Determination of oleuropein in herbal preparation and Olea europaea L. extracts by HPLC

• Autorzy: Szymański M. , Witkowska-Banaszczak E. , Matławska I. , Szymański A.
• Języki publikacji: EN

Abstrakty

EN

Oleuropein is a secoiridoide monoterpene. It is found primarily in all parts of the Olea europaea L. tree, mostly in its unripe fruit and leaves. It has a number of beneficial effects on the human body, being readily absorbed from the gastrointestinal tract due to its hydrophilic properties. The paper presents a simple, rapid and precise method for the assay of oleuropein in herbal formulations and the European Olive leaf extract. Chromatographic separation was performed using a C-18 column with an acetonitrile/water 20/80% vol. mixture as the mobile phase. The method has a wide range of linearity between 0.05 and 1.5 mg/mL, very good repeatability of retention time, and accuracies between 95.8 and 103.3%. Its limit of detection is 0.04 mg/mL. The developed method was tested on two herbal formulations which are commercially available in Poland.

Słowa kluczowe

EN

oleuropein; Olea europaea L.; herbal products; high performance liquid chromatography

• Wydawca: Faculty of Chemical Technology and Engineering, University of Technology and Life Sciences, Bydgoszcz
• Czasopismo: Ars Separatoria Acta
• Rocznik: 2012/2013
• Tom: No. 9/10
• Strony: 55--63
• Opis fizyczny: Bibliogr. 32 poz., rys., tab.

Twórcy

autor

Szymański M.

• Department of Pharmacognosy, Poznań University of Medical Sciences Święcickiego 4,60-781 Poznań, Poland

autor

Witkowska-Banaszczak E.

• Department of Pharmacognosy, Poznań University of Medical Sciences Święcickiego 4,60-781 Poznań, Poland

autor

Matławska I.

• Department of Pharmacognosy, Poznań University of Medical Sciences Święcickiego 4,60-781 Poznań, Poland

autor

Szymański A.

• Faculty of Chemistry, Adam Mickiewicz University Umultowska 89b, 61-614 Poznań, Poland

