Publication: Biomimetic transformation and biological activities of globiferin, a terpenoid benzoquinone from Cordia globifera
Issued Date
2009-05-22
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ISSN
01633864
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2-s2.0-66449085323
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Mahidol University
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SCOPUS
Bibliographic Citation
Journal of Natural Products. Vol.72, No.5 (2009), 861-865
Suggested Citation
Suppamit Dettrakul, Sanya Surerum, Shuleewan Rajviroongit, Prasat Kittakoop Biomimetic transformation and biological activities of globiferin, a terpenoid benzoquinone from Cordia globifera. Journal of Natural Products. Vol.72, No.5 (2009), 861-865. doi:10.1021/np9000703 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/27225
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Title
Biomimetic transformation and biological activities of globiferin, a terpenoid benzoquinone from Cordia globifera
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Abstract
A new 10-membered ring meroterpene (1), named globiferin, was isolated from root extracts of Cordia globifera. Biomimetic transformations of 1 and its derivatives, either by acid cyclization or by Cope rearrangement, provided information relating to the biogenesis of cordiachromes A-C. Globiferin (1) underwent Cope rearrangement upon refluxing in xylene and DMSO-d6 to yield cordiachrome C (3) and cordiaquinol C (4), respectively. Heating in DMSO-d6 resulted in an unexpected reduction of a quinone moiety. Globiferin diacetate (1b) cyclized under acidic conditions to give compounds 10 and 11, respective derivatives of natural cordiachromes B (2) and A (12). The present study indicates that globiferin (1) is a genuine intermediate for the biosynthesis of cordiachromes in Cordia species. Compounds 1 and 3 exhibited significant antimycobacterial activity, with MIC values of 6.2 and 1.5 μg/mL, respectively. Antimalarial, antifungal, and cytotoxic activities of 1 and its derivatives were also evaluated. © 2009 American Chemical Society and American Society of Pharmacognosy.