54522-52-0
Chemical Structure
Methyl protodioscin
Synonym(s): NSC-698790; Smilax saponin B
- CAS No.: 54522-52-0
- Formula:C52H86O22
- Molecular Weight:1063.23
IUPAC Name: (2S,2'S,3R,3'R,4R,4'R,5R,5'R,6S,6'S)-6,6'-(((2R,3S,4S,5R,6R)-4-hydroxy-2-(hydroxymethyl)-6-(((4S,6aR,6bS,8aS,8bR,9S,10R,11aS,12aS,12bS)-10-methoxy-6a,8a,9-trimethyl-10-((R)-3-methyl-4-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)butyl)-3,4,5,6,6a,6b,7,8,8a,8b,9,10,11a,12,12a,12b-hexadecahydro-1H-naphtho[2',1':4,5]indeno[2,1-b]furan-4-yl)oxy)tetrahydro-2H-pyran-3,5-diyl)bis(oxy))bis(2-methyltetrahydro-2H-pyran-3,4,5-triol)
InChIKey: HSSJYSJXBOCKQM-GVTGEURHSA-N
SMILES: C[C@@]1([C@]([C@@H]2C)([H])[C@](O[C@]2(OC)CC[C@@H](C)CO[C@@H]([C@@H]([C@@H](O)[C@@H]3O)O)O[C@@H]3CO)([H])C4)[C@]4([H])[C@@](CC=C5[C@@]6(CC[C@H](O[C@@](O[C@H](CO)[C@@H](O[C@@](O[C@@H](C)[C@H](O)[C@H]7O)([H])[C@@H]7O)[C@@H]8O)([H])[C@@H]8O[C@@](O[C@@H](C)[C@H](O)[C@H]9O)([H])[C@@H]9O)C5)C)([H])[C@]6([H])CC1
Biological Activity: Methyl protodioscin (NSC-698790; Smilax saponin B) is a multi-target, selective, steroidal diglycoside inhibitor with antitumor activity that induces cell cycle arrest. The mechanism of action of Methyl protodioscin is complex, involving the induction of G2/M cell cycle arrest, regulation of the Bcl-2/Bax apoptotic pathway, inhibition of the Akt1/c-Myc axis and MAPK/ERK signaling, while simultaneously downregulating ADAM15 and inducing FOXO1 to reduce cholesterol synthesis. It also inhibits the JNK/c-Jun pathway, reducing the production of inflammatory factors (IL-6, TNF-α). Methyl protodioscin exhibits significant antitumor (inhibiting proliferation, migration, invasion, and inducing apoptosis), anti-inflammatory, and anti-restenosis activities. Methyl protodioscin can be used in research on lung cancer, prostate cancer, pancreatic cancer, and other tumors, as well as inflammatory diseases such as airway inflammation and enteritis[1][2][3][4][5][6][7].
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Methyl protodioscin | 99.67% | Methyl protodioscin (NSC-698790; Smilax saponin B) is a multi-target, selective, steroidal diglycoside inhibitor with antitumor activity that induces cell cycle arrest. The mechanism of action of Methyl protodioscin is complex, involving the induction of G2/M cell cycle arrest, regulation of the Bcl-2/Bax apoptotic pathway, inhibition of the Akt1/c-Myc axis and MAPK/ERK signaling, while simultaneously downregulating ADAM15 and inducing FOXO1 to reduce cholesterol synthesis. It also inhibits the JNK/c-Jun pathway, reducing the production of inflammatory factors (IL-6, TNF-α). Methyl protodioscin exhibits significant antitumor (inhibiting proliferation, migration, invasion, and inducing apoptosis), anti-inflammatory, and anti-restenosis activities. Methyl protodioscin can be used in research on lung cancer, prostate cancer, pancreatic cancer, and other tumors, as well as inflammatory diseases such as airway inflammation and enteritis. | ||||||||||||||||||||
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- [1]. Hu K, et al. The cytotoxicity of methyl protodioscin against human cancer cell lines in vitro. Cancer Invest. 2003 Jun;21(3):389-93. [Content Brief]
- [2]. Bai Y, et al. Methyl protodioscin induces G2/M cell cycle arrest and apoptosis in A549 human lung cancer cells. Pharmacogn Mag. 2014 Jul;10(39):318-24. [Content Brief]
- [3]. Chen J, et al. Anticancer Activity of Methyl Protodioscin against Prostate Cancer by Modulation of Cholesterol-Associated MAPK Signaling Pathway via FOXO1 Induction. Biol Pharm Bull. 2023;46(4):574-585. [Content Brief]
- [4]. Chen L, et al. Natural Compound Methyl Protodioscin Suppresses Proliferation and Inhibits Glycolysis in Pancreatic Cancer. Evid Based Complement Alternat Med. 2018 Mar 15;2018:7343090. [Content Brief]
- [5]. Zhang R, et al. Natural compound methyl protodioscin protects against intestinal inflammation through modulation of intestinal immune responses. Pharmacol Res Perspect. 2015 Mar;3(2):e00118. [Content Brief]
- [6]. Chung YL, et al. Methyl Protodioscin, a Steroidal Saponin, Inhibits Neointima Formation in Vitro and in Vivo. J Nat Prod. 2016 Jun 24;79(6):1635-44. [Content Brief]
- [7]. Lee JH, et al. Methyl Protodioscin from the Roots of Asparagus cochinchinensis Attenuates Airway Inflammation by Inhibiting Cytokine Production. Evid Based Complement Alternat Med. 2015;2015:640846. [Content Brief]
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