Bergenin | Cuscutin | CAS#477-90-7

MedKoo Cat#: 600116 | Name: Bergenin

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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. 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.

Chemical Structure

Bergenin

CAS#477-90-7

Theoretical Analysis

MedKoo Cat#: 600116

Name: Bergenin

CAS#: 477-90-7

Chemical Formula: C14H16O9

Exact Mass: 328.0794

Molecular Weight: 328.27

Elemental Analysis: C, 51.22; H, 4.91; O, 43.86

Price and Availability

Size	Price	Availability	Quantity
500mg	USD 350.00	2 Weeks
1g	USD 600.00	2 Weeks

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Related CAS #

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Synonym

Cuscutin; (–)-Bergenin; NSC 661749; NSC-661749; NSC661749

IUPAC/Chemical 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

InChi Key

YWJXCIXBAKGUKZ-HJJNZUOJSA-N

InChi Code

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

SMILES Code

O=C1C2=C(C(O)=C(OC)C(O)=C2)[C@@]3([H])[C@]([C@@H](O)[C@H](O)[C@@H](CO)O3)([H])O1

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO.

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 328.27 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Li X, Wang Y, Liang J, Bi Z, Ruan H, Cui Y, Ma L, Wei Y, Zhou B, Zhang L, Zhou H, Yang C. Bergenin attenuates bleomycin-induced pulmonary fibrosis in mice via inhibiting TGF-β1 signaling pathway. Phytother Res. 2021 Oct;35(10):5808-5822. doi: 10.1002/ptr.7239. Epub 2021 Aug 10. PMID: 34375009. 2: Yang L, Zheng Y, Miao YM, Yan WX, Geng YZ, Dai Y, Wei ZF. Bergenin, a PPARγ agonist, inhibits Th17 differentiation and subsequent neutrophilic asthma by preventing GLS1-dependent glutaminolysis. Acta Pharmacol Sin. 2022 Apr;43(4):963-976. doi: 10.1038/s41401-021-00717-1. Epub 2021 Jul 15. PMID: 34267342; PMCID: PMC8975945. 3: Qiao S, Liu R, Lv C, Miao Y, Yue M, Tao Y, Wei Z, Xia Y, Dai Y. Bergenin impedes the generation of extracellular matrix in glomerular mesangial cells and ameliorates diabetic nephropathy in mice by inhibiting oxidative stress via the mTOR/β-TrcP/Nrf2 pathway. Free Radic Biol Med. 2019 Dec;145:118-135. doi: 10.1016/j.freeradbiomed.2019.09.003. Epub 2019 Sep 5. PMID: 31494242. 4: Madaan R, Singla RK, Kumar S, Dubey AK, Kumar D, Sharma P, Bala R, Singla S, Shen B. Bergenin - A Biologically Active Scaffold: Nanotechnological Perspectives. Curr Top Med Chem. 2022;22(2):132-149. doi: 10.2174/1568026621666211015092654. PMID: 34649489. 5: Liu J, Zhang Y, Yu C, Zhang P, Gu S, Wang G, Xiao H, Li S. Bergenin inhibits bladder cancer progression via activating the PPARγ/PTEN/Akt signal pathway. Drug Dev Res. 2021 Apr;82(2):278-286. doi: 10.1002/ddr.21751. Epub 2020 Oct 28. PMID: 33112006. 6: Yin Y, Xu R, Ning L, Yu Z. Bergenin alleviates Diabetic Retinopathy in STZ- induced rats. Appl Biochem Biotechnol. 2022 May 27. doi: 10.1007/s12010-022-03949-x. Epub ahead of print. PMID: 35622274. 7: Salimo ZM, Yakubu MN, da Silva EL, de Almeida ACG, Chaves YO, Costa EV, da Silva FMA, Tavares JF, Monteiro WM, de Melo GC, Koolen HHF. Chemistry and Pharmacology of Bergenin or Its Derivatives: A Promising Molecule. Biomolecules. 2023 Feb 21;13(3):403. doi: 10.3390/biom13030403. PMID: 36979338; PMCID: PMC10046151. 8: Lei D, Sun Y, Liu J, Chi J. Bergenin inhibits palmitic acid-induced pancreatic β-cell inflammatory death via regulating NLRP3 inflammasome activation. Ann Transl Med. 2022 Oct;10(19):1058. doi: 10.21037/atm-22-3781. PMID: 36330410; PMCID: PMC9622470. 