Enzyme inhibitory and antioxidant activities and HPLC quantification of chlorogenic acid in Helichrysum stoechas (L.) Moench and H. stoechas subsp. barrelieri (Ten) Nyman

Nurten Abacı Kaplan; Hasya Nazlı Gök; Mustafa Aslan; İlkay Erdoğan Orhan

doi:10.38093/cupmap.1314950

Research Article

Year 2023, Volume: 6 Issue: 1, 38 - 50, 02.07.2023

Nurten Abacı Kaplan Hasya Nazlı Gök Mustafa Aslan İlkay Erdoğan Orhan

https://doi.org/10.38093/cupmap.1314950

Abstract

References

References
1. Acet, T., Ozcan, K., & Zengin, G., (2020). An assessment of phenolic profiles, fatty acid compositions, and biological activities of two Helichrysum species: H. plicatum and H. chionophilum. Journal of Food Biochemistry, 44(2), https://doi.org/10.1111/jfbc.13128
2. Aksoy, A., Hamzaoğlu, E., & Budak, Ü., (2011). Taxonomic Revision of Turkey Helichrysum Mill. Asteraceae Species. Erciyes University, Research Project, Project No: FBA-08-519, Kayseri. 2011.
3. Aslan, M., (1994). Pharmacognostic Researches on Helichrysum plicatum ssp. plicatum. Department of Pharmacognosy, Institute of Health Sciences, Gazi University, Master's thesis. 76.
4. Aydın, T., (2020). Secondary metabolites of Helichrysum plicatum DC. subsp. plicatum flowers as strong carbonic anhydrase, cholinesterase and α-glycosidase inhibitors. Zeitschrift für Naturforschung C, 75(5-6), 153-159. https://doi.org/10.1515/znc-2020-0026
5. Barrantes, E., & Guinea, Ma., (2003). Inhibition of collagenase and metalloproteinases by aloins and aloe gel. Life Sciences, 72(7), 843-850. https://doi.org/10.1016/s0024-3205(02)02308-1
6. Barros, L., Baptista, P., & CFR, F. I., (2007). Effect of Lactarius piperatus fruiting body maturity stage on antioxidant activity measured by several biochemical assays. Food and Chemical Toxicology, 45(9), 1731-1737. https://doi.org/10.1016/j.fct.2007.03.006
7. Carter, P., (1971). Spectrophotometric determination of serum iron at the submicrogram level with a new reagent (ferrozine). Analytical Biochemistry, 40(2), 450-458. https://doi.org/10.1016/0003-2697(71)90405-2
8. Ellman, G. L., Courtney, K. D., Andres, V., Jr., & Feather-Stone, R. M., (1961). A new and rapid colorimetric determination of acetylcholinesterase activity. Biochemical Pharmacology, 7(2), 88-95. https://doi.org/10.1016/0006-2952(61)90145-9
9. Eroğlu, H. E., (2018). Names of Helichrysum taxa of Türkiye in Turkish and other languages. Avrasya Terim Dergisi, 6(1), 26-34.
10. Fraternale, D., Flamini, G., & Ascrizzi, R., (2019). In vitro anticollagenase and antielastase activities of essential oil of Helichrysum italicum subsp. italicum (Roth) G. Don. Journal of Medicinal Food, 22(10), 1041-1046. https://doi.org/10.1089/jmf.2019.0054
11. Gök, H., Pekacar, S., & Deliorman Orhan, D., (2022). Investigation of enzyme inhibitory activities, antioxidant activities, and chemical properties of Pistacia vera leaves using LC-QTOF-MS and RP-HPLC. Iranian Journal of Pharmaceutical Research, 21(1). https://doi.org/10.5812/ijpr-127033
12. Gras, A., Garnatje, T., Ibanez, N., Lopez-Pujol, J., Nualart, N., & Valles, J., (2017). Medicinal plant uses and names from the herbarium of Francesc Bolòs (1773-1844). Journal of Ethnopharmacology, 204, 142-168. https://doi.org/10.1016/j.jep.2017.04.002
13. Haddouchi, F., Chaouche, T. M., Ksouri, R., Medini, F., Sekkal, F. Z., & Benmansour, A., (2014). Antioxidant activity profiling by spectrophotometric methods of aqueous methanolic extracts of Helichrysum stoechas subsp. rupestre and Phagnalon saxatile subsp. saxatile. Chinese Journal of Natural Medicines, 12(6), 415-422. https://doi.org/10.1016/S1875-5364(14)60065-0
14. Hatano, T., Kagawa, H., Yasuhara, T., & Okuda, T., (1988). Two new flavonoids and other constituents in licorice root: their relative astringency and radical scavenging effects. Chemical and Pharmaceutical Bulletin, 36(6), 2090-2097. https://doi.org/10.1248/cpb.36.2090
15. Jovanović, M., Drinić, Z., Bigović, D., Alimpić-Aradski, A., Duletić-Laušević, S., & Šavikin, K., (2020). In vitro antineurodegenerative activity and in silico predictions of blood-brain barrier penetration of Helichrysum plicatum flower extract. Lekovite Sirovine, (40), 45-51. https://doi.org/10.5937/leksir2040045J
16. Kraunsoe, J. A., Claridge, T. D., & Lowe, G., (1996). Inhibition of human leukocyte and porcine pancreatic elastase by homologues of bovine pancreatic trypsin inhibitor. Biochemistry, 35(28), 9090-9096. https://doi.org/10.1021/bi953013b
