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berberrubine

Product Nameberberrubine
CAS15401-69-1
MFC19H16ClNO4
MW357.78764
EINECS
MOL File15401-69-1.mol

Chemical Properties

Melting point	245℃ (DEC.)
storage temp.	Hygroscopic, -20°C Freezer, Under inert atmosphere
solubility	DMSO (Slightly), Methanol (Slightly)
form	Solid
color	Off-White to Dark Yellow
Stability	Hygroscopic
InChI	InChI=1S/C19H15NO4.ClH/c1-22-16-3-2-11-6-15-13-8-18-17(23-10-24-18)7-12(13)4-5-20(15)9-14(11)19(16)21;/h2-3,6-9H,4-5,10H2,1H3;1H
InChIKey	GYFSYEVKFOOLFZ-UHFFFAOYSA-N
SMILES	[Cl-].O1C([H])([H])OC2=C1C([H])=C1C(=C2[H])C2C([H])=C3C([H])=C([H])C(=C(C3=C([H])[N+]=2C([H])([H])C1([H])[H])O[H])OC([H])([H])[H]

Usage And Synthesis

Chemical Properties

Soluble in acidic solution, insoluble in petroleum ether, chloroform and other solvents. Derived from the roots of Thalictrum polygamun Muhl.

Uses

Berberrubine Chloride is a novel alkaloid with novel nitric-oxide donating activity. Antitumor and an antimicrobial agent.

Definition

ChEBI: Berberrubine is an alkaloid.

Synthesis

A literature review of various methods to prepare berberrubine:
1. Vacuum pyrolysis; 2. Microwave irradiation; 3. Pyridine hydrochloride fusion; 4. Urea method; 5. Aluminum trichloride method; 6. Esterification-hydrolysis method. Steps for method 2 (microwave) are described in detail.

in vivo

Berberrubine (oral administration; 10-20 mg/kg; 7 days) has a beneficial effect in a mouse colitis model^[3].

Animal Model:	DSS (HY-116282) treated male Balb/c mice aged 6 weeks old^[3]
Dosage:	10 and 20 mg/kg
Administration:	Oral administration (p.o.); 7 days
Result:	Significantly reduced the disease activity index (DAI) with prolonged colon length and increased bodyweight at dose of 20 mg/kg. Significantly ameliorated the DSS-induced colonic pathological alternations and decreased histological scores. Markedly attenuated colonic inflammation by alleviating inflammatory cell infiltration and inhibiting myeloperoxidase (MPO) and cytokines (TNF-α, IFN-γ, IL-1β, IL-6, IL-4 and IL-10) productions in DSS mice. Substantially upregulated the expression of tight junction proteins (zonula occludens-1, zonula occludens-2, claudin-1, occludin) and mRNA expression of mucins (mucin-1 and mucin-2), and decreased the Bax/Bcl-2 ratio.

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