A sustainable application for the extraction of lichen metabolites from Usnea cornuta: nontargeted metabolomics and antioxidant activity

In this study, isolation and purification of lichen substances from Usnea cornuta were performed using conventional solvents, green solvents and green technologies. In addition, several lichen compounds were tentatively identified by UHPLC/ESI/MS/MS and usnic acid, diffractaic and galbinic acids wer...

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Autores:
Castañeta, Grover
Sepulveda, Beatriz
Vargas, Reinaldo
Garcia, Paula Andrea
Simirgiotis, Mario
Areche, Carlos
Tipo de recurso:
Article of investigation
Fecha de publicación:
2023
Institución:
Universidad de Ibagué
Repositorio:
Repositorio Universidad de Ibagué
Idioma:
eng
OAI Identifier:
oai:repositorio.unibague.edu.co:20.500.12313/5562
Acceso en línea:
https://hdl.handle.net/20.500.12313/5562
https://www.tandfonline.com/doi/full/10.1080/14786419.2022.2116703
Palabra clave:
Disolventes alternativos
Química verde
Líquenes
Alternative solvents
Antioxidants
Green chemistry
LC/MS
Lichens
Usnea
Rights
closedAccess
License
© 2022 Informa UK Limited, trading as Taylor & Francis Group.
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network_acronym_str UNIBAGUE2
network_name_str Repositorio Universidad de Ibagué
repository_id_str
dc.title.eng.fl_str_mv A sustainable application for the extraction of lichen metabolites from Usnea cornuta: nontargeted metabolomics and antioxidant activity
title A sustainable application for the extraction of lichen metabolites from Usnea cornuta: nontargeted metabolomics and antioxidant activity
spellingShingle A sustainable application for the extraction of lichen metabolites from Usnea cornuta: nontargeted metabolomics and antioxidant activity
Disolventes alternativos
Química verde
Líquenes
Alternative solvents
Antioxidants
Green chemistry
LC/MS
Lichens
Usnea
title_short A sustainable application for the extraction of lichen metabolites from Usnea cornuta: nontargeted metabolomics and antioxidant activity
title_full A sustainable application for the extraction of lichen metabolites from Usnea cornuta: nontargeted metabolomics and antioxidant activity
title_fullStr A sustainable application for the extraction of lichen metabolites from Usnea cornuta: nontargeted metabolomics and antioxidant activity
title_full_unstemmed A sustainable application for the extraction of lichen metabolites from Usnea cornuta: nontargeted metabolomics and antioxidant activity
title_sort A sustainable application for the extraction of lichen metabolites from Usnea cornuta: nontargeted metabolomics and antioxidant activity
dc.creator.fl_str_mv Castañeta, Grover
Sepulveda, Beatriz
Vargas, Reinaldo
Garcia, Paula Andrea
Simirgiotis, Mario
Areche, Carlos
dc.contributor.author.none.fl_str_mv Castañeta, Grover
Sepulveda, Beatriz
Vargas, Reinaldo
Garcia, Paula Andrea
Simirgiotis, Mario
Areche, Carlos
dc.subject.armarc.none.fl_str_mv Disolventes alternativos
Química verde
Líquenes
topic Disolventes alternativos
Química verde
Líquenes
Alternative solvents
Antioxidants
Green chemistry
LC/MS
Lichens
Usnea
dc.subject.proposal.eng.fl_str_mv Alternative solvents
Antioxidants
Green chemistry
LC/MS
Lichens
Usnea
description In this study, isolation and purification of lichen substances from Usnea cornuta were performed using conventional solvents, green solvents and green technologies. In addition, several lichen compounds were tentatively identified by UHPLC/ESI/MS/MS and usnic acid, diffractaic and galbinic acids were quantified as well. Limonene, ethyl lactate and methanol, were compared regarding their extraction properties and antioxidant capacities, determined by DPPH, ORAC, and FRAP assays. In the ethyl lactate, methanol and limonene extracts, 28 compounds in all, were detected for the first time by high resolution UHPLC-MS/MS fingerprinting. Untargeted metabolomics tentatively identified 14 compounds from the methanolic extract, 4 from limonene extract, and 20 metabolites from ethyl lactate extract. The green extract of ethyl lactate showed a similar antioxidant capacity to toxic methanol extract, except at ORAC assay where it was higher. Therefore, ethyl lactate can replace methanol, to provide more sustainable green chemistry methods.
