Phytochemical profiles and antimicrobial activity of the inflorescences of Sorbus domestica, S. aucuparia, and S. torminalis
Keywords:
rowans; inflorescences; floral metabolites; GC-MS profiling; chemotaxonomy; antimicrobial ability
Abstract
The genus Sorbus L. is known for its extremely complex taxonomical relationships and health-promoting phytochemicals included in the composition of its floral constituents. The inflorescences of three Sorbus species (rowans), characterized by distinct molecular-genetic traits, were studied in order to examine the possible chemotaxonomic and antimicrobial value of their metabolites. GC–MS profiling of the hexane extracts of S. domestica, S. aucuparia, and S. torminalis inflorescences identified a total of 87 components, which represented six chemical classes (hydrocarbons, alcohols, esters, fatty acid, aldehydes, and ketones) and miscellaneous minor floral constituents (1-methylinosine, 5-amino tetrazole, 1,4-dimethylbenzene, 3,5-bis(1,1-dimethylethyl)-phenol, 3-acetoxy-7,8-epoxylanostan-11-ol, cycloeucalenol acetate, etc.). Principal component analysis (PCA) of the qualitative and quantitative heterogeneity of the floral metabolites determined 1-hentetracontanol, nonacosane, pentadecyl acrylate, 1-methylhexacosane, cycloeucalenol acetate, butyl acetate, and urs-12-ene as the main components which contributed to the differences between S. domestica, S. aucuparia and S. torminalis and resulted in the distinction between the rowan species. Disc-diffusion assays showed variability in activity of inflorescence extracts against Gram-negative (Enterobacter dissolvens, Escherichia coli, Pseudomonas aeruginosa, and Klebsiella pneumoniae) and Gram-positive (Micrococcus lysodeikticus, Staphylococcus aureus, and S. epidermidis) bacterial and clinical fungal (Candida albicans) strains. The effect of S. torminalis was high against S. epidermidis and P. aeruginosa, while it was at its lowest against clinical C. albicans strains. Inflorescences of S. domestica showed the highest inhibition of P. aeruginosa, and moderate effects against S. epidermidis and C. albicans. Inflorescences of S. aucuparia caused low to moderate growth inhibition of both Gram-positive and Gram-negative bacterial strains, while it showed the highest effect on C. albicans. Antimicrobial properties of rowan inflorescences may be attributed to oleic, linoleic, arachidic, hexadecanoic, and pentadecanoic acids, 24-norursa-3,12-diene, hexahydrofarnesyl acetone, cycloeucalenol acetate, and other compounds which have known bioactivity. These findings indicated rowan inflorescences as a rich source of valuable secondary metabolites and allow us to assume an application of the floral constituents as chemotaxonomic markers of the genus Sorbus species.References
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Diab, T. A., Donia, T., & Saad-Allah, K. M. (2021). Characterization, antioxidant, and cytotoxic effects of some Egyptian wild plant extracts. Beni-Suef University Journal of Basic and Applied Sciences, 10, 13.
Dilika, F., Bremner, P. D., & Meyer, J. J. M. (2000). Antibacterial activity of linoleic and oleic acids isolated from Helichrysum pedunculatum: Plant used during circumcision rites. Fitoterapia, 71(4), 450–452.
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Gaivelyte, K., Jakstas, V., Razukas, A., & Janulis, V. (2014). Variation of quantitative composition of phenolic compounds in rowan (Sorbus aucuparia L.) leaves during the growth season. Natural Product Research, 28(13), 1018–1020.
Hamston, T. J., de Vere, N., King, R. A., Pellicer, J., Fay, M. F., Cresswell, J. E., & Stevens, J. R. (2018). Apomixis and hybridization drives reticulate evolution and phyletic differentiation in Sorbus L.: Implications for conservation. Frontiers in Plant Sciences, 9, 1796.
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Jin, X., Lv, Z., Gao, J., Zhang, R., Zheng, T., Yin, P., Li, D., Peng, L., Cao, X., Qin, Y., Persson, S., Zheng, B., & Chen, P. (2019). AtTrm5a catalyses 1-methylguanosine and 1-methylinosine formation on tRNAs and is important for vegetative and reproductive growth in Arabidopsis thaliana. Nucleic Acids Research, 47(2), 883–898.
