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Thionation of segetalins A and B, cyclic peptides with estrogen-like activity from seeds of Vaccaria segetalis.

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.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Morita H,Yun YS,Takeya K,Itokawa H,Shirota O

doi

10.1016/s0968-0896(97)00001-1

subject

Has Abstract

pub_date

1997-03-01 00:00:00

pages

631-6

issue

3

eissn

0968-0896

issn

1464-3391

pii

S0968089697000011

journal_volume

5

pub_type

杂志文章

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