MedKoo Cat#: 574136 | Name: Echinocystic acid
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Echinocystic acid is a triterpene that induces nuclear translocation of the glucocorticoid receptor (GR) and reduces TNF-α-induced NF-κB signaling in HEK293 cells. Echinocystic acid suppresses RANKL-induced NF-κB activation, ERK phosphorylation, and osteoclastogenesis in mouse bone marrow macrophages. It induces neurite outgrowth in Neuro2A cells in a concentration-dependent manner, an effect that can be blocked by the JNK inhibitor SP 600125. Echinocystic acid also recovers reductions in femoral bone mineral density and trabecular thickness and number in a rat model of ovariectomy-induced osteoporosis.5

Chemical Structure

Echinocystic acid
Echinocystic acid
CAS#510-30-5

Theoretical Analysis

MedKoo Cat#: 574136

Name: Echinocystic acid

CAS#: 510-30-5

Chemical Formula: C30H48O4

Exact Mass: 472.3553

Molecular Weight: 472.71

Elemental Analysis: C, 76.23; H, 10.24; O, 13.54

Price and Availability

Size Price Availability Quantity
50mg USD 450.00 2 Weeks
100mg USD 850.00 2 Weeks
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Synonym
Echinocystic acid; Echinocystate; Echinocystic-acid
IUPAC/Chemical Name
(4aR,5R,6aS,6bR,8aR,10S,12aR,12bR,14bS)-5,10-dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylic acid
InChi Key
YKOPWPOFWMYZJZ-PRIAQAIDSA-N
InChi Code
InChI=1S/C30H48O4/c1-25(2)14-15-30(24(33)34)19(16-25)18-8-9-21-27(5)12-11-22(31)26(3,4)20(27)10-13-28(21,6)29(18,7)17-23(30)32/h8,19-23,31-32H,9-17H2,1-7H3,(H,33,34)/t19-,20-,21+,22-,23+,27-,28+,29+,30+/m0/s1
SMILES Code
CC1(C)CC[C@]2(C(O)=O)[C@H](O)C[C@@]3(C)[C@]4(C)CC[C@@]5([H])C(C)(C)[C@@H](O)CC[C@]5(C)[C@@]4([H])CC=C3[C@]2([H])C1
Appearance
Solid powder
Purity
>95% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Biological target:
Echinocystic acid a pentacyclic triterpene isolated from the fruits of Gleditsia sinensis Lam, has potent antioxidant, anti-inflammatory and anti-tumor properties.
In vitro activity:
EA (echinocystic acid) promoted neurite outgrowth in a concentration-dependent manner (neurite-bearing cell: F5, 12=15.52, p<0.05, n=3/group, Fig. 2B, length of neurite: F5, 12=25.98, p<0.05, n=3/group, Fig. 2C, the number of neurite: F5, 12=17.24, p<0.05, n=3/group, Fig. 2D). Next, to examine the effects of EA on cell cytotoxicity, this study determined cell viability using EZ-Cytox cell viability assay kit. EA (0, 5, 10, 15, 20, 25 µM) has no influence on cell viability at the designated incubation time (6 h: F5, 12=0.8491, p>0.05, n=3/group; 12 h: F5, 18=1.143, p>0.05, n=4/group, Fig. 3). This result suggests that EA has no cytotoxic effect in Neuro2a cells and the effect of EA on neurite outgrowth is not due to its effect on cell viability. Reference: Biol Pharm Bull. 2017;40(10):1724-1729. https://pubmed.ncbi.nlm.nih.gov/28966244/
In vivo activity:
