Furanosesquiterpenoids of Commiphora myrrha

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-...

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Veröffentlicht in:	Journal of natural products (Washington, D.C.) D.C.), 2001-11, Vol.64 (11), p.1460-1462
Hauptverfasser:	ZHU, Nanqun, KIKUZAKI, Hiroe, SHENG, Shuqun, SANG, Shengmin, RAFI, Mohamed M., WANG, Mingfu, NAKATANI, Nobuji, DIPAOLA, Robert S., ROSEN, Robert T., HO, Chi-Tang
Format:	Artikel
Sprache:	eng
Schlagworte:	Antineoplastic Agents, Phytogenic - chemistry Antineoplastic Agents, Phytogenic - isolation & purification Antineoplastic Agents, Phytogenic - pharmacology Biological and medical sciences Breast Neoplasms Burseraceae - chemistry Chromatography, Thin Layer Drugs, Chinese Herbal - chemistry Drugs, Chinese Herbal - isolation & purification Drugs, Chinese Herbal - pharmacology Female General pharmacology Humans Medical sciences Molecular Conformation Molecular Structure Nuclear Magnetic Resonance, Biomolecular Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Plants, Medicinal - chemistry Sesquiterpenes - chemistry Sesquiterpenes - isolation & purification Sesquiterpenes - pharmacology Sesquiterpenes, Germacrane Stereoisomerism Tumor Cells, Cultured - drug effects
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Zusammenfassung:	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.
ISSN:	0163-3864 1520-6025
DOI:	10.1021/np010072j