| Identification | Back Directory | [Name]
OSW-1 | [CAS]
145075-81-6 | [Synonyms]
OSW-1
OSW-1 (Orsaponin)
OSW-1, >90%
(Orsaponin)
16beta-[2-O-Acetyl-3-O-[2-O-(4-Methoxybenzoyl)-beta-D-xylopyranosyl)-alpha-L-arabinopyranosyloxy]-3b
(3β,16β)-16-[[2-O-Acetyl-3-O-[2-O-(4-methoxybenzoyl)-β-D-xylopyranosyl]-α-L-arabinopyranosyl]oxy]-3,17-dihydroxycholest-5-en-22-one
Cholest-5-en-22-one,16-[[2-O-acetyl-3-O-[2-O-(4-methoxybenzoyl)-b-D-xylopyranosyl]-a-L-arabinopyranosyl]oxy]-3,17-dihydroxy-, (3b,16b)-
Cholest-5-en-22-one, 16-[[2-O-acetyl-3-O-[2-O-(4-methoxybenzoyl)-β-D-xylopyranosyl]-α-L-arabinopyranosyl]oxy]-3,17-dihydroxy-, (3β,16β)-
16beta-[2-O-Acetyl-3-O-[2-O-(4-methoxybenzoyl)-beta-D-xylopyranosyl)-alpha-L-arabinopyranosyloxy]-3beta,17alpha-dihydroxycholest-5-en-22-one | [Molecular Formula]
C47H68O15 | [MDL Number]
MFCD07779405 | [MOL File]
145075-81-6.mol | [Molecular Weight]
873.03 |
| Chemical Properties | Back Directory | [Boiling point ]
932.5±65.0 °C(Predicted) | [density ]
1.31±0.1 g/cm3(Predicted) | [storage temp. ]
Hygroscopic, Refrigerator, under inert atmosphere | [solubility ]
Chloroform (Slightly), Methanol (Slightly), Pyridine (Slightly) | [form ]
Solid | [pka]
12.65±0.70(Predicted) | [color ]
White to Off-White | [InChIKey]
MPXTYZZFIJTPPA-GMJJYARYNA-N |
| Hazard Information | Back Directory | [Description]
OSW-1 is a saponin that has been found in O. saundersiae and has antiviral and anticancer activities.1 It is an inhibitor of oxysterol-binding protein (OSBP) and its paralog OSBP-related protein 4 (ORP4) with Ki values of 16 and 71 nM, respectively, in radioligand binding assays using HEK293T cell lysates.2 It induces OSBP translocalization from the cytoplasm to the trans-Golgi network and decreases intracellular levels of OSBP in HEK293 cells.2,3 OSW-1 inhibits replication of a variety of enteroviruses (IC50s = 2.4-9.4 nM), including replication of coxsackievirus B3 (CVB3) in infected HeLa R19 cells in an OSBP-dependent manner when used at a concentration of 3 nM.4 It also inhibits replication of hepatitis C virus (HCV) but not mouse hepatitis virus (MHV), a coronavirus.5 It protects against CVA9 and echovirus 2 infection in HeLa cells when used at a concentration of 10 nM.4 OSW-1 inhibits growth of HeLa and HEK293 cells (GI50s = 0.33 and 0.22 nM, respectively).2 | [Uses]
OSW-1 is a unique steroidal saponin displaying selective cytotoxicity against cancer cell lines. From Ornithogalum Saundersiae bulbs. | [in vivo]
To ascertain whether or not OSW-1 is as effective in vivo, a nude mouse model inoculated by LoVo cells is adopted, in which OSW-1 treatment is performed when tumors became palpable. The results show that the size of tumors in treated mice is smaller on average than control mice. The significant difference is observed from the 15-17 th day following treatment, and this difference is gradually increased until the animals are sacrificed. Compared with the control group, the tumor weight of the OSW-1-treated group significantly decreases (P<0.05). Additionally, no apparent side effects are observed in OSW-1-treated mice. These results demonstrate that OSW-1 has powerful effects on suppressing colon tumor growth without significant side effects in vivo[2]. | [References]
[1] YOSHIHIRO MIMAKI ?. Cholestane glycosides with potent cytostatic activities on various tumor cells from Ornithogalum saundersiae bulbs[J]. Bioorganic & Medicinal Chemistry Letters, 1997, 7 5: Pages 633-636. DOI: 10.1016/s0960-894x(97)00071-1
[2] BRETT L. ROBERTS . Differing activities of oxysterol-binding protein (OSBP) targeting anti-viral compounds[J]. Antiviral research, 2019, 170: Article 104548. DOI: 10.1016/j.antiviral.2019.104548
[3] ANTHONY W G BURGETT. Natural products reveal cancer cell dependence on oxysterol-binding proteins[J]. Nature chemical biology, 2011, 7 9: 639-647. DOI: 10.1038/nchembio.625
[4] LUCIAN ALBULESCU . Broad-range inhibition of enterovirus replication by OSW-1, a natural compound targeting OSBP[J]. Antiviral research, 2015, 117: Pages 110-114. DOI: 10.1016/j.antiviral.2015.02.013
[5] JEROEN R P M STRATING. Itraconazole inhibits enterovirus replication by targeting the oxysterol-binding protein.[J]. Cell reports, 2015, 10 4: 600-615. DOI: 10.1016/j.celrep.2014.12.054 |
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