title: Ellagitannins, gallotannins, and gallo-ellagitannins from the galls of Tamarix aphylla.
abstract: Chromatographic separation of an aqueous acetone extract of the galls from Tamarix aphylla using gels resulted in isolation of an ellagitannin, phyllagallin M1 (13), a gallo-ellagitannin, phyllagallin D1 (14), and four gallotannins, phyllagallin M2 (15) and phyllagallins D2-D4 (16-18), in addition to four known ellagitannins and three phenolics of lower molecular weight structurally related to hydrolyzable tannins. The structures of the six new tannins were elucidated based on spectroscopic and chemical data. Among the phenolics, flavogallonic acid dilactone (8), which is presumed to be biogenetically produced by C-C oxidative coupling of an ellagic acid unit with a galloyl residue, shows an exceptional oxidative pattern of gallic acid residues in plants of the family Tamaricaceae. Although the ellagitannin tamarixellagic acid (4) was reported to be a constituent of the galls of T. aphylla, such compounds with anomalous location of the DHDG moiety at O-3 on the glucopyranose core have not been observed among the tannins of tamaricaceous plants.
authors.affiliation: Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University, Tsushima, Kita-ku, Okayama 700-8530, Japan.
authors.forename: Mohamed A A
authors.initials: MA
authors.lastname: Orabi
authors.affiliation: College of Pharmaceutical Sciences, Matsuyama University, Bunkyo-cho, Matsuyama 790-8578, Japan.
authors.forename: Morio
authors.initials: M
authors.lastname: Yoshimura
authors.affiliation: College of Pharmaceutical Sciences, Matsuyama University, Bunkyo-cho, Matsuyama 790-8578, Japan.
authors.forename: Yoshiaki
authors.initials: Y
authors.lastname: Amakura
authors.affiliation: Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University, Tsushima, Kita-ku, Okayama 700-8530, Japan. Electronic address: hatano@pharm.okayama-u.ac.jp.
authors.forename: Tsutomu
authors.initials: T
authors.lastname: Hatano
mesh_terms: D004610:Ellagic Acid / Q000737:chemistry / Q000302:isolation & purification; D005707:Gallic Acid / Q000737:chemistry / Q000302:isolation & purification; D047348:Hydrolyzable Tannins / Q000737:chemistry* / Q000302:isolation & purification; D015394:Molecular Structure; D010941:Plant Tumors; D032363:Tamaricaceae / Q000737:chemistry*
chemical_list: D047348:Hydrolyzable Tannins; C013515:ellagitannin; D004610:Ellagic Acid; D005707:Gallic Acid
keywords: Ellagitannins; Gall; Gallo-ellagitannins; Gallotannins; Tamaricaceae; Tamarix aphylla