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Structure Database (LMSD)

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Common Name

alpha-Spinasterol

Systematic Name

Stigmasta-7,22E-dien-3β-ol

Synonyms

24S-ethyl-5alpha-cholesta-7,22E-dien-3beta-ol
Bessisterol
Hitodesterol

LM ID

LMST01040126

Formula

C₂₉H₄₈O

Exact Mass

Calculate m/z

412.370516

Sum Composition

ST 29:2;O

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View NP-MRD ID(NMR) spectrum

Classification

Biological Context

α-Spinasterol is a bioavailable phytosterol originally isolated from spinach that acts as an antagonist at the transient receptor potential vanilloid type 1 (TRPV1) receptor (IC50 = 1.4 µM).^1,2 It has antinociceptive effects in a noxious heat-induced pain test and also reduces hyperalgesia and edema in a complete Freund’s adjuvant-induced inflammatory pain test in mice at a dose of 0.3 µmol/kg. α-Spinastrerol increases the seizure threshold in a dose-dependent manner and reduces depressive-like behavior in mice.^3,4 It also has anti-inflammatory activity in vivo and inhibits benign prostatic hyperplasia in rats.^5,6

This information has been provided by Cayman Chemical

References

1. Trevisan, G., Rossato, M.F., Walker, C.I., et al. Identification of the plant steroid α-spinasterol as a novel transient receptor potential vanilloid 1 antagonist with antinociceptive properties. J. Pharmacol. Exp. Ther. 343(2), 258-269 (2012).

2. Socala, K., and 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. 303, 19-25 (2016).

3. Socala, K., Nieoczym, D., Pieróg, M., et al. α-Spinasterol, a TRPV1 receptor antagonist, elevates the seizure threshold in three acute seizure tests in mice. J. Neural Transm. (Vienna) 122(9), 1239-1247 (2015).

4. Lee, M.-Y., Shin, I.-S., Kyoung, H., et al. α-Spinasterol from Melandrium firmum attenuates benign prostatic hyperplasia in a rat model. Mol. Med. Rep. 9(6), 2362-2366 (2014).

5. Hart, M.C., and Heyl, F.W. Spinasterol and some of its esters. J. Biol. Chem. 95(1), 311-315 (1931).

6. Borges, F.R., Silva, M.D., Córdova, M.M., et al. Anti-inflammatory action of hydroalcoholic extract, dichloromethane fraction and steroid α-spinasterol from Polygala sabulosa in LPS-induced peritonitis in mice. J. Ethnopharmacol. 151(1), 144-150 (2014).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Spinacia oleracea (#3562)

Magnoliopsida (#3398)

SPINASTEROL AND SOME OF ITS ESTERS,
J Biol Chem, 1932

Pubmed ID: 14241820

String Representations

InChiKey (Click to copy)

JZVFJDZBLUFKCA-FXIAWGAOSA-N

InChi (Click to copy)

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 (Click to copy)

C1[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@]([H])([C@]([H])(C)/C=C/[C@@H](CC)C(C)C)CC[C@@]4([H])C3=CC[C@@]2([H])C[C@@H](O)C1