17. Lee, S., Sandesh, S., Shruti, S., & Seo, S., (2009). Potent antielastase and antityrosinase activities of Astilbe chinensis. American journal of Pharmacology and Toxicology, 4(4), 127-129. https://doi.org/10.3844/ajptsp.2009.127.129
18. Memariani, Z., Moeini, R., Hamedi, S. S., Gorji, N., & Mozaffarpur, S. A., (2018). Medicinal plants with antithrombotic property in Persian medicine: a mechanistic review. Journal of Thrombosis and Thrombolysis, 45, 158-179. https://doi.org/10.1007/s11239-017-1580-3
19. Mukherjee, P. K., Maity, N., Nema, N. K., & Sarkar, B. K., (2011). Bioactive compounds from natural resources against skin aging. Phytomedicine, 19(1), 64-73. https://doi.org/10.1016/j.phymed.2011.10.003
20. Nejmi, I., Mükemre, M., Türker, R. S., Zengin, G., & Dalar, A., (2023). Analysis of phytochemical composition and biological activities of Helichrysum pallasii (Sprengel) ledeb leaves International Journal of Secondary Metabolite, 10(1), 71-85. https://doi.org/10.21448/ijsm.1132698
21. Oboh, G., Agunloye, O. M., Akinyemi, A. J., Ademiluyi, A. O., & Adefegha, S. A., (2013). Comparative study on the inhibitory effect of caffeic and chlorogenic acids on key enzymes linked to Alzheimer's disease and some pro-oxidant induced oxidative stress in rats' brain-in vitro. Neurochemical Research, 38, 413-419.
22. Oyaizu, M., (1986). Studies on products of browning reaction antioxidative activities of products of browning reaction prepared from glucosamine. The Japanese Journal of Nutrition and Dietetics, 44(6), 307-315. https://doi.org/10.5264/eiyogakuzashi.44.307
23. Sagbo, I. J., & Otang-Mbeng, W., (2020). Evaluation of the efficacy of ethanol leaf extract of Helichrysum petiolare Hilliard and BL Burtt against skin aging. Tropical Journal of Pharmaceutical Research, 19(12), 2631-2638. https://doi.org/10.4314/tjpr.v19i12.22
24. Silva, L., Rodrigues, A. M., Ciriani, M., Falé, P. L. V., Teixeira, V., Madeira, P., Machuqueiro, M., Pacheco, R., Florêncio, M. H., & Ascensão, L., (2017). Antiacetylcholinesterase activity and docking studies with chlorogenic acid, cynarin and arzanol from Helichrysum stoechas (Lamiaceae). Medicinal Chemistry Research, 26, 2942-2950. https://doi.org/10.1007/s00044-017-1994-7
25. Singleton, V. L., & Rossi, J. A., (1965). Colorimetry of total phenolics with phosphomolybdic-phosphotungstic acid reagents. American Journal of Enology and Viticulture, 16(3), 144-158.
26. Taşkın, T., Gezmiş, T., Çam, M. E., Taşkın, D., Çelik, B. Ö., Şenkardeş, İ., & Süzgeç-Selçuk, S., (2020). The in vitro and in vivo investigation of biological activities and phenolic analysis of Helichrysum plicatum subsp. plicatum. Brazilian Journal of Pharmaceutical Sciences, 56. https://doi.org/10.1590/s2175-97902019000418345
27. Terry, A. V., & Buccafusco, J. J., (2003). T The cholinergic hypothesis of age and Alzheimer's disease-related cognitive deficits: recent challenges and their implications for novel drug development. Journal of Pharmacology and Experimental Therapeutics, 306(3), 821-827. https://doi.org/10.1124/jpet.102.041616
28. Tsioutsiou, E. E., Amountzias, V., Vontzalidou, A., Dina, E., Stevanović, Z. D., Cheilari, A., & Aligiannis, N., (2022). Medicinal plants used traditionally for skin related problems in the South Balkan and East Mediterranean region-A review. Frontiers in Pharmacology, 13. https://doi.org/10.3389/fphar.2022.936047
29. Van Wart, H. E., & Steinbrink, D. R., (1981). A continuous spectrophotometric assay for Clostridium histolyticum collagenase. Analytical Biochemistry, 113(2), 356-365. https://doi.org/10.1016/0003-2697(81)90089-0
30. Version 7.2 of the Turkish Pharmacopoeia. Turkish Medicines and Medical Devices Agency, Ankara, Turkey, ISBN:978-975-590-733-8, 2019.
31. Woisky, R. G., & Salatino, A., (1998). Analysis of propolis: some parameters and procedures for chemical quality control. Journal of Apicultural Research, 37(2), 99-105. https://doi.org/10.1080/00218839.1998.11100961
32. Zengin, G., Cvetanović, A., Gašić, U., Tešić, Ž., Stupar, A., Bulut, G., Sinan, K. I., Uysal, S., Picot-Allain, M. C. N., & Mahomoodally, M. F., (2020). A comparative exploration of the phytochemical profiles and bio-pharmaceutical potential of Helichrysum stoechas subsp. barrelieri extracts obtained via five extraction techniques. Process Biochemistry, 91, 113-125. https://doi.org/10.1016/j.procbio.2019.12.002

