005AK2 - 230 Mini-Reviews in Organic Chemistry, 2010, 7,...

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230 Mini-Reviews in Organic Chemistry, 2010, 7, 230-254 1570-193X/10 $55.00+.00 © 2010 Bentham Science Publishers Ltd. Quinone/Hydroquinone Sesquiterpenes I.S. Marcos,* A. Conde, R.F. Moro, P. Basabe, D. Diez and J.G. Urones Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad de Salamanca, Plaza de los Caídos 1-5, 37008 Salamanca, Spain Abstract: The quinone/hydroquinone sesquiterpenes of drimane or rearranged drimane skeletons constitute a wide and diverse group of secondary metabolites of mixed biogenesis. These compounds are mainly of marine origin and their interest is not only for the variety of isolated structure but for the interesting biological activities that they present. In this paper a series of quinone/hydroquinone sesquiterpenes of natural origin that have been reported to date is presented. The structures of these compounds are gathered into eight groups with reference to their biological activities and compounds synthesised. Keywords: Sesquiterpenes quinone/hydroquinone, drimane, rearranged drimane. Sesquiterpene quinones/hydroquinones having a normal dri- mane skeleton or a rearranged drimane skeleton, represent a promi- nent class of mixed biogenesis metabolites that incorporate a bi- cyclic sesquiterpene unit coupled to a quinone or quinol [1]. Those compounds have attracted the attention of researchers both through the abundance of structural variants and the wide range of remark- able biological properties ascribed to specific samples [2]. Although most sesquiterpene quinones/hydroquinones have been isolated from sponges, some of them have been reported from brown algae [3] and at least three compounds were described from a fungus [4- 6]. We present herein a compilation of the naturally occurring ses- quiterpene quinones/hydroquinones, whose terpenoid unit is bi- cyclic, that have been isolated to date. The following collection comprises a listing of structures, along with tables that include the source of isolation, biological activities and the literature source. Some compounds have also been synthesised and these are marked with an asterisk. Listing of Structures In the first part of this review all the structures are shown. Each one is accompanied with its trivial name and is numbered. The compounds are presented in an order reflecting biogenetic path- ways. All the sesquiterpene quinones/hydroquinones presented in the review possess a drimane or rearranged drimane skeleton (Fig. 1 ). We propose the name avarane and aureane for the rearranged skele- tons considering the first compound isolated in each group (ava- rol/avarone [7] and aureol [8] respectively). Aureane and avarane skeletons arise from 1,2 rearrangements of the drimane skeleton. Within the avaranes two groups have been established owing to the fact that there is a large number of this class of compounds. The first one includes the avaranes ± 3 and the second one the avaranes ± 4(13) ( trans fusion in decalin system ) or ± 4(14) ( cis fusion in decalin system).
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005AK2 - 230 Mini-Reviews in Organic Chemistry, 2010, 7,...

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