The effects of grasping power after EA (echinocystic acid) treatment in ICH mice are shown in panel C of Figure 1. The grasping force in the ICH group (98.35±5.99 g, n=8) was significantly lower than that in the ICH + EA group (114.50±3.84 g, n=8, P<0.05). Furthermore, the rod-rotation persistence time in the EA + ICH group (71.25±7.09 s, n=8) was also significantly different from that in the ICH group (50.50±6.11 s, n=8, P<0.05), as shown in Figure 1A. Regarding the mNSS, the ICH + EA group (7.87±0.35, n=8) was significantly different from the ICH group (12.63±0.42, n=8) (P<0.05, Figure 1B). There were no statistically significant differences in body weight, claw force or rod-rotation persistence time between the groups before the model was established and the drug was administered. Reference: Ann Transl Med. 2020 Jan; 8(1): 6. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6995749/
Solvent mg/mL mM
Solubility
DMF 30.0 63.46
DMSO:PBS (pH 7.2) (1:2) 0.3 0.70
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 472.71 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Park HJ, Kwon H, Lee S, Jung JW, Ryu JH, Jang DS, Lee YC, Kim DH. Echinocystic Acid Facilitates Neurite Outgrowth in Neuroblastoma Neuro2a Cells and Enhances Spatial Memory in Aged Mice. Biol Pharm Bull. 2017;40(10):1724-1729. doi: 10.1248/bpb.b17-00324. PMID: 28966244. 2. Yang JH, Li B, Wu Q, Lv JG, Nie HY. Echinocystic acid inhibits RANKL-induced osteoclastogenesis by regulating NF-κB and ERK signaling pathways. Biochem Biophys Res Commun. 2016 Sep 2;477(4):673-677. doi: 10.1016/j.bbrc.2016.06.118. Epub 2016 Jun 24. PMID: 27349866. 3. Chen B, Zhao Y, Li W, Hang J, Yin M, Yu H. Echinocystic acid provides a neuroprotective effect via the PI3K/AKT pathway in intracerebral haemorrhage mice. Ann Transl Med. 2020 Jan;8(1):6. doi: 10.21037/atm.2019.12.35. PMID: 32055597; PMCID: PMC6995749. 4. Yu H, Li W, Cao X, Wang X, Zhao Y, Song L, Chen J, Wang S, Chen B, Xu Y. Echinocystic acid, a natural plant extract, alleviates cerebral ischemia/reperfusion injury via inhibiting the JNK signaling pathway. Eur J Pharmacol. 2019 Oct 15;861:172610. doi: 10.1016/j.ejphar.2019.172610. Epub 2019 Aug 16. Erratum in: Eur J Pharmacol. 2021 Feb 5;892:173790. PMID: 31425684.
In vitro protocol:
1. Park HJ, Kwon H, Lee S, Jung JW, Ryu JH, Jang DS, Lee YC, Kim DH. Echinocystic Acid Facilitates Neurite Outgrowth in Neuroblastoma Neuro2a Cells and Enhances Spatial Memory in Aged Mice. Biol Pharm Bull. 2017;40(10):1724-1729. doi: 10.1248/bpb.b17-00324. PMID: 28966244. 2. Yang JH, Li B, Wu Q, Lv JG, Nie HY. Echinocystic acid inhibits RANKL-induced osteoclastogenesis by regulating NF-κB and ERK signaling pathways. Biochem Biophys Res Commun. 2016 Sep 2;477(4):673-677. doi: 10.1016/j.bbrc.2016.06.118. Epub 2016 Jun 24. PMID: 27349866.
In vivo protocol:
