510-30-5

Usage

Uses

Used in Antiviral Applications:
Echinocystic acid is used as a potential entry inhibitor for the Hepatitis C Virus (HCV) infection, providing a potential therapeutic approach to combat this viral disease.
Used in Anti-inflammatory Applications:
In a mouse model of dermatitis, echinocystic acid is used as a topical treatment to reduce the expression of COX-2, inducible nitric oxide synthase (iNOS), TNF-α, and IL-1β, as well as to alleviate ear edema induced by phorbol 12-myristate 13-acetate (TPA).
Used in Bone Health Applications:
Echinocystic acid is used to recover reductions in femoral bone mineral density and trabecular thickness and number in a rat model of ovariectomy-induced osteoporosis, suggesting its potential use in promoting bone health and treating osteoporotic conditions.
Used in Neurological Applications:
Echinocystic acid is used to induce neurite outgrowth in Neuro2A cells in a concentration-dependent manner, which can be blocked by the JNK inhibitor SP 600125. In vivo, it is used to decrease escape latency in the Morris water maze and increase the length of neurite processes in the hippocampus of aged mice, indicating its potential role in enhancing cognitive function and neural regeneration.

Upstream product

• 124901-25-3 (2S,3S,4S,5R,6R)-6-((3S,6aR,6bS,8R,8aR,14bR)-8a-Carboxy-8-hydroxy-4,4,6a,6b,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-yloxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid 
• 134352-45-7 tragopogonoside A methyl ester 
• 1431884-70-6 congmuyenoside E 
• 131588-15-3 tragopogonoside A 

Downstream Products

• 2309-45-7 Echinocystsaeure-methylester 
• 6040-30-8 aegiceradienol 
• 2309-45-7 3β,16α-dihydroxy-olean-12-en-28-oic acid methyl ester 
• 465-95-2 primulagenin A 

Relevant academic research and scientific papers

New antimicrobial and cytotoxic acylated triterpenoidal saponins from Gleditsia aquatica

Phytochemical investigation on the fruits of Gleditsia aquatica resulted in the isolation and identification of two new bisdesmosidic triterpenoidal saponins, aquaticasaponin A (1) and aquaticasaponin B (2) acylated with two and one monoterpenic acids, respectively, and one known cytokinin, aquaticine C (3). The structural elucidation of isolated metabolites was established on the basis of 1D, 2D NMR, and MS spectral analyses. The antimicrobial activity of the isolated compounds [1-3] was evaluated. Compound 1 exhibited the highest degree of activity against Syncephalastrum racemosum with an MIC value of 9.2 μM, whereas compound 2 exhibited the highest degree of activity against Escherichia coli with an MIC value of 67.3 μM. The isolated compounds also exhibited good cytotoxic activity against human breast cancer (MCF-7) and human colon cancer (HCT-116) cell lines with values of IC50 from 0.5 to 1.0 μM. Compound 1 was found to be the most active against colon cancer HCT-116 cell line with IC50 value of 0.5 μM.

Studies on the constituents of Calliandra anomala (KUNTH) MACBR. II. Structure elucidation of four acylated triterpenoidal saponins

Four new triterpenoidal saponins, called calliandra saponins B (8), C (9), D (10), and F (12), were isolated from the branches of Calliandra anomala (KUNTH) MACBR. The structures of these compounds were established on the basis of NMR spectra, FAB-MS, and the chemical evidence. These saponins, interestingly, have a N-acetyl glucosamine at the 3 position of the genin, and one or two monoterpene glycosides at the position of the sugar chain.

Bioactive saponins from Acacia tenuifolia from the suriname rainforest

Bioassay-guided fractionation of the MeOH extract of Acacia tenuifolia using the engineered yeast strains 1138, 1140, 1353, and Sc7 as the bioassay tool resulted in the isolation of the three new saponins 3, 5, and 6 and the three known saponins 1, 2, and 4. The structures of the new compounds were established on the basis of HRMS, 1D and 2D NMR spectral data on the intact saponins, and GC-MS analyses of the sugars. Compounds 1,2 and 5,6 showed cytotoxicity against mammalian cell lines.

Triterpenoid saponins and anti-inflammatory activity of Codonopsis lanceolata

The ethanolic root extract of Codonopsis lanceolata were evaluated for anti-inflammatory activity using the carrageenan induced rat hind paw edema model and displayed a significant activity of 51.82% inhibition at 200 mg/kg at 3 h (p 0.05). Further isolation of the extract yielded two new triterpenoid saponins, named codonolaside I (1) and codonolaside II (2). The spectroscopic and chemical data revealed their structures to be 3-O-[β-D-xylopyranosyl (1→3)-(6′-O-methyl)-β-D-glucuronopyranosyl]-3β, 16α-dihydroxyolean-12-ene-28-oic acid 28-O-[β-D-xylopyranosyl (1→4)-α-L-rhamnpyranosyl (1→2)-α-L-arabinopyranosyl] ester (1), and 3β, 16α-dihydroxyolean-12-ene-28-oic acid 28-O [β-D-xylopyranosyl (1→3)-β-D-xylopyranosyl (1→4)-α-L- rhamnpyranosyl (1→2)-α-L-arabinopyranosyl] ester (2).

