595-15-3

Usage

Uses

Used in Pharmaceutical Industry:
SOYASAPOGENOL B(P) is used as a therapeutic agent for its neuroprotective properties. It has been demonstrated to attenuate lipopolysaccharide-induced memory impairment in mice, making it a promising candidate for the development of treatments targeting cognitive decline and memory-related disorders.
Used in Research and Development:
Due to its unique chemical structure, SOYASAPOGENOL B(P) can be utilized as a starting material or intermediate in the synthesis of various bioactive compounds, contributing to the advancement of pharmaceutical research and drug development.
Used in Nutraceutical Industry:
Given its potential neuroprotective effects, SOYASAPOGENOL B(P) may also find applications in the nutraceutical industry as an ingredient in dietary supplements or functional foods aimed at promoting brain health and cognitive function.

InChI:InChI=1/C30H50O3/c1-25(2)16-20-19-8-9-22-27(4)12-11-23(32)28(5,18-31)21(27)10-13-30(22,7)29(19,6)15-14-26(20,3)24(33)17-25/h8,20-24,31-33H,9-18H2,1-7H3/t20-,21+,22+,23-,24+,26+,27-,28+,29+,30+/m0/s1

Upstream product

• 142750-17-2 3-O-α-L-rhamnopyranosyl(1->2)-β-D-xylopyranosyl(1->2)-6-O-methyl-β-D-glucuronopyranosyl-soyasapogenol B 22-O-β-D-glucopyranoside 
• 51330-27-9 soyasaponin I 
• 143519-29-3 Cloversaponin IV methyl ester 
• 82793-03-1 3-O-[β-D-glucopyranosyl(1->2)-β-D-glucuronopyranosyl]olean-12-en-3β,22β,24-triol 
• 55319-36-3 astragaloside VIII 
• 82793-05-3 3-O-[α-L-rhamnopyranosyl(1->2)-β-D-glucopyranosyl(1->2)-β-D-glucuronopyranosyl]olean-12-en-3β,22β,24-triol 
• 67-56-1 methanol 
• 100201-62-5 prosapogenol 
• 100201-60-3 sophoraflavoside I 

Downstream Products

• 83689-13-8 (3S,4S,4aR,6aR,6bS,8aR,9R,12aS,14aR,14bR)-4,6a,6b,8a,11,11,14b-Heptamethyl-4-trityloxymethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydro-picene-3,9-diol 
• 187394-38-3 3,24-O-benzylidene soyasapogenol B 
• 187393-81-3 3β,22β-dibenzyloxy-24-trityloxyolean-12-ene 
• 191996-24-4 C₆₂H₉₄O₄Si₂ 
• 83689-14-9 C₆₃H₇₄N₂O₅ 
• 83689-15-0 C₄₄H₆₀N₂O₅ 
• 83689-16-1 C₄₄H₅₈N₂O₅ 
• 187394-39-4 Acetic acid (3S,4S,4aR,6aR,6bS,8aR,9R,12aS,14aR,14bR)-9-benzyloxy-4-benzyloxymethyl-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydro-picen-3-yl ester 
• 186415-79-2 (4R,4aR,6aS,6bR,8aR,9S,12aR,12bR,14bS)-4-Benzyloxy-9-benzyloxymethyl-2,2,4a,6a,6b,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,12,12a,12b,13,14b-octadecahydro-picene 
• 187394-34-9 24-acetoxy-3β,22β-dibenzyloxyolean-12-ene 
• 187393-82-4 (3S,4R,4aR,6aR,6bS,8aR,9R,12aS,14aR,14bR)-3,9-Bis-benzyloxy-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydro-picene-4-carboxylic acid 
• 186415-74-7 (3S,4R,4aR,6aR,6bS,8aR,9R,12aS,14aR,14bR)-3,9-Bis-benzyloxy-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydro-picene-4-carbaldehyde 
• 186415-77-0 C₄₄H₆₀O₃ 
• 187394-40-7 22β,24-dibenzyloxy-3β-methoxyolean-12-ene 

Relevant academic research and scientific papers

Artefact formation during acid hydrolysis of saponins from Medicago spp.