publishDate 2023
dc.date.issued.none.fl_str_mv 2023
dc.date.accessioned.none.fl_str_mv 2025-08-29T15:50:01Z
dc.date.available.none.fl_str_mv 2025-08-29T15:50:01Z
dc.type.none.fl_str_mv Artículo de revista
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dc.identifier.citation.none.fl_str_mv Castañeta, G., Sepulveda, B., Vargas, R., Garcia-Beltran, O., Simirgiotis, M. y Areche, C. (2023). A sustainable application for the extraction of lichen metabolites from Usnea cornuta: nontargeted metabolomics and antioxidant activity. Natural Product Research, 37(12), 2076 - 2082. DOI: 10.1080/14786419.2022.2116703
dc.identifier.doi.none.fl_str_mv 10.1080/14786419.2022.2116703
dc.identifier.eissn.none.fl_str_mv 14786427
dc.identifier.issn.none.fl_str_mv 14786419
dc.identifier.uri.none.fl_str_mv https://hdl.handle.net/20.500.12313/5562
dc.identifier.url.none.fl_str_mv https://www.tandfonline.com/doi/full/10.1080/14786419.2022.2116703
identifier_str_mv Castañeta, G., Sepulveda, B., Vargas, R., Garcia-Beltran, O., Simirgiotis, M. y Areche, C. (2023). A sustainable application for the extraction of lichen metabolites from Usnea cornuta: nontargeted metabolomics and antioxidant activity. Natural Product Research, 37(12), 2076 - 2082. DOI: 10.1080/14786419.2022.2116703
10.1080/14786419.2022.2116703
14786427
14786419
url https://hdl.handle.net/20.500.12313/5562
https://www.tandfonline.com/doi/full/10.1080/14786419.2022.2116703
dc.language.iso.none.fl_str_mv eng
language eng
dc.relation.citationendpage.none.fl_str_mv 2082
dc.relation.citationissue.none.fl_str_mv 17
dc.relation.citationstartpage.none.fl_str_mv 2076
dc.relation.citationvolume.none.fl_str_mv 37
dc.relation.ispartofjournal.none.fl_str_mv Natural Product Research
dc.relation.references.none.fl_str_mv Behera, 2005 Behera B.C., Verma N., Sonone A., Makhija U. Antioxidant and antibacterial activities of lichen Usnea ghattensis in vitro Biotechnol Lett, 27 (14) (2005), pp. 991-995
Calla-Quispe, 2020 Calla-Quispe E., Robles J., Areche C., Sepulveda B. Are ionic liquids better extracting agents than toxic volatile organic solvents? A combination of ionic liquids, microwave and LC/MS/MS, applied to the lichen Stereocaulon glareosum Front Chem, 8 (2020), p. 450
Cañadas, 2020 Cañadas R., González-Miquel M., González E.J., Díaz I., Rodríguez M. Overview of neoteric solvents as extractants in food industry: a focus on phenolic compounds separation from liquid streams Food Res Int, 136 (2020), p. 109558
Chae, 2021 Chae H.-J., Kim G.-J., Deshar B., Kim H.-J., Shin M.-J., Kwon H., Youn U.-J., Nam J.-W., Kim S.-H., Choi H. Anticancer activity of 2-O-caffeoyl alphitolic acid extracted from the Lichen, Usnea barbata 2017-KL-10 Molecules, 26 (13) (2021), p. 3937 10.3390/molecules26133937
Chemat, 2019 Chemat F., Abert-Vian M., Fabiano-Tixier A.S., Strube J., Uhlenbrock L., Gunjevic V., Cravotto G. Green extraction of natural products. Origins, current status, and future challenges TrAC Trends Anal Chem, 118 (2019), pp. 248-263
Doble, 2007 Doble M., Rollins K., Kumar A. Doble M., Kruthiventi A.K. (Eds.), Green chemistry and engineering, Academic Press, Burlington (2007), pp. xi-xiii
Elix, 1975 Elix J.A., Engkaninan U. The structure of galbinic acid. A depsidone from the lichen Usnea Undulata Aust J Chem, 28 (8) (1975), pp. 1793-1797
