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-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.
Zhu
N
N
Department of Food Science, Rutgers University, New Brunswick, New Jersey 08901, USA.
Kikuzaki
H
H
Sheng
S
S
Sang
S
S
Rafi
M M
MM
Wang
M
M
Nakatani
N
N
DiPaola
R S
RS
Rosen
R T
RT
Ho
C T
CT
D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001943:Breast Neoplasms; D029403:Burseraceae / Q000737:chemistry*; D002855:Chromatography, Thin Layer; D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D005260:Female; D006801:Humans; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010946:Plants, Medicinal / Q000737:chemistry; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D045788:Sesquiterpenes, Germacrane; D013237:Stereoisomerism; D014407:Tumor Cells, Cultured / Q000187:drug effects
D000972:Antineoplastic Agents, Phytogenic; D004365:Drugs, Chinese Herbal; D012717:Sesquiterpenes; D045788:Sesquiterpenes, Germacrane; C442567:rel-1S,2S-epoxy-4R-furanogermacr-10(15)-en-6-one; C442568:rel-2R-methyl-5S-acetoxy-4R-furanogermacr-1(10)Z-en-6-one