Enzyme inhibitory and antioxidant activities and HPLC quantification of chlorogenic acid in Helichrysum stoechas (L.) Moench and H. stoechas subsp. barrelieri (Ten) Nyman

Year 2023, Volume: 6 Issue: 1, 38 - 50, 02.07.2023

Nurten Abacı Kaplan Hasya Nazlı Gök Mustafa Aslan İlkay Erdoğan Orhan

https://doi.org/10.38093/cupmap.1314950

Abstract

The inhibitory effects of ethanol (80%) and aqueous extracts of Helichrysum stoechas (L.) Moench and H. stoechas subsp. barrelieri (Ten) Nyman on acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), two sister enzymes associated with pathogenesis of Alzheimer's disease (AD), as well as on elastase and collagenase, linked to inflammation and skin aging, were investigated. Simultaneously, antioxidant activity of the extracts was assessed through DPPH radical scavenging activity, ferric reducing antioxidant power (FRAP), and metal-chelating activity assays, since oxidative damage plays a critical role in both AD pathophysiology and skin aging. Total phenol and flavonoid contents in the extracts were spectrophotometrically determined. The highest AChE inhibitory activity (44.60 ± 4.4% at 2000 µg/mL) was found in the ethanol extract of H. stoechas subsp. barrelieri collected from Hatay, and the uppermost BChE inhibitory activity at same concentration was found in the aqueous extract of H. stoechas subsp. barrelieri collected from Izmir (80.24 ± 2.63%, IC50: 38.52 ± 1.41 µg/mL). Both of them inhibited AChE and BChE in a concentration-dependent manner. Nevertheless, none of the extracts from the two plants inhibited the elastase and collagenase. Although both ethanolic and aqueous extracts had significant antioxidant activity in DPPH radical scavenging and FRAP assays, they demonstrated inadequate antioxidant activity in metal-chelating assay. Chlorogenic acid was quantified in the extracts using HPLC. The mentioned two extracts having strong cholinesterase (ChE) inhibition had also the highest chlorogenic acid content. The ethanol extract of H. stoechas (Hatay sample) and the aqueous extract of H. stoechas (Izmir sample) seem to contain promising ChE inhibitors, which deserve further investigation.

