Journal article

Dihydro-beta-agarofurans from the Australian Endemic Rainforest Plant Denhamia pittosporoides Inhibit Leucine Transport in Prostate Cancer Cells

Mario Wibowo, Qian Wang, Jeff Holst, Jonathan M White, Andreas Hofmann, Rohan A Davis

Asian Journal of Organic Chemistry | WILEY-V C H VERLAG GMBH | Published : 2016

Abstract

Two previously unknown dihydro-β-agarofuran sesquiterpenoids, denhaminol I (1) and denhaminol J (2), together with four related and known metabolites, 1α,2α,6β,15-tetraacetoxy-9α-benzoyloxy-8-oxodihydro-β-agarofuran (3), wilforsinine F (4), 1α,2α,6β,8α,15-pentaacetoxy-9α-benzoyloxydihydro-β-agarofuran (5), and 1α,2α,6β,15-tetraacetoxy-9β-benzoyloxydihydro-β-agarofuran (6), were isolated from the leaves of an Australian rainforest plant, Denhamia pittosporoides. The structures of compounds 1 and 2 were determined by analysis of their 1D/2D NMR and MS data. The absolute configuration of compound 1 was established by single-crystal X-ray diffraction analysis. Compounds 1 and 4 were shown to inh..

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University of Melbourne Researchers

Grants

Awarded by National Health and Medical Research Council (NHMRC)


Awarded by Australian Research Council (ARC)


Awarded by Movember through the Prostate Cancer Foundation of Australia


Awarded by Australian Movember Revolutionary Team Award Targeting Advanced Prostate Cancer


Awarded by Cancer Council NSW


Funding Acknowledgements

The authors acknowledge the National Health and Medical Research Council (NHMRC) for financial support (Grant No. APP1024314 to R.A.D.) and thank the Australian Research Council (ARC) for support towards purchasing NMR and MS equipment (Grant Nos LE0668477 and LE0237908) and for financial support (Grant No. LP120200339 to R.A.D.). This work was supported by grants from Movember through the Prostate Cancer Foundation of Australia (Grant No. YI0813 to Q.W.) and the Australian Movember Revolutionary Team Award Targeting Advanced Prostate Cancer (Grant No. MRTA1 to J.H. and Q.W.); Cancer Council NSW (Grant No. APP1080503 to J.H.); and The University of Sydney through a Sydney Medical School PhD ECR Supervisor Grant to Q.W. and a HMR+ Implementation Grant to J.H. The authors thank R. Whyte, M. Novak, and R. Harisson from Save Our Waterways Now (SOWN) for performing the plant collection and identification. W. Loa-Kum-Cheung is acknowledged for performing the HRMS measurements. M. W. thanks Griffith University for the provision of PhD scholarships (GUPRS and GUIPRS).