Fernández-Moriano, 2016 Fernández-Moriano C., Gómez-Serranillos M.P., Crespo A. Antioxidant potential of lichen species and their secondary metabolites. A systematic review Pharm Biol, 54 (1) (2016), pp. 1-17
Okuyama, 1995 Okuyama E., Umeyama K., Yamazaki M., Kinoshita Y., Yamamoto Y. Usnic acid and diffractaic acid as analgesic and antipyretic components of Usnea diffracta Planta Med, 61 (2) (1995), pp. 113-115
Pathak, 2016 Pathak A., Upreti D.K., Dikshit A. Antidermatophytic activity of the fruticose lichen Usnea orientalis Medicines, 3 (3) (2016), p. 24
Pavithra, 2013 Pavithra G.M., Vinayaka K.S., Rakesh K.N., Syed J., Dileep N., Prashith Kekuda T.R., Saba S., Abhishiktha SN. Antimicrobial and antioxidant activities of a macrolichen Usnea pictoides G. Awasthi (Parmeliaceae) J. Appl. Pharm. Sci, 3 (2013), pp. 154-160
Pereira, 2011 Pereira C.S.M., Silva V.M.T.M., Rodrigues AE. Ethyl lactate as a solvent: properties, applications and production processes – a review Green Chem, 13 (10) (2011), pp. 2658-2671
Popovici, 2021 Popovici V., Bucur L., Popescu A., Schröder V., Costache T., Rambu D., Cucolea I.E., Gîrd C.E., Caraiane A., Gherghel D. Antioxidant and cytotoxic activities of Usnea barbata (L.) F.H. Wigg. Dry extracts in different solvents Plants, 10 (5) (2021), p. 909
Popovici, 2021 Popovici V., Matei E., Cozaru G.C., Aschie M., Bucur L., Rambu D., Costache T., Cucolea I.E., Vochita G., Gherghel D. Usnic acid and Usnea barbata (L.) F.H. wigg. Dry extracts promote apoptosis and DNA damage in human blood cells through enhancing ROS levels Antioxidants, 10 (8) (2021), p. 1171 https://doi.org/10.3390/antiox10081171
Prateeksha, 2016 Prateeksha P., Paliya B.S., Bajpai R., Jadaun V., Kumar J., Kumar S., Upreti D.K., Singh B.R., Nayaka S., Joshi Y. The genus Usnea: a potent phytomedicine with multifarious ethnobotany, phytochemistry and pharmacology RSC Adv, 6 (26) (2016), pp. 21672-21696
Reddy, 2019 Reddy S.D., Siva B., Kumar K., Babu V.S.P., Sravanthi V., Boustie J., Nayak V.L., Tiwari A.K., Rao C.V., Sridhar B. Comprehensive analysis of secondary metabolites in Usnea longissima. Lichenized Ascomycetes, Parmeliaceae) using UPLC-ESI-QTOF-MS/MS and pro-apoptotic activity of barbatic acid Molecules, 24 (2019), p. 2270
Salgado, 2020 Salgado F., Caballero J., Vargas R., Cornejo A., Areche C. Continental and Antarctic lichens: isolation, identification and molecular modeling of the depside tenuiorin from the Antarctic lichen Umbilicaria antarctica as tau protein inhibitor Nat Prod Res, 34 (5) (2020), pp. 646-650
Sepulveda, 2021 Sepulveda B., Benites D., Albornoz L., Simirgiotis M., Castro O., Garcia-Beltran O., Areche C. Green ultrasound-assisted extraction of lichen substances from Hypotrachyna cirrhata. Ethyl lactate, a better extracting agent than methanol toxic organic solvent? Nat Prod Res (2021) 10.1080/14786419.2021.1956922.34319194AQ1
Soquetta, 2018 Soquetta M.B., de Marsillac Terra L., Bastos CP. Green technologies for the extraction of bioactive compounds in fruits and vegetables CyTA-J Food, 16 (1) (2018), pp. 400-412
Tang, 2020 Tang J.-Y., Wu K.-H., Wang Y.-Y., Farooqi A.A., Huang H.-W., Yuan S.-S.F., Jian R.-I., Tsao L.-Y., Chen P.-A., Chang F.-R. Methanol extract of Usnea barbata induces cell killing, apoptosis, and DNA damage against oral cancer cells through oxidative stress Antioxidants, 9 (8) (2020), p. 694