Kandasamy, S., Ramu, S., & Aradhya, S. M. (2016). In vitro functional properties of crude extracts and isolated compounds from banana pseudostem and rhizome. Journal of the Science of the Food and Agriculture, 96(4), 1347–1355.
Kylli, P., Nohynek, L., Puupponen-Pimiä, R., Westerlund-Wikström, B., McDougall, G., Stewart, D., & Heinonen, M. J. (2010). Rowanberry phenolics: Compositional analysis and bioactivities. Agricultural and Food Chemistry, 58(22), 11985–11992.
Lens, C., Malet, G., & Cupferman, S. (2016). Antimicrobial activity of butyl acetate, ethyl acetate and isopropyl alcohol on undesirable microorganisms in cosmetic products. International Journal of Cosmetic Science, 38(5), 476–480.
Lipińska, M. M., Gołębiowski, M., Szlachetko, D. L., & Kowalkowska, A. K. (2022). Floral attractants in the black orchid Brasiliorchis schunkeana (Orchidaceae, Maxillariinae): Clues for presumed sapromyophily and potential antimicrobial activity. BMC Plant Biology, 22(1), 575.
Lykholat, Y. V., Khromykh, N. O., Didur, O. O., Drehval, O. A., Sklyar, T. V., & Anishchenko, A. O. (2021). Chaenomeles speciosa fruit endophytic fungi isolation and characterization of their antimicrobial activity and the secondary metabolites composition. Beni-Suef University Journal of Basic and Applied Sciences, 10, 83.
Mikulic-Petkovsek, M., Krska, B., Kiprovski, B., & Veberic, R. (2017). Bioactive components and antioxidant capacity of fruits from nine Sorbus genotypes. Journal of Food Science, 82(3), 647–658.
Mujeeb, F., Bajpai, P., & Pathak, N. (2014). Phytochemical evaluation, antimicrobial activity, and determination of bioactive components from leaves of Aegle marmelos. BioMed Research International, 2014, 497606.
Olszewska, M. A., & Michel, P. (2009). Antioxidant activity of inflorescences, leaves and fruits of three Sorbus species in relation to their polyphenolic composition. Natural Product Research, 23(16), 1507–1521.
Olszewska, M. A., Nowak, S., Michel, P., Banaszczak, P., & Kicel, A. (2010). Assessment of the content of phenolics and antioxidant action of inflorescences and leaves of selected species from the genus Sorbus sensu stricto. Molecules, 15(12), 8769–8783.
Orsavová, J., Juríková, T., Bednaříková, R., & Mlček, J. (2023). Total phenolic and total flavonoid content, individual phenolic compounds and antioxidant activity in sweet rowanberry cultivars. Antioxidants, 12(4), 913.
Raudonė, L., Raudonis, R., Gaivelytė, K., Pukalskas, A., Viškelis, P., Venskutonis, P. R., & Janulis, V. (2015). Phytochemical and antioxidant profiles of leaves from different Sorbus L. species. Natural Products Research, 29(3), 281–285.
Raudonis, R., Raudonė, L., Gaivelytė, K., Viškelis, P., Janulis, V. (2014). Phenolic and antioxidant profiles of rowan (Sorbus L.) fruits. Natural Products Research, 28(16), 1231–1240.
Robertson, K. R., Phipps, J. B., Rohrer, J. R., & Smith, P. G. (1991). A synopsis of genera in Maloideae (Rosaceae). Systematic Botany, 16(2), 376–394.
Shang, N., Saleem, A., Musallam, L., Walshe-Roussel, B., Badawi, A., Cuerrier, A., Arnason, J. T., & Haddad, P. S. (2015). Novel approach to identify potential bioactive plant metabolites: Pharmacological and metabolomics analyses of ethanol and hot water extracts of several canadian medicinal plants of the Cree of Eeyou Istchee. PLoS One, 10(8), e0135721.
