Abstract
Activity-directed fractionation of a stem extract of Azadirachta excelsa using KB (human oral epidermoid carcinoma) cells led to the isolation of four meliacin-type limonoids. Two of these constituents were novel, namely, 2,3-dihydronimbolide and 3-deoxymethylnimbidate, and these were purified along with the known compounds, nimbolide and 28-deoxonimbolide. The structures of the new compounds were determined by spectroscopic methods. Nimbolide and 28-deoxonimbolide were broadly cytotoxic when evaluated against a panel of human cancer cell lines, while the two novel compounds were inactive in this regard. The defection of nimbolide and 28-deoxonimbolide as cytotoxic constituents was facilitated by an electrospray LC/MS dereplication procedure.
Publication types
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Antineoplastic Agents, Phytogenic / chemistry
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Antineoplastic Agents, Phytogenic / isolation & purification*
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Antineoplastic Agents, Phytogenic / pharmacology
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Cholenes / chemistry
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Cholenes / isolation & purification*
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Cholenes / pharmacology
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Diterpenes / chemistry
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Diterpenes / isolation & purification*
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Diterpenes / pharmacology
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Drug Screening Assays, Antitumor
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Humans
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Lactones / chemistry
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Lactones / isolation & purification*
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Lactones / pharmacology
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Limonins*
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Plants, Medicinal / chemistry*
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Secosteroids / chemistry
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Secosteroids / isolation & purification*
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Secosteroids / pharmacology
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Spectrum Analysis
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Tumor Cells, Cultured
Substances
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2,3-dihydronimbolide
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3-deoxymethylnimbidate
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Antineoplastic Agents, Phytogenic
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Cholenes
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Diterpenes
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Lactones
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Limonins
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Secosteroids
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28-deoxonimbolide
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nimbolide