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Bioactive compounds of Arctostaphylos uva-ursi wild-growing populations from Bulgaria

Year 2024, Volume: 11 Issue: 1, 113 - 120, 05.02.2024
https://doi.org/10.21448/ijsm.1292525

Abstract

Arctostaphylos uva-ursi (L.) Sprengel (bearberry), Ericaceae is a valuable medicinal plant with diuretic and uroantiseptic action which is mainly due to arbutin. In Bulgaria the species is considered as rare. Content assessment of bioactive compounds of A. uva-ursi leaves from three natural populations from Bulgaria was the aim of the present study. Leaf samples were collected from Pirin, Vitosha, and Rhodope Mountains. Bioactive compounds in the methanolic extracts of the samples were analysed by GC/MS. Total phenolic content was determined using Folin–Ciocalteu reagent. Arbutin, quinic acid and gallic acid were detected in the highest amounts. Catechine, 4-hydroxybenzoic acid, chlorogenic acid, triterpenes (α- and β-amyrin, uvaol and lupeol) and other primary and secondary metabolites were found, also. Differences in the content of individual compounds between samples of different origin were established. The highest total phenolic (182.98 mg GAE g-1) and arbutin (8.4%) content was found in the sample from Vitosha Mountain. The presented data characterizes the profile of bioactive compounds in the Bulgarian bearberry raw material for the first time.

