Celastrofurans A-G: Dihydro-β-Agarofurans from the Australian Rainforest Vine Celastrus subspicata and Their Inhibitory Effect on Leucine Transport in Prostate Cancer Cells
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Wang, Qian
Holst, Jeff
White, Jonathan M
Hofmann, Andreas
Davis, Rohan A
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Abstract
Seven new dihydro-β-agarofurans, celastrofurans A–G (1–7), along with two known secondary metabolites, 9β-benzoyloxy-1α-furoyloxydihydro-β-agarofuran (8) and (1R,2R,4R,5S,7R,9S,10R)-2-acetoxy-9-benzoyloxy-1-furoyloxydihydro-β-agarofuran (9), were obtained from the leaves of the Australian rainforest vine, Celastrus subspicata. The structures of the new compounds were determined by detailed spectroscopic (1D/2D NMR) and MS data analysis. The absolute configurations of compounds 1–4 were defined by ECD and single-crystal X-ray diffraction studies. All compounds were found to exhibit inhibitory activity on leucine transport in the human prostate cancer cell line LNCaP with IC50 values ranging from 7.0 to 98.9 μM. Dihydro-β-agarofurans 1–9 showed better potency than the L-type amino acid transporter (LAT) family inhibitor, 2-aminobicyclo[2.2.1]-heptane-2-carboxylic acid (BCH).
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Journal of Natural Products
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80
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6
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This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Natural Products, copyright 2017 American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see 10.1021/acs.jnatprod.7b00220.
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Chemical sciences
Medicinal and biomolecular chemistry not elsewhere classified
Biological sciences
Biomedical and clinical sciences