title: Pycnanthuquinone C, an unusual 6,6,5-tricyclic Geranyltoluquinone from the Western Australian brown alga Cystophora harveyi.
abstract: 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.
authors.affiliation: Chemistry, School of Biological and Environmental Sciences, The University of Newcastle, Callaghan, NSW, 2308, Australia.
authors.forename: Damian W
authors.initials: DW
authors.lastname: Laird
authors.forename: Rachael
authors.initials: R
authors.lastname: Poole
authors.forename: Maria
authors.initials: M
authors.lastname: Wikström
authors.forename: Ian A van
authors.initials: IA
authors.lastname: Altena
mesh_terms: D003924:Diabetes Mellitus, Type 2 / Q000188:drug therapy*; D004365:Drugs, Chinese Herbal / Q000737:chemistry; D005231:Fatty Acids, Unsaturated / Q000096:biosynthesis / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D008386:Marine Biology; D015394:Molecular Structure; D009285:Naphthoquinones / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D000459:Phaeophyceae / Q000737:chemistry*; D013729:Terpenes; D014904:Western Australia
chemical_list: D004365:Drugs, Chinese Herbal; D005231:Fatty Acids, Unsaturated; D009285:Naphthoquinones; D013729:Terpenes; C519758:pycnanthuquinone C (Cystophora harveyi)