The alkaloid constituents of Euchresta japonica and the stereochemical assignment of two isomeric sophoridine N-oxides.

• OHMIYA SHIGERU

• OTOMASU HIROTAKA

• HAGINIWA JOJU

• MURAKOSHI ISAMU

Abstract

Nine known lupin alkaloids, (+)-matrine, (+)-matrine N-oxide, (+)-sophoranol, (+)-sophoranol N-oxide, (-)-sophoridine (1), (-)-cytisine, (-)-N-methylcytisine, (-)-N-formylcytisine, (-)-baptifoline, and (-)-sophoridine N-oxide (2a), were isolated from the aerial parts of Euchresta japonica BENTH., in addition to two alkaloids, (+)-5, 17-dehydromatrine N-oxide and (-)-12-cytisineacetic acid, reported previously. 2a was one of the two diastereoisomeric sophoridine N-oxides with different configurations of N-oxide nitrogen. Seasonal variations of the alkaloid contents in the aerial and ground parts of E. japonica were also examined. The N-oxidation of sophoridine with m-chloroperbenzoic acid gave two N-oxides in a ratio of ca. 1 : 5. The minor N-oxide was identical with 2a. The major N-oxide (2b) was characterized as the other diastereomer of sophoridine N-oxide by MS spectroscopy and deoxygenation to sophoridine. The stereochemical assignments of the two isomers were carried out by analysis of their ¹H- and ¹³C-NMR spectra.

Journal

• Chemical and Pharmaceutical Bulletin

  Chemical and Pharmaceutical Bulletin 28 (2), 546-551, 1980

  The Pharmaceutical Society of Japan

Keywords

• ^<13>C-NMR

Details

• CRID: 1390282679142943360
• NII Article ID: 110003623939
• NII Book ID: AA00602100
• DOI: 10.1248/cpb.28.546
• COI: 1:CAS:528:DyaL3cXltFSmsbw%3D
• ISSN: 13475223
• ISSN: 00092363
• ISSN: http://id.crossref.org/issn/00092363
• Web Site: http://www.jstage.jst.go.jp/article/cpb1958/28/2/28_2_546/_pdf
• Web Site: https://search.jamas.or.jp/link/ui/1981017661
• Text Lang: en
• Data Source:
  • JaLC
  • Crossref
  • CiNii Articles
• Abstract License Flag: Disallowed