Bergenin

Bergenin

Names
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)= 5956-63-8 (unspecified hydrate)
ChEMBL	ChEMBL273019
ChemSpider	59455
Jmol interactive 3D	Image
PubChem	66065
UNII	L84RBE4IDC
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 Key: YWJXCIXBAKGUKZ-HJJNZUOJSA-N
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
Properties
Chemical formula	C14H16O9
Molar mass	328.27 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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. It shows a potent immunomodulatory effect.^[1]

Bergenin can be isolated from Bergenia species like Bergenia ciliata and Bergenia ligulata,^[2] from rhizomes of Bergenia stracheyi. It is also found in the stem bark of Dryobalanops aromatica,^[3] in Ardisia elliptica and in Mallotus japonicus.^[4]

References

1. Nazir, N.; Koul, S.; Qurishi, M. A.; Taneja, S. C.; Ahmad, S. F.; Bani, S.; Qazi, G. N. (2007). "Immunomodulatory effect of bergenin and norbergenin against adjuvant-induced arthritis—A flow cytometric study". Journal of Ethnopharmacology 112 (2): 401–405. doi:10.1016/j.jep.2007.02.023. PMID 17408893.
2. Dhalwal, K.; Shinde, V. M.; Biradar, Y. S.; Mahadik, K. R. (2008). "Simultaneous quantification of bergenin, catechin, and gallic acid from Bergenia ciliata and Bergenia ligulata by using thin-layer chromatography". Journal of Food Composition and Analysis 21 (6): 496–500. doi:10.1016/j.jfca.2008.02.008. INIST:20528090.
3. Wibowo, A.; Ahmat, N.; Hamzah, A. S.; Sufian, A. S.; Ismail, N. H.; Ahmad, R.; Jaafar, F. M.; Takayama, H. (2011). "Malaysianol A, a new trimer resveratrol oligomer from the stem bark of Dryobalanops aromatica". Fitoterapia 82 (4): 676–681. doi:10.1016/j.fitote.2011.02.006. PMID 21338657.
4. Hepatoprotective effects of bergenin, a major constituent of Mallotus japonicus, on carbon tetrachloride-intoxicated rats. Lim HwaKyung, Kim HackSeang, Choi HongSerck, Oh SeiKwan and Choi JongWon, Journal of Ethnopharmacology, 2000, Volume 72 , Number 3, pages 469-474, doi:10.1016/S0378-8741(00)00260-9