Sphaerolone and dihydrosphaerolone, two bisnaphthyl-pigments from the fungus Sphaeropsidales sp. F-24'707

Two new bisnaphthalene compounds, sphaerolone (1) and dihydrosphaerolone (2), together with 2-hydroxyjuglone (9), were isolated from the culture broth of a Sphaeropsidales sp. (strain F-24'707) after inhibition of the regular proceeding 1,8-dihydroxynaphthalene (DHN) biosynthesis with tricyclaz...

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Bibliographic Details
Published in:Phytochemistry (Oxford) 2000-07, Vol.54 (6), p.597-601
Main Authors: BODE, H. B, ZEECK, A
Format: Article
Language:English
Subjects:
Benzofurans - chemistry
Benzofurans - isolation & purification
Benzofurans - metabolism
Biological and medical sciences
Fundamental and applied biological sciences. Psychology
Fungi - chemistry
Fungi - metabolism
Magnetic Resonance Spectroscopy
Microbiology
Morphology, structure, chemical composition
Mycology
Naphthalenes - chemistry
Naphthalenes - isolation & purification
Naphthalenes - metabolism
Naphthoquinones - chemistry
Naphthoquinones - isolation & purification
Naphthoquinones - metabolism
Pigments, Biological - biosynthesis
Pigments, Biological - chemistry
Pigments, Biological - isolation & purification
Stereoisomerism
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Summary:Two new bisnaphthalene compounds, sphaerolone (1) and dihydrosphaerolone (2), together with 2-hydroxyjuglone (9), were isolated from the culture broth of a Sphaeropsidales sp. (strain F-24'707) after inhibition of the regular proceeding 1,8-dihydroxynaphthalene (DHN) biosynthesis with tricyclazole. The structures of 1 and 2 were established by detailed spectroscopic analysis and present novel bisnaphthalenes. The biosynthetic origin of 1 and 2 as dimerization products of 1,3,8-trihydroxynaphthalene, an intermediate of the DHN biosynthesis, is discussed.
ISSN:0031-9422
DOI:10.1016/S0031-9422(00)00145-X