNET RESONANCE LAB,W-3300 BRAUNSCHWEIG,GERMANY
来源：
PHYTOCHEMISTRY | 1990年 / 29卷 / 01期
关键词：
caryophyllene; Diplodia gossypina; filamentous fungi; microbial hydroxylation; punctatin; sesquiterpene;
D O I：
10.1016/0031-9422(90)89023-3
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：
Fermentation of caryophyllene with Diplodia gossypina affords a number of products which are all derived from the 4,5-epoxide. Twelve of these are described here for the first time. The main products are 12-hydroxy-4,5-epoxy-caryophyllene and the corresponding acid. On side reactions additional hydroxylations occurred or the exo-methylene group was also epoxidized and further degraded. Two rearranged compounds were found, one resulting from an epoxide rearrangement leading to an eight-membered ring, the other one being a cyclization product possessing the rare skeleton of the punctatin antibiotics. © 1990.
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页码：115 / 120
页数：6
相关论文
共 18 条
  • [1] ABRAHAM WR, 1987, Z NATURFORSCH C, V42, P79
  • [2] ABRAHAM WR, 1987, Z NATURFORSCH C, V42, P414
  • [3] ABRAHAM WR, 1986, APPL MICROBIOL BIOT, V24, P24
  • [4] NEW TRANS-FUSED AFRICANOLS FROM LEPTOGRAPHIUM-LUNDBERGII
    ABRAHAM, WR
    ERNST, L
    WITTE, L
    HANSSEN, HP
    SPRECHER, E
    [J]. TETRAHEDRON, 1986, 42 (16) : 4475 - 4480
  • [5] PUNCTATIN-B AND PUNCTATIN-C (ANTIBIOTICS M95154 AND M95155) - FURTHER SESQUITERPENE ALCOHOLS FROM THE FUNGUS PORONIA-PUNCTATA
    ANDERSON, JR
    EDWARDS, RL
    FREER, AA
    MABELIS, RP
    POYSER, JP
    SPENCER, H
    WHALLEY, AJS
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (14) : 917 - 919
  • [6] PUNCTATIN-A (ANTIBIOTIC-M95464) - X-RAY CRYSTAL-STRUCTURE OF A SESQUITERPENE ALCOHOL WITH A NEW CARBON SKELETON FROM THE FUNGUS, PORONIA-PUNCTATA
    ANDERSON, JR
    BRIANT, CE
    EDWARDS, RL
    MABELIS, RP
    POYSER, JP
    SPENCER, H
    WHALLEY, AJS
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (07) : 405 - 406
  • [7] METABOLITES OF THE HIGHER FUNGI .23. THE PUNCTAPORONINS - NOVEL BI-CYCLIC, TRI-CYCLIC, AND TETRA-CYCLIC SESQUITERPENES RELATED TO CARYOPHYLLENE, FROM THE FUNGUS PORONIA-PUNCTATA (LINNAEUS, FRIES) FRIES
    ANDERSON, JR
    EDWARDS, RL
    POYSER, JP
    WHALLEY, AJS
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (04): : 823 - 831
  • [8] TERPENOID BIOTRANSFORMATION IN MAMMALS .4. BIOTRANSFORMATION OF (+)-LONGIFOLENE, (-)-CARYOPHYLLENE, (-)-CARYOPHYLLENE OXIDE, (-)-CYCLOCOLORENONE, (+)-NOOTKATONE, (-)-ELEMOL, (-)-ABIETIC ACID AND (+)-DEHYDROABIETIC ACID IN RABBITS
    ASAKAWA, Y
    ISHIDA, T
    TOYOTA, M
    TAKEMOTO, T
    [J]. XENOBIOTICA, 1986, 16 (08) : 753 - 767
  • [9] BACKENS S, 1984, LIEBIGS ANN CHEM, P1332
  • [10] NATURALLY-OCCURRING TERPENE DERIVATIVES .393. ALPHA-HUMULENE DERIVATIVES INCLUDING A SESQUITERPENE ACID WITH A REARRANGED CARBON SKELETON FROM LYCHOPHORA-COLUMNARIS
    BOHLMANN, F
    ZDERO, C
    ROBINSON, H
    KING, RM
    [J]. PHYTOCHEMISTRY, 1982, 21 (03) : 685 - 689
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