Cholinesterase and Tyrosinase Inhibitory Potential and Antioxidant Capacity of Lysimachia verticillaris L. and Isolation of the Major Compounds

Özgen, Ufuk; SENOL DENIZ, FATMA SEZER; Goren, Ahmet C; ERDOGAN ORHAN, ILKAY; Žemlička, Milan; Šmejkal, Karel; Vaclavik, Jiri; Svajdlenka, Emil; SENER, SILA OZLEM

doi:10.4274/tjps.galenos.2019.71598

Cholinesterase and Tyrosinase Inhibitory Potential and Antioxidant Capacity of Lysimachia verticillaris L. and Isolation of the Major Compounds

Ufuk ÖZGEN, (Karadeniz Teknik Üniversitesi, Eczacılık Fakültesi, Farmakognozi Anabilim Dalı, Trabzon, Türkiye)

Sıla Özlem ŞENER, (Karadeniz Teknik Üniversitesi, Eczacılık Fakültesi, Farmakognozi Anabilim Dalı, Trabzon, Türkiye)

Karel MEJKA, (Brno Veterinary and Pharmaceutical Sciences University, Faculty of Pharmacy, Department of Natural Drugs, Brno, Czechia)

Jiri VACLAVIK, (Brno Veterinary and Pharmaceutical Sciences University, Faculty of Pharmacy, Department of Natural Drugs, Brno, Czechia)

Fatma Sezer ŞENOL, (Gazi Üniversitesi, Eczacılık Fakültesi, Farmakognozi Anabilim Dalı, Ankara, Türkiye)

lkay ERDOĞAN ORHAN, (Gazi Üniversitesi, Eczacılık Fakültesi, Farmakognozi Anabilim Dalı, Ankara, Türkiye)

Emil SVAJDLENKA, (Brno Veterinary and Pharmaceutical Sciences University, Faculty of Pharmacy, Department of Natural Drugs, Brno, Czechia)

Ahmet C. GÖREN, (Bezmialem Vakıf Üniversitesi, Eczacılık Fakültesi, Kimya Bölümü, İstanbul, Türkiye)

Milan EMLI KA (Brno Veterinary and Pharmaceutical Sciences University, Faculty of Pharmacy, Department of Natural Drugs, Brno, Czechia)

Turkish Journal of Pharmaceutical Sciences

2 0

Yıl: 2020 Cilt: 17 Sayı: 5 Sayfa Aralığı: 528 - 534 Metin Dili: İngilizce DOI: 10.4274/tjps.galenos.2019.71598 İndeks Tarihi: 11-05-2021

Cholinesterase and Tyrosinase Inhibitory Potential and Antioxidant Capacity of Lysimachia verticillaris L. and Isolation of the Major Compounds

Öz:

Objectives: The scope of the present study was to specify the therapeutic potential for neurodegenerative diseases through evaluating cholinesterase and tyrosinase (TYR) inhibitory and antioxidant activity of Lysimachia verticillaris (LV), and to isolate the major compounds considering the most active fraction.Materials and Methods: The methanol extract (ME) of LV and the chloroform, ethyl acetate (EtOAC), and aqueous fractions obtained from it were used for biological activity and isolation studies. The ME and all fractions were tested for their acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and TYR inhibitory and antioxidant potentials using ELISA microtiter assays. Seven major compounds were isolated from the active EtOAC fraction by semi-preparative high performance liquid chromatography. The structures of the compounds were elucidated by several spectroscopic methods. Results: Marked AChE inhibitory activity was observed in the EtOAC fraction (6337±1.74%), BChE inhibitory activity in the ME and EtOAC fraction (85.84±3.01% and 83.82±3.93%), total phenol content in the EtOAC fraction (261.59±3.95 mg equivalent of gallic acid/1 g of extract) and total flavonoid contents in the EtOAC fraction (515.54±2.80 mg equivalent of quercetin/1 g of extract), and 2,2-diphenyl-1-picrylhydrazyl radical scavenging activity and ferric-reducing antioxidant power values in the aqueous and EtOAC fractions (92.54±0.67%, 92.11±0.30%; 2.318±0.054, 2.224±0.091, respectively). Accordingly, the isolation studies were carried out on the EtOAC fractions. Compounds 1-7 (gallic acid, (+)-catechin, myricetin 3-O-arabinofuranoside, myricetin 3-O-α-rhamnopyranoside, quercetin 3-O-β-glucopyranoside, quercetin 3-O-arabinofuranoside, and quercetin 3-O-α-rhamnopyranoside, respectively) were isolated from the active EtOAC fraction. Conclusion: LV may be a potential herbal source for treatment of neurodegenerative diseases based on its strong antioxidant activity and significant cholinesterase inhibition similar to that of the reference.

