Isolation and characterization of chemical constituents from Chaerophyllum bulbosum roots and their enzyme inhibitory and antioxidant effects
Abstract
Isolation and bioactive effects of the roots of Chaerophyllum bulbosum L. were firstly investigated herein. Enzyme (acetylcholinesterase, butyrylcholinesterase, urease, α-amylase, α-glucosidase, and tyrosinase) inhibitory effects of C. bulbosum root extracts were tested. Three known compounds, n-heptadecanyl eicosanoate (1), stigmasterol (2), and β-sitosterol-3-O-β-d-glucopyranoside (3) were isolated from C. bulbosum. Antioxidant and enzyme inhibitory effects of isolated compounds were investigated. The hexane extract (IC50: 349.58 ± 0.06 μg/mL) displayed a higher α-glucosidase inhibitory effect than the standard (IC50: 378.66 ± 0.14 μg/mL). The best inhibitory effect was found in compound 2 on AChE (46.40 ± 0.31%), BChE (56.41 ± 0.54%), and urease (92.47 ± 0.11%); compound 1 on α-amylase (22.27 ± 0.61%); and compound 3 on α-glucosidase (12.43 ± 0.25%) and tyrosinase (19.00 ± 0.16%). All isolated compounds showed moderate antioxidant effects in all assays. This study contributes to the therapeutic uses of Chaerophyllum roots and emphasizes the value of C. bulbosum species for the development of novel therapeutic agents.
Funding source: The Scientific and Technological Research Council of Turkey
Award Identifier / Grant number: TUBITAK-118Z610
Acknowledgments
The authors would like to thank Dr. Yeter Yeşil for the identification of the plant sample.
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Author contributions: G.T.Ç. designed, tested the biological assays, assisted in the isolation of compounds, resolved the structures of the compounds, analyzed data, supervised the project, and wrote the manuscript. E.D. performed the extraction, tested the biological assays, carried out the isolation of compounds, and wrote the manuscript. Z.M. performed the extraction, tested the biological assays, and carried out the isolation of compounds. M.E.D. analyzed data and contributed to the experiments. M.Ö. resolved the structures of the compounds.
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Research funding: This study was supported financially by The Scientific and Technological Research Council of Turkey (TUBITAK-118Z610).
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Conflict of interest statement: The authors declare no conflict of interest.
References
1. Karunamoorthi, K, Kegajeevanram, K, Vijayalakshmi, J, Mengistie, E. Traditional medicinal plants: a source of phytotherapeutic modality in resource-constrained health care settings. J Evid Base Compl Alternative Med 2012;18:67–74. https://doi.org/10.1177/2156587212460241.Search in Google Scholar
2. Shakya, AK. Medicinal plants: future source of new drugs. Int J Herb Med 2016;4:59–64.Search in Google Scholar
3. Sofowora, A, Ogunbodede, E, Onayade, A. The role and place of medicinal plants in the strategies for disease prevention. Afr J Tradit, Complementary Altern Med 2013;10:210–29. https://doi.org/10.4314/ajtcam.v10i5.2.Search in Google Scholar
4. Jain, C, Khatana, S, Vijayvergia, R. Bioactivity of secondary metabolites of various plants: a review. Int J Pharmaceut Sci Res 2019;10:494–504.Search in Google Scholar
5. Sayed-Ahmad, B, Talou, T, Saad, Z, Hijazi, A, Merah, O. The Apiaceae: ethnomedicinal family as source for industrial uses. Ind Crop Prod 2017;109:661–71. https://doi.org/10.1016/j.indcrop.2017.09.027.Search in Google Scholar
6. Zengin, G, Sinan, KI, Ak, G, Mahomoodally, MF, Paksoy, MY, Picot-Allain, C, et al.. Chemical profile, antioxidant, antimicrobial, enzyme inhibitory, and cytotoxicity of seven Apiaceae species from Turkey: a comparative study. Ind Crop Prod 2020;153:112572. https://doi.org/10.1016/j.indcrop.2020.112572.Search in Google Scholar
