54522-52-0

Basic information

• Product Name: methyl protodioscin
• Synonyms: methyl protodioscin;[(22R,25R)-22-Methoxy-26-(β-D-glucopyranosyloxy)furosta-5-ene-3β-yl]2-O,4-O-di-α-L-rhamnopyranosyl-β-D-glucopyranoside;[(25R)-26-(β-D-Glucopyranosyloxy)-22α-methoxyfurost-5-en-3β-yl]2-O,4-O-bis(α-L-rhamnopyranosyl)-β-D-glucopyranoside;3b,26-Dihydroxy-22a-methoxyfurost-5-ene 3-O-beta-chacotrioside 26-O-beta-D-glucopyranoside;Smilax saponin B;Methylprotodioscin(SMilax saponin B);22-Methoxylprotodioscin;22-O-Methylprotodioscin
• CAS NO: 54522-52-0
• Molecular Formula: C₅₂H₈₆O₂₂
• Molecular Weight: 1063.23
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 54522-52-0.mol
• Article Data: 1

Chemical Properties

• Melting Point: 175-177 °C
• Appearance: /
• Density: 1.43
• Refractive Index: 1.619
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Methanol (Slightly), Pyridine (Slightly), Water (Slightly)
• PKA: 12?+-.0.70(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: methyl protodioscin(CAS DataBase Reference)
• NIST Chemistry Reference: methyl protodioscin(54522-52-0)
• EPA Substance Registry System: methyl protodioscin(54522-52-0)

Safety Data

• Hazardous Substances Data: 54522-52-0(Hazardous Substances Data)

Usage

Uses

Methylprotodioscin is a steroidal saponin compound found in a number of plant species. It is known to be the active component of the herbal aphrodisiac plant Tribulus terrestris. It has also shown to produce significant increases in the levels of the hormonal levels in animal studies.

InChI:InChI=1/C52H86O22/c1-21(20-66-46-40(61)39(60)36(57)31(18-53)70-46)10-15-52(65-7)22(2)33-30(74-52)17-29-27-9-8-25-16-26(11-13-50(25,5)28(27)12-14-51(29,33)6)69-49-45(73-48-42(63)38(59)35(56)24(4)68-48)43(64)44(32(19-54)71-49)72-47-41(62)37(58)34(55)23(3)67-47/h8,21-24,26-49,53-64H,9-20H2,1-7H3/t21-,22+,23+,24+,26+,27-,28+,29+,30+,31-,32-,33+,34+,35+,36-,37-,38-,39+,40-,41-,42-,43+,44-,45?,46-,47+,48+,49-,50+,51+,52-/m1/s1

Upstream product

• 67-56-1 methanol 

Downstream Products

• 67-56-1 methanol 
• 6014-42-2 L-rhamnose 
• 78229-03-5 26-O-β-D-Glucopyranosylpseudodiosgenin-3-O-α-L-rhamnopyranosyl-(1->2)-β-D-glucopyranosid 
• 18615-48-0 L-arabino-6-deoxy-[2]hexosulose-bis-phenylhydrazone 
• 534-97-4 glucosazone 
• 109606-09-9 kryptogenin 3-O-β-chacotrioside 
• 21494-98-4 trigonelloside C 
• 19057-60-4 3-O-{α-L-rhamnopyranosyl-(1→4)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranosyl}-25(S)-spirost-5-en-3β-ol 
• 21494-98-4 proto-dioscin 
• 2280-44-6 D-Glucose 
• 19057-60-4 (25S)spirost-5-en-3β-ol-3-O-<α-L-rhamnopyranosyl(1-2)> <α-L-rhamnopyranosyl(1-4)>-β-D-glucopyranoside 
• 470-05-3 diosgenin 
• 73-34-7 L-rhamnose 
• 109617-40-5 3-O-β-chacotriosyl kryptogenin 26-O-β-D-glucoside 

Relevant articles and documents

Antineoplastic agents; II. Four furostanol glycosides from rhizomes of Dioscorea collettii var. hypoglauca

During activity-guided fractionations to screen for antineoplastic agents, further studies by means of preparative HPLC led to the isolation of four known furostanol saponins: protoneodioscin, protodioscin, protoneogracillin, protogracillin, along with their corresponding artifacts: methyl protoneodioscin, methyl protodioscin, methyl protoneogracillin, and methyl protogracillin, from the rhizomes of Dioscorea collettii var. hypoglauca. Among them, protoneodioscin, protodioscin, and protoneogracillin are first reported from the title plant. The structures of the compounds were established on the basis of chemical evidence and spectral analysis (1H-NMR, 13C-NMR, 1H-1H COSY, HMQC, HMBC, and FAB-MS). These eight compounds all caused morphological abnormality of Pyricularia oryzae mycelia. They also showed cytotoxic activities against the cancer cell line of K562 in vitro as antineoplastic agents.