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.
Publication types
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Research Support, U.S. Gov't, Non-P.H.S.
MeSH terms
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Amphotericin B / pharmacology
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Animals
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Anti-Bacterial Agents
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Anti-Infective Agents / chemistry
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Anti-Infective Agents / isolation & purification*
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Anti-Infective Agents / pharmacology
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Antimalarials / chemistry
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Antimalarials / isolation & purification*
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Antimalarials / pharmacology
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Benzopyrans / chemistry
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Benzopyrans / isolation & purification*
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Benzopyrans / pharmacology
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Benzoxazines
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Cannabinoids / pharmacology
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Cells, Cultured / drug effects
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Chloroquine / pharmacology
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Cryptococcus neoformans / drug effects
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Drug Resistance, Microbial
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Fabaceae / chemistry*
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Humans
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Inhibitory Concentration 50
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Magnetic Resonance Spectroscopy
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Mass Spectrometry
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Methicillin / pharmacology
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Molecular Conformation
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Molecular Structure
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Morpholines / pharmacology
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Naphthalenes / pharmacology
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Peru
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Plant Stems / chemistry
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Plants, Medicinal / chemistry*
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Plasmodium falciparum / drug effects
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Plasmodium falciparum / immunology
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Sesquiterpenes / chemistry
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Sesquiterpenes / isolation & purification*
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Sesquiterpenes / pharmacology
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Spectrophotometry, Infrared
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Spectrophotometry, Ultraviolet
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Spectroscopy, Fourier Transform Infrared
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Staphylococcus aureus / drug effects
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Structure-Activity Relationship
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Tetracycline / pharmacology
Substances
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Anti-Bacterial Agents
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Anti-Infective Agents
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Antimalarials
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Benzopyrans
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Benzoxazines
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Cannabinoids
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Morpholines
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Naphthalenes
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Sesquiterpenes
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kessane
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machaeriol A
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machaeriol B
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(3R)-((2,3-dihydro-5-methyl-3-((4-morpholinyl)methyl)pyrrolo-(1,2,3-de)-1,4-benzoxazin-6-yl)(1-naphthalenyl))methanone
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Amphotericin B
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Chloroquine
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Tetracycline
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Methicillin