A Total Synthesis of OSW-1

Xue, Junmin; Liu, Peng; Pan, Yu; Guo, Zhongwu

doi:10.1021/jo7018812

Cited by 48 publications

(27 citation statements)

References 34 publications

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“…Several studies have suggested that OSW-1 has a potent anti-proliferative effect against a variety of tumor cell lines, such as leukemia, pancreatic cancer, malignant brain tumor, and hepatocellular carcinoma cells, but is less toxic to non-malignant cells in vitro (5,6); however, it is so difficult to isolate the compound in certain stages that the application is restricted to research. Recent studies have shown that the synthesis of OSW-1 and its derivatives has gradually improved; however, this finding provides the premise for a possible therapeutic application for OSW-1 in the future (7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(21)(22)(23)(24). We determined whether the anti-proliferative effect of OSW-1, Effective cytotoxic activity of OSW-1 on colon cancer by inducing apoptosis in vitro and in vivo the mechanism of which is not completely understood, can be extrapolated to colon cancer cells.…”

Section: Introductionmentioning

confidence: 99%

Effective cytotoxic activity of OSW-1 on colon cancer by inducing apoptosis in vitro and in vivo

et al. 2017

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Abstract. As a natural compound, Ornithogalum caudatumAit is primarily used as an anti-inflammatory and antitumor agent in Chinese folk medicine. In 1992, OSW-1 was isolated from this compound, which is a new member of cholestane saponin family. In numerous recent studies, OSW-1 has been shown to have powerful cytotoxic anticancer effects against various malignant cells. However, the therapeutic efficacy of OSW-1 on colon cancer and the underlying mechanism are not understood. To explore the mechanism underlying OSW-1 in antitumor therapy, a therapeutic function analysis of OSW-1 on colon cancer was performed in vitro and in vivo. It was shown that with low toxicity on normal colonic cells, OSW-1 suppresses colon cancer cells in vitro and this inhibition was via the intrinsic apoptotic pathway, which increased cellular calcium, changed mitochondrial membrane potential, disrupted mitochondrial morphology, and led to the release of cytochrome c and the activation of caspase-3. Furthermore, in a nude mouse model, OSW-1 had a powerful effect on suppressing colon tumor proliferation without significant side effects through the apoptosis pathway. Taken together, these results demonstrate that OSW-1 is a potential drug for colon cancer treatment.

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Section: Introductionmentioning

confidence: 99%

Effective cytotoxic activity of OSW-1 on colon cancer by inducing apoptosis in vitro and in vivo

et al. 2017

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“…In the course of the planned synthesis of disaccharide block I for anticancer steroid OSW-1 based on the known components, glycosidedonor II and acceptor III [2,3] (Scheme 1) we tested 2,3-butanedione in conditions described in [4] for the selective protection of the 3,4-diol moiety of triol II in the form of butane 2,3-bisacetal. The butane 2,3-bisacetal and the other similar protective groups introduced into the synthetic practice by Liu group [5] are known to provide a selective blocking in cycles of trans-vicinal diols, impart the products a crystalline structure, desired conformational rigidity, etc.…”

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confidence: 99%

“…By repeated chromatography we succeeded to isolate and characterize α-anomer IX (δ 6.32, d, J 3.6 Hz), for the β-anomer δ 6.0, d, J 6.9 Hz (cf. [2]). Bringing into the coupling with diol III this α,β-anomeric mixture of imidates IX resulted in a complex mixture of compounds.…”

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confidence: 99%

Disaccharide blocks for analogs of OSW-1

et al. 2011

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The acetalization of phenyl 1-thio-α-L-arabinopyranoside with 2,3-butanedione in the medium of MeOH-CH(OMe) 3 -CSA proceeded with the prevailing formation of the corresponding 3,4-bisacetal that further was converted in compounds, which were regio-and stereoisomers of disaccharide block of OSW-1. O HO O SPh HO OH HO O SPh HO OAc I II IIIIn the sugar chemistry the necessity to work with awkward polyol systems makes the protective groups extremely important [1]. In the course of the planned synthesis of disaccharide block I for anticancer steroid OSW-1 based on the known components, glycosidedonor II and acceptor III [2, 3] (Scheme 1) we tested 2,3-butanedione in conditions described in [4] for the selective protection of the 3,4-diol moiety of triol II in the form of butane 2,3-bisacetal. The butane 2,3-bisacetal and the other similar protective groups introduced into the synthetic practice by Liu group [5] are known to provide a selective blocking in cycles of trans-vicinal diols, impart the products a crystalline structure, desired conformational rigidity, etc. [6].As seen from the structure of triol II all its hydroxy groups are located in the trans-equatorial reciprocal position, and here the possibility of the regiocontrolled acetalization depends mainly on the steric factors. In the experimental test of triol II acetalization by heating with excess 2,3-butanedione in the medium of MeOH-CH(OMe) 3 -camphorsulfonic acid (CSA) (catalyst) we obtained two expected acetals IV and V in the ratio ~3 : 1 and in the overall yield 80%. The main bisacetal IV is a crystalline substance easily isolated from compound V by chromatography on SiO 2 . Minor bisacetal V is oily substance containing ~10% of unidentifi ed isomeric compound. The assignment of the structure of regioisomeric acetals IV and V was carried out applying spectral data. Their 1 H NMR spectra contain a characteristic signal C 1 H which in the spectrum of 2,3-acetal V is located downfi eld (doublet, δ 4.77 ppm, J 9.6 Hz) with respect to the corresponding signal in the spectrum of compound IV (δ 4.47 ppm, d, J 9.35 Hz) because of the electron-withdrawing inductive effect of the closely Scheme 1.

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“…Subsequent to this work, other approaches have been developed for synthesizing OSW-1, wherein the glycosylations were realized in a similar manner. [98][99][100][101][102][103] Numerous analogues of OSW-1 (156) have been chemically synthesized for SAR and mechanism of action studies of OSW-1. 96 As depicted in Fig.…”

Section: Synthesis Of Plant Saponinsmentioning

confidence: 99%