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In Vitro Tyrosinase and Collagenase Inhibitory and Antioxidant Potential of Smyrnium rotundifolium Mill. and Euphorbia virgata Waldst.&Kit. from Türkiye

Year 2024, Volume: 45 Issue: 4, 756 - 762, 30.12.2024

Eda Sönmez Gürer , Ayşe Esra Karadağ , Rengin Baydar , Melek Demirel

https://doi.org/10.17776/csj.1568111

Abstract

Antioxidants help prevent signs of aging and skin tone inequalities by protecting our skin from free radicals. High tyrosinase inhibition has a whitening effect on the skin, while collagenase inhibition has an anti-sagging effect on the skin. Antioxidant activity and tyrosinase/collagenase enzyme inhibition capacities have mutually supporting effects. The aim of this study was to determine the antioxidant activities, tyrosinase and collagenase inhibitory potentials of ethanol extracts of two medicinal plants from Turkey (Smyrnium rotundifolium and Euphorbia virgata). In the study, 6 different reference substances and their chemical contents were investigated. Myricetin, quercetin and kaempferol were observed in S. rotundifolium extract, and quercetin was observed in E. virgata extract. According to the antioxidant capacity results measured by both analyses; S. rotundifolium (IC50 DPPH•: 4.9±0.15 µg/mL, IC50 ABTS•+: 4.3±0.2 µg/mL) and E. virgata (IC50 DPPH•: 4.6±0.11 µg/mL, IC50 ABTS•+: 4.1±0.13 µg/mL) extracts were observed to have antioxidant capacities similar to each other. It was determined that S. rotundifolium had higher anti-collagenase (27.9±0.13% inhibition) and anti-tyrosinase (11.1±0.14% inhibition) activities compared to E. virgata extract. These results showed us that S. rotundifolium can be considered as a strong candidate for the management of epidermal hyperpigmentation and skin elasticity and deserves further study.

