83541-38-2

Upstream product

• 84316-77-8 β-1-O-galloyl-2,3-(S)-hexahydroxydiphenoyl-D-glucose 
• 84316-77-8 1-O-galloyl-2,3-O-<(S)-hexahydroxydiphenoyl>-α-D-glucose 
• 82202-99-1 sanguiin H-1 
• 113866-64-1 pedunculagin 
• 79786-00-8 1-O-galloyl-2,3,4,6-bis[(S)-3,3',4,4',5,5'-hexahydroxydiphenoyl]-α-D-glucose 
• 113900-71-3 1,4,6-tri-O-galloyl-2,3-(R)-hexahydroxydiphenoyl-β-D-glucose 
• 113900-70-2 praecoxin B 
• 82202-99-1 nobotanin D 
• 104669-05-8 nobotanin F 

Relevant academic research and scientific papers

First and biomimetic total synthesis of a member of the C-glucosidic subclass of ellagitannins, 5-O-desgalloylepipunicacortein A

The first total synthesis of a member of the C-glucosidic subclass of ellagitannins, 5-O-desgalloylepipunicacortein A, was accomplished by relying on a biomimetic aldol-type formation of its characteristic C-aryl glucosidic bond through the exploitation of the inherent chemical reactivity of a glucopyranosic hemiacetal precursor.

Rhoipteleanins A and E, Dimeric Ellagitannins formed by Intermolecular C-C Oxidative Coupling from Rhoiptelea chiliantha

The first dimeric ellagitannins, rhoipteleanins A and E, generated biogenetically by intermoleuclar C-C oxidative coupling, are isolated from the fruits of Rhoiptelea chiliantha and structurally elucidated on the basis of spectroscopic and chemical evidence.

Tannins and related compounds. CXXIV. Five new ellagitannins, platycaryanins A, B, C, and D, and platycariin, and a new complex tannin, strobilanin, from the fruits and bark of Platycarya strobilacea Sieb et Zucc., and biomimetic synthesis of C-glycosidic

Five new ellagitannins, platycaryanins A (27), B (26), C (30), and D (25), and platycariin (31), and a new complex tannin, strobilanin (32), have been isolated from the fruits and bark of Platycarya strobilacea SIEB, et ZUCC, (Juglandaceae), together with

Dimeric ellagitannins from Alnus japonica

Two new hydrolysable tannins, alnusjaponins A and B, were isolated from the leaves of Alnus japonica, along with 12 known hydrolysable tannins and related compounds, namely 5-O-galloyl-(-)-shikimic acid, 2,3-(S)-hexahydroxydiphenoyl-d-glucose, 4,6-di-O-galloyl-d-glucose, 1,4-di-O-galloyl-β-d-glucose, 4,6-(S)-valoneoyl-d-glucose, strictinin, gemin D, pedunculagin, praecoxin A, flosin A, stachyurin and casuarinin. The structures of alnusjaponins A and B were elucidated on the basis of spectral and chemical evidence as dimeric ellagitannins consisting of pedunculagin and strictinin moieties in which the mode of linkage is different.

Tannins and Related Compounds. LXXVI. Isolation and Characterization of Cercidinins A and B and Cuspinin, Unusual 2,3-(R)-Hexahydroxydiphenoyl Glucoses from Cercidiphyllum japanicum and Castanopsis cuspidata var. sieboldii

Cercidinins A (1) and B (2) and cuspinin (3), unusual ellagitannins having an R-hexahydroxydiphenoyl ester group at the glucose 2,3-positions, have been isolated from the bark of Cercidiphyllum japonicum (Cercidiphyllaceae) and the leaves of Castanopsis cuspidata var. sieboldii (Fagaceae).On the basis of chemical and spectroscopic evidence, their structures were established as 1,4,6-tri-O-galloyl-2,3-(R)-hexahydroxydiphenoyl-β-D-glucose (1), 4,6-di-O-galloyl-2,3-(R)-hexahydroxydiphenoyl-D-glucose (2) and 1-O-galloyl-2,3-(R);4,6-(S)-hexahydroxydiphenoyl-β-D-glucose (3).The co-occurrence of 3 with the atropisomeric S-hexahydroxydiphenoyl derivative suggests the non-specificity of the enzyme which converts gallic acid to hexahydroxydiphenoic acid.Keywords: Cercidiphyllum japonicum; Cercidiphyllaceae; Castanopsis cuspidata var. sieboldii; Fagaceae; cercidinin A; cercidinin B; cuspinin; ellagitannin; 2,3-(R)-hexahydroxydiphenoyl glucose; atropisomerism

