510-30-5

Basic information

• Product Name: ECHINOCYSTIC ACID
• Synonyms: ECHINOCYSTIC ACID;3-B,16-A-DIHYDROXYOLEAN-12-EN-28-OIC ACID;3BETA,16ALPHA-DIHYDROXY-OLEAN-12-EN-28-OIC ACID;(3beta,16alpha)-3,16-dihydroxyolean-12-en-28-oic acid;Echinocystic;ECHINOCYSTIC ACID(SH);ECHINOCYSTIC ACID hplc;ECHINOCYSTIC ACID WITH HPLC
• CAS NO: 510-30-5
• Molecular Formula: C30H48O4
• Molecular Weight: 472.7
• EINECS: 208-112-3
• Product Categories: Tri-Terpenoids;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors
• Mol File: 510-30-5.mol
• Article Data: 27

Chemical Properties

• Melting Point: 299-300°C
• Boiling Point: 585°Cat760mmHg
• Flash Point: 321.6°C
• Appearance: /
• Density: 1.14
• Storage Temp.: 2-8°C
• PKA: 4.43±0.70(Predicted)
• CAS DataBase Reference: ECHINOCYSTIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: ECHINOCYSTIC ACID(510-30-5)
• EPA Substance Registry System: ECHINOCYSTIC ACID(510-30-5)

Safety Data

• Hazardous Substances Data: 510-30-5(Hazardous Substances Data)

Usage

Description

Echinocystic acid is a triterpene that has been found in G. sinensis and has diverse biological activities. It induces nuclear translocation of the glucocorticoid receptor (GR) and reduces TNF-α-induced NF-κB signaling in HEK293 cells overexpressing GFP-GR. Echinocystic acid (12.5, 25, and 50 μM) suppresses RANKL-induced NF-κB activation, ERK phosphorylation, and osteoclastogenesis in mouse bone marrow macrophages (BMMs). It induces neurite outgrowth in Neuro2A cells in a concentration-dependent manner, an effect that can be blocked by the JNK inhibitor SP 600125 . In vivo, echinocystic acid (10 mg/kg per day) decreases escape latency in the Morris water maze and increases the length of neurite processes in the hippocampus of aged mice. Topical administration of echinocystic acid reduces expression of COX-2, inducible nitric oxide synthase (iNOS), TNF-α, and IL-1β and ear edema induced by phorbol 12-myristate 13-acetate (TPA; ) in a mouse model of dermatitis. Echinocystic acid also recovers reductions in femoral bone mineral density and trabecular thickness and number in a rat model of ovariectomy-induced osteoporosis.

Uses

Echinocystic Acid is a potential entry inhibitor for the HCV infection.

Upstream product

• 1431884-70-6 congmuyenoside E 

Downstream Products

• 6040-30-8 aegiceradienol 
• 582-16-1 2,7-dimethylnaphthalene 
• 488-23-3 1,2,3,4-Tetramethylbenzene 
• 2131-43-3 1,2,5,6-tetramethylnaphthalene 
• 486-34-0 1,2,7-trimethylnaphthalene 
• 1601461-19-1 N-(3β,16α-dihydroxy-olean-12-en-28-oyl)-(1-benzyl-1H-1,2,3-triazol-4-yl)-methylamine 

Relevant articles and documents

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.

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.

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.

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.

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.