Keywords

Antioxidant Collagenase Euphorbia virgata Smyrnium rotundifolium Tyrosinase

References

  • [1] Yan W., J Jiang L., Zhixiang W.S., Suying T., Comparative Study of Anti-inflammatory Effect of Rosa laevigata Root and Stem., Modern Chinese Medicine, 3 (2010).
  • [2] Bilgin Sökmen B., Yılmazoglu B., Tirozinaz Enziminin Giresun Yöresinde Yetişen Yenilebilir Kanlıca Mantarından (Lactarius salmonicolor) Saflaştırılması ve Karakterizasyonu, Karadeniz Fen Bilimleri Dergisi, 8 (2018) 10–23.
  • [3] Zengin G., Mahomoodally M.F., Picot-Allain C.M.N., Cakmak Y.S., Uysal S., Aktumsek A., In Vitro Tyrosinase Inhibitory and Antioxidant Potential of Consolida orientalis, Onosma isauricum and Spartium junceum from Turkey, South African Journal of Botany, 120 (2019) 119–123.
  • [4] Trivedi M.K., Yang F.C., Cho B.K., A Review of Laser and Light Therapy in Melasma, Int. J. of Women’s Dermatology, 3 (2017) 11–20.
  • [5] Pillaiyar T., Manickam M., Namasivayam V., Skin Whitening Agents: Medicinal Chemistry Perspective of Tyrosinase Inhibitors, Journal of Enzyme Inhibition and Medicinal Chemistry, 32 (2017) 403–425.
  • [6] 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 Biotechnology Biochem., 69 (2005) 197–201.
  • [7] Silva R.M.G. da, Alves C.P., Barbosa F.C., Santos H.H., Adão K.M., Granero F.O., Antioxidant, Antitumoral, Antimetastatic Effect and Inhibition of Collagenase Enzyme Activity of Eleutherine bulbosa (Dayak onion) Extract: In Vitro, In Vivo and In Silico Approaches, Journal of Ethnopharmacol, 318 (2024) 117005.
  • [8] Freitas-Rodríguez S., Folgueras A.R., López-Otín C., The Role of Matrix Metalloproteinases in Aging: Tissue Remodeling and Beyond, Biochimica et Biophysica Acta (BBA) - Molecular Cell Research, 1863(11) (2017) 2015–2025.
  • [9] Lee K.K., Cho J.J., Park E.J., Choi J.D., Anti‐Elastase and Anti‐Hyaluronidase of Phenolic Substance from Areca catechu as a New Anti‐Ageing Agent, Int. J. Cosmet. Sci., 23 (2001) 341–346.
  • [10] Farage M.A., Miller K.W., Elsner P., Maibach H.I., Characteristics of the Aging Skin, Adv. Wound Care (New Rochelle), 2 (2013) 5–10.
  • [11] Pilipović K., Jurišić Grubešić R., Dolenec P., Kučić N., Juretić L., Mršić-Pelčić J., Plant-Based Antioxidants for Prevention and Treatment of Neurodegenerative Diseases: Phytotherapeutic Potential of Laurus nobilis, Aronia melanocarpa, and Celastrol, Antioxidants, 12 (2023).
  • [12] Negreanu-Pirjol B.S., Oprea O.C., Negreanu-Pirjol T., Roncea F.N., Prelipcean A.M., Craciunescu O., Health Benefits of Antioxidant Bioactive Compounds in the Fruits and Leaves of Lonicera caerulea L. and Aronia melanocarpa (Michx.) Elliot, Antioxidant, 12 (2023).
  • [13] Turkoglu A., Duru M.E., Mercan N., Kivrak I., Gezer K., Antioxidant and Antimicrobial Activities of Laetiporus sulphureus (Bull.) Murrill, Food Chem., 101 (2007) 267–273.
  • [14] Mungan F., Yıldız K., Kılıç M., Kuh M., A Morphological Study of Smyrnium (Apiaceae) from Turkey, Biological Diversity and Conservation, 8 (2015) 54–59.
  • [15] Ayaz F., Eruygur N., Doğru T., Bağcı Y., Doğu S., Biological Activities of the Methanol Extracts of Smyrnium connatum Boiss. and Kotschy, Kahramanmaraş Sütçü İmam Üniversitesi Tarım ve Doğa Dergisi, 25 (2022) 1216–1224.
  • [16] Özbilgin S., Küpeli Akkol E., Süntar İ., Tekin M., Saltan İşcan G., Wound-Healing Activity of Some Species of Euphorbia L., Records of Natural Products, 13 (2018) 104–113.
  • [17] Tang Q., Su Z., Han Z., Ma X., Xu D., Liang Y., LC–MS Method for Detecting Prostratin in Plant Extracts and Identification of a High-Yielding Population of Euphorbia fischeriana, Phytochem. Lett., 5 (2012) 214–218.
  • [18] Rojas-Jiménez S., Valladares-Cisneros M.G., Salinas-Sánchez D.O., Pérez-Ramos J., Sánchez-Pérez L., Pérez-Gutiérrez S., Anti-Inflammatory and Cytotoxic Compounds Isolated from Plants of Euphorbia Genus, Molecules, 29 (2024) 1083.