Sohn, E. J., Kang, D. G., Mun, Y. J., Woo, W. H., & Lee, H. S. (2005). Anti-atherogenic effects of the methanol extract of Sorbus cortex in atherogenic-diet rats. Biological and Pharmaceutical Bulletin, 28(8), 1444–1449.
Sołtys, A., Galanty, A., & Podolak, I. (2020). Ethnopharmacologically important but underestimated genus Sorbus: A comprehensive review. Phytochemistry Reviews, 19, 491–526.
Spikes, A. E., Pashen, M. A., Millar, J. G., Moreira, J. A., Hamel, P. B., Schiff, N. M., & Ginzel, M. D. (2010). First contact pheromone identified for a longhorned beetle (Coleoptera: Cerambycidae) in the subfamily Prioninae. Journal of Chemical Ecology, 36(9), 943–954.
Tahirovic, A., Mehic, E., Kjosevski, N., & Bašic, N. (2019). Phenolics content and antioxidant activity of three Sorbus species. Bulletin of Chemists and Technologists of Bosnia and Herzegovina, 53, 15–21.
Tang, C., Chen, X., Deng, Y., Geng, L., Ma, J., & Wei, X. (2022). Complete chloroplast genomes of Sorbus sensu stricto (Rosaceae): Comparative analyses and phylogenetic relationships. BMC Plant Biology, 22, 495.
Ullah, O., Shah, M., Ur Rehman, N., Ullah, S., Al-Sabahi, J. N., Alam, T., Khan, A., Khan, N. A., Rafiq, N., Bilal, S., & Al-Harrasi, A. (2022). Aroma profile and biological effects of Ochradenus arabicus essential oils: A comparative study of stem, flowers, and leaves. Molecules, 27(16), 5197.
Venn-Watson, S. K., & Butterworth, C. N. (2022). Broader and safer clinically-relevant activities of pentadecanoic acid compared to omega-3: Evaluation of an emerging essential fatty acid across twelve primary human cell-based disease systems. PLoS One, 17(5), e0268778.
Vianna, R., Brault, A., Martineau, L. C., Couture, P., Arnason, J. T., & Haddad, P. S. (2011). In vivo anti-diabetic activity of the ethanolic crude extract of Sorbus decora C. K. Schneid. (Rosacea): A medicinal plant used by Canadian James Bay Cree nations to treat symptoms related to diabetes. Evidence-Based Complementary and Alternative Medicine, 2011, 237941.
Walters, D., Raynor, L., Mitchell, A., Walker, R., & Walker, K. (2004). Antifungal activities of four fatty acids against plant pathogenic fungi. Mycopathologia, 157(1), 87–90.
Wink, M. (2003). Evolution of secondary metabolites from an ecological and molecular phylogenetic perspective. Phytochemistry, 64, 3–19.
Xu, Z., Gao, P., Liu, D., Song, W., Zhu, L., & Liu, X. (2022). Chemical composition and in vitro antioxidant activity of Sida rhombifolia L. volatile organic compounds. Molecules, 27(20), 7067.
Yu, T., Lee, Y. J., Jang, H. J., Kim, A. R., Hong, S., Kim, T. W., Kim, M. Y., Lee, J., Lee, Y. G., & Cho, J. Y. (2011). Anti-inflammatory activity of Sorbus commixta water extract and its molecular inhibitory mechanism. Journal of Ethnopharmacology, 134(2), 493–500.
Zheng, C. J., Yoo, J. S., Lee, T. G., Cho, H. Y., Kim, Y. H., & Kim, W. G. (2005). Fatty acids synthesis is a target for antibacterial activity of unsaturated fatty acids. FEBS Letters, 579(23), 5157–5162.
Zhu, S., Jiao, W. H., Xu, Y. L., Hou, L. J., Li, H., Shao, J. R., Zhang, X. L., Wang, R., & Kong, D. X. (2021). Palmitic acid inhibits prostate cancer cell proliferation and metastasis by suppressing the PI3K/Akt pathway. Life Sciences, 286, 120046.
