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rdf:type |
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lifeskim:mentions |
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pubmed:issue |
6
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pubmed:dateCreated |
1998-10-15
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pubmed:abstractText |
Bioassay-guided fractionation of a methanolic extract of a Thai crude drug, derived from heartwood of Anaxagorea luzonensis A. Gray (Annonaceae), resulted in the isolation of 8-isopentenylnaringenin (1) as an estrogen agonist with a activity of about an order of magnitude greater than genistein. Various flavonoids possessing isopentenyl side chains in the A-ring have been prepared and evaluated for their ability to bind estrogen receptor. In addition, enantiomers of 1 were separated and the respective enantiomers were assayed. These studies have demonstrated that the presence of an 8-isopentenyl group is an important factor for binding. Flavones, flavanones and flavonols having an isopentenyl substituent at C-8 exhibited an appreciable affinity for estrogen receptor. Conversely, isoflavones possessing an 8-isopentenyl substituent at C-8 did not show this activity. Movement of the isopentenyl group from position 8 to 6 resulted in loss of the activity. No significant difference was observed between 2(S)- and 2(R)-enantiomers of 1 in their binding affinity. Prenylflavonoids are reported to possess a wide range of biological activities; however, estrogenic activity has not been described.
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pubmed:language |
eng
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pubmed:journal |
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pubmed:citationSubset |
IM
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pubmed:chemical |
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pubmed:status |
MEDLINE
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pubmed:month |
Aug
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pubmed:issn |
0032-0943
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pubmed:author |
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pubmed:issnType |
Print
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pubmed:volume |
64
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
511-5
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pubmed:dateRevised |
2008-11-21
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pubmed:meshHeading |
pubmed-meshheading:9741295-Breast Neoplasms,
pubmed-meshheading:9741295-Cell Division,
pubmed-meshheading:9741295-Estradiol,
pubmed-meshheading:9741295-Estrogens, Non-Steroidal,
pubmed-meshheading:9741295-Female,
pubmed-meshheading:9741295-Genistein,
pubmed-meshheading:9741295-Humans,
pubmed-meshheading:9741295-Isoflavones,
pubmed-meshheading:9741295-Medicine, East Asian Traditional,
pubmed-meshheading:9741295-Molecular Structure,
pubmed-meshheading:9741295-Phytoestrogens,
pubmed-meshheading:9741295-Plant Extracts,
pubmed-meshheading:9741295-Plant Preparations,
pubmed-meshheading:9741295-Plants, Medicinal,
pubmed-meshheading:9741295-Receptors, Estradiol,
pubmed-meshheading:9741295-Stereoisomerism,
pubmed-meshheading:9741295-Structure-Activity Relationship,
pubmed-meshheading:9741295-Thailand,
pubmed-meshheading:9741295-Tumor Cells, Cultured
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pubmed:year |
1998
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pubmed:articleTitle |
Prenylflavonoids: a new class of non-steroidal phytoestrogen (Part 1). Isolation of 8-isopentenylnaringenin and an initial study on its structure-activity relationship.
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pubmed:affiliation |
Exploratory Chemistry Research Laboratories, Sankyo Co., Ltd., Shinagawa-ku, Tokyo, Japan.
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pubmed:publicationType |
Journal Article
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