Structure, Bioactivity, and Chemical Synthesis of OSW-1 and Other Steroidal Glycosides in the Genus Ornithogalum

Tang, Yuping; Li, Nian‐Guang; Duan, Jin‐Ao; Tao, Weiwei

doi:10.1021/cr300072s

Cited by 60 publications

(38 citation statements)

References 151 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In 1992, Kubo et al (3) isolated a steroidal glycoside, OSW-1, from OCA bulbs. The steroidal glycosides from Ornithogalum plants can be classified into four groups (cardenolide, cholestane, spirostane, and stigmastane glycosides (4). OSW-1 is classified as cholestane glycoside chemical structure formula: [3β,16β,17α-trihydroxycholest-5-en-22-one16-O-(2-O-4-methoxybenzoyl-β-D-xylopyranosyl)-(1→3)-(2-O-acetyl-α-Larabinopyranoside)].…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2017

View full text Add to dashboard Cite

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.

show abstract

Section: Introductionmentioning

confidence: 99%

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

et al. 2017

View full text Add to dashboard Cite

show abstract

“…5 The natural steroidal skeleton has been therefore developed as original anticancer drug candidates, for example, the notable of Withaferin A 6,7 and oxysterols. 8 Modification of some these natural products have yielded lots of better cytotoxic steroidal compounds, for example OSW-1 9 and other semi-synthetic cytotoxic steroids with platinum complex or alkylating agent hybrids. 10,11 Diosgenin is a C27 spiroacetal steroidal sapogenin abundantly available in Dioscorea species, fenugreek, and Costus speciosus, 12 which has been used as a healthy food, as well as the anti-hypercholesterolemia, antihypertriacyl glycerolemia, antidiabetes and antihyperglycemia ingredient in traditional Chinese medicine.…”

mentioning

confidence: 99%

Synthesis and cytotoxic activities of 2-substituted (25R)-spirostan-1,4,6-triene-3-ones via ring-opening/elimination and ‘click’ strategy

Yang

Huang

et al. 2015

Bioorganic & Medicinal Chemistry Letters

View full text Add to dashboard Cite

“…To fulfill these requirements, prior knowledge on the SAR of natural products is critical. The early studies on SAR of OSW‐1 indicated that both the sterol aglycone and the sugar moiety are required and their relative orientation to each other are important for its extremely potent cytotoxicity . In particular, the sterol side chain at C21 and the acyl groups of the disaccharide residue were found essential.…”

Section: Synthesis Of Fluorescent Probe By Site‐selective Acylation Omentioning

confidence: 99%

“…Because of the biomedical interest, several groups have achieved total synthesis of OSW‐1 and a number of its analogues have been synthesized to decipher the structure‐activity relationship (SAR) and to explore more potent analogues . In contrast, a relatively few studies have been reported on the development of chemical probes of OSW‐1 for investigation of its biological role .…”

Section: Introductionmentioning

confidence: 99%

“…Because of the biomedical interest, several groups have achieved total synthesis of OSW-1 and a number of its analogues have been synthesized to decipher the structureactivity relationship (SAR) and to explore more potent analogues. [8] In contrast, a relatively few studies have been reported on the development of chemical probes of OSW-1 for investigation of its biological role. [4,9,10] Here, we summarize our recent efforts in the synthesis, biological properties of probes derived from naturally occurring OSW-1 and their application to the analysis of intracellular localization and the interaction with known target proteins.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Development of Chemical Probes for Functional Analysis of Anticancer Saponin OSW‐1

Komatsu

Sakurai

2019

The Chemical Record

View full text Add to dashboard Cite

Chemical probe‐based approaches have proven powerful in recent years in the target identification studies of natural products. OSW‐1 is a saponin class of natural products with highly potent and selective cytotoxicity against various cancer cell lines. Understanding its mechanism of action is important for the development of anticancer drugs with potentially novel target pathways. This account reviews recent progress in the development of OSW‐1 derived probes for exploring the mechanism of its action. The key to the probe development is a judicious choice of functionalization sites and a selective functionalization strategy. The types of probes include fluorescent probes for cellular imaging analysis and affinity probes for target identification analysis.

show abstract

Structure, Bioactivity, and Chemical Synthesis of OSW-1 and Other Steroidal Glycosides in the Genus Ornithogalum

Cited by 60 publications

References 151 publications

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

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

Synthesis and cytotoxic activities of 2-substituted (25R)-spirostan-1,4,6-triene-3-ones via ring-opening/elimination and ‘click’ strategy

Development of Chemical Probes for Functional Analysis of Anticancer Saponin OSW‐1

Contact Info

Product

Resources

About