LIPID MAPS

Structure Database (LMSD)

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Common Name

beta-Sitostenone

Systematic Name

(2R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

Synonyms

LM ID

LMST01040249

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

β-Sitostenone is a phytosterol that has been found in A. occidentale and has diverse biological activities.^1,2,3,4 It inhibits basal nitric oxide (NO) production in RAW 264.7 macrophages (IC50 = 15.9 µM).¹ β-Sitostenone is active against T. evansi (IC50 = 150 nM).² It reduces mean blood pressure in normotensive rats when administered at a dose of 2 mg/kg.³ β-Sitostenone (1.3 and 3 mg/kg) decreases blood glucose levels in dogs.⁴

This information has been provided by Cayman Chemical

References

1. Tewtrakul, S., and Subhadhirasakul, S. Effects of compounds from Kaempferia parviflora on nitric oxide, prostaglandin E2 and tumor necrosis factor-alpha productions in RAW264.7 macrophage cells. J. Ethnopharmacol. 120(1), 81-84 (2008).

2. Nyunt, K.S., Elkhateeb, A., Tosa, Y., et al. Isolation of antitrypanosomal compounds from Vitis repens, a medicinal plant of Myanmar. Nat. Prod. Commun. 7(5), 609-610 (2012).

3. Barla, A., Birman, H., Kültür, Ş., et al. Secondary metabolites from Euphorbia helioscopia and their vasodepressor activity. Turk. J. Chem. 30(3), 325-332 (2006).

4. Alexander-Lindo, R.L., Morrison, E.Y.S.A., and Nair, M.G. Hypoglycaemic effect of stigmast-4-en-3-one and its corresponding alcohol from the bark of Anacardium occidentale (cashew). Phytother. Res. 18(5), 403-407 (2004).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Radermachera (#83956)

Magnoliopsida (#3398)

Antituberculosis cycloartane triterpenoids from Radermachera boniana.,
J Nat Prod, 2011

Pubmed ID: 21469696

DOI: 10.1021/np200022b

Geodia cydonium (#6047)

Demospongiae (#6042)

STEROIDAL KETONES FROM THE SPONGE GEODIA CYDONIUM,
J Nat Prod, 1990

DOI: 10.1021/np50071a019

String Representations

InChiKey (Click to copy)

RUVUHIUYGJBLGI-XJZKHKOHSA-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/h18-21,24-27H,7-17H2,1-6H3/t20-,21-,24+,25-,26+,27+,28+,29-/m1/s1

SMILES (Click to copy)

C1[C@]2(C)[C@]3([H])[C@]([H])([C@]4([H])CC[C@]([H])([C@H](C)CC[C@@H](CC)C(C)C)[C@@]4(C)CC3)CCC2=CC(=O)C1