Bioactive Dihydro-β-agarofuran Sesquiterpenoids from the Australian Rainforest PlantMaytenus bilocularis

Wibowo, Mario, Levrier, Claire, Sadowski, Martin C., Nelson, Colleen C., Wang, Qian, Holst, Jeff, Healy, Peter C., Hofmann, Andreas, & Davis, Rohan A. (2016) Bioactive Dihydro-β-agarofuran Sesquiterpenoids from the Australian Rainforest PlantMaytenus bilocularis. Journal of Natural Products, 79(5), pp. 1445-1453.

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Abstract

Chemical investigations of the CH2CI2 extract obtained from the leaves of the Australian rainforest tree Maytenus bilocularis afforded three new dihydro-β-agarofurans, bilocularins A–C (1–3), and six known congeners, namely, celastrine A (4), 1α,6β,8α-triacetoxy-9α-benzoyloxydihydro-β-agarofuran (5), 1α,6β-diacetoxy-9α-benzoyloxy-8α-hydroxydihydro-β-agarofuran (6), Ejap-10 (11), 1α,6β-diacetoxy-9β-benzoyloxydihydro-β-agarofuran (12), and Ejap-2 (13). The major compound 1 was used in semisynthetic studies to afford four ester derivatives (7–10). The chemical structures of 1–3 were elucidated following analysis of 1D/2D NMR and MS data. The absolute configurations of bilocularins A (1) and B (2) were determined by single-crystal X-ray diffraction analysis. All compounds were evaluated for cytotoxic activity against the human prostate cancer cell line LNCaP; none of the compounds were active. However, several compounds showed similar potency to the drug efflux pump inhibitor verapamil in reversing the drug resistance of the human leukemia CEM/VCR R cell line. In addition, similar to verapamil, compound 5 was found to inhibit leucine uptake in LNCaP cells (IC50 = 15.5 μM), which was more potent than the leucine analogue 2-aminobicyclo[2.2.1]heptane-2-carbocyclic acid. This is the first report of secondary metabolites from Maytenus bilocularis.

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3 citations in Scopus
3 citations in Web of Science®
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ID Code: 97733
Item Type: Journal Article
Refereed: Yes
Additional URLs:
DOI: 10.1021/acs.jnatprod.6b00190
ISSN: 1520-6025
Divisions: Current > QUT Faculties and Divisions > Faculty of Health
Current > Institutes > Institute of Health and Biomedical Innovation
Copyright Owner: Copyright 2016 American Chemical Society
Deposited On: 29 Jul 2016 04:25
Last Modified: 23 Jun 2017 14:48

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