19057-60-4, Dioscin, CAS:19057-60-4

19057-60-4, 薯蓣皂苷,
Dioscin,
Collettiside III
Polyphyllin III
CAS:19057-60-4
C45H72O16 / 869.04
MFCD02094174

Dioscin, 薯蓣皂苷

Dioscin is a natural compound that has been shown to have cytotoxic effects on human tumor cells. Dioscin has been found to be an apoptosis-inducing factor, which activates the mitochondrial pathway of apoptosis. It has also been shown to inhibit the proliferation of 3T3-L1 preadipocytes and HL-60 cells by affecting the bcl-2 protein and toll-like receptor pathways. Dioscin is effective in treating myocardial infarcts, as well as other injuries such as squamous cell carcinoma.

Dioscin is a natural steroid saponin that was first isolated from plants used in herbal remedies. Early studies indicated that it inhibits proliferation and induces apoptosis in cancer cells. Dioscin has antioxidant activity that can alter cell signaling in cancer cells. It also induces autophagy prior to apoptosis in human lung cancer cell lines.

Dioscin analytical standard provided with w/w absolute assay, to be used for quantitative titration.

Dioscin(CCRIS 4123; Collettiside III) is a natural steroid saponin derived from several plants, showing potent anti-cancer effect against a variety of tumor cell lines. IC50 value:Target: Anticancer agentin vitro: dioscin (1, 2 and 4 μmol/L) could significantly inhibit the viability of LNCaP cells in a time- and concentration-dependent manner. Flow cytometry revealed that the apoptosis rate was increased after treatment of LNCaP cells with dioscin for 24 h, indicating that apoptosis was an important mechanism by which dioscin inhibited cancer. dioscin abrogated AKT phosphorylation, which subsequently impaired RANKL-induced nuclear factor-kappaB (NF-κB) signaling pathway and inhibited NFATc1 transcriptional activity. Moreover, in vivo studies further verified the bone protection activity of dioscin in osteolytic animal model. Dioscin reduced cell death and lactate dehydrogenase (LDH) release in cells subjected to I/R. I/R induced apoptosis and cytochrome c release from mitochondria to the cytosol and this was prevented by dioscin. In support, dioscin decreased Bax but increased Bcl-2 mRNA expression. Dioscin prevented I/R induced dissipation of ΔΨm.

Title: Dioscin

CAS Registry Number: 19057-60-4

CAS Name: (25R)-Spirost-5-en-3b-yl O-6-deoxy-a-L-mannopyranosyl-(1®2)-O-[6-deoxy-a-L-mannopyranosyl-(1®4)]-b-D-glucopyranoside

Additional Names: diosgenin bis-a-L-rhamnopyranosyl-(1®2 and 1®4)-b-D-glucopyranoside

Molecular Formula: C45H72O16

Molecular Weight: 869.04

Percent Composition: C 62.19%, H 8.35%, O 29.46%

Literature References: From Dioscorea tokoro Mal., Dioscoreaceae. Isoln: Tsukamoto et al., Pharm. Bull. 4, 35 (1956); Heitz, Compt. Rend. 248, 283 (1958). Structure: Kawasaki, Yamauchi, Chem. Pharm. Bull. 10, 703 (1962).

Properties: Crystals, decomp 275-277°. [a]D13 -115° (c = 0.373 in ethanol).

Optical Rotation: [a]D13 -115° (c = 0.373 in ethanol)

CAS Number	19057-60-4
Product Name	Dioscin
IUPAC Name	(2S,3R,4R,5R,6S)-2-[(2R,3S,4S,5R,6R)-4-hydroxy-2-(hydroxymethyl)-6-[(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-16-yl]oxy-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
Molecular Formula	C45H72O16
Molecular Weight	869.04 g/mol
InChI	InChI=1S/C45H72O16/c1-19-9-14-45(54-18-19)20(2)30-28(61-45)16-27-25-8-7-23-15-24(10-12-43(23,5)26(25)11-13-44(27,30)6)57-42-39(60-41-36(52)34(50)32(48)22(4)56-41)37(53)38(29(17-46)58-42)59-40-35(51)33(49)31(47)21(3)55-40/h7,19-22,24-42,46-53H,8-18H2,1-6H3/t19-,20+,21+,22+,24+,25-,26+,27+,28+,29-,30+,31+,32+,33-,34-,35-,36-,37+,38-,39-,40+,41+,42-,43+,44+,45-/m1/s1
InChI Key	VNONINPVFQTJOC-ZGXDEBHDSA-N
SMILES	CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CC=C6C5(CCC(C6)OC7C(C(C(C(O7)CO)OC8C(C(C(C(O8)C)O)O)O)O)OC9C(C(C(C(O9)C)O)O)O)C)C)C)OC1
Synonyms	Collettiside III
Canonical SMILES	CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CC=C6C5(CCC(C6)OC7C(C(C(C(O7)CO)OC8C(C(C(C(O8)C)O)O)O)O)OC9C(C(C(C(O9)C)O)O)O)C)C)C)OC1
Isomeric SMILES	C[C@@H]1CC[C@@]2([C@H]([C@H]3[C@@H](O2)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC=C6[C@@]5(CC[C@@H](C6)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O[C@H]8[C@@H]([C@@H]([C@H]([C@@H](O8)C)O)O)O)O)O[C@H]9[C@@H]([C@@H]([C@H]([C@@H](O9)C)O)O)O)C)C)C)OC1

COA:

Name: Dioscin CAS: 19057-60-4 M.F.: C₄₅H₇₂O₁₆ M.W.: 869.04

Batch No: 090613 Quantity: 256 g

*Items*	*Standards*	*Results*
Appearance	White crystalline powder	Positive
NMR and MS	Should comply	Complies
Identification	IR and TLC	Positive
Loss Weight On Dryness	Max. 1%	Complies
TLC (15%H₂SO₄-C₂H₅OH)	One spot	Complies
Assay	Min. 98%	98.6%