human monoamine oxidase (hMAO) A and hMAO B inhibitors from Artemisia dracunculus L. herniarin and skimmin: human mononamine oxidase A and B inhibitors from A. dracunculus L.
-
Tuba Aydin
,
Hulya Akincioglu
,
Mehmet Gumustas
,
Ilhami Gulcin
,
Cavit Kazaz
und
Ahmet Cakir
Abstract
The aim of this study was to investigate the effects of extracts and pure Artemisia dracunculus L. (tarragon) metabolites on the antimonoamine oxidase and anticholinesterase activities. The compounds were characterized as stigmasterol (1), herniarin (2), (2E,4E)-1-(piperidin-1-yl)undeca-2,4-diene-8,10-diyn-1-one (3), (2E,4E)-N-isobutylundeca-2,4-dien-8,10-diynamide (4), 3,4-dehydroherniarin (5) and skimmin (6) by 1H-NMR, 13C-NMR, 1D and 2D NMR methods. The compounds 5 and 6 were isolated from tarragon for the first time. The extracts and pure compounds have inhibitory effects on the human monoamine oxidase (hMAO) A and B enzymes, whereas they did not exhibit any anticholinesterase activities. Among the tarragon compounds, only 2 and 6 compounds showed the inhibitory effects against hMAO A (IC50 = 51.76 and 73.47 μM, respectively) and hMAO B (IC50 = 0.84 and 1.63 mM, respectively). In the study, herniarin content in the extracts was also analysed by high-performance liquid chromatography and it was found that there was a relationship between the inhibition effects of the extracts and their herniarin content.
Funding source: Ağrı İbrahim Çeçen University Research Fund
Award Identifier / Grant number: BAP: ECZF.18.002BAP: FEF.18.003
Acknowledgments
This study was supported by grants of Ağrı İbrahim Çeçen University Research Fund (BAP: ECZF.18.002 and BAP: FEF.18.003).
Author contribution: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
References
1. Obolskiy, D, Pischel, I, Feistel, B, Glotov, N, Heinrich, M. Artemisia dracunculus L. (tarragon): A critical review of its traditional use, chemical composition, pharmacology, and safety. J Agr Food C 2011;59:11367–84. https://doi.org/10.1021/jf202277w.Suche in Google Scholar PubMed
2. Karimi, A, Hadian, J, Farzaneh, M, Khadivi-Khub, A. Phenotypic diversity and volatile composition of Iranian Artemisia dracunculus. Ind Crop Prod 2015;65:315–23. https://doi.org/10.1016/j.indcrop.2014.12.003.Suche in Google Scholar
3. Miraldi, E, Ferri, S, Mostaghimi, V. Botanical drugs and preparations in the traditional medicine of west Azerbaijan (Iran). J Ethnopharmacol 2001;75:77–87. https://doi.org/10.1016/s0378-8741(00)00381-0.Suche in Google Scholar PubMed
4. Bang, NC, Abyshev, AZ, Ivkin, DY. Synthesis and in vivo evaluation of new coumarin conjugates as potential indirect-action anticoagulants. Pharm Chem J 2019;53:419–22. https://doi.org/10.1007/s11094-019-02013-z.Suche in Google Scholar
5. Karatas, MO, Tekin, S, Alici, B, Sandal, S. Cytotoxic effects of coumarin substituted benzimidazolium salts against human prostate and ovarian cancer cells. J Chem Sci 2019;131:8. https://doi.org/10.1007/s12039-019-1647-0.Suche in Google Scholar
6. Sowa, P, Tarapatskyy, M, Puchalski, C, Jarecki, W, Dzugan, M. A novel honey-based product enriched with coumarin from melilotus flowers. J Food Meas Charact 2019;13:1748–54. https://doi.org/10.1007/s11694-019-00092-w.Suche in Google Scholar
