Abstract
Twelve new megastigmane sesquiterpenoids, wilsonols A-L (1-12), were isolated from the leaves of Cinnamomum wilsonii, along with seven known analogues (13-19). The structures of compounds 1-12 were established by spectroscopic analyses. The absolute configurations of 1-5 were determined by single-crystal X-ray diffraction analysis with Cu Kα irradiation, and the absolute configurations of 6-12 were determined by the modified Mosher's method. Compounds 1-9 and 13-19 were evaluated for in vitro cytotoxicity against five human cancer cell lines, HL-60, SMMC-7721, A-549, MCF-7, and SW-480, and compared against the Beas-2B immortalized (noncancerous) human bronchial epithelial cell line. Compound 13 exhibited IC50 values ranging from 2.5 to 12 μM and selectivity indices of >10 against SMMC-7721, A-549, and MCF-7 cell lines. Selected compounds were evaluated for in vitro immunomodulatory activity.
Publication types
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Research Support, Non-U.S. Gov't
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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Cinnamomum / chemistry*
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Crystallography, X-Ray
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Cyclohexanones / chemistry
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Cyclohexanones / isolation & purification*
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Cyclohexanones / pharmacology
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Drug Screening Assays, Antitumor
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Drugs, Chinese Herbal / chemistry
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Drugs, Chinese Herbal / isolation & purification*
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Drugs, Chinese Herbal / pharmacology
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Female
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Glucosides / chemistry
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Glucosides / isolation & purification*
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Glucosides / pharmacology
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HL-60 Cells
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Humans
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Immunologic Factors / chemistry
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Immunologic Factors / isolation & purification
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Immunologic Factors / pharmacology
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Molecular Conformation
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Molecular Structure
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Norisoprenoids / chemistry
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Norisoprenoids / isolation & purification*
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Norisoprenoids / pharmacology
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Nuclear Magnetic Resonance, Biomolecular
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Plant Leaves / chemistry
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Sesquiterpenes / chemistry
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Sesquiterpenes / isolation & purification*
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Sesquiterpenes / pharmacology
Substances
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Antineoplastic Agents, Phytogenic
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Cyclohexanones
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Drugs, Chinese Herbal
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Glucosides
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Immunologic Factors
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Norisoprenoids
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Sesquiterpenes
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megastigmane