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

Laird, D.W., Poole, R., Wikström, M. and van Altena, I.A. (2007) Pycnanthuquinone C, an Unusual 6,6,5-Tricyclic Geranyltoluquinone from the Western Australian Brown AlgaCystophora harveyi. Journal of Natural Products, 70 (4). pp. 671-674.

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.