| Identification | Back Directory | [Name]
Columbin | [CAS]
546-97-4 | [Synonyms]
Tinosporin
Columbin USP/EP/BP
Columbin >=95% (LC/MS-ELSD)
Columbin, 98%, from limacia sagittata
(1s,2s,3s,5s,8r,11r,12s)-5-(3-furyl)-12-hydroxy-3,11-dimethyl-6,14-dioxatetracyclo[10.2.2.02,11.03,8]hexadec-15-ene-7,13-dione
(1R,2S,3S,5S,8R,11R,12R)-5-(3-Furyl)-12-hydroxy-3,11-dimethyl-6,14-dioxatetracyclo[10.2.2.02,11.03,8]hexadec-15-ene-7,13-dione
(1R,4R,4aR,6aR,9S,10aS,10bS)-9-(3-Furanyl)decahydro-4-hydroxy-4a,10a-dimethyl-1,4-etheno-3H,7H-benzo[1,2-c:3,4-c']dipyran-3,7-dione
(1R,2S,3S,5S,8R,11R,12R)-5-(3-Furyl)-12-hydroxy-3,11-dimethyl-6,14-dioxatetracyclo[10.2.2.02,11.03,8]hexadec-15-ene-7,13-dione
(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
1,4-Etheno-3H,7H-benzo[1,2-c:3,4-c']dipyran-3,7-dione, 9-(3-furanyl)-1,4,4a,5,6,6a,9,10,10a,10b-decahydro-4-hydroxy-4a,10a-dimethyl-, (1R,4R,4aR,6aR,9S,10aS,10bS)- | [Molecular Formula]
C20H22O6 | [MDL Number]
MFCD02682955 | [MOL File]
546-97-4.mol | [Molecular Weight]
358.388 |
| Chemical Properties | Back Directory | [Melting point ]
190-191℃ | [alpha ]
D +52.5° (pyridine) | [Boiling point ]
410.82°C (rough estimate) | [density ]
1.36 | [refractive index ]
1.4450 (estimate) | [storage temp. ]
?20°C | [solubility ]
DMF: 30 mg/ml; DMSO: 30 mg/ml; Ethanol: 0.03 mg/ml | [form ]
Cryst. | [pka]
12.14±0.70(Predicted) | [color ]
White to off-white | [Major Application]
metabolomics
vitamins, nutraceuticals, and natural products | [InChIKey]
AALLCALQGXXWNA-QJNFORGASA-N | [SMILES]
C1(=O)O[C@H](C2C=COC=2)C[C@@]2(C)[C@@]3([H])[C@@](C)(CC[C@@]12[H])[C@]1(O)C=C[C@@]3([H])OC1=O |
| Hazard Information | Back Directory | [Chemical Properties]
White needle-shaped crystals, easily soluble in methanol and ethyl acetate, almost insoluble in water, derived from Jin Guolan. | [Uses]
Columbin is a furanolactone diterpene isolated from the roots of Jateorhiza and Tinospora species and is used in Asian and African folk medicine for analgesic and antipyretic properties. | [Definition]
ChEBI: Columbin is an organic heterotricyclic compound and an organooxygen compound. | [in vivo]
Columbin inhibits oedema formation in mice paw. At doses of 300 mg/kg and 700 mg/kg, columbin inhibits inflammation from 0 to 5 h and the results are comparable to that of aspirin as a standard anti-inflammatory drug. The inhibitory effect of columbin on carrageenan induced paw oedema in mice may be due to the suppression of the release of mediators responsible for inflammation including prostaglandin[1]. Columbin is poorly bioavailable (2.8% p.o. and 14% i.p.) in rats, but its transport is rapid across the Caco-2 cell monolayers, suggesting that extensive first-pass metabolism in the liver is the likely reason for its poor bioavailability[2]. | [IC 50]
Trypanosoma; COX-2: 53.1 μM (EC50); COX-1: 327 μM (EC50) |
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