Verma, 2008 Verma N., Behera B.C., Makhija U. Antioxidant and hepatoprotective activity of a lichen Usnea ghattensis in vitro Appl Biochem Biotechnol, 151 (2–3) (2008), pp. 167-181
Zugic, 2016 Zugic A., Jeremic I., Isakovic A., Arsic I., Savic S., Tadic V. Evaluation of anticancer and antioxidant activity of a commercially available CO2 supercritical extract of old man’s beard (Usnea barbata) PLoS One, 11 (1) (2016), p. e0146342
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spelling Castañeta, Groverf6ce73da-22f5-4391-958a-7fa62c5429b9-1Sepulveda, Beatriz0c4325ab-8765-4a63-9db5-9d1251af044a-1Vargas, Reinaldoee48d3f9-40d0-46ee-9ea7-90a48097cd3e-1Garcia, Paula Andreaa4e15700-17da-4d96-8175-328bd0dee82b600Simirgiotis, Mario6e012459-0e88-4d46-a491-c3cb8056c060-1Areche, Carlosb6d8fc85-e264-4a47-b13b-f39b0ae610ab-12025-08-29T15:50:01Z2025-08-29T15:50:01Z2023In this study, isolation and purification of lichen substances from Usnea cornuta were performed using conventional solvents, green solvents and green technologies. In addition, several lichen compounds were tentatively identified by UHPLC/ESI/MS/MS and usnic acid, diffractaic and galbinic acids were quantified as well. Limonene, ethyl lactate and methanol, were compared regarding their extraction properties and antioxidant capacities, determined by DPPH, ORAC, and FRAP assays. In the ethyl lactate, methanol and limonene extracts, 28 compounds in all, were detected for the first time by high resolution UHPLC-MS/MS fingerprinting. Untargeted metabolomics tentatively identified 14 compounds from the methanolic extract, 4 from limonene extract, and 20 metabolites from ethyl lactate extract. The green extract of ethyl lactate showed a similar antioxidant capacity to toxic methanol extract, except at ORAC assay where it was higher. Therefore, ethyl lactate can replace methanol, to provide more sustainable green chemistry methods.application/pdfCastañeta, G., Sepulveda, B., Vargas, R., Garcia-Beltran, O., Simirgiotis, M. y Areche, C. (2023). A sustainable application for the extraction of lichen metabolites from Usnea cornuta: nontargeted metabolomics and antioxidant activity. Natural Product Research, 37(12), 2076 - 2082. DOI: 10.1080/14786419.2022.211670310.1080/14786419.2022.21167031478642714786419https://hdl.handle.net/20.500.12313/5562https://www.tandfonline.com/doi/full/10.1080/14786419.2022.2116703engTaylor and Francis Ltd.Reino Unido208217207637Natural Product ResearchBehera, 2005 Behera B.C., Verma N., Sonone A., Makhija U. Antioxidant and antibacterial activities of lichen Usnea ghattensis in vitro Biotechnol Lett, 27 (14) (2005), pp. 991-995Calla-Quispe, 2020 Calla-Quispe E., Robles J., Areche C., Sepulveda B. Are ionic liquids better extracting agents than toxic volatile organic solvents? A combination of ionic liquids, microwave and LC/MS/MS, applied to the lichen Stereocaulon glareosum Front Chem, 8 (2020), p. 450Cañadas, 2020 Cañadas R., González-Miquel M., González E.J., Díaz I., Rodríguez M. Overview of neoteric solvents as extractants in food industry: a focus on phenolic compounds separation from liquid streams Food Res Int, 136 (2020), p. 109558Chae, 2021 Chae H.-J., Kim G.-J., Deshar B., Kim H.