Bergenin (Cuscutin) is a natural isocoumarin found in various medicinal plants. It shows mild anti-HIV activity,antihepatotoxic activity and antiulcer activity. It is trihydroxybenzoic acid glycoside and 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.

Physicochemical Properties

Molecular Formula	C14H16O9
Molecular Weight	328.27
Exact Mass	328.079
CAS #	477-90-7
Related CAS #	477-90-7
PubChem CID	66065
Appearance	White to off-white solid powder
Density	1.6±0.1 g/cm3
Boiling Point	658.9±55.0 °C at 760 mmHg
Melting Point	237-240 °C(lit.)
Flash Point	250.7±25.0 °C
Vapour Pressure	0.0±2.1 mmHg at 25°C
Index of Refraction	1.655
LogP	0.05
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	2
Heavy Atom Count	23
Complexity	458
Defined Atom Stereocenter Count	5
SMILES	COC1=C(C=C2C(=C1O)[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)OC2=O)O
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
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
Synonyms	Cuscutin
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro	HeLa cervical cancer cells' viability is reduced by bergenin (7.5–30 µM; 24 hours) (IC50=15 µM)[1]. HeLa cervical cancer cells undergo apoptosis when exposed to bergenin (7.5-30 µM; 24 hours)[1].
ln Vivo	Mice that are pretreated with Bergenin (12.5–100 mg/kg; ip; once) exhibit a dose-related reduction of writhing caused by acetic acid[3].
Cell Assay	Cell Viability Assay[1] Cell Types: HeLa cervical cancer cells Tested Concentrations: 7.5, 15, 30 µM Incubation Duration: 24 hrs (hours) Experimental Results: diminished the viability of HeLa cervical cancer cells. Cell Viability Assay[1] Cell Types: HeLa cervical cancer cells Tested Concentrations: 7.5, 15, 30 µM Incubation Duration: 24 hrs (hours) Experimental Results: Induced apoptosis in HeLa cervical cancer cells.
Animal Protocol	Animal/Disease Models: Male Swiss Webster C57BL/6 mice[3] Doses: 12.5, 25, 50, 100 mg/kg Route of Administration: ip; Once Experimental Results: Produced a dose-related inhibition of acetic acid-induced writhing in mice.
References	[1]. Anticancer activity of bergenin against cervical cancer cells involves apoptosis, cell cycle arrest, inhibition of cell migration and the STAT3 signalling pathway. Exp Ther Med. 2019 May;17(5):3525-3529. [2]. Bergenin decreases the morphine-induced physical dependence via antioxidative activity in mice. Arch Pharm Res. 2015 Jun;38(6):1248-54. [3]. Antinociceptive properties of bergenin. J Nat Prod. 2011 Oct 28;74(10):2062-8.
Additional Infomation	Bergenin is a trihydroxybenzoic acid. It has a role as a metabolite. Bergenin has been reported in Mallotus repandus, Peltophorum africanum, and other organisms with data available.

Solubility Data

Solubility (In Vitro)

DMSO: > 10 mM Water: NA Ethanol: NA

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (7.62 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (7.62 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (7.62 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	3.0463 mL	15.2314 mL	30.4627 mL
	5 mM	0.6093 mL	3.0463 mL	6.0925 mL
	10 mM	0.3046 mL	1.5231 mL	3.0463 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.