Thionation of segetalins A and B, cyclic peptides with estrogen-like activity from seeds of Vaccaria segetalis.
Bioorg Med Chem
; 5(3): 631-6, 1997 Mar.
Article
em En
| MEDLINE
| ID: mdl-9113340
ABSTRACT
Thionation of estrogen-like active cyclic peptides, segetalins A (1) and B (2), with Lawesson's reagent provided each two thiosegetalins; thiosegetalin A1 [Gly-1-psi(CS-NH)-Val-2; Trp-5-psi (CS-NH)-Ala-6]segetalin A, thiosegetalin A2 [Gly-1-psi(CS-NH)-Val-2; Ala-6-psi(CS-NH)-Gly-1]segetalin A, thiosegetalin B1 [Gly-1-psi (CS-NH)-Val-2; Ala-3-psi(CS-NH)-Trp-4]segetalin B, and thiosegetalin B2 [Gly-1-psi(CS-NH)-Val-2; Trp-4-psi(CS-NH)-Ala-1]segetalin B. Thiosegetalin A2 only showed estrogen-like activity against ovariectomized rats. On the basis of their conformations analysed by NMR experiments, the backbone conformation was considered to play an important role in estrogen-like activity for segetalins.
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Base de dados:
MEDLINE
Assunto principal:
Peptídeos Cíclicos
/
Sementes
/
Compostos de Sulfidrila
/
Estrogênios
Idioma:
En
Ano de publicação:
1997
Tipo de documento:
Article