7. Ruiz-Marcial, C, Chilpa, RR, Estrada, E, Reyes-Esparza, J, Farina, GG, Rodriguez-Fragoso, L. Anti proliferative, cytotoxic and antitumour activity of coumarins isolated from Calophyllum brasiliense. J Pharm Pharmacol 2007;59:719–25. https://doi.org/10.1211/jpp.59.5.0013.Suche in Google Scholar PubMed
8. Attia, G, Abou-El-Seoud, KA, Ibrahim, AS. Biotransformation of coumarins by Cunninghamella elegans. Afr J Pharm Pharmacol 2015;10:411–8, https://doi.org/10.5897/AJPP2015.4419.Suche in Google Scholar
9. Obistioiu, D, Cristina, RT, Schmerold, I, Chizzola, R, Stolze, K, Nichita, I, Chiurciu, V. Chemical characterization by gc-ms and in vitro activity against candida albicans of volatile fractions prepared from Artemisia dracunculus, Artemisia abrotanum, Artemisia absinthium and Artemisia vulgaris. Chem Cent J 2014;8:1–11. https://doi.org/10.1186/1752-153x-8-6.Suche in Google Scholar
10. Tipton, KF. Enzymology of monoamine-oxidase. Cell Biochem Funct 1986;4:79–87. https://doi.org/10.1002/cbf.290040202.Suche in Google Scholar PubMed
11. Vina, D, Serra, S, Lamela, M, Delogu, G. Herbal natural products as a source of monoamine oxidase inhibitors: A review. Curr Top Med Chem 2012;12:2131–44. https://doi.org/10.2174/156802612805219996.Suche in Google Scholar PubMed
12. Weyler, W, Hsu, YPP, Breakefield, XO. Biochemistry and genetics of monoamine-oxidase. Pharmacol Therapeut 1990;47:391–417. https://doi.org/10.1016/0163-7258(90)90064-9.Suche in Google Scholar PubMed
13. Vindis, C, Seguelas, MH, Bianchi, P, Parini, A, Cambon, C. Monoamine oxidase b induces erk-dependent cell mitogenesis by hydrogen peroxide generation. Biochem Bioph Res Co 2000;271:181–85. https://doi.org/10.1006/bbrc.2000.2524.Suche in Google Scholar PubMed
14. Cherrington, B, Englich, U, Niruntari, S, Grant, W, Hodgman, M. Monoamine oxidase a inhibition by toxic concentrations of metaxalone. Clin Toxicol 2019;2019:1–5. https://doi.org/10.1080/15563650.2019.1648815.Suche in Google Scholar PubMed
15. Bortolato, M, Floris, G, Shih, JC. From aggression to autism: New perspectives on the behavioral sequelae of monoamine oxidase deficiency. J Neural Transm 2018;125:1589–99. https://doi.org/10.1007/s00702-018-1888-y.Suche in Google Scholar PubMed PubMed Central
16. Erdemir, P, Celepci, DB, Aktas, A, Gok, Y, Kaya, R, Taslimi, P, Demir, Y, Gulcin, I. Novel 2-aminopyridine liganded pd(ii) n-heterocyclic carbene complexes: Synthesis, characterization, crystal structure and bioactivity properties. Bioorg Chem 2019;91:1–11. https://doi.org/10.1016/j.bioorg.2019.103134.Suche in Google Scholar PubMed
17. Rawa, MSA, Hassan, Z, Murugaiyah, V, Nogawa, T, Wahab, HA. Anti-cholinesterase potential of diverse botanical families from Malaysia: Evaluation of crude extracts and fractions from liquid-liquid extraction and acid-base fractionation. J Ethnopharmacol 2019;245. https://doi.org/10.1016/j.jep.2019.112160.Suche in Google Scholar PubMed
18. Al-Sayed, NAE, Farag, AES, Ezzat, MAF, Akincioglu, H, Gulc'in, İ, Abou-Seri, SM. Design, synthesis, in vitro and in vivo evaluation of novel pyrrolizine-basedcompounds with potential activity as cholinesterase inhibitors and anti-Alzheimer’s agents. Bioorg Chem 2019;93:103312, https://doi.org/10.1016/j.bioorg.2019.103312.Suche in Google Scholar PubMed