7. Prokopiou, L, Halahlah, A, Grigorakis, S, Fournarak, C, Kokkalou, E, Karioti, A. Threatened Cretan species Chaerophyllum creticum Boiss. & Heldr.: phenolic profile by HPLC-PDA-MS and in vitro antioxidant capacity. Nat Prod Res 2021;1–6. https://doi.org/10.1080/14786419.2021.1889545 [Epub ahead of print].Search in Google Scholar
8. Ebrahimabadi, AH, Djafari-Bidgoli, Z, Mazoochi, A, Kashi, FJ, Batooli, H. Essential oils composition, antioxidant and antimicrobial activity of the leaves and flowers of Chaerophyllum macropodum Boiss. Food Contr 2010;21:1173–8. https://doi.org/10.1016/j.foodcont.2010.01.014.Search in Google Scholar
9. Demirci, B, Koşar, M, Demirci, F, Dinç, M, Başer, KHC. Antimicrobial and antioxidant activities of the essential oil of Chaerophyllum libanoticum Boiss. Et Kotschy. Food Chem 2007;105:1512–7. https://doi.org/10.1016/j.foodchem.2007.05.036.Search in Google Scholar
10. Shafaghat, A, Salimi, F, Mahmoodi, R. Antioxidant, antimicrobial activity and chemical analysis of the flavonoid from Chaerophyllum macropodum (Boiss.). J Med Plants Res 2012;6:2111–6. https://doi.org/10.5897/jmpr11.1056.Search in Google Scholar
11. Rao, RS, Ravishankar, GA. Plant cell cultures: chemical factories of secondary metabolites. Biotechnol Adv 2002;20:101–53. https://doi.org/10.1016/s0734-9750(02)00007-1.Search in Google Scholar
12. Çayan, F, Tel, G, Duru, ME, Öztürk, M, Türkoğlu, A, Harmandar, M. Application of GC, GC-MSD, ICP-MS and spectrophotometric methods for the determination of chemical composition and in vitro bioactivities of Chroogomphus rutilus: the edible mushroom species. Food Anal Methods 2014;7:449–58. https://doi.org/10.1007/s12161-013-9644-2.Search in Google Scholar
13. Deveci, E, Çayan, F, Tel-Çayan, G, Duru, ME. Inhibitory activities of medicinal mushrooms on α-amylase and α-glucosidase-enzymes related to type 2 diabetes. South Afr J Bot 2021;137:19–23. https://doi.org/10.1016/j.sajb.2020.09.039.Search in Google Scholar
14. Çayan, F, Tel-Çayan, G, Deveci, E, Öztürk, M, Duru, ME. Chemical profile, in vitro enzyme inhibitory, and antioxidant properties of Stereum species (Agaricomycetes) from Turkey. Int J Med Mushrooms 2019;21:1075–87. https://doi.org/10.1615/intjmedmushrooms.2019032893.Search in Google Scholar
15. Nazreen, S, Alam, MM, Hamid, H, Ali, M, Alam, MS. Chemical constituents with antimicrobial and antioxidant activity from the aerial parts of Callistemon lanceolatus (Sm.) Sweet. Nat Prod Res 2020;34:3275–9. https://doi.org/10.1080/14786419.2018.1557174.Search in Google Scholar
16. Suttiarporn, P, Chumpolsri, W, Mahatheeranont, S, Luangkamin, S, Teepsawang, S, Leardkamolkarn, V. Structures of phytosterols and triterpenoids with potential anti-cancer activity in bran of black non-glutinous rice. Nutrients 2015;7:1672–87. https://doi.org/10.3390/nu7031672.Search in Google Scholar
17. Voutquenne, L, Lavauda, C, Massiot, G, Sevenet, T, Hadic, HA. Cytotoxic polyisoprenes and glycosides of long-chain fatty alcohols from Dimocarpus fumatus. Phytochemistry 1999;50:63–9. https://doi.org/10.1016/s0031-9422(98)00483-x.Search in Google Scholar
18. Mikaya, GA, Turabelidze, DG, Kemertelidze, EP, Vul’fson, NS. Kaerophyllin, a new lignan from Chaerophyllum maculatum. Planta Med 1981;43:378–80. https://doi.org/10.1055/s-2007-971527.Search in Google Scholar PubMed
19. Rollinger, JM, Zidorn, C, Dobner, MJ, Ellmerer, EP, Stuppner, H. Lignans, phenylpropanoids and polyacetylenes from Chaerophyllum aureum L. (Apiaceae). Z Naturforsch C Biosci 2003;58:553–7. https://doi.org/10.1515/znc-2003-7-818.Search in Google Scholar PubMed
20. Dall’Acqua, S, Innocenti, G. Antioxidant compounds from Chaerophyllum hirsutum extracts. Fitoterapia 2004;75:592–5.10.1016/j.fitote.2004.05.007Search in Google Scholar PubMed
21. Dall’Acqua, S, Viola, G, Piacente, S, Mariella Cappelletti, E, Innocenti, G. Cytotoxic constituents of roots of Chaerophyllum hirsutum. J Nat Prod 2004;67:1588–90.10.1021/np040046wSearch in Google Scholar PubMed