Zymone, K., Raudone, L., Raudonis, R., Marksa, M., Ivanauskas, L., & Janulis, V. (2018). Phytochemical profiling of fruit powders of twenty Sorbus L. cultivars. Molecules, 23(10), 2593.
Zymone, K., Raudone, L., Žvikas, V., Jakštas, V., & Janulis, V. (2022). Phytoprofiling of Sorbus L. inflorescences: A valuable and promising resource for phenolics. Plants, 11(24), 3421.
Choi, S. Y., Jeong, B., Jang, H. S., Lee, J., Ko, K., Kim, H., Hong, J., Bae, Y. S., & Yang, H. (2018). A new dibenzofuran from the barks of Sorbus commixta. Records of Natural Products, 12(2), 179–183.
Diab, T. A., Donia, T., & Saad-Allah, K. M. (2021). Characterization, antioxidant, and cytotoxic effects of some Egyptian wild plant extracts. Beni-Suef University Journal of Basic and Applied Sciences, 10, 13.
Dilika, F., Bremner, P. D., & Meyer, J. J. M. (2000). Antibacterial activity of linoleic and oleic acids isolated from Helichrysum pedunculatum: Plant used during circumcision rites. Fitoterapia, 71(4), 450–452.
Fahim, J. R., Darwish, A. G., Zawily, A. L. I., Wells, J., Abourehab, M. A. S., Desoukey, S. Y., & Attia, E. Z. (2023). Exploring the volatile metabolites of three Chorisia species: Comparative headspace GC–MS, multivariate chemometrics, chemotaxonomic significance, and anti-SARS-CoV-2 potential. Saudi Pharmaceutical Journal, 31(5), 706–726.
Fedoronchuk, M. M. (2017). Taksony Rosaceae flory Ukrajiny: Polozhennia v novij systemi rodyn, pobudovanij za danymy molekuliarno-filogenetychnogo analizu [Taxa of Rosaceae of the Ukrainian flora: Position in a new system of the family according to molecular phylogenetic data]. Ukrainian Botanical Journal, 4(1), 3–15 (in Ukrainian).
Fernandes, C. P., Corrêa, A. L., Lobo, J. F. R., Caramel, O. P., de Almeida, F. B., Castro, E. S., Souza, K. F. C. S., Burth, P., Amorim, L. M. F., Santos, M. G., Ferreira, J. L. P., Falcão, D. Q., Carvalho, J. C. T., & Rocha, L. (2013). Triterpene esters and biological activities from edible fruits of Manilkara subsericea (Mart.) Dubard, Sapotaceae. BioMed Research International, 2013, 280810.
Gaivelyte, K., Jakstas, V., Razukas, A., & Janulis, V. (2014). Variation of quantitative composition of phenolic compounds in rowan (Sorbus aucuparia L.) leaves during the growth season. Natural Product Research, 28(13), 1018–1020.
Hamston, T. J., de Vere, N., King, R. A., Pellicer, J., Fay, M. F., Cresswell, J. E., & Stevens, J. R. (2018). Apomixis and hybridization drives reticulate evolution and phyletic differentiation in Sorbus L.: Implications for conservation. Frontiers in Plant Sciences, 9, 1796.
Hukkanen, A. T., Pölönen, S. S., Kärenlampi, S. O., & Kokko, H. I. J. (2006). Antioxidant capacity and phenolic content of sweet rowanberries. Journal of Agricultural and Food Chemistry, 54(1), 112–119.
Jin, X., Lv, Z., Gao, J., Zhang, R., Zheng, T., Yin, P., Li, D., Peng, L., Cao, X., Qin, Y., Persson, S., Zheng, B., & Chen, P. (2019). AtTrm5a catalyses 1-methylguanosine and 1-methylinosine formation on tRNAs and is important for vegetative and reproductive growth in Arabidopsis thaliana. Nucleic Acids Research, 47(2), 883–898.
Kandasamy, S., Ramu, S., & Aradhya, S. M. (2016). In vitro functional properties of crude extracts and isolated compounds from banana pseudostem and rhizome. Journal of the Science of the Food and Agriculture, 96(4), 1347–1355.