Alnusnins A and B from the leaves of Alnus sieboldiana

Two new ellagitannins, alnusnins A and B, have been isolated from the leaves of Alnus sieboldiana (Betulaceae) and characterized as 1-O-galloyl-2,3-(S)-hexahydroxydiphenoyl-4,6-(S)-tergalloyl-β-d-glucose and 2,3-(S)-hexahydroxydiphenoyl-4,6-(S)-tergalloyl-d-glucose, respectively, by chemical and spectral evidence. The occurrence of eight known tannins, 1,2,6-tri-O-galloyl-β-d-glucose, strictinin, casuarinin, stachyurin, pedunculagin, 1(β)-O-galloylpedunculagin and stenophyllanin A, and two flavonoids, pinocembrin and quercetin 3-O-β-d-glucuronide, has also been demonstrated.

Tannins and Related Compounds. Part 28. Revision of the Structures of Sanguiins H-6, H-2 and H-3, and Isolation and Characterization of Sanguiin H-11, a Novel Tetrameric Hydrolysable Tannin and Seven Related Tannins, from Sanguisorba officinalis

The isolation and characterization of one tetrameric, three dimeric and four monomeric hydrolysable tannins from the underground parts of Sanguisorba officinalis (Rosaceae) are reported.The tetrameric and dimeric tannins contain both hexahydroxydiphenoyl and sanguisorboyl ester group(s) attached to the 2,3- and/or 4,6-positions in the α- and β-glucopyranose rings with the 4C1 conformation.The monomeric tannins are related to these tannins in that they contain either a hexahydroxydiphenoyl or sanguisorboyl ester group similarly bonded to the 4C1 glucopyranose moiety.The absence of a trimeric hydrolysable tannin suggests that the tetrameric tannin may be derived biosynthetically from two moles of sanguiin H-6 by a C-O oxidative coupling.A revision of the structures of sanguiins H-6, H-2 and H-3 isolated previously from the same plant source is also described.

The Metabolism of Gallic Acid and Hexahydroxydiphenic Acid in Plants. Part 2. Esters of (S)-Hexahydroxydiphenic Acid with D-Glucopyranose (4C1)

One form of further metabolism of β-penta-O-galloyl-D-glucose in higher plants is that in which intramolecular oxidative coupling takes place between adjacent galloyl ester groups (2,3 and 4,6).This route of biosynthesis is confined to certain plants and details of the structure elucidation of some of the principal metabolites are recorded.

Tannins and Related Compounds. Part 3. A New Phenolic Acid, Sanguisorbic Acid Dilactone, and Three New Ellagitannins, Sanguiins H-1, H-2, and H-3, from Sanguisorba officinalis

A new phenolic acid, sanguisorbic acid dilactone, and three new ellagitannins, sanguiins H-1, H-2, and H-3, have been isolated from the underground parts of Sanguisorba officinalis L. (Rosaceae).On the basis of chemical and spectroscopic evidence, sanguisorbic acid dilactone has been shown to possess a trimeric gallic acid structure and to be a structural isomer of valoneaic acid dilactone.Similarly, sanguiins H-1 and H-2 have been characterized as 1,6-digalloyl-2,3-(4,4',5,5',6,6'-hexahydroxydiphenoyl)glucose and 1-galloyl-2,4-(4,4',5,5',6,6'-hexahydroxydiphenoyl)-3,6-sanguisorboylglucose, respectively.Sanguiin H-3 has been shown mainly by spectroscopic data and analyses of partial hydrolysates to have a novel dimeric structure containing 2,3-(hexahydroxydiphenoyl)glucose and sanguiin H-2 moieties.