Biomimetic transformation and biological activities of Globiferin, a terpenoid benzoquinone from Cordia globifera.
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-d(6) to yield cordiachrome C (3) and cordiaquinol C (4), respectively. Heating in DMSO-d(6) 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 mug/mL, respectively. Antimalarial, antifungal, and cytotoxic activities of 1 and its derivatives were also evaluated.
Dettrakul
Suppamit
S
Department of Chemistry, Faculty of Science, Mahidol University, Bangkok 10400, Thailand.
Surerum
Sanya
S
Rajviroongit
Shuleewan
S
Kittakoop
Prasat
P
D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000378:metabolism / Q000494:pharmacology; D000962:Antimalarials / Q000737:chemistry / Q000302:isolation & purification* / Q000378:metabolism / Q000494:pharmacology; D000995:Antitubercular Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000378:metabolism / Q000494:pharmacology; D016227:Benzoquinones / Q000737:chemistry / Q000302:isolation & purification* / Q000378:metabolism / Q000494:pharmacology; D001711:Biotransformation; D002176:Candida albicans / Q000187:drug effects; D031213:Cordia / Q000737:chemistry*; D018432:Drug Resistance, Multiple / Q000187:drug effects; D020128:Inhibitory Concentration 50; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000187:drug effects; D018517:Plant Roots / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D010963:Plasmodium falciparum / Q000187:drug effects; D013729:Terpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000378:metabolism / Q000494:pharmacology; D013785:Thailand
D000935:Antifungal Agents; D000962:Antimalarials; D000995:Antitubercular Agents; D016227:Benzoquinones; D013729:Terpenes; C550791:globiferin