Abstract
A bioassay-guided purification of an EtOAc extract of the leaves of Croton mauritianus using a chikungunya virus-cell-based assay led to the isolation of 12-O-decanoylphorbol-13-acetate (1) and the new 12-O-decanoyl-7-hydroperoxy-phorbol-5-ene-13-acetate (2), along with loliolide, vomifoliol, dehydrovomifoliol, annuionone D and bluemol C. The planar structure and the relative configuration of compound 2 were elucidated based on spectroscopic analysis, including 1D- and 2D-NMR experiments, mass spectrometry, and comparison with literature data. Compounds 1 and 2 inhibited chikungunya virus-induced cell death in cell culture with EC50s of 2.4±0.3 and 4.0±0.8 μM, respectively.
Keywords:
Chikungunya; Croton mauritianus; Euphorbiaceae; HIV; Phorbol esters; Tigliane.
Copyright © 2014 Elsevier B.V. All rights reserved.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Antiviral Agents / chemistry
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Antiviral Agents / isolation & purification*
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Antiviral Agents / pharmacology
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Benzofurans / isolation & purification
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Benzofurans / pharmacology
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Butanols / isolation & purification
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Butanols / pharmacology
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Chikungunya virus / drug effects*
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Croton / chemistry*
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Cyclohexanones / isolation & purification
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Cyclohexanones / pharmacology
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Diterpenes / chemistry
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Diterpenes / isolation & purification
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Diterpenes / pharmacology
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Microbial Sensitivity Tests
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Norisoprenoids / isolation & purification*
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Norisoprenoids / pharmacology
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Phorbol Esters / isolation & purification*
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Phorbol Esters / pharmacology
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Plant Leaves / chemistry
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Virus Replication / drug effects
Substances
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Antiviral Agents
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Benzofurans
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Butanols
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Cyclohexanones
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Diterpenes
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Norisoprenoids
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Phorbol Esters
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dehydrovomifoliol
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vomifoliol
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loliolide