  • [19] Sarı A.O., Oğuz B., Bilgiç A., Tort N., Güvensen A., Şenol S.G., Ege ve Güney Marmara Bölgelerinde Halk İlacı Olarak Kullanılan Bitkiler, A.A.R.I., 20 (2010) 1–21.
  • [20] Mata A.T., Proença C., Ferreira A.R., Serralheiro M.L.M., Nogueira J.M.F., Araújo M.E.M., Antioxidant and Antiacetylcholinesterase Activities of Five Plants used as Portuguese Food Spices, Food Chem., 103 (2007) 778–786.
  • [21] Okur M.E., Ayla Ş., Karadağ A.E., Çiçek Polat D., Demirci S., Seçkin İ., Opuntia ficus indica Fruits Ameliorate Cisplatin-Induced Nephrotoxicity in Mice, Biol. Pharm. Bull., 43 (2020) 831–838.
  • [22] Blois M.S., Antioxidant Determinations by the Use of a Stable Free Radical, Nature, 181 (1958) 1199–1200.
  • [23] Karakaş N., Karadağ A.E., Yılmaz R., Demirci F., Okur M.E., In Vitro Cytotoxicity Evaluation of Marrubium vulgare L. Methanol Extract, Journal of Research in Pharmacy, 23 (2019) 711–718.
  • [24] Re R., Pellegrini N., Proteggente A., Pannala A., Yang M., Rice-Evans C., Antioxidant Activity Applying an Improved ABTS Radical Cation Decolorization Assay, Free Radic. Biol. Med., 26 (1999) 1231–1237.
  • [25] Hearing V.J., Jiménez M., Mammalian Tyrosinase—The Critical Regulatory Control Point in Melanocyte Pigmentation, International Journal of Biochemistry, 19 (1987) 1141–1147.
  • [26] Şahin D., Çağlar E.Ş., Boran T., Karadağ A.E., Özhan G., Üstündağ Okur N., Development, Characterization of Naringenin-Loaded Promising Microemulsion Formulations, and Demonstration of Anti-Aging Efficacy by In Vitro Enzyme Activity and Gene Expression, J. Drug Deliv. Sci. Technol., 84 (2023) 104422.
  • [27] Gören N., Ulubelen A., Jakupovic J., Bohlmann F., Grenz M., Sesquiterpene Lactones from the Fruits of Smyrnium rotundifolium, Phytochemistry, 23 (1984) 2281–2284.
  • [28] Gören N., Ulubelen A., Oxepine Derivatives from the Roots of Smyrnium rotundifolium, Phytochemistry, 24 (1985) 3051–3052.
  • [29] Rozimamat R., Kehrimen N., Aisa H.A., New Compound from Euphorbia alatavica Boiss., Nat. Prod. Res., 33 (2019) 380–385.
  • [30] Kaçar D., Bayraktar O., Erdem C., Alamri A.S., Galanakis C.M., Antioxidant and Antimicrobial Activities of Plants Grown in the Mediterranean Region, JSFA Reports, 2 (2022) 452–461.
  • [31] Kulevanova S., Stefova M., Panovska T.K., Stafilov T., HPLC Identification and Determination of Myricetin, Quercetin, Kaempferol and Total Flavonoids in Herbal Drugs, Macedonian Pharmaceutical Bulletin, 48 (2002) 25–30.
  • [32] Ersin M., Ergönül B., Kalyoncu F., Proximate Composition, Antimicrobial and Antioxidant Activities of Six Wild Edible Celeries (Smyrnium L.), Afr. J. Pharm. Pharmacol, 6 (2012).
  • [33] Orhan I., Tosun F., Skalicka-Woźniak K., Cholinesterase, Tyrosinase Inhibitory and Antioxidant Potential of Randomly Selected Umbelliferous Plant Species and Chromatographic Profile of Heracleum platytaenium Boiss. and Angelica sylvestris L. var. sylvestris, Journal of the Serbian Chemical Society, 81 (2016) 357–368.
  • [34] Ulubelen A., Abdolmaleky H., Mabry T.J., Flavonoid Glycosides from Smyrnium perfoliatum, Smyrnium creticum and Smyrnium rotundifolium, J. Nat. Products, 45 (1982) 507.
  • [35] Jassbi A.R., Chemistry and Biological Activity of Secondary Metabolites in Euphorbia from Iran, Phytochemistry, 67 (2006) 1977–1984.
  • [36] Kirbag S., Erecevit P., Zengin F., Guvenc A., Antimicrobial Activities of Some Euphorbia Species, African Journal of Traditional Complementary and Alternative Medicines, 10 (2013).
  • [37] Solimine J., Garo E., Wedler J., Rusanov K., Fertig O., Hamburger M., Tyrosinase Inhibitory Constituents from a Polyphenol Enriched Fraction of Rose Oil Distillation Wastewater, Fitoterapia, 108 (2016) 13–19.
  • [38] Laksmiani N.P.L., Widiantara I.W.A., Pawarrangan A.B.S., Potency of Moringa (Moringa oleifera L.) Leaves Extract Containing Quercetin as a Depigmentation Agent Inhibiting the Tyrosinase Enzyme Using In-Silico and In-Vitro Assay, Pharmacia, 69 (2022) 85–92.

