Bergenin

Bergenin: Bergenin

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

Other names

Cuscutin

Identifiers

CAS number 477-90-7 (anhydrous)^N=, 5956-63-8 (unspecified hydrate)

PubChem 66065

ChemSpider 59455^Y

UNII L84RBE4IDC^Y

ChEMBL CHEMBL273019^Y

Jmol-3D images Image 1

SMILES

OC[C@@H](O1)[C@@H](O)[C@H](O)[C@@H]2[C@@H]1c3c(O)c(OC)c(O)cc3C(=O)O2

InChI

InChI=1S/C14H16O9/c1-21-11-5(16)2-4-7(9(11)18)12-13(23-14(4)20)10(19)8(17)6(3-15)22-12/h2,6,8,10,12-13,15-19H,3H2,1H3/t6-,8-,10+,12+,13-/m1/s1^Y
Key: YWJXCIXBAKGUKZ-HJJNZUOJSA-N^Y

Properties

Molecular formula C₁₄H₁₆O₉

Molar mass 328.27 g/mol

Exact mass 328.079432 u

N (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references

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. Bergenin can be isolated from Bergenia species like Bergenia ciliata and Bergenia ligulata^[1] and from rhizomes of Bergenia stracheyi. It shows a potent immunomodulatory effect.^[2] It is also found in Ardisia elliptica.

References

^ Simultaneous quantification of bergenin, catechin, and gallic acid from Bergenia ciliata and Bergenia ligulata by using thin-layer chromatography. Dhalwal K., Shinde V.M., Biradar Y.S. and Mahadik K.R., Journal of food composition and analysis, 2008, vol. 21, no6, pp. 496-500, INIST:20528090

^ Immunomodulatory effect of bergenin and norbergenin against adjuvant-induced arthritis—A flow cytometric study Nighat Nazira, Surrinder Koulb, Mushtaq A. Qurishia, Sachin C. Tanejab, Sheikh F. Ahmadc, Sarang Banic and Ghulam N. Qazi, 2006

v · phenolic acids

Monohydroxybenzoic acids
3-Hydroxybenzoic acid | 4-Hydroxybenzoic acid | Salicylic acid

Dihydroxybenzoic acids
Gentisic acid | Homogentisic acid | Orsellinic acid | Protocatechuic acid | 2,3-Dihydroxybenzoic acid | 2,4-Dihydroxybenzoic acid | 2,6-Dihydroxybenzoic acid | 3,5-Dihydroxybenzoic acid

Trihydroxybenzoic acids
Bergenin | Chebulic acid | Ethyl gallate | Eudesmic acid | Gallic acid | Norbergenin | Phloroglucinol carboxylic acid | Syringic acid | Theogallin

This article about a natural phenol is a stub. You can help Wikipedia by expanding it.

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Bergenin

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Bergenin

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
Other names Cuscutin
Identifiers
CAS number	477-90-7 (anhydrous)^N=, 5956-63-8 (unspecified hydrate)
PubChem	66065
ChemSpider	59455^Y
UNII	L84RBE4IDC^Y
ChEMBL	CHEMBL273019^Y
Jmol-3D images	Image 1
SMILES OC[C@@H](O1)[C@@H](O)[C@H](O)[C@@H]2[C@@H]1c3c(O)c(OC)c(O)cc3C(=O)O2
InChI InChI=1S/C14H16O9/c1-21-11-5(16)2-4-7(9(11)18)12-13(23-14(4)20)10(19)8(17)6(3-15)22-12/h2,6,8,10,12-13,15-19H,3H2,1H3/t6-,8-,10+,12+,13-/m1/s1^Y Key: YWJXCIXBAKGUKZ-HJJNZUOJSA-N^Y
Properties
Molecular formula	C₁₄H₁₆O₉
Molar mass	328.27 g/mol
Exact mass	328.079432 u
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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Bergenin

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