639-14-5

Usage

Uses

Used in Pharmaceutical Industry:
(3beta,4alpha)-3-hydroxy-23-oxoolean-12-en-28-oic acid is used as a pharmaceutical agent for its potential therapeutic properties. Its unique structure allows it to exhibit various biological activities, such as anti-inflammatory, anti-tumor, and immunomodulatory effects. This makes it a promising candidate for the development of new drugs targeting various diseases.
Used in Cosmetic Industry:
In the cosmetic industry, (3beta,4alpha)-3-hydroxy-23-oxoolean-12-en-28-oic acid is used as an active ingredient for its potential skin benefits. Its anti-inflammatory and immunomodulatory properties may contribute to the development of skincare products that promote skin health and address various skin concerns.
Used in Nutraceutical Industry:
(3beta,4alpha)-3-hydroxy-23-oxoolean-12-en-28-oic acid is also used in the nutraceutical industry as a dietary supplement. Its potential health benefits, such as anti-inflammatory and anti-tumor properties, make it a valuable addition to products aimed at promoting overall health and well-being.

Upstream product

• 32448-19-4 28-Hydroxy-23,28-dioxoolean-12-en-3β-yl β-D-Glucopyranoside 
• 1028100-31-3 gypsogenin 28-O-α-D-galactopyranosyl’-(1→6)-β-D-glucopyranosyl-(1 →6)[β-D-glucopyranosyl-(1→3)]-β-D-glucopyranosylester 
• 1028100-33-5 3-O-β-D-galactopyranosyl-(1->2)-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-xylopyranosyl-(1->4)-α-L-rhamnopyranosyl-(1->2)-β-D-fucopyranoside 
• 1028100-34-6 3-O-β-D-galactopyranosyl-(1->2)-[β-D-xylopyranosyl-(1->3)]-β-D-glucuronopyranosyl gypsogenin 28-O-α-L-arabinopyranosyl-(1->3)-β-D-xylopyranosyl-(1->4)-α-L-rhamnopyranosyl-(1->2)-β-D-fucopyranoside 
• 1028100-35-7 3-O-β-D-galactopyranosyl-(1->2)-[β-D-xylopyranosyl-(1->3)]-β-D-glucuronopyranosyl gypsogenin 28-O-(6-O-acetyl)-β-D-glucopyranosyl-(1->3)-[β-D-xylopyranosyl-(1->4)]-α-L-rhamnopyranosyl-(1->2)-β-D-fucopyranoside 
• 1207550-40-0 3-O-β-D-galactopyranosyl-(1->2)-[β-D-xylopyranosyl-(1->3)]-β-D-glucuronopyranosyl gypsogenin 28-O-α-L-arabinopyranosyl-(1->4)-α-L-arabinopyranosyl-(1->3)-β-D-xylopyranosyl-(1->4)-α-L-rhamnopyranosyl-(1->2)-β-D-fucopyranosyl ester 
• 1207550-42-2 3-O-β-D-galactopyranosyl-(1->3)-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-xylopyranosyl-(1->3)-β-D-xylopyranosyl-(1->4)-α-L-rhamnopyranosyl-(1->2)-β-D-fucopyranosyl ester 
• 465-99-6 hedaragenin 
• 96552-97-5 C₄₉H₇₆O₁₉ 

Downstream Products

• 486-34-0 1,2,7-trimethylnaphthalene 
• 465-99-6 hedaragenin 
• 582-16-1 2,7-dimethylnaphthalene 
• 108368-99-6 6-Hydroxy-1.2.5-trimethyl-naphthalin 
• 1679-02-3 2,9-dimethyl-picene 
• 641-91-8 1,2,5-trimethylnaphthalene 
• 1616947-39-7 benzyl 3-(acetyloxy)-23-oxoolean-12-en-28-oate 
• 1616947-29-5 benzyl 3-hydroxy-23-oxoolean-12-en-28-oate 
• 466-02-4 hedragonic acid 

Relevant academic research and scientific papers

New triterpenoidal saponins from Gypsophila repens

Six new triterpene glycosides, repensosides A-F (1-6, resp.), were isolated from the roots of Gypsophila repens L. Their structures, established by extensive 1D- and 2D-NMR spectroscopic experiments as well as MS analyses, were found to be based on gypsogenic acid (or gypsogenin) as aglycone, with three to nine branched or unbranched sugar moieties.

