Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Studies on Coumarins from the Root of Angelica decursiva FR. et SAV. : II. Stereostructures of Decursin, Decursidin, and Other New Pyranocoumarin Derivatives
KIYONORI SANOITIRO YOSIOKAISAO KITAGAWA
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1975 Volume 23 Issue 1 Pages 20-28

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Abstract

The stereostructures of pyranocoumarin derivatives named decursin (I), decursidin (II), AD-I (III), AD-II (IV) isolated from the root of the titled plant have been elucidated on the basis of chemical and physicochemical evidence. Decursin is expressed as 3'(S)-senecioyloxy-3', 4'-dihydroxanthyletin (I) and decursidin as -3'(S), 4'(R)-disenecioyloxy-3', 4'-dihydroxanthyletin (II). AD-I has been revealed to be a mixture of two diastereoisomers being isomeric at C-4' and is expressed as 3'(S)-angeloyloxy-4'(R and S)-isovaleroyloxy-3', 4'-dihydroxanthyletin (III). Finally, AD-II has been established to be -3'(S)-angeloyloxy- 4'(R)-senecioyloxy-3', 4'-dihydroxanthyletin (IV) and it has been suggested on the basis of close similarity of the physical properties of AD-II with those of andelin that the structure proposed for andelin by Avramenko, et al. might be revised.

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