Project Number

Grant КП-06-Н26/6, 13.12.2018

References

  • Asensio, E., Vitales, D., Pérez, I., Peralba, L., Viruel, J., Montaner, C., Vallès, J., Garnatje, T., & Sales, E. (2020). Phenolic Compounds Content and Genetic Diversity at Population Level across the Natural Distribution Range of Bearberry (Arctostaphylos uva-ursi, Ericaceae) in the Iberian Peninsula. Plants, 9(9), 1250. https://doi.org/10.3390/plants9091250
  • Bhalla, M., R. Mittal, M., Kumar, A., & Kushwah S. (2023). Pharmacological Aspects of a Bioactive Compound Arbutin: A Comprehensive Review. Biointerface Research in Applied Chemistry, 13(2), 119. https://doi.org/10.33263/BRIAC132.119
  • Berkov, S., Pechlivanova, D., Denev, R., Nikolova, M., Georgieva, L., Sidjimova, B., Bakalov, D., Tafradjiiska, R., Stoynev, A., Momekov, G., & Bastida J. (2021). GC-MS analysis of Amaryllidaceae and Sceletium-type alkaloids in bioactive fractions from Narcissus cv. Hawera. Rapid Communications in Mass Spectrometry, 35(14), e9116. https://doi.org/10.1002/rcm.9116
  • Boo, Y.C. (2021). Arbutin as a Skin Depigmenting Agent with Antimelanogenic and Antioxidant Properties. Antioxidants, 10(7), 1129. https://doi.org/10.3390/antiox10071129
  • de Arriba, S.G,, Naser, B., & Nolte, K.U. (2013). Risk assessment of free hydroquinone derived from Arctostaphylos uva-ursi folium herbal preparations. International Journal of Toxicology, 32(6), 442-53. https://doi.org/10.1177/1091581813507721.
  • EMA European Medicine Agency. (2016). Assessment report on Arctostaphylos uva-ursi (L.) Spreng., folium EMA/HMPC/750266/2016
  • Jurica, K., Karačonji, I.B., Šegan, S., Opsenica, D.M., & Kremer D. (2015). Quantitative analysis of arbutin and hydroquinone in strawberry tree (Arbutus unedo L., Ericaceae) leaves by gas chromatography-mass spectrometry. Archives of Industrial Hygiene and Toxicology, 66, 197-202. https://doi.org/10.1515/aiht-2015-66-2696
  • Ingram, J., & Bartels, D. (1996). The molecular basis of dehydration tolerance in plants. Annual Review of Plant Physiology and Plant Molecular Biology, 47, 377 403. https://doi.org/10.1146/annurev.arplant.47.1.377
  • Kozhuharov, S. (Ed.). (1992). A field guide to the vascular plants in Bulgaria. Nauka & Izkustvo, Sofia (in Bulgarian).
  • Kurkin, V.A., Ryazanova, T.K., Daeva, E.D., & Kadentsev V.I. (2018). Constituents of Arctostaphylos uva ursi Leaves. Chemistry of Natural Compounds, 54, 278 280. https://doi.org/10.1007/s10600-018-2323-1
  • Olennikov, D.N., & Chekhirova, G.V. (2013). 6″-Galloylpicein and other phenolic compounds from Arctostaphylos uva ursi. Chemistry of Natural Compounds, 49, 1 7. https://doi.org/10.1007/s10600-013-0491-6
  • Parejo, I., Viladomat, F., Bastida, J.,& Codina, C. (2002). Variation of the arbutin content in different wild populations of Arctostaphylos uva-ursi in Catalonia, Spain. Journal of Herbs, Spices and Medicinal Plants, 9, 329-333.
  • Petrova, A., & Vladimirov, V. (2009). Red List of Bulgarian vascular plants. Phytologia Balcanica, 15, 63-94.
  • Sugier, P., Sęczyk, Ł., Sugier, D., Krawczyk, R., Wójcik, M., Czarnecka, J., Okoń, S., & Plak, A. (2021). Chemical Characteristics and Antioxidant Activity of Arctostaphylos uva-ursi L. Spreng. at the Southern Border of the Geographical Range of the Species in Europe. Molecules, 26(24), 7692. https://doi.org/10.3390/molecules26247692
  • Shamilov, A.A., Bubenchikova, V.N., Chernikov, M.V., Pozdnyakov, D.I., Garsiya, E.R., & Larsky, M.V. (2021). Bearberry (Arctostaphylos Uva-Ursi (L.) Spreng.): Chemical Content and Pharmacological Activity. Journal of Excipients and Food Chemicals, 12(3), 49-66.
  • Song, X.C., Canellas, E., Dreolin, N., Nerin, C., & Goshawk, J. (2021). Discovery and characterization of phenolic compounds in bearberry (Arctostaphylos uva-ursi) leaves using liquid chromatography-ion mobility-high-resolution mass spectrometry. Journal of Agricultural and Food Chemistry, 69(37), 10856 10868. https://doi.org/10.1021/acs.jafc.1c02845
  • Stefkov, G., Cvetkovikj-Karanfilova, I., Labroska, V., Krsteska, O., Qazimi, B., Karapandzova, M., Gjoni, Z., Bardhi, N., & Kulevanova, S. (2021). Variability of the arbutin content in wild growing populations of Arctostaphylos uva-ursi (L.) Spreng from Korab Mountain, Western Balkan. Macedonian Journal of Chemistry and Chemical Engineering, 40(1), 69-74. https://doi.org/10.20450/mjcce.2021.2095
  • Yang, L.,Wen, K.-S., Ruan, X., Zhao, Y.-X., Wei, F., & Wang, Q. (2018). Response of plant secondary metabolites to environmental factors. Molecules, 23, 762. https://doi.org/10.3390/molecules23040762

Bioactive compounds of Arctostaphylos uva-ursi wild-growing populations from Bulgaria

Year 2024, Volume: 11 Issue: 1, 113 - 120, 05.02.2024
https://doi.org/10.21448/ijsm.1292525

