Phytochemical profile and angiotensin I converting enzyme (ACE) inhibitory activity of Limonium michelsonii Lincz
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Members of the genus Limonium are widely used as medicinal herbs due to their health-promoting effects, such as an ability to improve blood circulation by inhibiting angiotensin I converting enzyme (ACE). While the potential of L. michelsonii Lincz. (a medicinal plant endemic to Kazakhstan) to inhibit ACE has been demonstrated, the inhibitory activities of its secondary metabolites have not been explored. In this work, the principal phenolic compounds (1–20) among these metabolites were isolated to determine the components responsible for ACE inhibition. The natural abundances of the active constituents within the target plant were characterized by UPLC-Q-TOF/MS analysis. All of the isolated compounds except for gallates 10–12 were found to significantly inhibit ACE, with IC50 values of between 7.1 and 138.4 μM. Unexpectedly, the flavonol glycosides 16–20 were observed to be more potent than the corresponding aglycones 4 and 5. For example, quercetin (4) had IC50 = 30.3 μM, whereas its glycosides (16, 17) had IC50 = 10.2 and 14.5 μM, respectively. A similar trend was observed for myricetin (5) and its glycosides (18–20). In a kinetic study, the flavonols 3–5 and 16–20 and the dihydroflavonols 8 and 9 behaved as competitive inhibitors, whereas other flavones (1, 2, 13–15) and flavanones (6, 7) performed noncompetitive inhibition.
KeywordsLimonium michelsonii Lincz. Angiotensin I converting enzyme Phenolic metabolites Competitive inhibitors
Angiotensin I converting enzyme
Inhibitor concentration that produces a 50% decrease in activity
This work was done with research funds from the Ministry of Agriculture, Food and Rural Affairs (No. 315032-04-2-SB010) and the Next-Generation BioGreen 21 program, Rural Development Administration (SSAC, No. PJ01107001), Republic of Korea. The BK21 PLUS program supported scholarships for senior researchers and all other students.
Compliance with ethical standards
Conflict of interest
The authors declare no conflict of interest.
- 1.Baytenov MC (1963) Flora of Kazakhstan, part 7. Science Press, Almaty, p 75Google Scholar
- 2.Compiling Groups of Countrywide Herbal Medicine of China (1996) Compilation of countrywide herbal medicine of China, part 1, 2nd edn. People’s Medical Publishing House, Beijing, pp 407–408Google Scholar
- 3.Xu X, Bahargul K, Hang B, Jia XG (2009) Kazakh herbal medicine, part 1. The Ethnic Press, Beijing, pp 90–92Google Scholar
- 5.Sihem B, Nicola M, Teresa M, Tiziana E, Rita PA, Noureddine B, Samir B, Massimiliano DA, Antonio V (2015) Phenolic compounds from Limonium pruinosum. Nat Pro Com 10:319–321Google Scholar
- 8.Kazuyoshi K, Mami T, Kotaro M, Yoshishisa T (2005) A novel drime-type sesquiterpene from Limonium wrightii. J Nat Med 59(4):186–188Google Scholar
- 9.Faten M, Wided M, Vakhtang M, Andre P, Jean L, St-G Alexis, Riadh K (2014) Antiviral-guided fractionation and isolation of phenolic compounds from Limonium densiflorum hydroalcoholic extract. C R Chimie 19:726–732Google Scholar
- 12.Murray AP, Rodriguez S, Frontera MA, Tomas MA, Mulet MC (2004) Antioxidant metabolites from Limonium brasiliense (Boiss.) Kuntze. Z Naturforsch 59:477–480Google Scholar
- 16.Felmeden DC, Lip GY (2000) The renin–angiotensin–aldosterone system and fibrinolysis. JRAAS 1(3):240–244Google Scholar
- 23.Guvenalp Z, Ozbek H, Kuruuzum-uz A, Kazaz C, Demirezer LO (2009) Secondary metabolites from Nepeta heliotropifolia. Turk J Chem 33:667–675Google Scholar
- 25.Hilbert G, Temsamani H, Bordenave L, Pedrot E, Chaher N, Cluzet S, Delaunay JC, Ollat N, Delrot S, Merillon JM, Gomes E, Richard T (2015) Flavonol profiles in berries of wild Vitis accessions using liquid chromatography coupled to mass spectrometry and nuclear magnetic resonance spectrometry. Food Chem 169:49–58Google Scholar
- 26.Dawidar AM, Abdel-Mogib M, El-Nagga ME, Mostafa ME (2014) Isolation and characterization of Polygonum equisetiforme flavonoids and their acaricidal activity against Tetranychus urticae Koch. Res J Pharm Biol Chem Sci 5(4):140–148Google Scholar
- 27.Korul′kina LM, Shul′ts EE, Zhusupova GE, Abilov ZhA, Erzhanov KB, Chaudri MI (2014) Biologically active compounds from Limonium gmelinii and L. popovii. I. Chem Nat Compd 40(5):465–471Google Scholar
- 28.Sentandreu MA, Toldrá FA (2006) A fluorescence-based protocol for quantifying angiotensin-converting enzyme activity. Nat Protoc 1(5):2423–2437Google Scholar