Keywords

Helichrysum stoechas, enzyme inhibition, Alzheimer’s disease, antioxidant activity

References

References
1. Acet, T., Ozcan, K., & Zengin, G., (2020). An assessment of phenolic profiles, fatty acid compositions, and biological activities of two Helichrysum species: H. plicatum and H. chionophilum. Journal of Food Biochemistry, 44(2), https://doi.org/10.1111/jfbc.13128
2. Aksoy, A., Hamzaoğlu, E., & Budak, Ü., (2011). Taxonomic Revision of Turkey Helichrysum Mill. Asteraceae Species. Erciyes University, Research Project, Project No: FBA-08-519, Kayseri. 2011.
3. Aslan, M., (1994). Pharmacognostic Researches on Helichrysum plicatum ssp. plicatum. Department of Pharmacognosy, Institute of Health Sciences, Gazi University, Master's thesis. 76.
4. Aydın, T., (2020). Secondary metabolites of Helichrysum plicatum DC. subsp. plicatum flowers as strong carbonic anhydrase, cholinesterase and α-glycosidase inhibitors. Zeitschrift für Naturforschung C, 75(5-6), 153-159. https://doi.org/10.1515/znc-2020-0026
5. Barrantes, E., & Guinea, Ma., (2003). Inhibition of collagenase and metalloproteinases by aloins and aloe gel. Life Sciences, 72(7), 843-850. https://doi.org/10.1016/s0024-3205(02)02308-1
6. Barros, L., Baptista, P., & CFR, F. I., (2007). Effect of Lactarius piperatus fruiting body maturity stage on antioxidant activity measured by several biochemical assays. Food and Chemical Toxicology, 45(9), 1731-1737. https://doi.org/10.1016/j.fct.2007.03.006
7. Carter, P., (1971). Spectrophotometric determination of serum iron at the submicrogram level with a new reagent (ferrozine). Analytical Biochemistry, 40(2), 450-458. https://doi.org/10.1016/0003-2697(71)90405-2
8. Ellman, G. L., Courtney, K. D., Andres, V., Jr., & Feather-Stone, R. M., (1961). A new and rapid colorimetric determination of acetylcholinesterase activity. Biochemical Pharmacology, 7(2), 88-95. https://doi.org/10.1016/0006-2952(61)90145-9
9. Eroğlu, H. E., (2018). Names of Helichrysum taxa of Türkiye in Turkish and other languages. Avrasya Terim Dergisi, 6(1), 26-34.
10. Fraternale, D., Flamini, G., & Ascrizzi, R., (2019). In vitro anticollagenase and antielastase activities of essential oil of Helichrysum italicum subsp. italicum (Roth) G. Don. Journal of Medicinal Food, 22(10), 1041-1046. https://doi.org/10.1089/jmf.2019.0054
11. Gök, H., Pekacar, S., & Deliorman Orhan, D., (2022). Investigation of enzyme inhibitory activities, antioxidant activities, and chemical properties of Pistacia vera leaves using LC-QTOF-MS and RP-HPLC. Iranian Journal of Pharmaceutical Research, 21(1). https://doi.org/10.5812/ijpr-127033
12. Gras, A., Garnatje, T., Ibanez, N., Lopez-Pujol, J., Nualart, N., & Valles, J., (2017). Medicinal plant uses and names from the herbarium of Francesc Bolòs (1773-1844). Journal of Ethnopharmacology, 204, 142-168. https://doi.org/10.1016/j.jep.2017.04.002
13. Haddouchi, F., Chaouche, T. M., Ksouri, R., Medini, F., Sekkal, F. Z., & Benmansour, A., (2014). Antioxidant activity profiling by spectrophotometric methods of aqueous methanolic extracts of Helichrysum stoechas subsp. rupestre and Phagnalon saxatile subsp. saxatile. Chinese Journal of Natural Medicines, 12(6), 415-422. https://doi.org/10.1016/S1875-5364(14)60065-0