New triterpenoid saponin glycosides from the fruit fibers of: Trichosanthes cucumerina L.

Five new triterpenoid saponin glycosides, trichocucumerisides A-E (1-5), together with eleven known compounds (6-16) were isolated from Trichosanthes cucumerina fruit fibers. The structures of the new compounds were elucidated by detailed analysis of NMR and mass spectroscopic data as well as chemical reactions. The anti-inflammatory study against nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW264.7 cells shows that compounds 7 and 9 exhibited stronger NO inhibitory activity, with IC50 values of 3.0 and 2.7 μM, respectively, with comparison to positive references Celecoxib and aminoguanidine (IC50 values 75.7 and 75.0 μM, respectively). Compounds 7 and 9 also possessed a greater selectivity index (SI) of approximately 3-4-fold activity than that of the positive references.

Interconversion of hederagenin and gypsogenin and accessing 4-epi-hedragonic acid

Gypsogenin (1) and hederagenin (2) were isolated by extracting the powdered roots of Saponaria officinalis and the pericarp of Sapindus saponaria, respectively. While the gypsophila derived saponin can be obtained easily and in large quantities as a technical product, the plant material from Sapindus saponaria is difficult to obtain in Europe and the North-Americas, whereas in Latin America it is readily available (unlike the gypsophila saponin). In order to achieve a better accessibility of both aglycones, gypsogenin (1) and hederagenin (2), a simple synthesis for their interconversion was developed. Modification of the reaction conditions led to the first synthesis of 4-epi-hedragonic acid (3).

MINIMAL SAPONIN ANALOGUES, SYNTHESIS AND USE THEREOF

Truncated triterpene saponin analogues containing a trisaccharide or tetrasaccharide ester are disclosed. Also disclosed are pharmaceutical compositions comprising truncated saponin analogues and synthetic methods of producing the truncated saponin analogues. Another aspect of the present application relates to a method for immunizing a subject, comprising administering to the subject the pharmaceutical composition comprising a minimal saponin analogue and an antigen.

Three new sulfated triterpenoids from the roots of Gypsophila pacifica

Three new sulfated triterpenoids (1-3), along with one known compound (4), were isolated from the roots of Gypsophila pacifica Kom. The structures of the new compounds were established as 3β-O-sulfate gypsogenin 28-O-β-d-glucopyranosyl ester (1), 3β-O-sulfate gypsogenin (2), and 3β-O-sulfate quillaic acid (3) on the basis of 1D, 2D NMR, and HR-ESI-MS methods.

New triterpenoid saponins from the roots of Gypsophila perfoliata Linn.

Nine new triterpenoid saponins (1-9) have been isolated from the roots of Gypsophila perfoliata Linn. Their structures were established on the basis of extensive NMR (1H, 13C, HSQC and HMBC) and ESIMS studies.

New triterpenoid saponins from the roots of Gypsophila pacifica Kom.

Six new triterpenoid saponins (1-6) have been isolated from the roots of Gypsophila pacifica Kom. Their structures were established on the basis of extensive NMR (1H, 13C, TOCSY, HSQC, and HMBC) and ESIMS studies.