19. Genc Bilgicli, H, Kestane, A, Taslimi, P, Karabay, O, Bytyqi-Damoni, A, Zengin, M, Gulc'in, İ. Novel eugenol bearing oxypropanolamines: Synthesis, characterization, antibacterial, antidiabetic, and anticholinergic potentials. Bioorg Chem 2019;88:102931. https://doi.org/10.1016/j.bioorg.2019.102931.Suche in Google Scholar PubMed
20. Sharma, K. Cholinesterase inhibitors as alzheimer’s therapeutics. Mol Med Rep 2019;20:1479–87, https://doi.org/10.3892/mmr.2019.10374.Suche in Google Scholar PubMed PubMed Central
21. Silman, I, Sussman, JL. Acetylcholinesterase: ’Classical’ and ’non-classical’ functions and pharmacology. Curr Opin Pharmacol 2005;5:293–302. https://doi.org/10.1016/j.coph.2005.01.014.Suche in Google Scholar PubMed
22. Bartus, RT, Dean, RL, Beer, B, Lippa, AS. The cholinergic hypothesis of geriatric memory dysfunction. Sci 1982;217:408–17. https://doi.org/10.1126/science.7046051.Suche in Google Scholar PubMed
23. Jayaprakash, V, Yabanoglu, S, Sinha, BN, Ucar, G. Pyrazoline-based mycobactin analogues as dual inhibitors of MAO/cholinesterase. Turk J Biochem 2010;35:89–96, https://doi.org/10.1016/j.bmcl.2008.10.084.Suche in Google Scholar PubMed
24. Jayaprakash, V, Sinha, BN, Ucar, G, Ercan, A. Pyrazoline-based mycobactin analogues as MAO-inhibitors. Bioorg Med Chem Lett 2008;18:6362–68. https://doi.org/10.1016/j.bmcl.2008.10.084.Suche in Google Scholar
25. Cavalli, A, Bolognesi, ML, Minarini, A, Rosini, M, Tumiatti, V, Recanatini, M, Melchiorre, C. Multi-target-directed ligands to combat neurodegenerative diseases. J Med Chem 2008;51:347–72. https://doi.org/10.1021/jm7009364.Suche in Google Scholar PubMed
26. Aydin, T, Yurtvermez, B, Senturk, M, Kazaz, C, Cakir, A. Inhibitory effects of metabolites isolated from Artemisia dracunculus L. against the human carbonic anhydrase I (hCA I) and II (hCA II). Rec Nat Prod 2019;13:216–25, http://doi.org/10.25135/rnp.102.18.07.329.10.25135/rnp.102.18.07.329Suche in Google Scholar
27. Guvenalp, Z, Ozbek, H, Dursunoglu, B, Yuca, H, Gozcu, S, Cil, YM, Kazaz, C, Kara, K, Demirezer, OL. Alpha-amylase and alpha-glucosidase inhibitory activities of the herbs of Artemisia dracunculus L. and its active constituents. Med Chem Res 2017;26:3209–15. https://doi.org/10.1007/s00044-017-2014-7.Suche in Google Scholar
28. Gunes, A, Kordali, S, Turan, M, Bozhuyuk, AU. Determination of antioxidant enzyme activity and phenolic contents of some species of the Asteraceae family from medicanal plants. Ind Crop Prod 2019;137:208–13, https://doi.org/10.1016/j.indcrop.2019.05.042.Suche in Google Scholar
29. Mumivand, H, Babalar, M, Tabrizi, L, Craker, LE, Shokrpour, M, Hadian, J. Antioxidant properties and principal phenolic phytochemicals of iranian tarragon (Artemisia dracunculus L.) accessions. Hortic Environ Biote 2017;58:414–22. https://doi.org/10.1007/s13580-017-0121-5.Suche in Google Scholar
30. Wang, J, Fernandez, AE, Tiano, S, Huang, J, Floyd, E, Poulev, A, Ribnicky, D, Pasinetti, GM. An extract of Artemisia dracunculus L. Promotes psychological resilience in a mouse model of depression. Oxid Med Cell Longev 2018. https://doi.org/10.1155/2018/7418681.Suche in Google Scholar PubMed PubMed Central
