Chemical synthesis of 9(Z)-octadecenamide and its hypolipidemic effect: a bioactive agent found in the essential oil of mountain celery seeds - PubMed

Affiliations

• PMID: 20078072
• DOI: 10.1021/jf903573g

Chemical synthesis of 9(Z)-octadecenamide and its hypolipidemic effect: a bioactive agent found in the essential oil of mountain celery seeds

Ming-Ching Cheng et al. J Agric Food Chem. 2010.

Abstract

The unusual hypolipidemic activity of the methanolic fractionate of the essential oil (EOM) obtained from the mountain celery seed was previously reported. The most enriched 9(Z)-octadecenamide (oleamide) was speculated to be responsible for the relevant bioactivity. Chemically syntheized oleamide (CSO) yielded 85.1% with a purity of 98.6% when identified by RP-HPLC, FTIR, HREIMS, (1)H NMR, and (13)C NMR. CSO was tested for its antioxidative and hypolipidemic bioactivities. Results indicated CSO was potently hypolipidemic with regard to serum TG, TC, LDL-C, LDL-C/HDL-C, and hepatic TG (p < 0.05), but not for serum HDL-C and hepatic TC. In addition, CSO exhibited only poor antioxidative activity, implicating the possibility that the hypolipidemic and antioxidative bioactivity of original EOM was due to another coexisting constituent, probably gamma-selinene. Conclusively, oleamide is a potent hypolipidemic agent as regarding its effects on decreasing serum TG, TC, LDL-C and hepatic TG.

Similar articles

• Hypolipidemic and antioxidant activity of mountain celery (Cryptotaenia japonica Hassk) seed essential oils.

  Cheng MC, Lin LY, Yu TH, Peng RY. Cheng MC, et al. J Agric Food Chem. 2008 Jun 11;56(11):3997-4003. doi: 10.1021/jf703593v. Epub 2008 May 13. J Agric Food Chem. 2008. PMID: 18473476

• Optimization of bioactive compounds in buckwheat sprouts and their effect on blood cholesterol in hamsters.

  Lin LY, Peng CC, Yang YL, Peng RY. Lin LY, et al. J Agric Food Chem. 2008 Feb 27;56(4):1216-23. doi: 10.1021/jf072886x. Epub 2008 Jan 24. J Agric Food Chem. 2008. PMID: 18217700

• Arabinogalactan present in the mountain celery seed extract potentiated hypolipidemic bioactivity of coexisting polyphenols in hamsters.

  Lin LY, Ker YB, Chang CH, Chen KC, Peng RY. Lin LY, et al. Pharm Biol. 2011 Mar;49(3):319-26. doi: 10.3109/13880209.2010.516753. Pharm Biol. 2011. PMID: 21323484

• Hypolipidemic effects of different angiocarp parts of Alpinia zerumbet.

  Chuang CM, Wang HE, Peng CC, Chen KC, Peng RY. Chuang CM, et al. Pharm Biol. 2011 Dec;49(12):1257-64. doi: 10.3109/13880209.2011.589856. Epub 2011 Aug 16. Pharm Biol. 2011. PMID: 21846199

• Chemistry, technology, and nutraceutical functions of celery (Apium graveolens L.): an overview.

  Sowbhagya HB. Sowbhagya HB. Crit Rev Food Sci Nutr. 2014;54(3):389-98. doi: 10.1080/10408398.2011.586740. Crit Rev Food Sci Nutr. 2014. PMID: 24188309 Review.

Cited by

• Bioprospecting Endophytic Fungi of Forest Plants for Bioactive Metabolites with Antibacterial, Antifungal, and Antioxidant Potentials.

  El-Sayed ER, Baskaran A, Pomarańska O, Mykhailova D, Dunal A, Dudek A, Satam S, Strzała T, Łyczko J, Olejniczak T, Boratyński F. El-Sayed ER, et al. Molecules. 2024 Oct 8;29(19):4746. doi: 10.3390/molecules29194746. Molecules. 2024. PMID: 39407685 Free PMC article.

• Milk-based culture of Penicillium camemberti and its component oleamide affect cognitive function in healthy elderly Japanese individuals: a multi-arm randomized, double-blind, placebo-controlled study.

  Sasaki M, Oba C, Nakamura K, Takeo H, Toya H, Furuichi K. Sasaki M, et al. Front Nutr. 2024 Mar 27;11:1357920. doi: 10.3389/fnut.2024.1357920. eCollection 2024. Front Nutr. 2024. PMID: 38600994 Free PMC article.

• Lime (Citrus aurantifolia (Christm.) Swingle) Essential Oils: Volatile Compounds, Antioxidant Capacity, and Hypolipidemic Effect.

  Lin LY, Chuang CH, Chen HC, Yang KM. Lin LY, et al. Foods. 2019 Sep 7;8(9):398. doi: 10.3390/foods8090398. Foods. 2019. PMID: 31500259 Free PMC article.

• First report of the production of a potent biosurfactant with α,β-trehalose by Fusarium fujikuroi under optimized conditions of submerged fermentation.

  Reis CBLD, Morandini LMB, Bevilacqua CB, Bublitz F, Ugalde G, Mazutti MA, Jacques RJS. Reis CBLD, et al. Braz J Microbiol. 2018 Nov;49 Suppl 1(Suppl 1):185-192. doi: 10.1016/j.bjm.2018.04.004. Epub 2018 Apr 24. Braz J Microbiol. 2018. PMID: 29728339 Free PMC article.

• Subcritical Water Extraction of Undaria pinnatifida: Comparative Study of the Chemical Properties and Biological Activities across Different Parts.

  Park JS, Han JM, Park SW, Kim JW, Choi MS, Lee SM, Haq M, Zhang W, Chun BS. Park JS, et al. Mar Drugs. 2024 Jul 27;22(8):344. doi: 10.3390/md22080344. Mar Drugs. 2024. PMID: 39195460 Free PMC article.

MeSH terms

Substances

LinkOut - more resources

• Full Text Sources

  • American Chemical Society

• Other Literature Sources

  • The Lens - Patent Citations Database

• Medical

  • MedlinePlus Health Information

• Miscellaneous

  • NCI CPTAC Assay Portal