Austrocolorins A1 and B1:: Atropisomeric 10,10′-linked dihydroanthracenones from an Australian Dermocybe sp.

被引:11
作者
Beattie, K [1 ]
Elsworth, C [1 ]
Gill, M [1 ]
Milanovic, NM [1 ]
Prima-Putra, D [1 ]
Raudies, E [1 ]
机构
[1] Univ Melbourne, Sch Chem, Parkville, Vic 3010, Australia
基金
澳大利亚研究理事会;
关键词
Dermocybe sp WAT 26641; cortinariaceae; pigments; dihydroanthracenone dimers; atropisomers; austrocolorins;
D O I
10.1016/j.phytochem.2003.09.023
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 [生物化学与分子生物学]; 081704 [应用化学];
摘要
The atropisomeric austrocolorins A(1) (7) and B-1 (8), new members of the rare tricolorin class of 10,10'-coupled dihydro-anthracenones, are isolated from an indigenous Australian toadstool belonging to the subgenus Dermocybe of Cortinarius, and their structure and absolute central and axial configuration is deduced from the spectroscopic data, and confirmed by chemical degradation and chiral HPLC analysis. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1033 / 1038
页数:6
相关论文
共 18 条
[1]
[Anonymous], CIRCULARLY DICHROIC
[2]
BESL H, 1977, Z PILZKUNDE, V43, P311
[3]
BESL H, 1987, UNPUB
[4]
Pigments of fungi.: Part 51.: Structure and stereochemistry of coupled pre-anthraquinones of the pseudophlegmacin type from Australian toadstools belonging to the genus Dermocybe [J].
Buchanan, MS ;
Gill, M ;
Millar, PA ;
Phonh-Axa, S ;
Raudies, E ;
Yu, J .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (07) :795-801
[5]
Pigments of fungi.: Part 70.: Total synthesis of (R)-semixanthomegnin and the X-ray crystal structure of (±)-7-chloro-10-methoxy-3-methyl-3, 4-dihydro-1H-naphtho[2,3-c]pyran-1,6,9-trione [J].
Cotterill, AS ;
Donner, CD ;
Gill, M ;
White, JM .
AUSTRALIAN JOURNAL OF CHEMISTRY, 2003, 56 (01) :49-57
[6]
Eliel E.L., 1994, STEREOCHEMISTRY ORGA, P682
[7]
Pigments of fungi.: Part 50.: Structure, biosynthesis and stereochemistry of new dimeric dihydroanthracenones of the phlegmacin type from Cortinarius sinapicolor Cleland [J].
Elsworth, C ;
Gill, M ;
Giménez, A ;
Milanovic, NM ;
Raudies, E .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (02) :119-125
[8]
ANTI-MICROBIAL AND ANTI-SPASMODIC TETRAHYDROANTHRACENES FROM CASSIA-SINGUEANA [J].
ENDO, M ;
NAOKI, H .
TETRAHEDRON, 1980, 36 (17) :2449-2452
[9]
PIGMENTS OF FUNGI .19. A DEGRADATIVE METHOD FOR THE DETERMINATION OF CENTRAL CHIRALITY IN NATURALLY-OCCURRING 3-HYDROXY-3-METHYL-3,4-DIHYDROANTHRACEN-1(2H)-ONES - APPLICATION TO PIGMENTS OF THE FLAVOMANNIN TYPE [J].
GILL, M ;
GIMENEZ, A ;
JHINGRAN, AG ;
PALFREYMAN, AR .
TETRAHEDRON-ASYMMETRY, 1990, 1 (09) :621-634
[10]
Gill M, 1987, Fortschr Chem Org Naturst, V51, P1