31. Chaleshtori, RS, Taghizadeh, M, Arani, NM, Sharafati Chaleshtori, F. A comparative study on the antibacterial activity of Artemisia dracunculus L. and Ocimum basilicum essential oils on multidrug resistant bacteria isolated from ready to eat foods. J Essent Oil Bear Pl 2018;21:701–12, https://doi.org/10.1080/0972060X.2018.1491328.Suche in Google Scholar
32. Liu, TM, Lin, PC, Bao, TW, Ding, Y, Lha, Q, Nan, P, Huang, YY, Gu, ZY, Zhong, Y. Essential oil composition and antimicrobial activity of Artemisia dracunculus L. var. Qinghaiensis y. R. Ling (Asteraceae) from qinghai-tibet plateau. Ind Crop Prod 2018;125:1–4. https://doi.org/10.1016/j.indcrop.2018.08.085.Suche in Google Scholar
33. Watcho, P, Stavniichuk, R, Tane, P, Shevalye, H, Maksimchyk, Y, Pacher, P, Obrosova, IG. Evaluation of pmi-5011, an ethanolic extract of Artemisia dracunculus L., on peripheral neuropathy in streptozotocin-diabetic mice. Int J Mol Med 2011;27:299–307, https://doi.org/10.3892/ijmm.2011.597.Suche in Google Scholar PubMed PubMed Central
34. Vandanmagsar, B, Haynie, KR, Wicks, SE, Bermudez, EM, Mendoza, TM, Ribnicky, D, Cefalu, WT, Mynatt, RL. Artemisia dracunculus L. extract ameliorates insulin sensitivity by attenuating inflammatory signalling in human skeletal muscle culture. Diabetes Obes Metab 2014;16:728–38. https://doi.org/10.1111/dom.12274.Suche in Google Scholar PubMed PubMed Central
35. Stafford, GI, Pedersen, PD, Jager, AK, Van Staden, J. Monoamine oxidase inhibition by southern African traditional medicinal plants. S Afr J Bot 2007;73:384–90. https://doi.org/10.1016/j.sajb.2007.03.001.Suche in Google Scholar
36. Holt, A, Sharman, DF, Baker, GB, Palcic, MM. A continuous spectrophotometric assay for monoamine oxidase and related enzymes in tissue homogenates. Anal Biochem 1997;244:384–92. https://doi.org/10.1006/abio.1996.9911.Suche in Google Scholar PubMed
37. Ellman, GL, Courtney, KD, Andres, V, Featherston, RM. A new and rapidcolorimetric determination of acetylcholinesterase activity. Biochem Pharmacol 1961;7:88–95. https://doi.org/10.1016/0006-2952(61)90145-9.Suche in Google Scholar PubMed
38. Oztaskin, N, Kaya, R, Maraş, A, Sahin, E, Gülçin, İ, Göksu, S. Synthesis and characterization of novel bromophenols: Determination of their anticholinergic, antidiabetic and antioxidant activities. Bioorg Chem 2019;87:91–102, https://doi.org/10.1016/j.bioorg.2019.03.010.Suche in Google Scholar PubMed
39. Talbi, M, Saadali, B, Boriky, D, Bennani, L, Elkouali, M, Ainane, T. Two natural compounds - a benzofuran and a phenylpropane - from Artemisia dracunculus. J Asian Nat Prod Res 2016;18:724–29. https://doi.org/10.1080/10286020.2016.1158708.Suche in Google Scholar PubMed
40. Saadali, B, Boriky, D, Blaghen, M, Vanhaelen, M, Talbi, M. Alkamides from Artemisia dracunculus. Phytochemistry 2001;58:1083–86. https://doi.org/10.1016/s0031-9422(01)00347-8.Suche in Google Scholar PubMed
41. Yamada, M, Nakamura, K, Watabe, T, Ohno, O, Kawagoshi, M, Maru, N, Uotsu, N, Chiba, T, Yamaguchi, K, Uemura, D. Melanin biosynthesis inhibitors from tarragon Artemisia dracunculus. Biosci Biotech Bioch 2011;75:1628–30. https://doi.org/10.1271/bbb.110306.Suche in Google Scholar PubMed
42. Meepagala, KM, Sturtz, G, Wise, D, Wedge, DE. Molluscicidal and antifungal activity of erigeron speciosus steam distillate. Pest Manag Sci 2002;58:1043–47. https://doi.org/10.1002/ps.542.Suche in Google Scholar PubMed
