Pycnanthuquinone C, an Unusual 6,6,5-Tricyclic Geranyltoluquinone from the Western Australian Brown Alga Cystophora harveyi

Chemical investigation of the Western Australian marine brown alga Cystophora harveyi resulted in the isolation of the new linearly fused 6,6,5-tricyclic compound pycnanthuquinone C (1), in addition to four previously reported geranyltoluquinol derivatives. Structures were elucidated by interpretati...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2007-04, Vol.70 (4), p.671-674
Main Authors: Laird, Damian W, Poole, Rachael, Wikström, Maria, van Altena, Ian A
Format: Article
Language:English
Subjects:
1,4-Dimethoxy-(3',7'-dimethylocta-2',6'-dienyl)-6-methylbenzene
2-(3',7'-Dimethylocta-2',6'-dienyl)-4-hydroxy-1-methoxy-6-methylbenzene
2-(3',7'-Dimethylocta-2',6'-dienyl)-6-methyl-2,5-cyclohexadiene-1,4-dione
algae and seaweeds
atractylochromene
Biological and medical sciences
chemical structure
Cystophora
Cystophora harveyi
Diabetes Mellitus, Type 2 - drug therapy
Drugs, Chinese Herbal - chemistry
Fatty Acids, Unsaturated - biosynthesis
Fatty Acids, Unsaturated - chemistry
Fatty Acids, Unsaturated - isolation & purification
Fatty Acids, Unsaturated - pharmacology
General pharmacology
geranyltoluquinone
Marine Biology
Medical sciences
Molecular Structure
Naphthoquinones - chemistry
Naphthoquinones - isolation & purification
Naphthoquinones - pharmacology
Phaeophyceae - chemistry
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
pycnanthuquinone
quinones
Sargassaceae
spectral analysis
Terpenes
Western Australia
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Summary:Chemical investigation of the Western Australian marine brown alga Cystophora harveyi resulted in the isolation of the new linearly fused 6,6,5-tricyclic compound pycnanthuquinone C (1), in addition to four previously reported geranyltoluquinol derivatives. Structures were elucidated by interpretation of spectrometric data. Compounds with the same cyclic skeleton as 1 have been reported to be useful drug leads for the treatment of type 2 diabetes, while compounds 4 and 7 are known constituents of Chinese medicinal herbs. A biosynthetic scheme encompassing all of the geranyltoluquinol derivatives isolated from C. harveyi is proposed.
ISSN:0163-3864
1520-6025
DOI:10.1021/np060566m