19083-00-2

Basic information

• Product Name: gracillin
• Synonyms: (25R)-3β-(2-O-α-L-Rhamnopyranosyl-3-O-β-D-glucopyranosyl-β-D-glucopyranosyloxy)spirosta-5-ene;[(25R)-Spirost-5-en-3β-yl]2-O-(6-deoxy-α-L-mannopyranosyl)-3-O-(β-D-glucopyranosyl)-β-D-glucopyranoside;[(25R)-Spirosta-5-ene-3β-yl]3-O-β-D-glucopyranosyl-2-O-α-L-rhamnopyranosyl-β-D-glucopyranoside;Diosgenin 3-O-β-gracillimatrioside;Gracilline;Diosgenin 3-O-beta-gracillimatrioside;DulcaMarinC;LilioglycosideG
• CAS NO: 19083-00-2
• Molecular Formula: C₄₅H₇₂O₁₇
• Molecular Weight: 248.32
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 19083-00-2.mol
• Article Data: 5

Chemical Properties

• Melting Point: 290-293℃ (DEC.)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.42
• Refractive Index: 1.622
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 12.78±0.70(Predicted)
• CAS DataBase Reference: gracillin(CAS DataBase Reference)
• NIST Chemistry Reference: gracillin(19083-00-2)
• EPA Substance Registry System: gracillin(19083-00-2)

Safety Data

• Hazardous Substances Data: 19083-00-2(Hazardous Substances Data)

Usage

Description

Gracillin is a steroidal saponin that has been found in C. speciosus and has diverse biological activities. It reduces cell growth in a panel of 58 leukemia, non-small cell lung, colon, CNS, prostate, melanoma, ovarian, renal, and breast cancer cell lines (GI50s = 0.58-2.44 μM). Gracillin reduces growth of fish Ich parasite (I. multifiliis) theronts (EC50 = 0.53 mg/L) and induces 100 and 92.5% mortality of I. multifiliis protomonts and encysted tomonts, respectively, when used at a concentration of 0.8 mg/L. It decreases the number of I. multifiliis-infected goldfish by approximately 75% when used at a concentration of 1 mg/L in tank water. Gracillin (100 mg/kg) reduces ear edema induced by arachidonic acid in mice.

Uses

Gracillin is a steroidal glycoside from the rhizomes of the family Dioscoreaceae with potential anti-proliferative effects.

InChI:InChI=1/C45H72O17/c1-19-8-13-45(55-18-19)20(2)30-27(62-45)15-26-24-7-6-22-14-23(9-11-43(22,4)25(24)10-12-44(26,30)5)57-42-39(61-40-36(53)34(51)31(48)21(3)56-40)38(33(50)29(17-47)59-42)60-41-37(54)35(52)32(49)28(16-46)58-41/h6,19-21,23-42,46-54H,7-18H2,1-5H3/t19-,20+,21+,23+,24-,25+,26+,27+,28-,29-,30+,31+,32-,33-,34-,35+,36-,37-,38+,39-,40+,41+,42-,43+,44+,45-/m1/s1

Upstream product

• 54848-30-5 proto-gracillin 
• 79975-20-5 balanitin-2 
• 512-04-9 diosgenin 
• 211797-93-2 diosgenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1-2)-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-β-D-glucopyranoside 
• 211797-94-3 diosgenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)-4,6-O-benzylidene-β-D-glucopyranoside 
• 14218-11-2 2,3,4,6-tetra-O-benzoylglucosyl bromide 
• 211797-95-4 diosgenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1-2)-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1-3)-4,6-O-benzylidene-β-D-glucopyranoside 

Downstream Products

• 2280-44-6 D-Glucose 
• 73-34-7 L-rhamnose 

Related news

Quantitative determination of gracillin (cas 19083-00-2) by HPLC–MS/MS after oral administration and its application to a pharmacokinetic study07/22/2019

A sensitive and credible high performance liquid chromatography hyphenated to mass spectrometry (HPLC–MS/MS) was established to quantify the concentration of gracillin in rat plasma. The plasma samples were subjected to a direct protein precipitation process with acetonitrile as a precipitant i...detailed

Relevant articles and documents

The substrate specificity of a glucoamylase with steroidal saponin-rhamnosidase activity from Curvularia lunata

In previous work, we studied and reported that an enzyme from Curvularia lunata 3.4381 had the novel specificity to hydrolyze the terminal rhamnosyl at C-3 position of steroidal saponin and obtained four transformed products; the enzyme was purified and ascertained as glucoamylase (EC 3.2.1.3 GA). In this work, the enzyme exhibiting steroidal saponin-rhamnosidase activity was systematically studied on 21?steroidal saponins and 6 ginsenosides. The results showed that the α-1,2-linked end-rhamnosyl residues at C-3 position of steroidal saponins could be hydrolyzed to corresponding secondary steroidal saponins, among which 18 compounds were isolated and identified, including 3 new secondary compounds. For the furostanosides having glucosyl residues at the C-26 position, hydrolysis occurred first at end-rhamnosyl at C-3 position to produce secondary furostanosides. The reaction of hydrolyzing glucosyl at C-26 position depended considerably on longer reaction times yielding the corresponding secondary spirostanosides (without rhamnosyl and glucosyl residues). The enzyme had the strict specificity for the terminal α-1,2-linked rhamnosyl residues of linear chain, or the terminal α-1,2-linked rhamnosyl residues with branched chain of 1,4-linked glycosyl residues of sugar chain at C-3 position of steroidal saponins, it was not specific for different aglycones, different glycons, and the number of glycon of sugar chain of steroidal saponin. The end-rhamnosyl of ginsenosides and p-nitrophenyl-α-l-rhamnopyranoside (pNPR) could not be hydrolyzed by the enzyme from C. lunata.

Synthesis of diosgenyl α-L-rhamnopyranosyl-(1 → 2)-[β-D- glucopyranosyl-(1 → 3)]-β-D-glucopyranoside (gracillin) and related saponins

Diosgenyl α-L-rhamnopyranosyl-(1 → 2)-[β-D-glucopyranosyl-(1 → 3)]- β-D-glucopyranoside (gracillin), a monodesmosidic saponin isolated from paris, dioscorea, and costacea species with promising cardiovascular and antitumor activities, was synthesized by s

A Micromethod for Determining the Branching Points in Oligosaccharides Based on Circular Dichroism

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