Rare, seven-membered cyclic ether labdane diterpenoid from Dodonaea polyandra

Bradley Simpson, David Claudie, Nick Smith, Ross McKinnon, Susan Semple

    Research output: Contribution to journalArticle

    13 Citations (Scopus)

    Abstract

    Previous phytochemical studies on the leaf resin of dioecious plant species Dodonaea polyandra have identified the presence of furanoclerodane diterpenoids. As part of ongoing research on this species the chemical profile of an individual plant displaying male flowers was investigated. Repeated chromatographic separation of a resinous extract from the leaves of the plant yielded three labdane diterpenoids, 13,17-epoxy-13-methyl-15-oxo-labda-7-ene (1), 17-hydroxy-13-methyl-labda-7,13Z-diene-15-oic acid (2) and 13-methyl-17-oxo-labda-7,13Z-diene-15-oic acid (3) and a fourth known labdane diterpenoid (4) reported as being isolated from a natural source for the first time. Structural elucidation was carried out using conventional 1D and 2D NMR and mass spectrometry together with other complementary techniques (UV and IR). The leaf extract from this individual of D. polyandra with male flowers present displays a marked difference in the chemical composition of diterpenoids compared to previously studied extracts from the leaves of this species.

    Original languageEnglish
    Pages (from-to)141-146
    Number of pages6
    JournalPhytochemistry
    Volume84
    DOIs
    Publication statusPublished - 2012

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