14. Hatano, T., Kagawa, H., Yasuhara, T., & Okuda, T., (1988). Two new flavonoids and other constituents in licorice root: their relative astringency and radical scavenging effects. Chemical and Pharmaceutical Bulletin, 36(6), 2090-2097. https://doi.org/10.1248/cpb.36.2090
15. Jovanović, M., Drinić, Z., Bigović, D., Alimpić-Aradski, A., Duletić-Laušević, S., & Šavikin, K., (2020). In vitro antineurodegenerative activity and in silico predictions of blood-brain barrier penetration of Helichrysum plicatum flower extract. Lekovite Sirovine, (40), 45-51. https://doi.org/10.5937/leksir2040045J
16. Kraunsoe, J. A., Claridge, T. D., & Lowe, G., (1996). Inhibition of human leukocyte and porcine pancreatic elastase by homologues of bovine pancreatic trypsin inhibitor. Biochemistry, 35(28), 9090-9096. https://doi.org/10.1021/bi953013b
17. Lee, S., Sandesh, S., Shruti, S., & Seo, S., (2009). Potent antielastase and antityrosinase activities of Astilbe chinensis. American journal of Pharmacology and Toxicology, 4(4), 127-129. https://doi.org/10.3844/ajptsp.2009.127.129
18. Memariani, Z., Moeini, R., Hamedi, S. S., Gorji, N., & Mozaffarpur, S. A., (2018). Medicinal plants with antithrombotic property in Persian medicine: a mechanistic review. Journal of Thrombosis and Thrombolysis, 45, 158-179. https://doi.org/10.1007/s11239-017-1580-3
19. Mukherjee, P. K., Maity, N., Nema, N. K., & Sarkar, B. K., (2011). Bioactive compounds from natural resources against skin aging. Phytomedicine, 19(1), 64-73. https://doi.org/10.1016/j.phymed.2011.10.003
20. Nejmi, I., Mükemre, M., Türker, R. S., Zengin, G., & Dalar, A., (2023). Analysis of phytochemical composition and biological activities of Helichrysum pallasii (Sprengel) ledeb leaves International Journal of Secondary Metabolite, 10(1), 71-85. https://doi.org/10.21448/ijsm.1132698
21. Oboh, G., Agunloye, O. M., Akinyemi, A. J., Ademiluyi, A. O., & Adefegha, S. A., (2013). Comparative study on the inhibitory effect of caffeic and chlorogenic acids on key enzymes linked to Alzheimer's disease and some pro-oxidant induced oxidative stress in rats' brain-in vitro. Neurochemical Research, 38, 413-419.
22. Oyaizu, M., (1986). Studies on products of browning reaction antioxidative activities of products of browning reaction prepared from glucosamine. The Japanese Journal of Nutrition and Dietetics, 44(6), 307-315. https://doi.org/10.5264/eiyogakuzashi.44.307
23. Sagbo, I. J., & Otang-Mbeng, W., (2020). Evaluation of the efficacy of ethanol leaf extract of Helichrysum petiolare Hilliard and BL Burtt against skin aging. Tropical Journal of Pharmaceutical Research, 19(12), 2631-2638. https://doi.org/10.4314/tjpr.v19i12.22
24. Silva, L., Rodrigues, A. M., Ciriani, M., Falé, P. L. V., Teixeira, V., Madeira, P., Machuqueiro, M., Pacheco, R., Florêncio, M. H., & Ascensão, L., (2017). Antiacetylcholinesterase activity and docking studies with chlorogenic acid, cynarin and arzanol from Helichrysum stoechas (Lamiaceae). Medicinal Chemistry Research, 26, 2942-2950. https://doi.org/10.1007/s00044-017-1994-7