Anahtar Kelime:

Lysimachia verticillaris L.’nin Kolinesteraz ve Tirozinaz İnhibitör Etki Potansiyeli ve Antioksidan Kapasitesi ile Ana Bileşiklerinin İzolasyonu

Öz:

maç: Bu çalışmanın amacı, Lysimachia verticillaris’in (LV) kolinesteraz, tirozinaz inhibitör etkisini ve antioksidan aktivitesini değerlendirerek nörodejeneratif hastalıklar için terapötik potansiyelini belirlemek ve en etkili fraksiyondan hareketle ana bileşiklerini izole etmektir.Gereç ve Yöntemler: Biyolojik aktivite ve izolasyon çalışmaları için LV’nin metanol ekstresinden hareketle kloroform, EtOAC ve sulu fraksiyonları elde edilmiştir. Etkili EtOAC fraksiyonundan, yarı preparatif yüksek performanslı sıvı kromatografisi (YBSK) yöntemi ile 7 ana bileşik izole edilmiştir. İzole edilen bileşiklerin yapıları çeşitli spektroskopik yöntemler kullanılarak aydınlatılmıştır. Metanol ekstresi (ME) ve tüm fraksiyonların asetilkolinesteraz (AChE), butirilkolinesteraz (BChE), tirozinaz inhibitor etkileri ve antioksidan potansiyelleri ELISA yöntemleri kullanılarak belirlenmiştir.Bulgular: En yüksek AChE inhibitor etki EtOAc fraksiyonunda (%63,37±1,74), en yüksek BChE inhibitör etki ME’de ve etil asetat fraksiyonunda (%85,84±3,01 ve %83,82±3,93), en yüksek total fenolik içeriği etil asetat fraksiyonunda (261,59±3,95 mg gallik asit eşdeğeri/g ekstre), en yüksek total flavonoit içeriği etil asetat fraksiyonunda (515,54±2,80 mg kersetin eşdeğeri/1 g ekstre) gözlenmiştir. En yüksek 2,2-difenil-1-pikrilhidrazil radikal süpürücü etki ve demir azaltıcı antioksidan güç değerleri ise su ve EtOAC fraksiyonlarında sırasıyla %92,54±0.67, %92,11±0,30 ve 2,318±0,054 2,224±0,091 olarak belirlenmiştir. Aktivite sonuçlarına dayanarak izolasyon çalışmalarının etil asetat fraksiyonunda yürütülmesine karar verilmiştir. Etil asetat fraksiyonundan, gallik asit (1), (+) kateşin (2), mirsetin 3-O-arabinofuranozit (3), mirsetin 3-O-α-ramnopiranozit (4), kersetin 3-O-β-glukopiranozit (5), kersetin 3-O-arabinofuranozit (6) ve kersetin 3-O-α-ramnopiranozit (7) ana bileşikleri izole edilmiştir.Sonuç: LV, güçlü antioksidan aktivitesiye sahip olması ve referans bileşiklerle karşılaştırıldığında benzer kolinesteraz inhibitor etki göstermesi nedeniyle nörodejeneratif hastalıkların tedavisi için potansiyel bir bitkisel ilaç kaynağı olabilir.