-J., Shin M.-J., Kwon H., Youn U.-J., Nam J.-W., Kim S.-H., Choi H. Anticancer activity of 2-O-caffeoyl alphitolic acid extracted from the Lichen, Usnea barbata 2017-KL-10 Molecules, 26 (13) (2021), p. 3937 10.3390/molecules26133937Chemat, 2019 Chemat F., Abert-Vian M., Fabiano-Tixier A.S., Strube J., Uhlenbrock L., Gunjevic V., Cravotto G. Green extraction of natural products. Origins, current status, and future challenges TrAC Trends Anal Chem, 118 (2019), pp. 248-263Doble, 2007 Doble M., Rollins K., Kumar A. Doble M., Kruthiventi A.K. (Eds.), Green chemistry and engineering, Academic Press, Burlington (2007), pp. xi-xiiiElix, 1975 Elix J.A., Engkaninan U. The structure of galbinic acid. A depsidone from the lichen Usnea Undulata Aust J Chem, 28 (8) (1975), pp. 1793-1797Fernández-Moriano, 2016 Fernández-Moriano C., Gómez-Serranillos M.P., Crespo A. Antioxidant potential of lichen species and their secondary metabolites. A systematic review Pharm Biol, 54 (1) (2016), pp. 1-17Okuyama, 1995 Okuyama E., Umeyama K., Yamazaki M., Kinoshita Y., Yamamoto Y. Usnic acid and diffractaic acid as analgesic and antipyretic components of Usnea diffracta Planta Med, 61 (2) (1995), pp. 113-115Pathak, 2016 Pathak A., Upreti D.K., Dikshit A. Antidermatophytic activity of the fruticose lichen Usnea orientalis Medicines, 3 (3) (2016), p. 24Pavithra, 2013 Pavithra G.M., Vinayaka K.S., Rakesh K.N., Syed J., Dileep N., Prashith Kekuda T.R., Saba S., Abhishiktha SN. Antimicrobial and antioxidant activities of a macrolichen Usnea pictoides G. Awasthi (Parmeliaceae) J. Appl. Pharm. Sci, 3 (2013), pp. 154-160Pereira, 2011 Pereira C.S.M., Silva V.M.T.M., Rodrigues AE. Ethyl lactate as a solvent: properties, applications and production processes – a review Green Chem, 13 (10) (2011), pp. 2658-2671Popovici, 2021 Popovici V., Bucur L., Popescu A., Schröder V., Costache T., Rambu D., Cucolea I.E., Gîrd C.E., Caraiane A., Gherghel D. Antioxidant and cytotoxic activities of Usnea barbata (L.) F.H. Wigg. Dry extracts in different solvents Plants, 10 (5) (2021), p. 909Popovici, 2021 Popovici V., Matei E., Cozaru G.C., Aschie M., Bucur L., Rambu D., Costache T., Cucolea I.E., Vochita G., Gherghel D. Usnic acid and Usnea barbata (L.) F.H. wigg. Dry extracts promote apoptosis and DNA damage in human blood cells through enhancing ROS levels Antioxidants, 10 (8) (2021), p. 1171 https://doi.org/10.3390/antiox10081171Prateeksha, 2016 Prateeksha P., Paliya B.S., Bajpai R., Jadaun V., Kumar J., Kumar S., Upreti D.K., Singh B.R., Nayaka S., Joshi Y. The genus Usnea: a potent phytomedicine with multifarious ethnobotany, phytochemistry and pharmacology RSC Adv, 6 (26) (2016), pp. 21672-21696Reddy, 2019 Reddy S.D., Siva B., Kumar K., Babu V.S.P., Sravanthi V., Boustie J., Nayak V.L., Tiwari A.K., Rao C.V., Sridhar B. Comprehensive analysis of secondary metabolites in Usnea longissima. Lichenized Ascomycetes, Parmeliaceae) using UPLC-ESI-QTOF-MS/MS and pro-apoptotic activity of barbatic acid Molecules, 24 (2019), p. 2270Salgado, 2020 Salgado F., Caballero J., Vargas R., Cornejo A., Areche C. Continental and Antarctic lichens: isolation, identification and molecular modeling of the depside tenuiorin from the Antarctic lichen Umbilicaria antarctica as tau protein inhibitor Nat Prod Res, 34 (5) (2020), pp. 