COLUMBIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H22O6
Molecular Weight	358.3851
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12OC(=O)[C@](O)(C=C1)[C@]3(C)CC[C@@]4([H])C(=O)O[C@@H](C[C@@]4(C)[C@]23[H])C5=COC=C5

InChI

InChIKey=AALLCALQGXXWNA-DURQJQQASA-N

InChI=1S/C20H22O6/c1-18-9-14(11-5-8-24-10-11)25-16(21)12(18)3-6-19(2)15(18)13-4-7-20(19,23)17(22)26-13/h4-5,7-8,10,12-15,23H,3,6,9H2,1-2H3/t12-,13-,14-,15-,18+,19+,20+/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22227329

Columbin is a diterpenoid furanolactone, was isolated from the plant species Tinspora bakis. It displays anti-inflammatory activity, protects from azoxymethane-induced rat colon carcinogenesis and possess trypanocidal mechanism.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cyclooxygenase-2 196 Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22227329	Inhibitor 8297		53.1 µM [IC50]
cholesterol import 1 Target ID: GO:0070508 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16206831	Blocker 537

Conditions

Condition	Modality	Targets	Highest Phase	Product
Trypanosomiasis 9 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16206831	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Structure of columbin, a diterpenoid furanolactone from Tinospora cordifolia Miers.	1989 Feb 15	2610972
A bitter diterpenoid furanolactone columbin from Calumbae Radix inhibits azoxymethane-induced rat colon carcinogenesis.	2002 Sep 26	12065087
In vitro and in vivo anti-inflammatory activities of columbin through the inhibition of cycloxygenase-2 and nitric oxide but not the suppression of NF-κB translocation.	2012 Mar 5	22227329

Patents

Sample Use Guides

In Vivo Use Guide

In anti-canrogenesis experiments rats were fed by experimental diets, made by mixing columbin at doses of 4, 20, and 100 ppm with a powdered CE-2 basal diet. Anti-inflammatory activity was evaluated in carrageenan-induced mice paw oedema test. Columbin was intra-peritoneally administered to mice at the dose of 30, 100, 300 and 700 mg/kg.

Route of Administration: Oral

In Vitro Use Guide

COX-2 activity was tested using COX-inhibitor screening kit (Cayman Chemical, USA). This assay measures the production of PGF2-alpha generated by SnCl2, in the presence of PGH2. Columbin inhibits COX-2 with IC50 of 53 uM.

Name

Type

Language

COLUMBIN

Common Name

English

COLUMBIN [MI]

Common Name

English

(1R,4R,4AR,6AR,9S,10AS,10BS)-9-(3-FURANYL)-1,4,4A,5,6,6A,9,10,10A,10B-DECAHYDRO-4-HYDROXY-4A,10A-DIMETHYL-1,4-ETHENO-3H,7H-BENZO(1,2-C:3,4-C')DIPYRAN-3,7-DIONE

Common Name

English

Code System Code Type Description

FDA UNII

KKI91P85GE