1. Chen B, Zhao Y, Li W, Hang J, Yin M, Yu H. Echinocystic acid provides a neuroprotective effect via the PI3K/AKT pathway in intracerebral haemorrhage mice. Ann Transl Med. 2020 Jan;8(1):6. doi: 10.21037/atm.2019.12.35. PMID: 32055597; PMCID: PMC6995749. 2. Yu H, Li W, Cao X, Wang X, Zhao Y, Song L, Chen J, Wang S, Chen B, Xu Y. Echinocystic acid, a natural plant extract, alleviates cerebral ischemia/reperfusion injury via inhibiting the JNK signaling pathway. Eur J Pharmacol. 2019 Oct 15;861:172610. doi: 10.1016/j.ejphar.2019.172610. Epub 2019 Aug 16. Erratum in: Eur J Pharmacol. 2021 Feb 5;892:173790. PMID: 31425684.
1: Li Y, Chen L, Zheng D, Liu JX, Liu C, Qi SH, Hu PC, Yang XF, Min JW. Echinocystic acid alleviated hypoxic-ischemic brain damage in neonatal mice by activating the PI3K/Akt/Nrf2 signaling pathway. Front Pharmacol. 2023 Feb 9;14:1103265. doi: 10.3389/fphar.2023.1103265. PMID: 36843928; PMCID: PMC9947717. 2: Hyam SR, Jang SE, Jeong JJ, Joh EH, Han MJ, Kim DH. Echinocystic acid, a metabolite of lancemaside A, inhibits TNBS-induced colitis in mice. Int Immunopharmacol. 2013 Feb;15(2):433-41. doi: 10.1016/j.intimp.2012.12.017. Epub 2013 Jan 23. PMID: 23352442. 3: Geng D, Li Y, Zheng R, Wang R, Yang B, Zhang H, Zhang Y, Zhang F. Modulation of Kv7 Channel Currents by Echinocystic Acid. Mol Pharmacol. 2023 Aug;104(2):42-50. doi: 10.1124/molpharm.122.000640. Epub 2023 Jun 6. PMID: 37280100. 4: Miyase T, Melek FR, Ghaly NS, Warashina T, El-Kady M, Nabil M. Echinocystic acid 3,16-O-bisglycosides from Albizia procera. Phytochemistry. 2010 Aug;71(11-12):1375-80. doi: 10.1016/j.phytochem.2010.05.004. Epub 2010 Jun 4. PMID: 20621796. 5: Xiao L, Li M, Xiao Y, Yu L, Li Y, Zhang Z, Zhang G, Li Y, Zhou L, Liang Y. Echinocystic acid prevents obesity and fatty liver via interacting with FABP1. Phytother Res. 2023 Aug;37(8):3617-3630. doi: 10.1002/ptr.7839. Epub 2023 Apr 24. PMID: 37092723. 6: Joh EH, Gu W, Kim DH. Echinocystic acid ameliorates lung inflammation in mice and alveolar macrophages by inhibiting the binding of LPS to TLR4 in NF-κB and MAPK pathways. Biochem Pharmacol. 2012 Aug 1;84(3):331-40. doi: 10.1016/j.bcp.2012.04.020. Epub 2012 May 4. PMID: 22564908. 7: He D, Hu G, Zhou A, Liu Y, Huang B, Su Y, Wang H, Ye B, He Y, Gao X, Fu S, Liu D. Echinocystic Acid Inhibits Inflammation and Exerts Neuroprotective Effects in MPTP-Induced Parkinson's Disease Model Mice. Front Pharmacol. 2022 Jan 19;12:787771. doi: 10.3389/fphar.2021.787771. PMID: 35126128; PMCID: PMC8807489. 8: Chen B, Zhao Y, Li W, Hang J, Yin M, Yu H. Echinocystic acid provides a neuroprotective effect via the PI3K/AKT pathway in intracerebral haemorrhage mice. Ann Transl Med. 2020 Jan;8(1):6. doi: 10.21037/atm.2019.12.35. PMID: 32055597; PMCID: PMC6995749. 9: Cheng YC, Zhang X, Lin SC, Li S, Chang YK, Chen HH, Lin CC. Echinocystic Acid Ameliorates Arthritis in SKG Mice by Suppressing Th17 Cell Differentiation and Human Rheumatoid Arthritis Fibroblast-Like Synoviocytes Inflammation. J Agric Food Chem. 2022 Dec 28;70(51):16176-16187. doi: 10.1021/acs.jafc.2c05802. Epub 2022 Dec 14. PMID: 36516328. 10: Kang YM, Kim HM, Lee M, An HJ. Effects of Echinocystic Acid on Atopic Dermatitis and Allergic Inflammation of the Skin and Lungs. Phytomedicine. 