PIGMENTS OF FUNGI .11. (+)-AUSTROCORTICIN, AUSTROCORTICINIC ACID, AUSTROCORTICONE, AND RELATED PIGMENTS - THE 1ST NATURALLY-OCCURRING ANTHRAQUINONES DERIVED FROM A PROPIONATE-TRIGGERED OCTAKETIDE

被引:16
作者
GILL, M
GIMENEZ, A
机构
[1] Department of Organic Chemistry, University of Melbourne, Parkville
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1990年 / 04期
关键词
D O I
10.1039/p19900001159
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The anthraquinones (7), (9), (11), (13), (15), and (17) have been isolated from the orange fruit bodies of an Australian toadstool belonging to the genus Dermocybe. Five of these six pigments bear a unique C2 side chain at C-3 in the anthraquinone nucleus, the biogenetic origin of which has been studied by feeding 13C labelled precursors to young toadstools. High specific incorporation of isotope from sodium [3-13C]propionate into the C-3′ methyl group of pigments (7), (11), (13), (15), and (17) indicates that a propionate 'starter' effect is operating. The sixth pigment (9) is derived in the same organism by 'normal' acetate-triggered octaketide assembly.
引用
收藏
页码:1159 / 1167
页数:9
相关论文
共 28 条
[1]  
Aldridge DC, 1983, FUNGAL METABOLITES, V2
[2]   ANTHRAQUINONE PIGMENTS FROM CRINOID COMANTHUS-BENNETTI [J].
BARTOLINI, GL ;
ERDMAN, TR ;
SCHEUER, PJ .
TETRAHEDRON, 1973, 29 (22) :3699-3702
[3]  
Bu'Lock J. D., 1979, COMPREHENSIVE ORGANI, V5, P927
[4]   STUDIES OF POLYKETIDE CHAIN ASSEMBLY PROCESSES - INCORPORATION OF [2-C-13]MALONATE INTO AVERUFIN IN ASPERGILLUS-PARASITICUS [J].
CHANDLER, IM ;
SIMPSON, TJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (01) :17-18
[5]  
COLE FM, 1984, FIELD GUIDE COMMON G
[6]  
FUHRER BA, 1985, FIELD COMPANION AUST, P33
[7]   MECHANISM OF BIOLOGICAL FORMATION OF ANTHRAQUINONES [J].
GATENBECK, S .
ACTA CHEMICA SCANDINAVICA, 1962, 16 (04) :1053-&
[8]   ON THE BIOSYNTHESIS OF THE PIGMENTS OF PENICILLIUM-ISLANDICUM .2. [J].
GATENBECK, S .
ACTA CHEMICA SCANDINAVICA, 1960, 14 (02) :296-302
[9]   INCORPORATION OF LABELLED ACETATE IN EMODIN IN PENICILLIUM-ISLANDICUM [J].
GATENBECK, S .
ACTA CHEMICA SCANDINAVICA, 1958, 12 (06) :1211-1214