Anahtar Kelime:

Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık

1. Orhan IE. Current concepts on selected plant secondary metabolites with promising inhibitory effects against enzymes linked to Alzheimer’s disease. Curr Med Chem. 2012;19:2252-2261.
2. Mendes E, Perry MJ, Francisco AP. Design and discovery of mushroom tyrosinase inhibitors and their therapeutic applications. Expert Opin Drug Disc. 2014;9:533-554.
3. Terzioglu S, Karaer F. An Alien Species New to the Flora of Turkey. Lysimachia japonica Thunb. (Primulaceae) Turk J Bot. 2009;33:123-126.
4. Kızılarslan Ç, Özhatay N. Wild plants used as medicinal purpose in the south part of İzmit (Northwest Turkey). Turk J Med Sci. 2012;9:199-218.
5. Tóth A, Riethmüller E, Alberti Á, Végh K, Kéry Á. Comparative phytochemical screening of phenoloids in Lysimachia species. Eur Chem Bull. 2012;1:27-30.
6. Marr KL, Bohm BA, Cooke C, Gunning P. Flavonoids of Hawaiian endemic Lysimachia in honour of professor GH Neil Towers 75thbirthday. Phytochemistry. 1998;49:553-557.
7. Hanganu D, Olah NK, Mocan A, Vlase L, Benedec D, Raita O, Toma CC. Comparative polyphenolic content and antioxidant activities of two Romanian Lysimachia species. Studies. Rev Chim. 2016;67:227-231.
8. Podolak I, Koczurkiewicz P, Michalik M, Galanty A, Zajdel P, Janeczko Z. A new cytotoxic triterpene saponin from Lysimachia nummularia L. Carbohydrate Res. 2013;375:16-20.
9. Wang J, Zhang Y, Zhang Y, Cui Y, Liu J, Zhang B. Protective effect of Lysimachia christinae against acute alcohol-induced liver injury in mice. Biosci Trends. 2012; 6:89-97.
10. Lee JO, Chang K, Kim CY, Jung SH, Lee SW, Oak MH. Lysimachia clethroides extract promote vascular relaxation via endothelium-dependent mechanism. J Cardiovasc Pharmacol. 2010;55:481-488.
11. Ellman GL, Courtney KD, Andres V, Featherstone RM. A new and rapidcolorimetric determination of acetylcholinesterase activity. Biochem Pharmacol. 1961;7:88-95.
12. Khan MTH, Orhan I, Senol FS, Kartal M, Sener B, Dvorská M, Smejkal K, Slapetová T. Cholinesterase inhibitory activities of some flavonoid derivatives and chosen xanthone and their molecular docking studies. Chem-Biol Interact. 2009;181:383-389.
13. Masuda T, Yamashita D, Takeda Y, Yonemori S. Screening for tyrosinase inhibitors among extracts of seashore plants and identification of potent inhibitors from Garcinia subelliptica. Biosci Biotechnol Biochem. 2005;69:197-201.
14. Blois MS. Antioxidant determinations by the use of a stable free radical. Nature. 1958;181:1199-1200.
15. Oyaizu M. Studies on products of browning reactions-antioxidative activities of products of browning reaction prepared from glucosamine. Jpn J Nutr. 1986;44:307-315.
16. Singleton VL, Rossi Jr. JA. Colorimetry of total phenolics withphosphomolibdic-phosphotungtic acid reagents. Am J Enol Viticult. 1965;16:144-158.
17. Woisky R, Salatino A. Analysis of propolis: some parameters and procedures for chemical quality control. J Apicol Res. 1998;37:99-105.
18. Eldashan OA. Isolation and structure elucidation of phenolic compounds of carob leaves grown in Egypt. Curr Res J Biol Sci. 2011;3:52-55.
19. Adrienne LD, Ya C, Alan PD, Lewis JR. 1H and 13C NMR assignments of some green tea polyphenols. Magnetic Res Chem. 1996;34:887-890.
20. Ek S, Kartimo H, Mattila S, Tolonen A. Characterization of phenolic compounds from Lingonberry (Vaccinium vitis-idaeae). J Agric Food Chem. 2006;54:9834-9842.
21. Aderogba MA, Ndhlala AR, Rengasamy KRR, Van Staden J. Antimicrobial and selected in vitro enzyme inhibitory effects of leaf extracts, flavonols and indole alkaloids isolated from Croton menyharthii. Molecules. 2013;18:12633-12644.
22. Ko JH, Kim BG, Kim JH, Kim H, Lim CE, Lim J, Lee C, Lim Y, Ahn, JH. Four glucosyltransferases from rice: cDNA cloning, expression, and characterization. J Plant Physiology. 2008;165:435-444.
23. Mansouri A, Embarek G, Kokkalou E, Kefalas P. Phenolic profile and antioxidant activity of the Algerian ripe date palm fruit (Phoenix dactylifera). Food Chem. 2005;89:411-420.
24. Verma AK, Rajkumar V, Banerjee R, Biswas S, Das AK. Guava (Psidium guajava L.) Powder as an Antioxidant Dietary Fibre in Sheep Meat Nuggets. Asian-Australas J Anim Sci. 2013;26:886-895.