22. Deka, P, Kumar, A, Nayak, BK, Eloziia, N. Some plants as a source of acetyl cholinesterase inhibitors: a review. Int Res J Pharm 2017;8:5–13. https://doi.org/10.7897/2230-8407.08565.Search in Google Scholar
23. Modolo, LV, de Souza, AX, Horta, LP, Araujo, DP, Fátima, AP. An overview on the potential of natural products as ureases inhibitors: a review. J Adv Res 2015;6:35–44. https://doi.org/10.1016/j.jare.2014.09.001.Search in Google Scholar PubMed PubMed Central
24. Salehi, B, Ata, A, Kumar, NVA, Sharopov, F, Ramírez-Alarcón, K, Ruiz-Ortega, A, et al.. Antidiabetic potential of medicinal plants and their active components. Biomolecules 2019;9:551. https://doi.org/10.3390/biom9100551.Search in Google Scholar PubMed PubMed Central
25. Raman, BV, Krishna, ANV, Rao, BN, Saradhi, MP, Rao, MVB. Plants with antidiabetic activities and their medicinal values. Int Res J Pharm 2012;3:11–5.Search in Google Scholar
26. Mukherjee, P, Biswas, R, Sharma, A, Banerjee, S, Biswas, S, Katiyar, CK. Validation of medicinal herbs for anti-tyrosinase potential. J Herb Med 2018;14:1–16. https://doi.org/10.1016/j.hermed.2018.09.002.Search in Google Scholar
27. Abbas-Mohammadi, M, Farimani, MM, Salehi, P, Ebrahimi, SN, Sonboli, A, Kelso, C, et al.. Acetylcholinesterase-inhibitory activity of Iranian plants: combined HPLC/bioassay-guided fractionation, molecular networking and docking strategies for the dereplication of active compound. J Pharmaceut Biomed Anal 2018;5:471–9. https://doi.org/10.1016/j.jpba.2018.06.026.Search in Google Scholar PubMed
28. Dall’Acqua, S, Ak, G, Sut, S, Ferrarese, I, Zengin, G, Yıldıztugay, E, et al.. Phenolics from Scorzonera tomentosa L.: exploring the potential use in industrial applications via an integrated approach. Ind Crop Prod 2020;154:112751.10.1016/j.indcrop.2020.112751Search in Google Scholar
29. Zengin, G, Sarikurkcu, C, Aktumsek, A, Ceylan, R. Sideritis galatica Bornm.: a source of multifunctional agents for the management of oxidative damage, Alzheimer’s and diabetes mellitus. J Funct Foods 2014;11:538–47. https://doi.org/10.1016/j.jff.2014.08.011.Search in Google Scholar
30. Gohari, AR, Nabati, F, Saeidnia, S, Malmir, M, Amanlou, M. Urease inhibitory activity of some Iranian medicinal plants. Asian J Chem 2012;24:1527–9.Search in Google Scholar
31. Sichaem, J, Ruksilp, T, Sawasdee, P, Khumkratok, S. Tip-pyang S. Chemical constituents of the stems of Spatholobus parviflorus and their cholinesterase inhibitory activity. Chem Nat Compd 2018;54:356–7. https://doi.org/10.1007/s10600-018-2344-9.Search in Google Scholar
32. Parveen, S, Riaz, N, Saleem, M, Ashraf, M, Qurat-ul-Ain, Khatoon, T, et al.. A new cyclic terephthalate from the methanolic extract of Carissa opaca. J Chem Soc Pakistan 2017;39:610–3.Search in Google Scholar
33. Dawe, A, Mbiantcha, M, Fongang, Y, Nana, WY, Yakai, F, Ateufack, G, et al.. Piptadenin, a novel 3,4-secooleanane triterpene and piptadenamide, a new ceramide from the stem bark of Piptadeniastrum africanum (HOOK.f.) BRENA. Chem Biodivers 2017;14:e1600215. https://doi.org/10.1002/cbdv.201600215.Search in Google Scholar PubMed
34. Demirkiran, O, Topcu, G, Azarpira, A, Choudhary, MI. Tyrosinase inhibitory activity of chemical constituents of Euphorbia macrostegia. Chem Nat Compd 2014;50:810–3. https://doi.org/10.1007/s10600-014-1089-3.Search in Google Scholar
35. Khan, S, Khan, MTH, Kardar, MN. Tyrosinase inhibitors from the fruits of Madhuca latifolia. Curr Bioact Compd 2014;10:31–6. https://doi.org/10.2174/1573407210666140311234806.Search in Google Scholar
36. Sadasivam, M, Kumarasamy, C, Thangaraj, A, Govindan, M, Kasirajan, G, Vijayan, V, et al.. Phytochemical constituents from dietary plant Citrus hystrix. Nat Prod Res 2018;32:1721–6. https://doi.org/10.1080/14786419.2017.1399386.Search in Google Scholar