Artefact compounds obtained during acid hydrolysis of saponins from Medicago spp. (Fabaceae), have been monitored and evaluated by GC-FID. Their identification has been performed by GC-MS and 1H and 13C NMR. Saponins with different substituents on the triterpenic pentacyclic aglycones were considered, and their hydrolysis products were detected and quantified during 10?h of time course reaction. From soyasapogenol B glycoside the well known soyasapogenols B, C, D and F were obtained together with a previously undescribed sapogenol artefact identified as 3β,22β,24-trihydroxyolean-18(19)-en and named soyasapogenol H. From a zanhic acid saponin two major artefact compounds identified as 2β,3β,16α-trihydroxyolean-13(18)-en-23,28-dioic acid and 2β,3β,16α-trihydroxyolean-28,13β-olide-23-oic acid were obtained, together with some zanhic acid. Other compounds, detected in very small amount in the reaction mixture, were also tentatively identified based on their GC-MS and UV spectra. The other most characteristic saponins in Medicago spp., hederagenin, bayogenin and medicagenic acid glycosides, under acidic condition of hydrolysis, released instead the correspondent aglycones and generated a negligible amount of artefacts. Nature of artefacts and mechanism of their formation, involving a stable tertiary carbocation, is here proposed and discussed for the first time.

New triterpenic saponins from the aerial parts of Medicago arabica (L.) Huds

The reinvestigation of saponin composition from Medicago arabica from Italy allowed the detection of nineteen (1-19) saponins. All of them were purified by reverse-phase chromatography and their structures elucidated by spectroscopic and spectrometric (1D and 2D NMR; ESI-MS/MS) and chemical methods. Fourteen were known saponins, previously found in other plants including other Medicago species. They have been identified as glycosides of oleanolic acid, 2β,3β-dihydroxyolean-12-en-28-oic acid, hederagenin, bayogenin and soyasapogenol B. Five saponins, identified as 3-O-[-α-L- arabinopyranosyl(1→2)-β-D-glucuronopyranosyl]-30-O-β-D- glucopyranosyl 2β,3β,30-trihydroxyolean-12-en-28-oic acid (1), 3-O-[α-L-arabinopyranosyl(1→2)-β-D-glucuronopyranosyl] -30-O-[β-D-glucopyranosyl]3β,30-dihydroxyolean-12-en-28-oic acid (2), 3-O-|β-D-glucuronopyranosyl]-30-O-[α-L-arabinopyranosyl(1→2) -β-D-glucopyranosyl] 2β,3β,30-trihydroxyolean-12-en-28-oic acid (3), 3-O-[β-D-glucuronopyranosyl]-30-O-[α-L- arabinopyranosyl(1→2)-β-D-glucopyranosyl] 3β,30-dihydroxyolean- 12-en-28-oic acid (4) and 3-O-[β-D-glucuronopyranosyl]-30-O-[β-D- glucopyranosyl] 2β,3β,30-trihydroxyolean-12-en-28-oic acid (5), are reported here as new natural compounds. These new saponins, possessing a hydroxy group at the 30-methyl position of the triterpenic skeleton, have never been previously found in the genus Medicago.

A γ-PYRONYL-TRITERPENOID SAPONIN FROM PISUM SATIVUM

A new triterpenoid saponin was isolated from Pisum sativum and characterized as 3-O-2)-β-D-galactopyranosyl(12)-β-D-glucuronopyranosyl(1)>-22-O-)>-3β,22β,24-trihydroxyolean-12-ene.The name chromosaponin I is proposed.Chromosaponin I yielded soyasaponin I, known as phytochrome inhibitor, during extraction, but the latter was not found in the free form in this plant. Key Word Index - Pisum sativum; Leguminosae; pea: phytochrome inhibitor; triterpenoid saponin; soyasaponin I derivative; chromosaponin I.

Four new oleanene derivatives from the sseeds of Astragalus complanatus

Four new methyl ester derivatives of oleanene glycosides (3-6) were isolated from the seeds of Astragalus complanatus R. BR. together with two known triterpene glycosides, astragaloside VIII methyl ester (1) and soyasaponin I methyl ester (2) after treatment with diazomethane during separation procedure. The structures of 3-6 were elucidated as 3-O-α-L-rhamnopyranosyl(1→2)-β-D-xylopyranosyl(1→2)-6-O-methy-β-D- glucuronopyranosyl-soyasapogenol B 22-O-β-D-glucopyranoside, 3-O-α-L-rhamnopyranosyl(1 →2)-β-D-galactopyranosyl(1→2)-6-O-methyl-β-D-glucuronopyranosyl-soy asapogenol B 22-O-β-D-glucopyranoside, 3-O-α-L-rhamnopyranosyl(1→2)-β-D-xylopyranosyl(1→2)-6-O-methyl-β-D -glucuronopyranosyl 3β,22β,24-trihydroxy-11-oxo-olean-12-ene and 3-O-α-L-rhamnopyranosyl (1→2)-β-D-galactopyranosyl(1→2)-6-O-methyl-β-D-glucuronopyranosyl 3β,22β,24-trihydroxy-11-oxo-olean-12-ene, respectively.