25. Okoth DA, Chenia HY, Koorbanally NA. Antibacterial and antioxidant activities of flavonoids from Lannea alata (Engl.) Engl. (Anacardiaceae). Phytochem Lett. 2013;6:476-481.
26. Ramzi AA, Mothana MS, Al-Said AJ, Al-Rehaily TM, Thabet NA, Awad M, Lalk UL. Anti-inflammatory, antinociceptive, antipyretic and antioxidant activities and phenolic constituents from Loranthus regularis Steud. ex Sprague. Food Chem. 2012;130:344-349.
27. Sun LJ, Zhang JB, Lu XY, Zhang, LY, Zhang YL. Evaluation to the antioxidant activity of total flavonoids extract from persimmon (Diospyros kaki L.) leaves. Food Chem Toxicol. 2011;49:2689-2696.
28. Cao J, Xia X, Chen X, Xiao J, Wang Q. Characterization of flavonoids from Dryopteris erythrosora and evaluation of their antioxidant, anticancer and acetylcholinesterase inhibition activities. Food Chem Toxicol. 2013;51:242-250.
29. Orhan IE. Implications of some selected flavonoids towards Alzheimer’s disease with the emphasis on cholinesterase inhibition and their bioproduction by metabolic engineering. Curr Pharm Biotechnol. 2014;15:352-361.
30. Anand P, Singh B. Flavonoids as lead compounds modulating the enzyme targets in Alzheimer’s disease. Med Chem Res. 2013;22:3061-3075.
31. Odontuya G. Anti-oxidative, acetylcholinesterase and pancreatic lipase inhibitory activities of compounds from Dasiphora fruticosa, Myricaria alopecuroides and Sedum hybridum. Mongolian Journal of Chemistry. 2017;43:42-49.
32. Gasca CA, Castillo WO, Takahashi CS, Fagg CW, Magalhães PO, Fonseca-Bazzo YM, Silveira D. Assessment of anti-cholinesterase activity and cytotoxicity of cagaita (Eugenia dysenterica) leaves. Food and Chemical Toxicology. 2017;109:996-1002.
33. Farhoosh R, Nyströmm L. Antioxidant potency of gallic acid, methyl gallate and their combinations in sunflower oil triacylglycerols at high temperature. Food Chem. 2018;244:29-35.
34. Ado MA, Abas F, Ismail IS, Ghazali HM, Shaari K. Chemical profile and antiacetylcholinesterase, antityrosinase, antioxidant and α-glucosidase inhibitory activity of Cynometra cauliflora L. leaves. J Sci Food Agric. 2015;95:635-642.
35. Russo D, Valentão P, Andrade PB, Fernandez EC, Milella L. Evaluation of antioxidant, antidiabetic and anticholinesterase activities of Smallanthus sonchifolius landraces and correlation with their phytochemical profiles. Int J Mol Sci. 2015;16:17696-71718.
36. Wang S, Wang D, Liu Z. Synergistic, additive and antagonistic effects of Potentilla fruticosa combined with EGb761 on antioxidant capacities and the possible mechanism. Ind Crops Prods. 2015;67:227-238.
37. Altunkaya A, Gökmen V, Skibsted LH. PH dependent antioxidant activity of lettuce (L. sativa) and synergism with added phenolic antioxidants. Food Chem. 2016;190:25-32.
38. Colon M, Nerín C. Synergistic, antagonistic and additive interactions of green tea polyphenols. Eur Food Res Technol. 2015;242:211-220.
39. Gupta S, Sarma S, Mao AA, Seal T. Antioxidant activity of different parts of Lysimachia laxa and Gymnocladus assamicus, a comparison using three different solvent extraction systems. J Chem Pharm Res. 2013;5:33-40.
40. Toth A, Toth G, Kery A. Polyphenol composition and antioxidant capacity of three Lysimachia species. Nat Prod Commun. 2014;9:1473-1478.
41. Li HY, Hao ZB, Wang XL, Huang L, Li JP. Antioxidant activities of extracts and fractions from Lysimachia foenum-graecum Hance. Bioresour Technol. 2009;100:970-974.
42. Wei JF, Zhang ZJ, Cui LL, Kang WY. Flavonoids in different parts of Lysimachia clethroides duby extracted by ionic liquid: analysis by HPLC and antioxidant activity assay. J Chem. 2017;2017:1-10.
43. Yildirim AB, Guner B, Karakas FP, Turker AU. Evaluation of antibacterial, antitumor, antioxidant activities and phenolic constituents of field-grown and in vitro-grown Lysimachia vulgaris L. Afr J Tradit Complement Altern Med. 2017;14:177-187.
44. Kaufmann D, Kaur Dogra A, Tahrani A, Herrmann F, Wink M. Extracts from traditional Chinese medicinal plants inhibit acetylcholinesterase, a known Alzheimer’s disease target. Molecules. 2016; 21:1161-1177.