37. Naveed, MA, Riaz, N, Saleem, M, Mussadiq, S, Jabeen, B, Ashraf, M, et al.. New enzyme inhibitory constituents from Tribulus longipetalus. Record Nat Prod 2016;10:128–36.Search in Google Scholar
38. Boğa, M, Yılmaz, PK, Cebe, DB, Fatima, M, Siddiquid, BS, Kolak, U. Chemical constituents and biological activities of Cirsium leucopsis, C. sipyleum, and C. eriophorum. Z Naturforsch 2014;69c:381–90.10.5560/znc.2014-0071Search in Google Scholar
39. Rahal, A, Kumar, A, Singh, V, Yadav, B, Tiwari, R, Chakraborty, S, et al.. Oxidative stress, prooxidants, and antioxidants: the interplay. BioMed Res Int 2014;2014:19. https://doi.org/10.1155/2014/761264.Search in Google Scholar
40. Liguori, I, Russo, G, Curcio, F, Bulli, G, Aran, L, Della-Morte, D, et al.. Oxidative stress, aging, and diseases. Clin Interv Aging 2018;13:757–72. https://doi.org/10.2147/cia.s158513.Search in Google Scholar
41. Perrotta, I, Aquila, S. The role of oxidative stress and autophagy in atherosclerosis. Oxid Med Cell Longev 2015;2015:10. https://doi.org/10.1155/2015/130315.Search in Google Scholar
42. Rao, GM, Rao, AV, Raja, A, Rao, S, Rao, A. Role of antioxidant enzymes in brain tumours. Clin Chim Acta 2000;296:203–12. https://doi.org/10.1016/s0009-8981(00)00219-9.Search in Google Scholar
43. Miras-Moreno, B, Sabater-Jara, AB, Pedreno, MA, Almagro, L. Bioactivity of phytosterols and their production in plant in vitro cultures. J Agric Food Chem 2016;6:7049–58. https://doi.org/10.1021/acs.jafc.6b02345.Search in Google Scholar PubMed
44. Teng, H, Lu, Y, Li, J, Yang, ZG, Mei, ZN. Two new steroidal glycosides from the root of Cynanchum auriculatum. Chin Chem Lett 2011;22:77–80. https://doi.org/10.1016/j.cclet.2010.09.009.Search in Google Scholar
45. Khatun, A, Rahman, M, Rahman, MS, Hossain, MK, Rashid, MA. Terpenoids and phytosteroids isolated from Commelina benghalensis Linn. with antioxidant activity. J Basic Clin Physiol Pharmacol 2020;26:31. https://doi.org/10.1515/jbcpp-2018-0218.Search in Google Scholar PubMed
46. Khan, I, Zahoor, M, Zeb, A, Sahibzada, MUK, Bari, WU, Naz, S. Isolation, characterization, pharmacological evaluation and in silico modeling of bioactive secondary metabolites from Ziziphus oxyphylla a member of Rhamnaceae family. Trop J Pharmaceut Res 2020;19:351–9. https://doi.org/10.4314/tjpr.v19i2.18.Search in Google Scholar
47. Lu, SH, Zuo, HJ, Shi, JX, Li, CR, Li, YH, Wang, X, et al.. Two new glycosides from the leaves of Ligustrum robustum and their antioxidant activities and inhibitory effects on α-glucosidase and α-amylase. South Afr J Bot 2019;125:521–6. https://doi.org/10.1016/j.sajb.2019.07.028.Search in Google Scholar
Supplementary material
The online version of this article offers supplementary material (https://doi.org/10.1515/znc-2021-0119).
© 2021 Walter de Gruyter GmbH, Berlin/Boston
Articles in the same Issue
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- Research Articles
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Articles in the same Issue
- Frontmatter
- Research Articles
- Isolation and characterization of chemical constituents from Chaerophyllum bulbosum roots and their enzyme inhibitory and antioxidant effects
- Monascin and monascinol, azaphilonoid pigments from Mortierella polycephala AM1: in silico and in vitro targeting of the angiogenic VEGFR2 kinase
- Novel Ag(I)-NHC complex: synthesis, in vitro cytotoxic activity, molecular docking, and quantum chemical studies
- NLRP3 inflammasome activation and oxidative stress status in the mild and moderate SARS-CoV-2 infected patients: impact of melatonin as a medicinal supplement
- Oxidative stress and cyto-genotoxicity induced by poly-d-glucosamine in human blood cells in vitro
- A synergy interaction of artocarpin and tetracycline against Pseudomonas aeruginosa and its mechanism of action on membrane permeability
- Review Articles
- Cytokine storm syndrome in SARS-CoV-2: a review
- A comprehensive review on the development of probiotic supplemented confectioneries