α-Spinasterol | CAS#481-18-5 | TRPV1 receptor antagonist

MedKoo Cat#: 584429 | Name: α-Spinasterol

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Description:

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

α-Spinasterol is a plant-derived compound which was reported to act as a selective antagonist for the transient receptor potential vanilloid 1 (TRPV1) receptor.

Chemical Structure

α-Spinasterol

CAS#481-18-5

Theoretical Analysis

MedKoo Cat#: 584429

Name: α-Spinasterol

CAS#: 481-18-5

Chemical Formula: C29H48O

Exact Mass: 412.3705

Molecular Weight: 412.70

Elemental Analysis: C, 84.40; H, 11.72; O, 3.88

Price and Availability

Size	Price	Availability
1mg	USD 250.00	2 weeks
5mg	USD 475.00	2 weeks
10mg	USD 650.00	2 weeks

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Related CAS #

No Data

Synonym

Spinasterol; alpha-Spinasterin; Bessisterol; Hitodesterol

IUPAC/Chemical Name

5-alpha-Stigmasta-7,22-dien-3-beta-ol, (E)-

InChi Key

JZVFJDZBLUFKCA-FXIAWGAOSA-N

InChi Code

InChI=1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h8-9,11,19-23,25-27,30H,7,10,12-18H2,1-6H3/b9-8+/t20-,21-,22+,23+,25-,26+,27+,28+,29-/m1/s1

SMILES Code

CC[C@@H](C(C)C)/C=C/[C@@H](C)[C@H]1CC[C@@]2([H])C3=CC[C@@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C

Appearance

Solid powder

Purity

>98% (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

>2 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

Product Data

Instruction

View handling instruction

Biological target:

α-Spinasterol is a TRPV1 receptor antagonist (IC50 = 1.4 µM).

In vitro activity:

α-Spinasterol could be a potential candidate for anti-type 2 diabetes (T2D) therapy. α-Spinasterol may improve hyperglycemia by improving glucose uptake into skeletal muscle cells and enhancing insulin secretion in pancreatic β-cells. α-Spinasterol enhanced glucose uptake with no toxic effects on C2C12 cells. α-Spinasterol enhanced insulin secretion in response to high glucose concentrations, with no toxic effects on INS-1 cells Reference: Plants (Basel). 2022 Feb 28;11(5):658. https://pubmed.ncbi.nlm.nih.gov/35270128/

In vivo activity:

α-Spinasterol shows promise as a potential analgesic drug, with demonstrated effectiveness in reducing postoperative and neuropathic pain in mice. It was found to alleviate mechanical allodynia and reduce cell infiltration in injured tissue. Moreover, α-spinasterol inhibited COX-1 and COX-2 enzyme activities without affecting animal body temperature or locomotor activity. Reference: Br J Pharmacol. 2017 Dec;174(23):4247-4262. https://pubmed.ncbi.nlm.nih.gov/28849589/

	Solvent	mg/mL	mM
Solubility
	DMF	1.0	2.42
	Ethanol	0.3	0.61

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 412.70 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.

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. Lee D, Kim JY, Kwon HC, Kwon J, Jang DS, Kang KS. Dual Beneficial Effects of α-Spinasterol Isolated from Aster pseudoglehnii on Glucose Uptake in Skeletal Muscle Cells and Glucose-Stimulated Insulin Secretion in Pancreatic β-Cells. Plants (Basel). 2022 Feb 28;11(5):658. doi: 10.3390/plants11050658. PMID: 35270128; PMCID: PMC8912510. 2. Sedky NK, El Gammal ZH, Wahba AE, Mosad E, Waly ZY, El-Fallal AA, Arafa RK, El-Badri N. The molecular basis of cytotoxicity of α-spinasterol from Ganoderma resinaceum: Induction of apoptosis and overexpression of p53 in breast and ovarian cancer cell lines. J Cell Biochem. 2018 May;119(5):3892-3902. doi: 10.1002/jcb.26515. Epub 2018 Jan 25. PMID: 29143969. 3. Brusco I, Camponogara C, Carvalho FB, Schetinger MRC, Oliveira MS, Trevisan G, Ferreira J, Oliveira SM. α-Spinasterol: a COX inhibitor and a transient receptor potential vanilloid 1 antagonist presents an antinociceptive effect in clinically relevant models of pain in mice. Br J Pharmacol. 2017 Dec;174(23):4247-4262. doi: 10.1111/bph.13992. Epub 2017 Oct 18. PMID: 28849589; PMCID: PMC5715973. 4. Socała K, Wlaź P. Evaluation of the antidepressant- and anxiolytic-like activity of α-spinasterol, a plant derivative with TRPV1 antagonistic effects, in mice. Behav Brain Res. 2016 Apr 15;303:19-25. doi: 10.1016/j.bbr.2016.01.048. Epub 2016 Jan 22. PMID: 26808607.

