Abstract
Calanolides are tetracyclic 4-substituted dipyranocoumarins. Calanolide A, isolated from the leaves and twigs of Calophyllum lanigerum var. austrocoriaceum (Whitmore) P. F. Stevens, is the first member of this group of compounds with anti-HIV-1 activity mediated by reverse transcriptase inhibition. Calanolides are classified pharmacologically as non-nucleoside reverse transcriptase inhibitors (NNRTI). There are at least 15 naturally occurring calanolides distributed mainly within the genus Calophyllum, but some of them are also present in the genus Clausena. Besides significant anti-HIV properties, which have been exploited towards potential development of new NNRTIs for anti-HIV therapy, calanolides have also been found to possess anticancer, antimicrobial and antiparasitic potential. This review article provides a comprehensive update on all aspects of naturally occurring calanolides, including their chemistry, natural occurrence, biosynthesis, pharmacological and toxicological aspects including mechanism of action and structure activity relationships, pharmacokinetics, therapeutic potentials and available patents.
Highlights
Calanolides are tetracyclic 4-substituted dipyranocoumarins, and their C-ring contains a gem-dimethyl group (Figure 1), e.g., (+)-calanolide A (1), (−)-calanolide B (14) (Figure 2).The discovery of calanolides from the leaves and twigs of the tree Calophyllum lanigerum var.austrocoriaceum (Whitmore) P
This study demonstrated that, like many other plant secondary metabolites, the biosynthesis of calanolides, albeit genetically controlled, may be affected by environmental conditions, e.g., soil nutrients
The outcome form this study indicated that (±)-11-demethyl-calanolide had a slightly more potent anti-HIV activity than (±)-calanolide A, suggesting the methyl functionality at C-11 in calanolide A (1) might not be an essential structural feature for anti-HIV activity
Summary
Calanolides are tetracyclic 4-substituted dipyranocoumarins, and their C-ring contains a gem-dimethyl group (Figure 1), e.g., (+)-calanolide A (1), (−)-calanolide B (costatolide) (14) (Figure 2). Calanolides are among the first plant-based compounds to demonstrate potential anti-HIV-1 activity. There is a review [7] and a book chapter on calanolides [8], published about six years ago, that mainly cover anti-HIV activity, and the literature published until early 2014. This present review is not on the genus Calophyllum, the family Calophyllaceae or pyranocoumarins a such, but it exclusively focuses on various aspects of naturally occurring calanolides. This review is significantly different from any other previous articles on calanolides in its approach and coverage, and is a comprehensive update on naturally occurring calanolides, encompassing their chemistry, natural occurrence, biosynthesis, pharmacological and toxicological aspects including mechanism of action and structure activity relationships, pharmacokinetics, therapeutic potentials and available patents
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