Stachyssaponins I-VIII, new oleanane-type triterpene saponins from Stachys riederi Chamisso

Water extracts from the whole plant of Stachys riederi gave eight new bisdesmosides of echinocystic acid. The structures of these compounds were elucidated by chemical and spectroscopic evidence.

Murine metabolism and absorption of lancemaside A, an active compound in the roots of Codonopsis lanceolata

Lancemaside A, a triterpenoid saponin isolated from the roots of Codonopsis lanceolata, has been reported to ameliorate the reduction of blood testosterone levels induced by immobilization stress in mice. In the present study, we investigated the metabolism and absorption of lancemaside A in mice. After oral administration of lancemaside A at 100 mg/kg body weight, the unmetabolized compound appeared rapidly in plasma (tmax = 0.5 h). Lancemaside A has a low bioavailability (1.1%) because of its metabolism by intestinal bacteria and its poor absorption in the gastrointestinal tract. Furthermore, we identified four metabolites from the cecum of mice after oral administration of lancemaside A: codonolaside II, echinocystic acid, echinocystic acid 28-O-β-D-xylopyranosyl-(1 → 4)- α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl ester, and echinocystic acid 28-O-α-L- rhamnopyranosyl-(1 → 2)- α-L-arabinopyranosyl ester. Among these metabolites, codonolaside II and echinocystic acid were detected in plasma, and their tmax values were 4 and 8 h, respectively. These findings should be helpful for understanding the mechanism of the biological effect of lancemaside A. The Japanese Society of Pharmacognosy and Springer 2010.

Isolation and Structural Characterization of Echinocystic Acid Triterpenoid Saponins from the Australian Medicinal and Food Plant Acacia ligulata

The Australian plant Acacia ligulata has a number of traditional food and medicinal uses by Australian Aboriginal people, although no bioactive compounds have previously been isolated from this species. Bioassay-guided fractionation of an ethanolic extract of the mature pods of A. ligulata led to the isolation of the two new echinocystic acid triterpenoid saponins, ligulatasides A (1) and B (2), which differ in the fine structure of their glycan substituents. Their structures were elucidated on the basis of 1D and 2D NMR, GC-MS, LC-MS/MS, and saccharide linkage analysis. These are the first isolated compounds from A. ligulata and the first fully elucidated structures of triterpenoid saponins from Acacia sensu stricto having echinocystic acid reported as the aglycone. Compounds 1 and 2 were evaluated for cytotoxic activity against a human melanoma cancer cell line (SK-MEL28) and a diploid fibroblast cell line (HFF), but showed only weak activity.

Albidosides H and I, two new triterpene saponins from the barks of Acacia albida Del. (Mimosaceae)

Two new triterpene saponins, albidosides H (1) and I (2), along with the three known saponins were isolated from the barks of Acacia albida. Their structures were elucidated on the basis of extensive 1D- and 2D-NMR studies and mass spectrometry. Albidosid

New triterpene saponins from the roots of Acacia macrostachya (Mimosaceae)

Four new oleanane-type saponins, macrostachyaosides A, B, C, and D (1–4) were isolated from the roots of Acacia macrostachya. Their structures were elucidated on the basis of extensive 1D- and 2D-NMR data and HR-ESI-MS analyses. At concentrations of 100 μM of each compounds, none of the tested compounds caused a significant growth reduction against HL60 cells.

Pro-apoptotic activity of acylated triterpenoid saponins from the stem bark of Albizia chevalieri harms

As a continuation of our interest in apoptosis-inducing triterpenoid saponins from Albizia genus, phytochemical investigation of the stem bark of Albizia chevalieri led to the isolation of three new oleanane-type saponins, named chevalierosides A–C (1–3). Their structures were established on the basis of extensive analysis of 1D and 2D NMR (1H-, 13C NMR, DEPT, COSY, TOCSY, ROESY, HSQC and HMBC) experiments, HRESIMS studies, and by chemical evidence. The pro-apoptotic effect of the three saponins was evaluated on two human cell lines (pancreatic carcinoma AsPC-1 and hematopoietic monocytic THP-1). Cytometric analyses showed that saponins 1–3 induced apoptosis of both human cell lines (AsPC-1 and THP-1) in a dose-dependent manner.