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Titolo:
Stereochemistry of cis- and trans-hinokiresinol and their estrogen-like activity
Autore:
Minami, E; Taki, M; Takaishi, S; Iijima, Y; Tsutsumi, S; Akiyama, T;
Indirizzi:
Sankyo Co Ltd, Exploratory Chem Res Labs, Shinagawa Ku, Tokyo 1408710, Japan Sankyo Co Ltd Tokyo Japan 1408710 bs, Shinagawa Ku, Tokyo 1408710, Japan Sankyo Co Ltd, Pharmacol & Mol Biol Res Labs, Shinagawa Ku, Tokyo 1408710,Japan Sankyo Co Ltd Tokyo Japan 1408710 abs, Shinagawa Ku, Tokyo 1408710,Japan Sankyo Co Ltd, Analyt & Metab Res Labs, Shinagawa Ku, Tokyo 1408710, JapanSankyo Co Ltd Tokyo Japan 1408710 bs, Shinagawa Ku, Tokyo 1408710, Japan
Titolo Testata:
CHEMICAL & PHARMACEUTICAL BULLETIN
fascicolo: 3, volume: 48, anno: 2000,
pagine: 389 - 392
SICI:
0009-2363(200003)48:3<389:SOCATA>2.0.ZU;2-X
Fonte:
ISI
Lingua:
ENG
Soggetto:
AFRICAN MEDICINAL-PLANTS; HYPOXIS-NYASICA BAK; REPLACEMENT THERAPY; BREAST-CANCER; RECEPTOR; PRENYLFLAVONOIDS; PHYTOESTROGENS; GLUCOSIDES; AGONIST;
Keywords:
phytoestrogen; hinokiresinol; stereochemistry; nyasol; Chamaecyparis obtusa; Anemarrhena asphodeloides;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Citazioni:
30
Recensione:
Indirizzi per estratti:
Indirizzo: Akiyama, T Sankyo Co Ltd, Exploratory Chem Res Labs, Shinagawa Ku, 2-58 Hiromachi 1-Chome, Tokyo 1408710, Japan Sankyo Co Ltd 2-58 Hiromachi 1-Chome Tokyo Japan 1408710 Japan
Citazione:
E. Minami et al., "Stereochemistry of cis- and trans-hinokiresinol and their estrogen-like activity", CHEM PHARM, 48(3), 2000, pp. 389-392

Abstract

Naturally occurring phenylpropanoids, hinokiresinol (trans-hinokiresinol) and nyasol (cis-hinokiresinol) were found to possess appreciable estrogen receptor binding activity. Strong differences in activity were observed between the geometrical isomers and enantiomers, Among these, (3S)-cis-hinokiresinol displayed the highest activity, one order of magnitude greater than the activity of genistein. Furthermore, cis- and trans-hinokiresinol stimulated the proliferation of estrogen-dependent T47D breast cancer cells, and their stimulatory effects were blocked by an estrogen antagonist, indicatingthat the compounds are estrogen agonists, In addition, the absolute configuration of C-3 in (+)-cis-hinokiresinol has been assigned as S by comparison with the circular dichroism spectra of the hydrogenated products preparedfrom cis and trans ((3S)-trans-hinokiresinol: previously assigned) isomers, These results incidentally provide us with an unambiguous answer to contradictory reports regarding the assignment of the full stereochemisry of cis- and trans-hinokiresinol that have existed in the literature for more thantwo decades.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 23/09/20 alle ore 08:34:08