Abstract

Arctostaphylos uva-ursi (L.) Sprengel (bearberry), Ericaceae is a valuable medicinal plant with diuretic and uroantiseptic action which is mainly due to arbutin. In Bulgaria the species is considered as rare. Content assessment of bioactive compounds of A. uva-ursi leaves from three natural populations from Bulgaria was the aim of the present study. Leaf samples were collected from Pirin, Vitosha, and Rhodope Mountains. Bioactive compounds in the methanolic extracts of the samples were analysed by GC/MS. Total phenolic content was determined using Folin–Ciocalteu reagent. Arbutin, quinic acid and gallic acid were detected in the highest amounts. Catechine, 4-hydroxybenzoic acid, chlorogenic acid, triterpenes (α- and β-amyrin, uvaol and lupeol) and other primary and secondary metabolites were found, also. Differences in the content of individual compounds between samples of different origin were established. The highest total phenolic (182.98 mg GAE g-1) and arbutin (8.4%) content was found in the sample from Vitosha Mountain. The presented data characterizes the profile of bioactive compounds in the Bulgarian bearberry raw material for the first time.

Supporting Institution

Bulgarian National Science Fund, Bulgarian Ministry of Education and Science

Project Number

Grant КП-06-Н26/6, 13.12.2018

Thanks

The authors are grateful for the financial support by the Bulgarian National Science Fund, Bulgarian Ministry of Education and Science