43. Aglarova, AM, Zilfikarov, IN, Severtseva, OV. Biological characteristics and useful properties of tarragon (Artemisia dracunculus L.) (review). Pharm Chem J 2008;42:81–86. https://doi.org/10.1007/s11094-008-0064-3.Suche in Google Scholar
44. Ribnicky, DM, Poulev, A, Watford, M, Cefalu, WT, Raskin, I. Antihyperglycemic activity of tarralin (tm), an ethanolic extract of Artemisia dracunculus L. Phytomedicine 2006;13:550–57. https://doi.org/10.1016/j.phymed.2005.09.007.Suche in Google Scholar PubMed
45. Ribnicky, DM, Kuhn, P, Poulev, A, Logendra, S, Zuberi, A, Cefalu, WT, Raskin, I. Improved absorption and bioactivity of active compounds from an anti-diabetic extract of Artemisia dracunculus L. Int J Pharmaceut 2009;370:87–92. https://doi.org/10.1016/j.ijpharm.2008.11.012.Suche in Google Scholar PubMed PubMed Central
46. Wang, ZQ, Ribnicky, D, Zhang, XH, Raskin, I, Yu, YM, Cefalu, WT. Bioactives of Artemisia dracunculus L. enhance cellular insulin signaling in primary human skeletal muscle culture. Metabolism 2008;57:S58–S64. https://doi.org/10.1016/j.metabol.2008.04.003.Suche in Google Scholar PubMed PubMed Central
47. Benli, M, Kaya, I, Yigit, N. Screening antimicrobial activity of various extracts of Artemisia dracunculus L. Cell Biochem Funct 2007;25:681–86. https://doi.org/10.1002/cbf.1373.Suche in Google Scholar PubMed
48. Shahriyary, L, Yazdanparast, R. Inhibition of blood platelet adhesion, aggregation and secretion by Artemisia dracunculus leaves extracts. J Ethnopharmacol 2007;114:194–98. https://doi.org/10.1016/j.jep.2007.07.029.Suche in Google Scholar PubMed
49. Sayyah, M, Nadjafnia, L, Kamalinejad, M. Anticonvulsant activity and chemical composition of Artemisia dracunculus L. essential oil. J Ethnopharmacol 2004;94:283–87. https://doi.org/10.1016/j.jep.2004.05.021.Suche in Google Scholar PubMed
50. Mattsson, C, Svensson, P, Sonesson, C. A novel series of 6-substituted 3-(pyrrolidin-1-ylmethyl)chromen-2-ones as selective monoamine oxidase (MAO) a inhibitors. Eur J Med Chem 2014;73:177–86. https://doi.org/10.1016/j.ejmech.2013.11.035.Suche in Google Scholar PubMed
51. Gnerre, C, Catto, M, Leonetti, F, Weber, P, Carrupt, PA, Altomare, C, Carotti, A, Testa, B. Inhibition of monoamine oxidases by functionalized coumarin derivatives: Biological activities, qsars, and 3d-qsars. J Med Chem 2000;43:4747–58. https://doi.org/10.1021/jm001028o.Suche in Google Scholar PubMed
52. Seong, SH, Ali, MY, Jung, HA, Choi, JS. Umbelliferone derivatives exert neuroprotective effects by inhibiting monoamine oxidase a, self-amyloid beta aggregation, and lipid peroxidation. Bioorg Chem 2019;92. https://doi.org/10.1016/j.bioorg.2019.103293.Suche in Google Scholar PubMed
53. Ibrar, A, Shehzadi, SA, Saeed, F, Khan, I. Developing hybrid molecule therapeutics for diverse enzyme inhibitory action: Active role of coumarin-based structural leads in drug discovery. Bioorgan Med Chem 2018;26:3731–62. https://doi.org/10.1016/j.bmc.2018.05.042.Suche in Google Scholar PubMed
© 2020 Walter de Gruyter GmbH, Berlin/Boston
Artikel in diesem Heft
- Frontmatter
- Research articles
- Modulation of antibiotic resistance by the essential oil of Ocimum gratissimum L. in association with light-emitting diodes (LED) lights
- Dynamic analysis of the mathematical model of COVID-19 with demographic effects