2022 Sep;104:154211. doi: 10.1016/j.phymed.2022.154211. Epub 2022 Jun 6. PMID: 35717808. 11: Li S, Han J, Wang DS, Feng B, Deng YT, Wang XS, Yang Q, Zhao MG. Echinocystic acid reduces reserpine-induced pain/depression dyad in mice. Metab Brain Dis. 2016 Apr;31(2):455-63. doi: 10.1007/s11011-015-9786-6. Epub 2016 Jan 4. PMID: 26729203. 12: Joh EH, Jeong JJ, Kim DH. Inhibitory effect of echinocystic acid on 12-O-tetradecanoylphorbol-13-acetate-induced dermatitis in mice. Arch Pharm Res. 2014 Feb;37(2):225-31. doi: 10.1007/s12272-013-0092-8. Epub 2013 Mar 21. PMID: 23515933. 13: Tchegnitegni BT, Ahmed T, Ngouafong FT, Kamso VFK, Teponno RB, Lenta BN, Tapondjou LA, Ali A, Musharraf SG. Echinocystic Acid Bidesmoside Saponins from Microglossa afzelii O. Hoffm and Their Cytotoxic Activity against the CAL-27 Oral Squamous Carcinoma Cell Line. Metabolites. 2022 Oct 25;12(11):1018. doi: 10.3390/metabo12111018. PMID: 36355102; PMCID: PMC9694296. 14: Zhu D, Li B, Wang C, Jiang P, Tang F, Li Y. Echinocystic acid induces the apoptosis, and inhibits the migration and invasion of non-small cell lung cancer cells. Med Oncol. 2023 May 19;40(6):182. doi: 10.1007/s12032-023-02029-2. PMID: 37202561. 15: Ryu S, Shin JS, Jung JY, Cho YW, Kim SJ, Jang DS, Lee KT. Echinocystic acid isolated from Eclipta prostrata suppresses lipopolysaccharide-induced iNOS, TNF-α, and IL-6 expressions via NF-κB inactivation in RAW 264.7 macrophages. Planta Med. 2013 Aug;79(12):1031-7. doi: 10.1055/s-0032-1328767. Epub 2013 Jul 22. PMID: 23877917. 16: Huang CF, Wang WN, Sun CC, Wang YQ, Li L, Li Y, Li DJ. Echinocystic acid ameliorates hyperhomocysteinemia-induced vascular endothelial cell injury through regulating NF-κB and CYP1A1. Exp Ther Med. 2017 Nov;14(5):4174-4180. doi: 10.3892/etm.2017.5097. Epub 2017 Sep 1. PMID: 29104633; PMCID: PMC5658691. 17: Yang JH, Li B, Wu Q, Lv JG, Nie HY. Echinocystic acid inhibits RANKL-induced osteoclastogenesis by regulating NF-κB and ERK signaling pathways. Biochem Biophys Res Commun. 2016 Sep 2;477(4):673-677. doi: 10.1016/j.bbrc.2016.06.118. Epub 2016 Jun 24. PMID: 27349866. 18: Ma Z, Wang Y, Piao T, Liu J. Echinocystic Acid Inhibits IL-1β-Induced COX-2 and iNOS Expression in Human Osteoarthritis Chondrocytes. Inflammation. 2016 Apr;39(2):543-9. doi: 10.1007/s10753-015-0278-y. PMID: 26499345. 19: Baglin I, Mitaine-Offer AC, Nour M, Tan K, Cavé C, Lacaille-Dubois MA. A review of natural and modified betulinic, ursolic and echinocystic acid derivatives as potential antitumor and anti-HIV agents. Mini Rev Med Chem. 2003 Sep;3(6):525-39. doi: 10.2174/1389557033487917. PMID: 12871156. 20: Georgatza D, Gorgogietas VA, Kylindri P, Charalambous MC, Papadopoulou KK, Hayes JM, Psarra AG. The triterpene echinocystic acid and its 3-O-glucoside derivative are revealed as potent and selective glucocorticoid receptor agonists. Int J Biochem Cell Biol. 2016 Oct;79:277-287. doi: 10.1016/j.biocel.2016.08.028. Epub 2016 Aug 31. PMID: 27592454.