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Spirostanols obtained by cyclization of pseudosaponin derivatives and comparison of anti-platelet agglutination activities of spirostanol glycosides.

Abstract：

:Naturally occurring saponins 3 and 4 have a normal type F ring and alpha-arranged CH(3)-21 group. Treatments of pseudosaponin peracetates 18 and 19 derived from 3 and 4, respectively, with alcoholic KOH, followed by acidification with acetic acid, gave spirostanols 20 and 22 having iso type F rings as major products. Structural analyses of sapogenins and saponins derived from pseudo derivatives 11, 12, 18 and 19 were performed by comparisons of their 1H-NMR spectral data and the X-ray analytical data of 3-O-p-bromobenzoyl sarsasapogenin 7, 3-O-acetyl diosgenin 13 and saponin 20. The mechanisms of ring-closure reaction of the side chain at C-22 of pseudosapogenins and pseudosaponins were deduced using stereomodels of the spirostanols derived from 11 under various reaction conditions. Inhibitory activities of saponin diglycosides 3, 4, 20, 21 and 25 on human platelet agglutinations induced by ADP and ristocetin were compared.

journal_name

Eur J Med Chem

journal_title

European journal of medicinal chemistry

authors

Tobari A,Teshima M,Koyanagi J,Kawase M,Miyamae H,Yoza K,Takasaki A,Nagamura Y,Saito S

doi

10.1016/s0223-5234(00)00151-3

subject

Has Abstract

pub_date

2000-05-01 00:00:00

pages

511-27

issue

5

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(00)00151-3

journal_volume

35

pub_type

杂志文章

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