- Biochemical evidences for M1-, M17- and M18-like aminopeptidases in marine invertebrates from Cuban coastline
- Hexanal inhalation affects cognition and anxiety-like behavior in mice
- Overexpression of a novel E3 ubiquitin ligase gene from Coptis chinensis Franch enhances drought tolerance in transgenic tobacco
- Topiroxostat ameliorates oxidative stress and inflammation in sepsis-induced lung injury
- A computational study of the interactions between anthocyans and cyclodextrins
- Chemical characterization of the lipids in femoral gland secretions of wild male tegu lizards, Salvator merianae (Squamata, Teiidae) in comparison with captive-bred males
- Metabolite profiling by means of GC-MS combined with principal component analyses of natural populations of Nectaroscordum siculum ssp. bulgaricum (Janka) Stearn
- human monoamine oxidase (hMAO) A and hMAO B inhibitors from Artemisia dracunculus L. herniarin and skimmin: human mononamine oxidase A and B inhibitors from A. dracunculus L.
- Rapid communications
- Chemical composition and anticholinesterase inhibitory activity of Pavetta graciliflora Wall. ex Ridl. essential oil
- Chemical composition of the essential oils of four Polyalthia species from Malaysia
- Composition of the essential oils of three Malaysian Xylopia species (Annonaceae)
- Chemical characterization of Goniothalamus macrophyllus and Goniothalamus malayanus leaves’ essential oils
- Effect of pH on xylitol production by Candida species from a prairie cordgrass hydrolysate
Artikel in diesem Heft
- Frontmatter
- Research articles
- Modulation of antibiotic resistance by the essential oil of Ocimum gratissimum L. in association with light-emitting diodes (LED) lights
- Dynamic analysis of the mathematical model of COVID-19 with demographic effects
- Biochemical evidences for M1-, M17- and M18-like aminopeptidases in marine invertebrates from Cuban coastline
- Hexanal inhalation affects cognition and anxiety-like behavior in mice
- Overexpression of a novel E3 ubiquitin ligase gene from Coptis chinensis Franch enhances drought tolerance in transgenic tobacco
- Topiroxostat ameliorates oxidative stress and inflammation in sepsis-induced lung injury
- A computational study of the interactions between anthocyans and cyclodextrins
- Chemical characterization of the lipids in femoral gland secretions of wild male tegu lizards, Salvator merianae (Squamata, Teiidae) in comparison with captive-bred males
- Metabolite profiling by means of GC-MS combined with principal component analyses of natural populations of Nectaroscordum siculum ssp. bulgaricum (Janka) Stearn
- human monoamine oxidase (hMAO) A and hMAO B inhibitors from Artemisia dracunculus L. herniarin and skimmin: human mononamine oxidase A and B inhibitors from A. dracunculus L.
- Rapid communications
- Chemical composition and anticholinesterase inhibitory activity of Pavetta graciliflora Wall. ex Ridl. essential oil
- Chemical composition of the essential oils of four Polyalthia species from Malaysia
- Composition of the essential oils of three Malaysian Xylopia species (Annonaceae)
- Chemical characterization of Goniothalamus macrophyllus and Goniothalamus malayanus leaves’ essential oils
- Effect of pH on xylitol production by Candida species from a prairie cordgrass hydrolysate