APA	Özgen U, SENER S, Šmejkal K, Vaclavik J, SENOL DENIZ F, ERDOGAN ORHAN I, Svajdlenka E, Goren A, Žemlička M (2020). Cholinesterase and Tyrosinase Inhibitory Potential and Antioxidant Capacity of Lysimachia verticillaris L. and Isolation of the Major Compounds. , 528 - 534. 10.4274/tjps.galenos.2019.71598
Chicago	Özgen Ufuk,SENER SILA OZLEM,Šmejkal Karel,Vaclavik Jiri,SENOL DENIZ FATMA SEZER,ERDOGAN ORHAN ILKAY,Svajdlenka Emil,Goren Ahmet C,Žemlička Milan Cholinesterase and Tyrosinase Inhibitory Potential and Antioxidant Capacity of Lysimachia verticillaris L. and Isolation of the Major Compounds. (2020): 528 - 534. 10.4274/tjps.galenos.2019.71598
MLA	Özgen Ufuk,SENER SILA OZLEM,Šmejkal Karel,Vaclavik Jiri,SENOL DENIZ FATMA SEZER,ERDOGAN ORHAN ILKAY,Svajdlenka Emil,Goren Ahmet C,Žemlička Milan Cholinesterase and Tyrosinase Inhibitory Potential and Antioxidant Capacity of Lysimachia verticillaris L. and Isolation of the Major Compounds. , 2020, ss.528 - 534. 10.4274/tjps.galenos.2019.71598
AMA	Özgen U,SENER S,Šmejkal K,Vaclavik J,SENOL DENIZ F,ERDOGAN ORHAN I,Svajdlenka E,Goren A,Žemlička M Cholinesterase and Tyrosinase Inhibitory Potential and Antioxidant Capacity of Lysimachia verticillaris L. and Isolation of the Major Compounds. . 2020; 528 - 534. 10.4274/tjps.galenos.2019.71598
Vancouver	Özgen U,SENER S,Šmejkal K,Vaclavik J,SENOL DENIZ F,ERDOGAN ORHAN I,Svajdlenka E,Goren A,Žemlička M Cholinesterase and Tyrosinase Inhibitory Potential and Antioxidant Capacity of Lysimachia verticillaris L. and Isolation of the Major Compounds. . 2020; 528 - 534. 10.4274/tjps.galenos.2019.71598
IEEE	Özgen U,SENER S,Šmejkal K,Vaclavik J,SENOL DENIZ F,ERDOGAN ORHAN I,Svajdlenka E,Goren A,Žemlička M "Cholinesterase and Tyrosinase Inhibitory Potential and Antioxidant Capacity of Lysimachia verticillaris L. and Isolation of the Major Compounds." , ss.528 - 534, 2020. 10.4274/tjps.galenos.2019.71598
ISNAD	Özgen, Ufuk vd. "Cholinesterase and Tyrosinase Inhibitory Potential and Antioxidant Capacity of Lysimachia verticillaris L. and Isolation of the Major Compounds". (2020), 528-534. https://doi.org/10.4274/tjps.galenos.2019.71598

