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  • Title: Antimalarial (+)-trans-hexahydrodibenzopyran derivatives from Machaerium multiflorum.
    Author: Muhammad I, Li XC, Dunbar DC, ElSohly MA, Khan IA.
    Journal: J Nat Prod; 2001 Oct; 64(10):1322-5. PubMed ID: 11678659.
    Abstract:
    Bioassay-guided fractionation of Machaerium multiflorum yielded the hitherto unreported (+)-trans-hexahydrodibenzopyrans machaeriol A (1) and machaeriol B (2), as well as the known guaiane sesquiterpene (-)-kessane. Structure elucidation was based on (1)H and (13)C NMR data, mainly 2D NMR (1)H-(1)H COSY, (1)H-(13)C HMQC, (1)H-(13)C HMBC, and (1)H-(1)H NOESY experiments. This is the first report of the hexahydrodibenzopyrans from a higher plant other than the genus Cannabis. The cannabimimetic activity was thus evaluated by radioligand binding assay for cannabinoid receptor CB1, which indicated, notably, that both 1 and 2 were inactive. In addition, the cross reactivity of 1 and 2 toward antibodies designed for urinary metabolites of cannabinoids was evaluated with the EMIT and On Line cannabinoids assays. Both compounds showed no response at 100 000 ng/mL in both assays. Machaeriol B (2) demonstrated in vitro antimalarial activity (IC(50) = 120 ng/mL) against Plasmodium falciparum W-2 clone.
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