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Chuulangun Aboriginal Corporation and University of South Australia | Date: 2010-11-10

New clerodane compounds isolated from plant material from

Simpson B.S.,University of South Australia | Claudie D.J.,Chuulangun Aboriginal Corporation | Smith N.M.,University of South Australia | McKinnon R.A.,Flinders University | Semple S.J.,University of South Australia
Phytochemistry | Year: 2012

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. © 2012 Elsevier Ltd. All rights reserved. Source

Simpson B.S.,University of South Australia | Claudie D.J.,Chuulangun Aboriginal Corporation | Smith N.M.,University of South Australia | Gerber J.P.,University of South Australia | And 3 more authors.
Phytochemistry | Year: 2011

Three prenylated flavonoids 5,7,4′-trihydroxy-3′(3-methylbut-2- enyl)-3-methoxy flavone, 5,7-dihydroxy-3′(3-methylbut-2-enyl)-3,4′- dimethoxy flavone and 5,7,4′-trihydroxy-3′,5′(3-methylbuyt-2- enyl)-3-methoxy flavone together with three other known flavonoids were isolated from the medicinal plant Dodonaea polyandra. The plant is used in the traditional medicine system of Northern Kaanju people of Cape York Peninsula, Queensland, Australia. The extracts studied have previously been found to possess anti-inflammatory activity. Successive fractionation of leaf and stem extracts by column and high performance liquid chromatography led to the isolation of these compounds. Their structures were determined using a number of spectroscopic techniques including 1D and 2D NMR and high resolution mass spectroscopy. The structural elucidation is reported herein accompanied by full 1H and 13C NMR spectroscopic data. Spectroscopic data of known compounds was in agreement with that previously reported in literature. © 2011 Elsevier Ltd. All rights reserved. Source

Simpson B.S.,University of South Australia | Claudie D.J.,Chuulangun Aboriginal Corporation | Gerber J.P.,University of South Australia | Pyke S.M.,University of Adelaide | And 3 more authors.
Journal of Natural Products | Year: 2011

Four new benzoyl ester clerodane diterpenoids, 15,16-epoxy-8α- (benzoyloxy)methylcleroda-3,13(16),14-trien-18-oic acid (1), 15,16-epoxy-8α-(benzoyloxy)methyl-2α-hydroxycleroda-3,13(16), 14-trien-18-oic acid (2), 15,16-epoxy-8α-(benzoyloxy)methyl-2-oxocleroda- 3,13(16),14-trien-18-oic acid (3), and 15,16-epoxy-2α-benzoyloxycleroda-3, 13(16),14-trien-18-oic acid (4), have been isolated from the leaves and stems of Dodonaea polyandra. The anti-inflammatory activities of compounds 1, 2, and 4 were evaluated by means of 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced mouse ear edema. Compounds 2 and 4 exhibited maximum inhibition of inflammation (70-76%) at doses of 0.22 and 0.9 μmol/ear, respectively. Modest activity (45% inhibition) was maintained at nanomole/ear doses. © 2011 The American Chemical Society and American Society of Pharmacognosy. Source

Ndi C.P.,Flinders University | Ndi C.P.,University of South Australia | Sykes M.J.,University of South Australia | Claudie D.J.,Chuulangun Aboriginal Corporation | And 5 more authors.
Australian Journal of Chemistry | Year: 2016

Australian Aboriginal people have a long history of relying on plants for the treatment of various ailments and illnesses. Our ongoing collaborative research project initiated by Chuulangun Aboriginal Corporation (Cape York, Australia) has recently focussed on revealing whether Kuuku I'yu plant medicines possess anticancer-related activities and the chemistry responsible for this. Here, we present results from a study of the plant Litsea glutinosa, used traditionally for the treatment of gastrointestinal disorders. Four known aporphine alkaloids N-methylactinodaphnine (1), boldine (2), N-methyllaurotetanine (3), and isoboldine (4) were isolated by activity-guided fractionation and tested for cytotoxicity against HT29, SKMEL28, and primary human keratinocytes. Compound 1 was the most cytotoxic and this observation may be explained by the presence of a 1,2-methylenedioxy group. In silico docking revealed that a plausible mechanism for the observed cytotoxicity is the stabilization of a topoisomerase II (β) DNA-enzyme complex. The ethnopharmacological relevance of this study is discussed in the context of researching and using traditional knowledge in biomolecular discovery. © CSIRO 2016. Source

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