Bibliografia

• [1] Soler-Rivas C, Espin J.C., Wichers H.J., 2000. Oleuropein and related compounds. J. Sci. Food Agric. 80 1013-1023.
• [2] Vissers M.N., Zock P.L., Roodenburg A.J.C., Leenen R., Katan M.B., 2002. Olive oil phenols are absorbed in humans. J. Nutr. 132, 409-417.
• [3] Keceli T., Gordon M.H., 2001. The antioxidant activity and stability of the phenolic fraction of green olives and extra virgin olive oil. J. Sci. Food Agric. 81, 1391-1396.
• [4] Owen R.W., Giacosa A., Hull W.E., Haubner R., Spiegelhalder B., Bartsch H., 2000. The antioxidant/anticancer potential of phenolic compounds isolated from olive oil. Eur. J. Cancer 36, 1235-1247.
• [5] Haloui E., Marzouk B., Marzouk Z., Bouraoui A., Fenina N., 2011. Hydroxytyrosol and oleuropein from olive leaves: Potent anti-inflammatory and analgesic activities. J. Food Agric. & Environ., 9(3-4), 128-133.
• [6] Susalit E., Agus N., Effendi I., Tjandrawinata R.R., Nofiarny D., Perrinjaquet-Moccetti T., Verbruggen M., 2011. Olive (Olea europaea) leaf extract effective in patients with stage-1 hypertension: comparison with captopril. Phytomedicine 15;18(4):251-8.
• [7] Khayyal M.T., El-Ghazaly M.A., Abdall D.M., Okpanyi S.N., Kreuter M.H., 2002. Blood pressure lowering effect of an olive leaf extract (Olea europaea) in L-NAME induced hypertension in rats. Arzneimittelforschung 52(11), 797-802.
• [8] Perrinjaquet-Moccettil T., Busjahn A., Schmidlin C., Schmidt A., Brad B., Aydogan C., Food supplementation with an olive (Olea europaea L.) leaf extract reduces blood pressure in borderline hypertensive monozygotic twins. Phytother. Res. 22 1239-42.
• [9] Hertog M.L.G., Feskens E.J.M., Katan M.B., Kromhout D.,1993. Dietary antioxidant flavonoids and risk of coronary heart disease: the Zutphen Elderly Study. Lancet 342, 1007.
• [10] Visioli F., Bellomo G., Montedoro G., Galli C., 1995. Low density lipoprotein oxidation is inhibited in vitro by olive oil constituents. Atheroscler 19. Keys A. Mediterranean diet and public health: personal reflections. Am. J. Clin. Nutr. 61 1321S-1323S.
• [11] Cao G., Sofic E., Prior R.L., 1997. Antioxidant and prooxidant behavior of flavonoids: structure-activity relationships. Free Radical Biol. Med. 22, 749-760.
• [12] Benkhalti F., Prost J., Paz E., Perez-Jimenez F., El Modafar C., El Boustani E., 2002. Effects of feeding virgin olive oil or their polyphenols on lipid of rat liver. Adv. Food Nutr. Res. 22 1067-1075.
• [13] Carluccio M.A., Siculella L., Ancora M.A., Massaro M., Scoditti E., Storelli C., Visioli F., Distante A., De Caterina R., 2003. Olive oil and red wine antioxidant polyphenols inhibit endothelial activation: antiatherogenic properties of Mediterranean diet phytochemicals. Arterioscler. Thromb. Vasc. Biol. 23(4) 622-629.
• [14] Manna C., Migliardi V., Golino P., Scognmiglio A., Galetti P., Chiariello M., Zappia V.. 2004. Oleuropein prevents oxidative myocardial injury by ischemia and reperfusion. J. Nutr. Biochem. 15, 461-468.
• [15] Huang M.T., Osawa T., Ho C.T., Rosen R.T., 1994. Food phytochemicals for cancer prevention. In Fruits and Vegetables. ACS Symposium Series no. 46. Washington, DC: American Chemical Society.
• [16] Johnson I.T., Williamson G., Musk S.R.R., 1994. Anticarcinogenic factors in plant foods. A new class of nutrients. Nutrition Research Rev. 7, 1-30.
• [17] Hamdi H.K., Castellon R., 2005. Oleuropein, a non-toxic olive iridoid, is an antitumor agent and cytoskeleton disruptor. Biochem Biophys Res Commun. 334 769-778.
• [18] Menendez J.A., Vazquez-Martin A., Garcia-Villalba R., Carrasco-Pancorbo A., Oliveras-Ferraros C., Fernandez-Gutierrez A., Segura-Carretero A., 2008. tabAnti-HER2 (erbB-2) oncogene effects of phenolic compounds directly isolated from commercial Extra-Virgin Olive Oil (EVOO). BMC Cancer. 8, 377.
• [19] Han J., Talorete T.P., Yamada P., Isoda H., 2009. Anti-proliferative and apoptotic effects of oleuropein and hydroxytyrosol on human breast cancer MCF-7 cells. Cytotechnology 59, 45-53.
• [20] Goulas V., Exarchou V., Troganis A.N., Psomiadou E., Fotsis T., Briasoulis E., Gerothanassis I.P., 2009. Phytochemicals in olive-leaf extracts and their antiproliferative activity against cancer and endothelial cells. Mol. Nutr. Food. Res. 53, 600-608.
• [21] Medina E., de Castro A., Romero C., Brenes M., 2006. Comparison of the concentrations of phenolic compounds in olive oils and other plant oils: correlation with antimicrobial activity. J. Agric. Food. Chem. 54, 4954-4961.
• [22] Caturla N., Perez Fons L., Estepa A., Micol V., 2005. Differential effects of oleuropein, a biophenol from Olea europaea, on anionic and zwiterionic phospholipid model membranes. Chem. Phys. Lipids. 137, 2-17.
• [23] Saija A., Uccella N., 2001. Olive biophenols: functional effects on human wellbeing. Trends Food Sci. Technol. 11, 357-363.
• [24] Bisignano, G., Tomaino, A., Lo Cascio, R., Crisafi, G., Uccella, N., Saija, A., 1999. On the in vitro antimicrobial activity of oleuropein and hydroxytyrosol. J. Pharm. Pharmacol. 51, 971-974.
• [25] Aziz N.H., Farag S.E., Mousa L.A.A., Abo Zaid M.A., 1998. Comparative antibacterial and antifungal effects of some phenolic compounds. Microbios. 93, 43-54.
• [26] Jemai H., El Feki A., Sayadi S., 2009. Antidiabetic and Antioxidant Effects of Hydroxytyrosol and Oleuropein from Olive Leaves in Alloxan-Diabetic Rats. J. Agric. Food Chem. 57(19), 8798-8804.
• [27] Al-Azzawiea H.F., Alhamdanib M.S., 2006. Hypoglycemic and antioxidant effect of oleuropein in alloxan-diabetic rabbits. Life Sci. 78(12), 1371-1377.
• [28] Corey E.J., 2007. Molecules and medicine. Hoboken: Wiley, 156.
• [29] Liu S, Zhao Q, Jiang S., 2003. Determination of the HIV-1 gp41 fusogenic core conformation modeled by synthetic peptides: applicable for identification of HIV-1 fusion inhibitors. Peptides 24, 1303-1313.
• [30] Zhao G., Yin Z., Donga J., 2009. Antiviral efficacy against hepatitis B virus replication of oleuropein isolated from Jasminum officinale L. var. grandiflorum, J. Ethnopharmacol 125, 265-268.
• [31] Shuang-Cheng M.A., Zhen-Dan H.E., Xue-Long D., Pui-Hay B. P., Eng-Choon V.O., Hong-Xi X., Hon-Sun L.S, Song-Fong L., 2001. In Vitro Evaluation of Secoiridoid Glucosides from the Fruits of Ligustrum lucidum as Antiviral Agents. Chem. Pharm. Bull. 49(11), 1471-1473.
• [32] Farmakopea VIII. PTF 2008; Vol. III:2533-4.