bergenin

Also known as Cuscutin, (2R,3S,4S,4aR,10bS)-3,4,8,10-Tetrahydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydropyrano[3,2-c]isochromen-6(2H)-one

Bergenin, alias cuscutin, is trihydroxybenzoic acid glycoside. It is the C-glycoside of 4-O-methyl gallic acid. It possesses an O-demethylated derivative called norbergenin. These are chemical compounds and drugs of Ayurveda, commonly known as Paashaanbhed. It shows a potent immunomodulatory effect.

Chemical data

Formula: C14H16O9
Molecular weight: 328.27 g/mol
IUPAC name: (2R,3S,4S,4aR,10bS)-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-6-one

via PubChem

Drug data · ChEMBL

Molecule type: Small molecule

via ChEMBL · EBI

Wikidata facts

Mass: 328.079

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chemical formula: C₁₄H₁₆O₉
canonical SMILES: COC1=C(C=C2C(=C1O)C3C(C(C(C(O3)CO)O)O)OC2=O)O
isomeric SMILES: COC1=C(C=C2C(=C1O)[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)OC2=O)O
Commons category: Bergenin

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Bergenin can be isolated from Bergenia species like Bergenia ciliata and Bergenia ligulata, from rhizomes of Bergenia stracheyi. It is also found in the stem bark of Dryobalanops aromatica, in Ardisia elliptica and in Mallotus japonicus.