In vitro protocol:

In vivo protocol:

1. Brusco I, Camponogara C, Carvalho FB, Schetinger MRC, Oliveira MS, Trevisan G, Ferreira J, Oliveira SM. α-Spinasterol: a COX inhibitor and a transient receptor potential vanilloid 1 antagonist presents an antinociceptive effect in clinically relevant models of pain in mice. Br J Pharmacol. 2017 Dec;174(23):4247-4262. doi: 10.1111/bph.13992. Epub 2017 Oct 18. PMID: 28849589; PMCID: PMC5715973. 2. Socała K, Wlaź P. Evaluation of the antidepressant- and anxiolytic-like activity of α-spinasterol, a plant derivative with TRPV1 antagonistic effects, in mice. Behav Brain Res. 2016 Apr 15;303:19-25. doi: 10.1016/j.bbr.2016.01.048. Epub 2016 Jan 22. PMID: 26808607.

1: Trevisan G, Rossato MF, Walker CI, Klafke JZ, Rosa F, Oliveira SM, Tonello R, Guerra GP, Boligon AA, Zanon RB, Athayde ML, Ferreira J. Identification of the plant steroid α-spinasterol as a novel transient receptor potential vanilloid 1 antagonist with antinociceptive properties. J Pharmacol Exp Ther. 2012 Nov;343(2):258-69. doi: 10.1124/jpet.112.195909. Epub 2012 Jul 26. PubMed PMID: 22837009. 2: Lee TH, Jung M, Bang MH, Chung DK, Kim J. Inhibitory effects of a spinasterol glycoside on lipopolysaccharide-induced production of nitric oxide and proinflammatory cytokines via down-regulating MAP kinase pathways and NF-κB activation in RAW264.7 macrophage cells. Int Immunopharmacol. 2012 Jul;13(3):264-70. doi: 10.1016/j.intimp.2012.05.005. Epub 2012 May 14. PubMed PMID: 22595195. 3: Socała K, Nieoczym D, Pieróg M, Wlaź P. α-Spinasterol, a TRPV1 receptor antagonist, elevates the seizure threshold in three acute seizure tests in mice. J Neural Transm (Vienna). 2015 Sep;122(9):1239-47. doi: 10.1007/s00702-015-1391-7. Epub 2015 Mar 13. PubMed PMID: 25764210; PubMed Central PMCID: PMC4540766. 4: Villaseñor IM, Domingo AP. Anticarcinogenicity potential of spinasterol isolated from squash flowers. Teratog Carcinog Mutagen. 2000;20(3):99-105. PubMed PMID: 10820420. 5: Badreddine A, Karym el M, Zarrouk A, Nury T, El Kharrassi Y, Nasser B, Cherkaoui Malki M, Lizard G, Samadi M. An expeditious synthesis of spinasterol and schottenol, two phytosterols present in argan oil and in cactus pear seed oil, and evaluation of their biological activities on cells of the central nervous system. Steroids. 2015 Jul;99(Pt B):119-24. doi: 10.1016/j.steroids.2015.01.005. Epub 2015 Jan 13. PubMed PMID: 25595450. 6: El Kharrassi Y, Samadi M, Lopez T, Nury T, El Kebbaj R, Andreoletti P, El Hajj HI, Vamecq J, Moustaid K, Latruffe N, El Kebbaj MS, Masson D, Lizard G, Nasser B, Cherkaoui-Malki M. Biological activities of Schottenol and Spinasterol, two natural phytosterols present in argan oil and in cactus pear seed oil, on murine miroglial BV2 cells. Biochem Biophys Res Commun. 2014 Apr 11;446(3):798-804. doi: 10.1016/j.bbrc.2014.02.074. Epub 2014 Feb 25. PubMed PMID: 24582563. 7: Lee MY, Shin IS, Kyoung H, Seo CS, Son JK, Shin HK. α-Spinasterol from Melandrium firmum attenuates benign prostatic hyperplasia in a rat model. Mol Med Rep. 2014 Jun;9(6):2362-6. doi: 10.3892/mmr.2014.2081. Epub 2014 Mar 28. PubMed PMID: 24682042. 