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Bergenin information


Bergenin
Chemical structure of bergenin
Chemical structure of bergenin in ball-and-stick format
Names
Preferred IUPAC name
(2R,3S,4S,4aR,10bS)-3,4,8,10-Tetrahydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydropyrano[3,2-c][2]benzopyran-6(2H)-one
Other names
Cuscutin
Identifiers
CAS Number
  • 477-90-7 (anhydrous) checkY
  • 5956-63-8 (unspecified hydrate) ☒N
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL273019 checkY
ChemSpider
  • 59455 checkY
ECHA InfoCard 100.230.534 Edit this at Wikidata
PubChem CID
  • 66065
UNII
  • L84RBE4IDC checkY
CompTox Dashboard (EPA)
  • DTXSID4048141 Edit this at Wikidata
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 checkY
    Key: YWJXCIXBAKGUKZ-HJJNZUOJSA-N checkY
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).
☒N verify (what is checkY☒N ?)
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]

  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

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Bergenin

Last Update:

Bergenin, alias cuscutin, is trihydroxybenzoic acid glycoside. It is the C-glycoside of 4-O-methyl gallic acid. It possesses an O-demethylated derivative...

Word Count : 286

Bergenia

Last Update:

'notched' outline which can detract from the appearance of the plant. Bergenin, C-glycoside of 4-O-methyl gallic acid, and its O-demethylated derivative...

Word Count : 980

Bergenia ligulata

Last Update:

500 m (4,900 ft) elevation. Bergenia ligulata contains a phenolic compound bergenin, and afzelechin, a type of flavan-3-ol. Umashankar D.C.; Chawla A.S.; Deepak...

Word Count : 278

Bergenia ciliata

Last Update:

Afghanistan, south Tibet, Northern Nepal, Bhutan (Haa and Mongar districts). Bergenin, catechin, gallic acid, gallicin, catechin-7-O-glucoside and β-sitosterol...

Word Count : 339

Bergenia stracheyi

Last Update:

the Western Himalayas, from 2700 to 4700 m, Afghanistan and Tajikistan. Bergenin and norbergenin are chemical compounds that can be isolated from rhizomes...

Word Count : 115

Dryobalanops aromatica

Last Update:

at least two protected areas (Lambir and Gunung Mulu National Parks). Bergenin, malaysianol A, laevifonol, ampelopsin E, α-viniferin, ε-viniferin and...

Word Count : 357

Norbergenin

Last Update:

Norbergenin is a chemical compound. It is the O-demethylated derivative of bergenin. It can be isolated from rhizomes of Bergenia stracheyi. Nighat Nazira;...

Word Count : 75

Ardisia elliptica

Last Update:

amyrin, and the phenolic compounds syringic acid, isorhamnetin, quercetin, bergenin, 5-(Z-heptadec-4'-enyl)resorcinol and 5-pentadecylresorcinol can be found...

Word Count : 660

Sacoglottis gabonensis

Last Update:

drupe, greenish to yellow when ripe, 1-5 seeded. The chemical compound, Bergenin has been isolated from the stem bark of Sacoglottis gabonensis. Stem bark...

Word Count : 547

Mallotus japonicus

Last Update:

leaf age and abiotic habitat conditions,. Mallotus japonicus contains bergenin. The pericarp contains mallotophenone, mallotochromene mallophenone, mallotojaponin...

Word Count : 690

Vateria indica

Last Update:

bark gained neuro-protection and enhanced memory. Several stilbenoids (bergenin, hopeaphenol, vaticanol B, vaticanol C, and ε‐viniferin) found in resins...

Word Count : 3564

Daniel Riihilahti

Last Update:

at the Wayback Machine, fotball.no Daniel Riihilahti sopimukseen Brann Bergenin kanssa Archived 2023-12-18 at the Wayback Machine, hjk.fi, 16 December...

Word Count : 332

Cnestis polyphylla

Last Update:

Connarus species are known to contain the glycosides rapanone, embelin and bergenin. "Cnestis polyphylla". Germplasm Resources Information Network. Agricultural...

Word Count : 376

Afzelechin

Last Update:

proanthocyanidin. High pressure liquid chromatographic determination of bergenin and (+) -afzelechin from different parts of Paashaanbhed (Bergenia ligulata...

Word Count : 324

Diospyros abyssinica

Last Update:

inhibitors have been found. The attraction is caused by phenolic smell of bergenin and flavanol that the plant releases. It also releases betulinic acid and...

Word Count : 462

Bark isolate

Last Update:

oil, α-Santalol, β-Santalol Sandalwood (Santalum) Ayurvedic component Bergenin, α-viniferin, ε-viniferin, diptoindonesin A Bergenia ligulata, Dryobalanops...

Word Count : 166

Dictionary of natural phenols and polyphenols molecular formulas

Last Update:

p-Coumaric acid glucoside 326.100168 C20H22O4 Acutifolin A 326.151809 C14H16O9 Bergenin 328.079432 C18H16O6 Salvigenin, others 328.094688 C16H24O7 Rhododendrin...

Word Count : 54

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