New triterpenoid saponins with strong α-glucosidase inhibitory activity from the roots of Gypsophila oldhamiana

Seven new triterpenoid saponins (1-7), have been isolated and elucidated from the roots of Gypsophila oldhamiana together with five known triterpenoid saponins (8-12). These saponins which could be classified into three series: 3-O-monoglucosides (1, 8, 9), 28-O-monoglucosides (2-4, 12) and 3, 28-O-bidesmosides (5-7, 10, 11), have been evaluated for their α-glucosidase inhibition activity. As a result, the preliminary structure-activity relationships were discussed based on the position of sugar linkage attached to the aglycone, and 28-O-monoglucosides 2-4 and 12 showed significant inhibitory activities on α-glucosidase.

Triterpene saponins from Chenopodium quinoa Willd.

Twenty triterpene saponins (1-20) have been isolated from different parts of Chenopodium quinoa (flowers, fruits, seed coats, and seeds) and their structures have been elucidated by analysis of chemical and spectroscopic data including 1D- and 2D-NMR. Four compounds (1-4) were identified: 3β-[(O-β-d-glucopyranosyl-(1 → 3)-α-l-arabinopyranosyl)oxy]-23-oxo-olean-12-en-28-oic acid β-d-glucopyranoside (1), 3β-[(O-β-d-glucopyranosyl-(1 → 3)-α-l-arabinopyranosyl)oxy]-27-oxo-olean-12-en-28-oic acid β-d-glucopyranoside (2), 3-O-α-l-arabinopyranosyl serjanic acid 28-O-β-d-glucopyranosyl ester (3), and 3-O-β-d-glucuronopyranosyl serjanic acid 28-O-β-d-glucopyranosyl ester (4). The following known compounds have not previously been reported as saponin constituents from the flowers and the fruits of this plant: two bidesmosides of serjanic acid (5, 6), four bidesmosides of oleanolic acid (7-10), five bidesmosides of phytolaccagenic acid (11-15), four bidesmosides of hederagenin (16-19), and one bidesmoside of 3β,23,30-trihydroxy olean-12-en-28-oic acid (20). The cytotoxicity of these saponins and their aglycones was tested in HeLa cells. Induction of apoptosis in Caco-2 cells by bidesmosidic saponins 1-4 and their aglycones I-III was determined by flow cytometric DNA analysis. The saponins with an aldehyde group were most active. The relationships between structure and cytotoxic activity of saponins and their aglycones are discussed.

Triterpenoid saponins and sapogenins from Vaccaria segetalis

Four new triterpenoid saponins, vaccarosides E, F, G and H were isolated from the seeds of Vaccaria segetalis and were respectively defined to be 3- O-β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranosyl] quillaic acid 28- O-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-[α-L- arabinofuranosyl-(1 → 3)]-β-D-4-O-acetylfucopyranoside; 3-O-[β-D- galactopyranosyl-(1 → 2)-β-D-glucuronopyranosyl] 3β,4α,16α-trihydroxy- 23-norolean-12-en-28-oic acid 28-O-β-D-xylopyranosyl-(1 → 4)-α-L- rhamnopyranosyl-(1 → 2)-[α-L-arabinofuranosyl-(1 → 3)]-β-D-4-O- acetylfucopyranoside; 3-O-[β-D-galactopyranosyl-(1 → 2)-β-D- glucuronopyranosyl] gypsogenin 28-O-β-D-xylopyranosyl-(1 → 4)-α-L- rhamnopyranosyl-(1 → 2)-[α-L-arabinofuranosyl-(1 → 3)]-β-D-4-O- acetylfucopyranoside; and 3-O-[β-D-galactopyranosyl-(1 → 2)-β-D- glucuronopyranosyl] 3β,4α-dihydroxy-23-norolean-12-en-28-oic acid 28-O-β- D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-[α-L- arabinofuranosyl-(1 → 3)]-β-D-4-O-acetylfucopyranoside. Their structures were established on the basis of extensive NMR (DEPT, COSY, HOHAHA, HETCOR, HMBC AND NOESY), FAB-MS and ESI-MS studies as well as chemical strategies and enzymatic degradation. The new aglycones of two of the saponins have been designated as segetalic acid and vaccaric acid, respectively.