Abstract
An investigation on the gum exudates of Commiphora myrrha has led to the isolation of six sesquiterpenoids. On the basis of spectroscopic data interpretation, they were determined as two new furanosesquiterpenoids, rel-1S,2S-epoxy-4R-furanogermacr-10(15)-en-6-one (1) and rel-2R-methyl-5S-acetoxy-4R-furanogermacr-1(10)Z-en-6-one (2), and four known furanosesquiterpenoids, rel-3R-methoxy-4S-furanogermacra-1E,10(15)-dien-6-one (3), rel-2R-methoxy-4R-furanogermacr-1(10)E-en-6-one (4), furanogermacra-1(10)Z,4Z-dien-6-one, and curzerenone [6,7-dihydro-5beta-isopropenyl-3,6beta-dimethyl-6-vinylbenzofuran-4(5H)-one]. This is the first report of the relative stereochemistry for the known compounds 3 and 4. Compound 1 exhibited weak cytotoxic activity against a MCF-7 breast tumor cell line in a clonogenic assay, while the other five compounds were inactive in this assay.
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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Breast Neoplasms
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Burseraceae / chemistry*
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Chromatography, Thin Layer
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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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Humans
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Molecular Conformation
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Molecular Structure
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Nuclear Magnetic Resonance, Biomolecular
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Plants, Medicinal / chemistry
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Sesquiterpenes / chemistry
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Sesquiterpenes / isolation & purification*
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Sesquiterpenes / pharmacology
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Sesquiterpenes, Germacrane*
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Stereoisomerism
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Tumor Cells, Cultured / drug effects
Substances
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Antineoplastic Agents, Phytogenic
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Drugs, Chinese Herbal
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Sesquiterpenes
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Sesquiterpenes, Germacrane
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rel-1S,2S-epoxy-4R-furanogermacr-10(15)-en-6-one
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rel-2R-methyl-5S-acetoxy-4R-furanogermacr-1(10)Z-en-6-one