8: Lee TH, Lee SM, Lee DY, Son Y, Chung DK, Baek NI, Kim J. A glycosidic spinasterol from Koreana stewartia promotes procollagen production and inhibits matrix metalloproteinase-1 expression in UVB-irradiated human dermal fibroblasts. Biol Pharm Bull. 2011;34(5):768-73. PubMed PMID: 21532171. 9: Jeong GS, Li B, Lee DS, Kim KH, Lee IK, Lee KR, Kim YC. Cytoprotective and anti-inflammatory effects of spinasterol via the induction of heme oxygenase-1 in murine hippocampal and microglial cell lines. Int Immunopharmacol. 2010 Dec;10(12):1587-94. doi: 10.1016/j.intimp.2010.09.013. Epub 2010 Oct 8. PubMed PMID: 20933625. 10: Borges FR, Silva MD, Córdova MM, Schambach TR, Pizzolatti MG, Santos AR. Anti-inflammatory action of hydroalcoholic extract, dichloromethane fraction and steroid α-spinasterol from Polygala sabulosa in LPS-induced peritonitis in mice. J Ethnopharmacol. 2014;151(1):144-50. doi: 10.1016/j.jep.2013.10.009. Epub 2013 Oct 23. PubMed PMID: 24161429. 11: Uchida K, Mizuno H, Hirota K, Takeda K, Takeuchi N, Ishikawa Y. Effects of spinasterol and sitosterol on plasma and liver cholesterol levels and biliary and fecal sterol and bile acid excretions in mice. Jpn J Pharmacol. 1983 Feb;33(1):103-12. PubMed PMID: 6876509. 12: WALTER ED. ISOLATION OF ALPHA-SPINASTERYL-D-GLUCOSIDE AND ALPHA-SPINASTEROL FROM ALFALFA. J Pharm Sci. 1964 Aug;53:970. PubMed PMID: 14241820. 13: Villaseñor IM, Lemon P, Palileo A, Bremner JB. Antigenotoxic spinasterol from Cucurbita maxima flowers. Mutat Res. 1996 Jun 10;360(2):89-93. PubMed PMID: 8649469. 14: Ragasa CY, Espineli DL, Shen CC. A new triterpene from Barringtonia asiatica. Nat Prod Res. 2012;26(20):1869-75. Epub 2011 Sep 19. PubMed PMID: 21929282. 15: Socała K, Wlaź P. Evaluation of the antidepressant- and anxiolytic-like activity of α-spinasterol, a plant derivative with TRPV1 antagonistic effects, in mice. Behav Brain Res. 2016 Apr 15;303:19-25. doi: 10.1016/j.bbr.2016.01.048. Epub 2016 Jan 22. PubMed PMID: 26808607. 16: Jeong SI, Kim KJ, Choi MK, Keum KS, Lee S, Ahn SH, Back SH, Song JH, Ju YS, Choi BK, Jung KY. alpha-Spinasterol isolated from the root of Phytolacca americana and its pharmacological property on diabetic nephropathy. Planta Med. 2004 Aug;70(8):736-9. PubMed PMID: 15326549. 17: Zhou CC, Sun XB, Liu JY, Luo SQ, Lu CY. [Anti-inflammatory effect of alpha-spinasterol]. Yao Xue Xue Bao. 1985 Apr;20(4):257-61. Chinese. PubMed PMID: 4072696. 18: Wang GK, Liu JS, Zhang CE, Wang Z, Cai BX, Wang G. [Study on Chemical Constituents of Kalimeris indica]. Zhong Yao Cai. 2015 Jan;38(1):81-4. Chinese. PubMed PMID: 26214873. 19: Ragasa CY, Espineli DL, Shen CC. New triterpenes from Barringtonia asiatica. Chem Pharm Bull (Tokyo). 2011;59(6):778-82. PubMed PMID: 21628919. 20: Tomimatsu T. [Isolation of sucrose and alpha-spinasterol from the roots of Bupleurum longiradiatum Turcz]. Yakugaku Zasshi. 1969 Apr;89(4):589-90. Japanese. PubMed PMID: 5816929.