Year 2024, Volume: 45 Issue: 4, 756 - 762, 30.12.2024

Eda Sönmez Gürer , Ayşe Esra Karadağ , Rengin Baydar , Melek Demirel

https://doi.org/10.17776/csj.1568111

Abstract

References

  • [1] Yan W., J Jiang L., Zhixiang W.S., Suying T., Comparative Study of Anti-inflammatory Effect of Rosa laevigata Root and Stem., Modern Chinese Medicine, 3 (2010).
  • [2] Bilgin Sökmen B., Yılmazoglu B., Tirozinaz Enziminin Giresun Yöresinde Yetişen Yenilebilir Kanlıca Mantarından (Lactarius salmonicolor) Saflaştırılması ve Karakterizasyonu, Karadeniz Fen Bilimleri Dergisi, 8 (2018) 10–23.
  • [3] Zengin G., Mahomoodally M.F., Picot-Allain C.M.N., Cakmak Y.S., Uysal S., Aktumsek A., In Vitro Tyrosinase Inhibitory and Antioxidant Potential of Consolida orientalis, Onosma isauricum and Spartium junceum from Turkey, South African Journal of Botany, 120 (2019) 119–123.
  • [4] Trivedi M.K., Yang F.C., Cho B.K., A Review of Laser and Light Therapy in Melasma, Int. J. of Women’s Dermatology, 3 (2017) 11–20.
  • [5] Pillaiyar T., Manickam M., Namasivayam V., Skin Whitening Agents: Medicinal Chemistry Perspective of Tyrosinase Inhibitors, Journal of Enzyme Inhibition and Medicinal Chemistry, 32 (2017) 403–425.
  • [6] 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 Biotechnology Biochem., 69 (2005) 197–201.
  • [7] Silva R.M.G. da, Alves C.P., Barbosa F.C., Santos H.H., Adão K.M., Granero F.O., Antioxidant, Antitumoral, Antimetastatic Effect and Inhibition of Collagenase Enzyme Activity of Eleutherine bulbosa (Dayak onion) Extract: In Vitro, In Vivo and In Silico Approaches, Journal of Ethnopharmacol, 318 (2024) 117005.
  • [8] Freitas-Rodríguez S., Folgueras A.R., López-Otín C., The Role of Matrix Metalloproteinases in Aging: Tissue Remodeling and Beyond, Biochimica et Biophysica Acta (BBA) - Molecular Cell Research, 1863(11) (2017) 2015–2025.
  • [9] Lee K.K., Cho J.J., Park E.J., Choi J.D., Anti‐Elastase and Anti‐Hyaluronidase of Phenolic Substance from Areca catechu as a New Anti‐Ageing Agent, Int. J. Cosmet. Sci., 23 (2001) 341–346.
  • [10] Farage M.A., Miller K.W., Elsner P., Maibach H.I., Characteristics of the Aging Skin, Adv. Wound Care (New Rochelle), 2 (2013) 5–10.
  • [11] Pilipović K., Jurišić Grubešić R., Dolenec P., Kučić N., Juretić L., Mršić-Pelčić J., Plant-Based Antioxidants for Prevention and Treatment of Neurodegenerative Diseases: Phytotherapeutic Potential of Laurus nobilis, Aronia melanocarpa, and Celastrol, Antioxidants, 12 (2023).
  • [12] Negreanu-Pirjol B.S., Oprea O.C., Negreanu-Pirjol T., Roncea F.N., Prelipcean A.M., Craciunescu O., Health Benefits of Antioxidant Bioactive Compounds in the Fruits and Leaves of Lonicera caerulea L. and Aronia melanocarpa (Michx.) Elliot, Antioxidant, 12 (2023).
  • [13] Turkoglu A., Duru M.E., Mercan N., Kivrak I., Gezer K., Antioxidant and Antimicrobial Activities of Laetiporus sulphureus (Bull.) Murrill, Food Chem., 101 (2007) 267–273.