Kylli, P., Nohynek, L., Puupponen-Pimiä, R., Westerlund-Wikström, B., McDougall, G., Stewart, D., & Heinonen, M. J. (2010). Rowanberry phenolics: Compositional analysis and bioactivities. Agricultural and Food Chemistry, 58(22), 11985–11992.
Lens, C., Malet, G., & Cupferman, S. (2016). Antimicrobial activity of butyl acetate, ethyl acetate and isopropyl alcohol on undesirable microorganisms in cosmetic products. International Journal of Cosmetic Science, 38(5), 476–480.
Lipińska, M. M., Gołębiowski, M., Szlachetko, D. L., & Kowalkowska, A. K. (2022). Floral attractants in the black orchid Brasiliorchis schunkeana (Orchidaceae, Maxillariinae): Clues for presumed sapromyophily and potential antimicrobial activity. BMC Plant Biology, 22(1), 575.
Lykholat, Y. V., Khromykh, N. O., Didur, O. O., Drehval, O. A., Sklyar, T. V., & Anishchenko, A. O. (2021). Chaenomeles speciosa fruit endophytic fungi isolation and characterization of their antimicrobial activity and the secondary metabolites composition. Beni-Suef University Journal of Basic and Applied Sciences, 10, 83.
Mikulic-Petkovsek, M., Krska, B., Kiprovski, B., & Veberic, R. (2017). Bioactive components and antioxidant capacity of fruits from nine Sorbus genotypes. Journal of Food Science, 82(3), 647–658.
Mujeeb, F., Bajpai, P., & Pathak, N. (2014). Phytochemical evaluation, antimicrobial activity, and determination of bioactive components from leaves of Aegle marmelos. BioMed Research International, 2014, 497606.
Olszewska, M. A., & Michel, P. (2009). Antioxidant activity of inflorescences, leaves and fruits of three Sorbus species in relation to their polyphenolic composition. Natural Product Research, 23(16), 1507–1521.
Olszewska, M. A., Nowak, S., Michel, P., Banaszczak, P., & Kicel, A. (2010). Assessment of the content of phenolics and antioxidant action of inflorescences and leaves of selected species from the genus Sorbus sensu stricto. Molecules, 15(12), 8769–8783.
Orsavová, J., Juríková, T., Bednaříková, R., & Mlček, J. (2023). Total phenolic and total flavonoid content, individual phenolic compounds and antioxidant activity in sweet rowanberry cultivars. Antioxidants, 12(4), 913.
Raudonė, L., Raudonis, R., Gaivelytė, K., Pukalskas, A., Viškelis, P., Venskutonis, P. R., & Janulis, V. (2015). Phytochemical and antioxidant profiles of leaves from different Sorbus L. species. Natural Products Research, 29(3), 281–285.
Raudonis, R., Raudonė, L., Gaivelytė, K., Viškelis, P., Janulis, V. (2014). Phenolic and antioxidant profiles of rowan (Sorbus L.) fruits. Natural Products Research, 28(16), 1231–1240.
Robertson, K. R., Phipps, J. B., Rohrer, J. R., & Smith, P. G. (1991). A synopsis of genera in Maloideae (Rosaceae). Systematic Botany, 16(2), 376–394.
Shang, N., Saleem, A., Musallam, L., Walshe-Roussel, B., Badawi, A., Cuerrier, A., Arnason, J. T., & Haddad, P. S. (2015). Novel approach to identify potential bioactive plant metabolites: Pharmacological and metabolomics analyses of ethanol and hot water extracts of several canadian medicinal plants of the Cree of Eeyou Istchee. PLoS One, 10(8), e0135721.
Sohn, E. J., Kang, D. G., Mun, Y. J., Woo, W. H., & Lee, H. S. (2005). Anti-atherogenic effects of the methanol extract of Sorbus cortex in atherogenic-diet rats. Biological and Pharmaceutical Bulletin, 28(8), 1444–1449.
Sołtys, A., Galanty, A., & Podolak, I. (2020). Ethnopharmacologically important but underestimated genus Sorbus: A comprehensive review. Phytochemistry Reviews, 19, 491–526.
