Studies on Chemical Constituents of Antitumor Fraction from Periploca sepium Bge. I

Hideji Itokawa, Junping Xu, Koichi Takeya

Research output: Contribution to journalArticle

42 Scopus citations

Abstract

When the CHC13 extract obtained by partitioning the methanolic extract of Periploca sepium between H20. and CHC13 was subjected to column chromatography on silica gel, the antitumor activity against Sarcoma 180 ascites in mice was concentrated in the fraction eluted with CHC13-MeOH (10:1). From the antitumor fraction, eight products, S-l—S-8, were isolated. S-l was identified as 12β-hydroxypregna-4,6,16-triene-3,20-dione (neridienone-A), obtained for the first time from Asclepiadaceous plants, by direct comparison with an authentic sample and the others were found to be steroidal glycosides. A new compound S-2A (named periplocogenin), and two known aglycones S-3A and S-5A, obtained by hydrolyzing the above glycosides with diluted acid, were respectively identified as 3β-0-(4’,6’-dideoxy-3’-O-methyl-/l3-D-2’-hexosulosyl)-d5-pregnene-17α,20(5)-diol, periplogenin, and △5-pregnene-3β,20(5)-diol from the proton and carbon-13 nuclear magnetic resonance spectral data. The structure of S-6A was identical with that of S-5A, and S-7A and S-8A were identical with S-2A.

Original languageEnglish (US)
Pages (from-to)4524-4529
Number of pages6
JournalChemical and Pharmaceutical Bulletin
Volume35
Issue number11
DOIs
StatePublished - 1987

Keywords

  • Periploca sepium
  • antitumor activity
  • neridienone-A
  • periplocogenin
  • periplogenin
  • △-pregnene-3β,20(5)-diol

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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