References

  • Asensio, E., Vitales, D., Pérez, I., Peralba, L., Viruel, J., Montaner, C., Vallès, J., Garnatje, T., & Sales, E. (2020). Phenolic Compounds Content and Genetic Diversity at Population Level across the Natural Distribution Range of Bearberry (Arctostaphylos uva-ursi, Ericaceae) in the Iberian Peninsula. Plants, 9(9), 1250. https://doi.org/10.3390/plants9091250
  • Bhalla, M., R. Mittal, M., Kumar, A., & Kushwah S. (2023). Pharmacological Aspects of a Bioactive Compound Arbutin: A Comprehensive Review. Biointerface Research in Applied Chemistry, 13(2), 119. https://doi.org/10.33263/BRIAC132.119
  • Berkov, S., Pechlivanova, D., Denev, R., Nikolova, M., Georgieva, L., Sidjimova, B., Bakalov, D., Tafradjiiska, R., Stoynev, A., Momekov, G., & Bastida J. (2021). GC-MS analysis of Amaryllidaceae and Sceletium-type alkaloids in bioactive fractions from Narcissus cv. Hawera. Rapid Communications in Mass Spectrometry, 35(14), e9116. https://doi.org/10.1002/rcm.9116
  • Boo, Y.C. (2021). Arbutin as a Skin Depigmenting Agent with Antimelanogenic and Antioxidant Properties. Antioxidants, 10(7), 1129. https://doi.org/10.3390/antiox10071129
  • de Arriba, S.G,, Naser, B., & Nolte, K.U. (2013). Risk assessment of free hydroquinone derived from Arctostaphylos uva-ursi folium herbal preparations. International Journal of Toxicology, 32(6), 442-53. https://doi.org/10.1177/1091581813507721.
  • EMA European Medicine Agency. (2016). Assessment report on Arctostaphylos uva-ursi (L.) Spreng., folium EMA/HMPC/750266/2016
  • Jurica, K., Karačonji, I.B., Šegan, S., Opsenica, D.M., & Kremer D. (2015). Quantitative analysis of arbutin and hydroquinone in strawberry tree (Arbutus unedo L., Ericaceae) leaves by gas chromatography-mass spectrometry. Archives of Industrial Hygiene and Toxicology, 66, 197-202. https://doi.org/10.1515/aiht-2015-66-2696
  • Ingram, J., & Bartels, D. (1996). The molecular basis of dehydration tolerance in plants. Annual Review of Plant Physiology and Plant Molecular Biology, 47, 377 403. https://doi.org/10.1146/annurev.arplant.47.1.377
  • Kozhuharov, S. (Ed.). (1992). A field guide to the vascular plants in Bulgaria. Nauka & Izkustvo, Sofia (in Bulgarian).
  • Kurkin, V.A., Ryazanova, T.K., Daeva, E.D., & Kadentsev V.I. (2018). Constituents of Arctostaphylos uva ursi Leaves. Chemistry of Natural Compounds, 54, 278 280. https://doi.org/10.1007/s10600-018-2323-1
  • Olennikov, D.N., & Chekhirova, G.V. (2013). 6″-Galloylpicein and other phenolic compounds from Arctostaphylos uva ursi. Chemistry of Natural Compounds, 49, 1 7. https://doi.org/10.1007/s10600-013-0491-6
  • Parejo, I., Viladomat, F., Bastida, J.,& Codina, C. (2002). Variation of the arbutin content in different wild populations of Arctostaphylos uva-ursi in Catalonia, Spain. Journal of Herbs, Spices and Medicinal Plants, 9, 329-333.
  • Petrova, A., & Vladimirov, V. (2009). Red List of Bulgarian vascular plants. Phytologia Balcanica, 15, 63-94.
  • Sugier, P., Sęczyk, Ł., Sugier, D., Krawczyk, R., Wójcik, M., Czarnecka, J., Okoń, S., & Plak, A. (2021). Chemical Characteristics and Antioxidant Activity of Arctostaphylos uva-ursi L. Spreng. at the Southern Border of the Geographical Range of the Species in Europe. Molecules, 26(24), 7692. https://doi.org/10.3390/molecules26247692
  • Shamilov, A.A., Bubenchikova, V.N., Chernikov, M.V., Pozdnyakov, D.I., Garsiya, E.R., & Larsky, M.V. (2021). Bearberry (Arctostaphylos Uva-Ursi (L.) Spreng.): Chemical Content and Pharmacological Activity. Journal of Excipients and Food Chemicals, 12(3), 49-66.
  • Song, X.C., Canellas, E., Dreolin, N., Nerin, C., & Goshawk, J. (2021). Discovery and characterization of phenolic compounds in bearberry (Arctostaphylos uva-ursi) leaves using liquid chromatography-ion mobility-high-resolution mass spectrometry. Journal of Agricultural and Food Chemistry, 69(37), 10856 10868. https://doi.org/10.1021/acs.jafc.1c02845
  • Stefkov, G., Cvetkovikj-Karanfilova, I., Labroska, V., Krsteska, O., Qazimi, B., Karapandzova, M., Gjoni, Z., Bardhi, N., & Kulevanova, S. (2021). Variability of the arbutin content in wild growing populations of Arctostaphylos uva-ursi (L.) Spreng from Korab Mountain, Western Balkan. Macedonian Journal of Chemistry and Chemical Engineering, 40(1), 69-74. https://doi.org/10.20450/mjcce.2021.2095
  • Yang, L.,Wen, K.-S., Ruan, X., Zhao, Y.-X., Wei, F., & Wang, Q. (2018). Response of plant secondary metabolites to environmental factors. Molecules, 23, 762. https://doi.org/10.3390/molecules23040762
There are 18 citations in total.

Details

Primary Language English
Subjects Organic Chemistry
Journal Section Articles
Authors

Milena Nikolova 0000-0002-8513-0562

Ina Aneva This is me 0000-0002-6476-5438

Petar Zhelev This is me 0000-0002-4273-3400

Strahil Berkov This is me 0000-0002-4210-3070

Elina Yankova-tsvetkova This is me 0000-0002-4455-9768

Project Number Grant КП-06-Н26/6, 13.12.2018
Publication Date February 5, 2024
Submission Date May 4, 2023
Published in Issue Year 2024 Volume: 11 Issue: 1

Cite

APA Nikolova, M., Aneva, I., Zhelev, P., Berkov, S., et al. (2024). Bioactive compounds of Arctostaphylos uva-ursi wild-growing populations from Bulgaria. International Journal of Secondary Metabolite, 11(1), 113-120. https://doi.org/10.21448/ijsm.1292525
International Journal of Secondary Metabolite

e-ISSN: 2148-6905