Isolation and structure elucidation of an isoflavone and a sesterterpenoic acid from Henriettella fascicularis.
A new isoflavone, 4',5,7-trihydroxy-6,8-dimethylisoflavone (1), and a new sesterterpenoic acid (2), together with five known compounds, lichexanthone (3), (-)-pinoresinol (4), betulinic acid, palmitic acid, and beta-sitosterol, were isolated from a dichloromethane extract of the branches of Henriettella fascicularis. Their structures were established by extensive spectroscopic methods. An attempt to determine the absolute stereochemistry of (2E,6S)-6-[(1R,5Z,3aS,9R,10Z,12aR)-1,2,3,3a,4,7,8,9,12,12a-decahydro-9-hydroxy-3a,6,10-trimethylcyclopentanocycloundecen-1-yl]-2-methylhept-2-enoic acid (2) was performed by single-crystal X-ray analysis, using Cu Kalpha radiation. Compound 1 showed significant competitive binding to estrogen receptor beta and moderate antiestrogenic activity with cultured Ishikawa cells.
Calderón
Angela I
AI
Institut de Pharmacognosie et Phytochimie, Université de Lausanne, BEP, CH-1015 Lausanne, Switzerland.
Terreaux
Christian
C
Schenk
Kurt
K
Pattison
Phil
P
Burdette
Joanna E
JE
Pezzuto
John M
JM
Gupta
Mahabir P
MP
Hostettmann
K
K
D000469:Alkaline Phosphatase / Q000378:metabolism; D001665:Binding Sites; D002460:Cell Line / Q000187:drug effects; D018360:Crystallography, X-Ray; D004717:Endometrium / Q000187:drug effects; D004965:Estrogen Antagonists / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D020847:Estrogen Receptor Modulators / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D005260:Female; D005663:Furans; D006801:Humans; D007529:Isoflavones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D017705:Lignans / Q000737:chemistry / Q000302:isolation & purification; D035322:Melastomataceae / Q000737:chemistry*; D008745:Methylation; D008968:Molecular Conformation; D015394:Molecular Structure; D019308:Palmitic Acid / Q000737:chemistry / Q000302:isolation & purification; D010176:Panama; D010840:Phytosterols / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D018520:Plant Shoots / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D012855:Sitosterols / Q000737:chemistry / Q000302:isolation & purification; D013237:Stereoisomerism; D013729:Terpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
C472851:(2E,6S)-6-((1R,5Z,3aS,9R,10Z,12aR)-1,2,3,3a,4,7,8,9,12,12a-decahydro-9-hydroxy-3a,6,10-trimethylcyclopentanocycloundecen-1-yl)-2-methylhept-2-enoic acid; C472850:4',5,7-trihydroxy-6,8-dimethylisoflavone; D004965:Estrogen Antagonists; D020847:Estrogen Receptor Modulators; D005663:Furans; D007529:Isoflavones; D017705:Lignans; D010840:Phytosterols; D012855:Sitosterols; D013729:Terpenes; D019308:Palmitic Acid; C025473:gamma-sitosterol; D000469:Alkaline Phosphatase; C103298:pinoresinol