APA	Özgen U, SENER S, Šmejkal K, Vaclavik J, SENOL DENIZ F, ERDOGAN ORHAN I, Svajdlenka E, Goren A, Žemlička M (2020). Cholinesterase and Tyrosinase Inhibitory Potential and Antioxidant Capacity of Lysimachia verticillaris L. and Isolation of the Major Compounds. Turkish Journal of Pharmaceutical Sciences, 17(5), 528 - 534. 10.4274/tjps.galenos.2019.71598
Chicago	Özgen Ufuk,SENER SILA OZLEM,Šmejkal Karel,Vaclavik Jiri,SENOL DENIZ FATMA SEZER,ERDOGAN ORHAN ILKAY,Svajdlenka Emil,Goren Ahmet C,Žemlička Milan Cholinesterase and Tyrosinase Inhibitory Potential and Antioxidant Capacity of Lysimachia verticillaris L. and Isolation of the Major Compounds. Turkish Journal of Pharmaceutical Sciences 17, no.5 (2020): 528 - 534. 10.4274/tjps.galenos.2019.71598
MLA	Özgen Ufuk,SENER SILA OZLEM,Šmejkal Karel,Vaclavik Jiri,SENOL DENIZ FATMA SEZER,ERDOGAN ORHAN ILKAY,Svajdlenka Emil,Goren Ahmet C,Žemlička Milan Cholinesterase and Tyrosinase Inhibitory Potential and Antioxidant Capacity of Lysimachia verticillaris L. and Isolation of the Major Compounds. Turkish Journal of Pharmaceutical Sciences, vol.17, no.5, 2020, ss.528 - 534. 10.4274/tjps.galenos.2019.71598
AMA	Özgen U,SENER S,Šmejkal K,Vaclavik J,SENOL DENIZ F,ERDOGAN ORHAN I,Svajdlenka E,Goren A,Žemlička M Cholinesterase and Tyrosinase Inhibitory Potential and Antioxidant Capacity of Lysimachia verticillaris L. and Isolation of the Major Compounds. Turkish Journal of Pharmaceutical Sciences. 2020; 17(5): 528 - 534. 10.4274/tjps.galenos.2019.71598
Vancouver	Özgen U,SENER S,Šmejkal K,Vaclavik J,SENOL DENIZ F,ERDOGAN ORHAN I,Svajdlenka E,Goren A,Žemlička M Cholinesterase and Tyrosinase Inhibitory Potential and Antioxidant Capacity of Lysimachia verticillaris L. and Isolation of the Major Compounds. Turkish Journal of Pharmaceutical Sciences. 2020; 17(5): 528 - 534. 10.4274/tjps.galenos.2019.71598
IEEE	Özgen U,SENER S,Šmejkal K,Vaclavik J,SENOL DENIZ F,ERDOGAN ORHAN I,Svajdlenka E,Goren A,Žemlička M "Cholinesterase and Tyrosinase Inhibitory Potential and Antioxidant Capacity of Lysimachia verticillaris L. and Isolation of the Major Compounds." Turkish Journal of Pharmaceutical Sciences, 17, ss.528 - 534, 2020. 10.4274/tjps.galenos.2019.71598
ISNAD	Özgen, Ufuk vd. "Cholinesterase and Tyrosinase Inhibitory Potential and Antioxidant Capacity of Lysimachia verticillaris L. and Isolation of the Major Compounds". Turkish Journal of Pharmaceutical Sciences 17/5 (2020), 528-534. https://doi.org/10.4274/tjps.galenos.2019.71598