25. Singleton, V. L., & Rossi, J. A., (1965). Colorimetry of total phenolics with phosphomolybdic-phosphotungstic acid reagents. American Journal of Enology and Viticulture, 16(3), 144-158.
26. Taşkın, T., Gezmiş, T., Çam, M. E., Taşkın, D., Çelik, B. Ö., Şenkardeş, İ., & Süzgeç-Selçuk, S., (2020). The in vitro and in vivo investigation of biological activities and phenolic analysis of Helichrysum plicatum subsp. plicatum. Brazilian Journal of Pharmaceutical Sciences, 56. https://doi.org/10.1590/s2175-97902019000418345
27. Terry, A. V., & Buccafusco, J. J., (2003). T The cholinergic hypothesis of age and Alzheimer's disease-related cognitive deficits: recent challenges and their implications for novel drug development. Journal of Pharmacology and Experimental Therapeutics, 306(3), 821-827. https://doi.org/10.1124/jpet.102.041616
28. Tsioutsiou, E. E., Amountzias, V., Vontzalidou, A., Dina, E., Stevanović, Z. D., Cheilari, A., & Aligiannis, N., (2022). Medicinal plants used traditionally for skin related problems in the South Balkan and East Mediterranean region-A review. Frontiers in Pharmacology, 13. https://doi.org/10.3389/fphar.2022.936047
29. Van Wart, H. E., & Steinbrink, D. R., (1981). A continuous spectrophotometric assay for Clostridium histolyticum collagenase. Analytical Biochemistry, 113(2), 356-365. https://doi.org/10.1016/0003-2697(81)90089-0
30. Version 7.2 of the Turkish Pharmacopoeia. Turkish Medicines and Medical Devices Agency, Ankara, Turkey, ISBN:978-975-590-733-8, 2019.
31. Woisky, R. G., & Salatino, A., (1998). Analysis of propolis: some parameters and procedures for chemical quality control. Journal of Apicultural Research, 37(2), 99-105. https://doi.org/10.1080/00218839.1998.11100961
32. Zengin, G., Cvetanović, A., Gašić, U., Tešić, Ž., Stupar, A., Bulut, G., Sinan, K. I., Uysal, S., Picot-Allain, M. C. N., & Mahomoodally, M. F., (2020). A comparative exploration of the phytochemical profiles and bio-pharmaceutical potential of Helichrysum stoechas subsp. barrelieri extracts obtained via five extraction techniques. Process Biochemistry, 91, 113-125. https://doi.org/10.1016/j.procbio.2019.12.002

There are 33 citations in total.

Details

Primary Language	English
Subjects	Pharmacology and Pharmaceutical Sciences (Other)
Journal Section	Research Articles
Authors	Nurten Abacı Kaplan 0000-0002-4144-7074 Hasya Nazlı Gök 0000-0003-4115-7509 Mustafa Aslan 0000-0003-3630-1764 İlkay Erdoğan Orhan 0000-0002-7379-5436
Early Pub Date	June 30, 2023
Publication Date	July 2, 2023
Published in Issue	Year 2023 Volume: 6 Issue: 1

Cite

APA	Abacı Kaplan, N., Gök, H. N., Aslan, M., Erdoğan Orhan, İ. (2023). Enzyme inhibitory and antioxidant activities and HPLC quantification of chlorogenic acid in Helichrysum stoechas (L.) Moench and H. stoechas subsp. barrelieri (Ten) Nyman. Current Perspectives on Medicinal and Aromatic Plants, 6(1), 38-50. https://doi.org/10.38093/cupmap.1314950

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