9: Jayakody RS, Wijewardhane P, Herath C, Perera S. Bergenin: a computationally proven promising scaffold for novel galectin-3 inhibitors. J Mol Model. 2018 Oct 2;24(10):302. doi: 10.1007/s00894-018-3831-4. PMID: 30276553. 10: Chen M, Chen C, Gao Y, Li D, Huang D, Chen Z, Zhao X, Huang Q, Wu D, Lai T, Su G, Wu B, Zhou B. Bergenin-activated SIRT1 inhibits TNF-α-induced proinflammatory response by blocking the NF-κB signaling pathway. Pulm Pharmacol Ther. 2020 Jun;62:101921. doi: 10.1016/j.pupt.2020.101921. Epub 2020 Jun 29. PMID: 32615160. 11: Liu Y, Tan Y, Cao G, Shi L, Song Y, Shan W, Zhang M, Li P, Zhou H, Zhang B, Sun Y, Yi W. Bergenin alleviates myocardial ischemia-reperfusion injury via SIRT1 signaling. Biomed Pharmacother. 2023 Feb;158:114100. doi: 10.1016/j.biopha.2022.114100. Epub 2022 Dec 18. PMID: 36538860. 12: Chen M, Ye C, Zhu J, Zhang P, Jiang Y, Lu X, Wu H. Bergenin as a Novel Urate-Lowering Therapeutic Strategy for Hyperuricemia. Front Cell Dev Biol. 2020 Jul 29;8:703. doi: 10.3389/fcell.2020.00703. PMID: 32850823; PMCID: PMC7403512. 13: Bajracharya GB. Diversity, pharmacology and synthesis of bergenin and its derivatives: potential materials for therapeutic usages. Fitoterapia. 2015 Mar;101:133-52. doi: 10.1016/j.fitote.2015.01.001. Epub 2015 Jan 14. PMID: 25596093. 14: El-Hawary SS, Mohammed R, AbouZid S, Zaki MA, Ali ZY, Elwekeel A, Elshemy HAH. Antitrypanosomal activity of new semi-synthetic bergenin derivatives. Chem Biol Drug Des. 2022 Feb;99(2):179-186. doi: 10.1111/cbdd.14000. Epub 2021 Dec 29. PMID: 34967118. 15: Singla RK, Dhonchak K, Sodhi RK, Arockia Babu M, Madan J, Madaan R, Kumar S, Sharma R, Shen B. Bergenin ameliorates cognitive deficits and neuropathological alterations in sodium azide-induced experimental dementia. Front Pharmacol. 2022 Sep 29;13:994018. doi: 10.3389/fphar.2022.994018. PMID: 36249784; PMCID: PMC9556967. 16: Rajput SA, Mirza MR, Choudhary MI. Bergenin protects pancreatic beta cells against cytokine-induced apoptosis in INS-1E cells. PLoS One. 2020 Dec 21;15(12):e0241349. doi: 10.1371/journal.pone.0241349. PMID: 33347462; PMCID: PMC7751853. 17: Lee KH, Choi EM. Effects of bergenin on methylglyoxal-induced damage in osteoblastic MC3T3-E1 cells. J Appl Toxicol. 2018 Apr;38(4):585-593. doi: 10.1002/jat.3565. Epub 2017 Nov 17. PMID: 29148590. 18: Zeng Q, Zhou T, Zhao F, Xiong D, He B, Hua Q, Lin M, Deng L, Sang X, Xie W, Chen J, Wang Z, Ren L, Luo Z, Huang X, Liu W, Tang S. p62-Nrf2 Regulatory Loop Mediates the Anti-Pulmonary Fibrosis Effect of Bergenin. Antioxidants (Basel). 2022 Feb 3;11(2):307. doi: 10.3390/antiox11020307. PMID: 35204190; PMCID: PMC8868171. 19: Huang D, Sun C, Chen M, Bai S, Zhao X, Wang W, Geng K, Huang W, Zhao T, Wu B, Zhang G, Wu D, Xu Y. Bergenin ameliorates airway inflammation and remodeling in asthma by activating SIRT1 in macrophages to regulate the NF-κB pathway. Front Pharmacol. 2022 Oct 13;13:994878. doi: 10.3389/fphar.2022.994878. PMID: 36313381; PMCID: PMC9606584. 20: Zhang G, Wang H, Zhang Q, Zhao Z, Zhu W, Zuo X. Bergenin alleviates H2 O2 -induced oxidative stress and apoptosis in nucleus pulposus cells: Involvement of the PPAR-γ/NF-κB pathway. Environ Toxicol. 2021 Dec;36(12):2541-2550. doi: 10.1002/tox.23368. Epub 2021 Sep 9. PMID: 34499403.