Spikes, A. E., Pashen, M. A., Millar, J. G., Moreira, J. A., Hamel, P. B., Schiff, N. M., & Ginzel, M. D. (2010). First contact pheromone identified for a longhorned beetle (Coleoptera: Cerambycidae) in the subfamily Prioninae. Journal of Chemical Ecology, 36(9), 943–954.
Tahirovic, A., Mehic, E., Kjosevski, N., & Bašic, N. (2019). Phenolics content and antioxidant activity of three Sorbus species. Bulletin of Chemists and Technologists of Bosnia and Herzegovina, 53, 15–21.
Tang, C., Chen, X., Deng, Y., Geng, L., Ma, J., & Wei, X. (2022). Complete chloroplast genomes of Sorbus sensu stricto (Rosaceae): Comparative analyses and phylogenetic relationships. BMC Plant Biology, 22, 495.
Ullah, O., Shah, M., Ur Rehman, N., Ullah, S., Al-Sabahi, J. N., Alam, T., Khan, A., Khan, N. A., Rafiq, N., Bilal, S., & Al-Harrasi, A. (2022). Aroma profile and biological effects of Ochradenus arabicus essential oils: A comparative study of stem, flowers, and leaves. Molecules, 27(16), 5197.
Venn-Watson, S. K., & Butterworth, C. N. (2022). Broader and safer clinically-relevant activities of pentadecanoic acid compared to omega-3: Evaluation of an emerging essential fatty acid across twelve primary human cell-based disease systems. PLoS One, 17(5), e0268778.
Vianna, R., Brault, A., Martineau, L. C., Couture, P., Arnason, J. T., & Haddad, P. S. (2011). In vivo anti-diabetic activity of the ethanolic crude extract of Sorbus decora C. K. Schneid. (Rosacea): A medicinal plant used by Canadian James Bay Cree nations to treat symptoms related to diabetes. Evidence-Based Complementary and Alternative Medicine, 2011, 237941.
Walters, D., Raynor, L., Mitchell, A., Walker, R., & Walker, K. (2004). Antifungal activities of four fatty acids against plant pathogenic fungi. Mycopathologia, 157(1), 87–90.
Wink, M. (2003). Evolution of secondary metabolites from an ecological and molecular phylogenetic perspective. Phytochemistry, 64, 3–19.
Xu, Z., Gao, P., Liu, D., Song, W., Zhu, L., & Liu, X. (2022). Chemical composition and in vitro antioxidant activity of Sida rhombifolia L. volatile organic compounds. Molecules, 27(20), 7067.
Yu, T., Lee, Y. J., Jang, H. J., Kim, A. R., Hong, S., Kim, T. W., Kim, M. Y., Lee, J., Lee, Y. G., & Cho, J. Y. (2011). Anti-inflammatory activity of Sorbus commixta water extract and its molecular inhibitory mechanism. Journal of Ethnopharmacology, 134(2), 493–500.
Zheng, C. J., Yoo, J. S., Lee, T. G., Cho, H. Y., Kim, Y. H., & Kim, W. G. (2005). Fatty acids synthesis is a target for antibacterial activity of unsaturated fatty acids. FEBS Letters, 579(23), 5157–5162.
Zhu, S., Jiao, W. H., Xu, Y. L., Hou, L. J., Li, H., Shao, J. R., Zhang, X. L., Wang, R., & Kong, D. X. (2021). Palmitic acid inhibits prostate cancer cell proliferation and metastasis by suppressing the PI3K/Akt pathway. Life Sciences, 286, 120046.
Zymone, K., Raudone, L., Raudonis, R., Marksa, M., Ivanauskas, L., & Janulis, V. (2018). Phytochemical profiling of fruit powders of twenty Sorbus L. cultivars. Molecules, 23(10), 2593.
Zymone, K., Raudone, L., Žvikas, V., Jakštas, V., & Janulis, V. (2022). Phytoprofiling of Sorbus L. inflorescences: A valuable and promising resource for phenolics. Plants, 11(24), 3421.
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2023-07-19
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