  • [14] Mungan F., Yıldız K., Kılıç M., Kuh M., A Morphological Study of Smyrnium (Apiaceae) from Turkey, Biological Diversity and Conservation, 8 (2015) 54–59.
  • [15] Ayaz F., Eruygur N., Doğru T., Bağcı Y., Doğu S., Biological Activities of the Methanol Extracts of Smyrnium connatum Boiss. and Kotschy, Kahramanmaraş Sütçü İmam Üniversitesi Tarım ve Doğa Dergisi, 25 (2022) 1216–1224.
  • [16] Özbilgin S., Küpeli Akkol E., Süntar İ., Tekin M., Saltan İşcan G., Wound-Healing Activity of Some Species of Euphorbia L., Records of Natural Products, 13 (2018) 104–113.
  • [17] Tang Q., Su Z., Han Z., Ma X., Xu D., Liang Y., LC–MS Method for Detecting Prostratin in Plant Extracts and Identification of a High-Yielding Population of Euphorbia fischeriana, Phytochem. Lett., 5 (2012) 214–218.
  • [18] Rojas-Jiménez S., Valladares-Cisneros M.G., Salinas-Sánchez D.O., Pérez-Ramos J., Sánchez-Pérez L., Pérez-Gutiérrez S., Anti-Inflammatory and Cytotoxic Compounds Isolated from Plants of Euphorbia Genus, Molecules, 29 (2024) 1083.
  • [19] Sarı A.O., Oğuz B., Bilgiç A., Tort N., Güvensen A., Şenol S.G., Ege ve Güney Marmara Bölgelerinde Halk İlacı Olarak Kullanılan Bitkiler, A.A.R.I., 20 (2010) 1–21.
  • [20] Mata A.T., Proença C., Ferreira A.R., Serralheiro M.L.M., Nogueira J.M.F., Araújo M.E.M., Antioxidant and Antiacetylcholinesterase Activities of Five Plants used as Portuguese Food Spices, Food Chem., 103 (2007) 778–786.
  • [21] Okur M.E., Ayla Ş., Karadağ A.E., Çiçek Polat D., Demirci S., Seçkin İ., Opuntia ficus indica Fruits Ameliorate Cisplatin-Induced Nephrotoxicity in Mice, Biol. Pharm. Bull., 43 (2020) 831–838.
  • [22] Blois M.S., Antioxidant Determinations by the Use of a Stable Free Radical, Nature, 181 (1958) 1199–1200.
  • [23] Karakaş N., Karadağ A.E., Yılmaz R., Demirci F., Okur M.E., In Vitro Cytotoxicity Evaluation of Marrubium vulgare L. Methanol Extract, Journal of Research in Pharmacy, 23 (2019) 711–718.
  • [24] Re R., Pellegrini N., Proteggente A., Pannala A., Yang M., Rice-Evans C., Antioxidant Activity Applying an Improved ABTS Radical Cation Decolorization Assay, Free Radic. Biol. Med., 26 (1999) 1231–1237.
  • [25] Hearing V.J., Jiménez M., Mammalian Tyrosinase—The Critical Regulatory Control Point in Melanocyte Pigmentation, International Journal of Biochemistry, 19 (1987) 1141–1147.
  • [26] Şahin D., Çağlar E.Ş., Boran T., Karadağ A.E., Özhan G., Üstündağ Okur N., Development, Characterization of Naringenin-Loaded Promising Microemulsion Formulations, and Demonstration of Anti-Aging Efficacy by In Vitro Enzyme Activity and Gene Expression, J. Drug Deliv. Sci. Technol., 84 (2023) 104422.
  • [27] Gören N., Ulubelen A., Jakupovic J., Bohlmann F., Grenz M., Sesquiterpene Lactones from the Fruits of Smyrnium rotundifolium, Phytochemistry, 23 (1984) 2281–2284.
  • [28] Gören N., Ulubelen A., Oxepine Derivatives from the Roots of Smyrnium rotundifolium, Phytochemistry, 24 (1985) 3051–3052.
