1984•Chemical and Pharmaceutical BulletinOpen access

Tannins and related compounds. XXIII. Rhubarb (4): Isolation and structures of new classes of gallotannins.

Yoshiki Kashiwada, Gen‐ichiro Nonaka, Itsuo Nishioka

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Abstract

A chemical examination of hydrolyzable tannins in a rhubarb of high quality (commercial name : ?? ?? ?? ?? ) has revealed the occurrence of four new acylated sugars, i.e., 2-O-cinnamoyl-β-D-glucose (I), 2-O-cinnamoyl-1, 6-di-O-galloyl-β-D-glucose (II), 2-O-p-coumaroyl-1-O-galloyl-β-D-glucose (III) and 1-O-galloylfructose (IV), as well as the known compounds 2-O-cinnamoyl-1-O-galloyl-β-D-glucose (VII), (-)-epicatechin 3-O-gallate (VIII), 1-O-galloyl-β-D-glucose (IX) and 1, 6-di-O-galloyl-β-D-glucose (X). A low-quality rhubarb (commercial name : ?? ?? ?? ) was found to contain three new gallates, 1-O-galloylfructose (IV), 2, 6-di-O-galloylglucose (V) and 3, 5-dihydroxyphenol 1-O-β-D-(6-O-galloyl)-glucopyranoside (VI), together with five known compounds, VIII, X, 6-O-galloylglucose (XI), 1, 2, 6-tri-O-galloyl-β-D-glucose (XII) and procyanidin B-1 3-O-gallate (XIII).

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A chemical examination of hydrolyzable tannins in a rhubarb of high quality (commercial name : ?? ?? ?? ?? ) has revealed the occurrence of four new acylated sugars, i.e., 2-O-cinnamoyl-β-D-glucose (I), 2-O-cinnamoyl-1, 6-di-O-galloyl-β-D-glucose (II), 2-O-p-coumaroyl-1-O-galloyl-β-D-glucose (III) and 1-O-galloylfructose (IV), as well as the known compounds 2-O-cinnamoyl-1-O-galloyl-β-D-glucose (VII), (-)-epicatechin 3-O-gallate (VIII), 1-O-galloyl-β-D-glucose (IX) and 1, 6-di-O-galloyl-β-D-glucose (X). A low-quality rhubarb (commercial name : ?? ?? ?? ) was found to contain three new gallates, 1-O-galloylfructose (IV), 2, 6-di-O-galloylglucose (V) and 3, 5-dihydroxyphenol 1-O-β-D-(6-O-galloyl)-glucopyranoside (VI), together with five known compounds, VIII, X, 6-O-galloylglucose (XI), 1, 2, 6-tri-O-galloyl-β-D-glucose (XII) and procyanidin B-1 3-O-gallate (XIII).

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Available abstract

A chemical examination of hydrolyzable tannins in a rhubarb of high quality (commercial name : ?? ?? ?? ?? ) has revealed the occurrence of four new acylated sugars, i.e., 2-O-cinnamoyl-β-D-glucose (I), 2-O-cinnamoyl-1, 6-di-O-galloyl-β-D-glucose (II), 2-O-p-coumaroyl-1-O-galloyl-β-D-glucose (III) and 1-O-galloylfructose (IV), as well as the known compounds 2-O-cinnamoyl-1-O-galloyl-β-D-glucose (VII), (-)-epicatechin 3-O-gallate (VIII), 1-O-galloyl-β-D-glucose (IX) and 1, 6-di-O-galloyl-β-D-glucose (X). A low-quality rhubarb (commercial name : ?? ?? ?? ) was found to contain three new gallates, 1-O-galloylfructose (IV), 2, 6-di-O-galloylglucose (V) and 3, 5-dihydroxyphenol 1-O-β-D-(6-O-galloyl)-glucopyranoside (VI), together with five known compounds, VIII, X, 6-O-galloylglucose (XI), 1, 2, 6-tri-O-galloyl-β-D-glucose (XII) and procyanidin B-1 3-O-gallate (XIII).

Key concepts: Chemistry, Hydrolyzable Tannin, Gallic acid, Polyphenol, Methyl gallate, Tannin, D-Glucose, Stereochemistry

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