646-650Sepulveda, 2021 Sepulveda B., Benites D., Albornoz L., Simirgiotis M., Castro O., Garcia-Beltran O., Areche C. Green ultrasound-assisted extraction of lichen substances from Hypotrachyna cirrhata. Ethyl lactate, a better extracting agent than methanol toxic organic solvent? Nat Prod Res (2021) 10.1080/14786419.2021.1956922.34319194AQ1Soquetta, 2018 Soquetta M.B., de Marsillac Terra L., Bastos CP. Green technologies for the extraction of bioactive compounds in fruits and vegetables CyTA-J Food, 16 (1) (2018), pp. 400-412Tang, 2020 Tang J.-Y., Wu K.-H., Wang Y.-Y., Farooqi A.A., Huang H.-W., Yuan S.-S.F., Jian R.-I., Tsao L.-Y., Chen P.-A., Chang F.-R. Methanol extract of Usnea barbata induces cell killing, apoptosis, and DNA damage against oral cancer cells through oxidative stress Antioxidants, 9 (8) (2020), p. 694Verma, 2008 Verma N., Behera B.C., Makhija U. Antioxidant and hepatoprotective activity of a lichen Usnea ghattensis in vitro Appl Biochem Biotechnol, 151 (2–3) (2008), pp. 167-181Zugic, 2016 Zugic A., Jeremic I., Isakovic A., Arsic I., Savic S., Tadic V. Evaluation of anticancer and antioxidant activity of a commercially available CO2 supercritical extract of old man’s beard (Usnea barbata) PLoS One, 11 (1) (2016), p. e0146342© 2022 Informa UK Limited, trading as Taylor & Francis Group.info:eu-repo/semantics/closedAccesshttp://purl.org/coar/access_right/c_14cbAtribución-NoComercial 4.0 Internacional (CC BY-NC 4.0)https://creativecommons.org/licenses/by-nc/4.0/https://www.sciencedirect.com/org/science/article/pii/S1478641923002838Disolventes alternativosQuímica verdeLíquenesAlternative solventsAntioxidantsGreen chemistryLC/MSLichensUsneaA sustainable application for the extraction of lichen metabolites from Usnea cornuta: nontargeted metabolomics and antioxidant activityArtículo de revistahttp://purl.org/coar/resource_type/c_2df8fbb1http://purl.org/coar/version/c_970fb48d4fbd8a85Textinfo:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionPublicationTEXTArtículo.pdf.txtArtículo.pdf.txtExtracted texttext/plain2498https://repositorio.unibague.edu.co/bitstreams/144ac8aa-c321-46bd-b694-6a3d838adbc4/download4c2534975665e26a956f389426e58480MD53THUMBNAILArtículo.pdf.jpgArtículo.pdf.jpgIM Thumbnailimage/jpeg22875https://repositorio.unibague.edu.co/bitstreams/43d3fda2-204b-4f62-9af9-3199e1be8d1c/download34b8d84e853e47b0d1c9a6af57f26b1aMD54LICENSElicense.txtlicense.txttext/plain; charset=utf-8134https://repositorio.unibague.edu.co/bitstreams/91497854-11e0-4ab8-99fe-db39696d6475/download2fa3e590786b9c0f3ceba1b9656b7ac3MD51ORIGINALArtículo.pdfArtículo.pdfapplication/pdf135042https://repositorio.unibague.edu.co/bitstreams/3895969d-95a6-427b-a2fc-bd709cea0d58/downloadc7cba3a22c7f1d1951ea0ac6fae1ef96MD5220.500.12313/5562oai:repositorio.unibague.edu.co:20.500.12313/55622025-09-12 12:15:44.002https://creativecommons.org/licenses/by-nc/4.0/© 2022 Informa UK Limited, trading as Taylor & Francis Group.https://repositorio.unibague.edu.coRepositorio Institucional Universidad de Ibaguébdigital@metabiblioteca.comQ3JlYXRpdmUgQ29tbW9ucyBBdHRyaWJ1dGlvbi1Ob25Db21tZXJjaWFsLU5vRGVyaXZhdGl2ZXMgNC4wIEludGVybmF0aW9uYWwgTGljZW5zZQ0KaHR0cHM6Ly9jcmVhdGl2ZWNvbW1vbnMub3JnL2xpY2Vuc2VzL2J5LW5jLW5kLzQuMC8=

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