  • [29] Rozimamat R., Kehrimen N., Aisa H.A., New Compound from Euphorbia alatavica Boiss., Nat. Prod. Res., 33 (2019) 380–385.
  • [30] Kaçar D., Bayraktar O., Erdem C., Alamri A.S., Galanakis C.M., Antioxidant and Antimicrobial Activities of Plants Grown in the Mediterranean Region, JSFA Reports, 2 (2022) 452–461.
  • [31] Kulevanova S., Stefova M., Panovska T.K., Stafilov T., HPLC Identification and Determination of Myricetin, Quercetin, Kaempferol and Total Flavonoids in Herbal Drugs, Macedonian Pharmaceutical Bulletin, 48 (2002) 25–30.
  • [32] Ersin M., Ergönül B., Kalyoncu F., Proximate Composition, Antimicrobial and Antioxidant Activities of Six Wild Edible Celeries (Smyrnium L.), Afr. J. Pharm. Pharmacol, 6 (2012).
  • [33] Orhan I., Tosun F., Skalicka-Woźniak K., Cholinesterase, Tyrosinase Inhibitory and Antioxidant Potential of Randomly Selected Umbelliferous Plant Species and Chromatographic Profile of Heracleum platytaenium Boiss. and Angelica sylvestris L. var. sylvestris, Journal of the Serbian Chemical Society, 81 (2016) 357–368.
  • [34] Ulubelen A., Abdolmaleky H., Mabry T.J., Flavonoid Glycosides from Smyrnium perfoliatum, Smyrnium creticum and Smyrnium rotundifolium, J. Nat. Products, 45 (1982) 507.
  • [35] Jassbi A.R., Chemistry and Biological Activity of Secondary Metabolites in Euphorbia from Iran, Phytochemistry, 67 (2006) 1977–1984.
  • [36] Kirbag S., Erecevit P., Zengin F., Guvenc A., Antimicrobial Activities of Some Euphorbia Species, African Journal of Traditional Complementary and Alternative Medicines, 10 (2013).
  • [37] Solimine J., Garo E., Wedler J., Rusanov K., Fertig O., Hamburger M., Tyrosinase Inhibitory Constituents from a Polyphenol Enriched Fraction of Rose Oil Distillation Wastewater, Fitoterapia, 108 (2016) 13–19.
  • [38] Laksmiani N.P.L., Widiantara I.W.A., Pawarrangan A.B.S., Potency of Moringa (Moringa oleifera L.) Leaves Extract Containing Quercetin as a Depigmentation Agent Inhibiting the Tyrosinase Enzyme Using In-Silico and In-Vitro Assay, Pharmacia, 69 (2022) 85–92.
There are 38 citations in total.

Details

Primary Language English
Subjects Plant Biochemistry, Botany (Other)
Journal Section Natural Sciences
Authors

Eda Sönmez Gürer 0000-0003-0319-6312

Ayşe Esra Karadağ 0000-0002-3412-0807

Rengin Baydar 0009-0008-3754-0293

Melek Demirel 0000-0002-8477-1122

Publication Date December 30, 2024
Submission Date October 19, 2024
Acceptance Date December 19, 2024
Published in Issue Year 2024Volume: 45 Issue: 4

Cite

APA Sönmez Gürer, E., Karadağ, A. E., Baydar, R., Demirel, M. (2024). In Vitro Tyrosinase and Collagenase Inhibitory and Antioxidant Potential of Smyrnium rotundifolium Mill. and Euphorbia virgata Waldst.&Kit. from Türkiye. Cumhuriyet Science Journal, 45(4), 756-762. https://doi.org/10.17776/csj.1568111
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