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However, there is a lack of knowledge about the chemical characterization of 3\u2010aminospirostane alkaloids, an important class related to pharmacological activities. This work aimed to characterize the alkaloids using liquid chromatography with tandem mass spectrometry (LC\/MS\/MS) supported by molecular networking and theoretical calculations as well as to evaluate the contribution to hepatoprotective activity.\n                    <\/jats:p>\n                  <\/jats:sec>\n                  <jats:sec>\n                    <jats:title>Methods<\/jats:title>\n                    <jats:p>\n                      <jats:styled-content style=\"fixed-case\">\n                        <jats:italic>S. paniculatum<\/jats:italic>\n                      <\/jats:styled-content>\n                      roots were collected and macerated with MeOH\/H\n                      <jats:sub>2<\/jats:sub>\n                      O (8:2) obtaining the crude extract (SP\u2010CE). From this, partition using EtOAc with pH variation yielded the alkaloidic fraction (SP\u2010AF). Both were evaluated in an acute liver injury model (100 and 200\u2009mg\/kg), after intraperitoneal administration of carbon tetrachloride (CCl\n                      <jats:sub>4<\/jats:sub>\n                      ) in mice. AST (aspartate transaminase) and ALT (alanine transaminase) serum levels were investigated, as well as the histopathological characteristics. The SP\u2010CE and SP\u2010AF were analyzed by LC\/MS\/MS, using quadrupole\/time\u2010of\u2010flight and ion\u2010trap systems. The alkaloids annotated by the GNPS molecular network had their structures defined using gas\u2010phase ionization and fragmentation reaction supported by theoretical calculations.\n                    <\/jats:p>\n                  <\/jats:sec>\n                  <jats:sec>\n                    <jats:title>Results<\/jats:title>\n                    <jats:p>The SP\u2010CE and SP\u2010AF decreased the ALT serum levels compared with the negative control. The group treated with the SP\u2010CE (at the highest dose) demonstrated a significant decrease of ALT. Hepatic cell degeneration decrease was observed mainly at the highest dose of the treatment. Detailed electrospray ionization MS\/MS data allowed us to identify alkaloids not previously reported, to propose their gas\u2010phase reactions and to redefine the initial open ring fragmentation mechanism of the steroidal alkaloids with the jurubidine moiety.<\/jats:p>\n                  <\/jats:sec>\n                  <jats:sec>\n                    <jats:title>Conclusions<\/jats:title>\n                    <jats:p>The results allowed us to identify seven steroidal alkaloids from jurubeba and redefine the initial mechanism of fragmentation. A significant hepatoprotective effect was also demonstrated, corroborating its traditional use.<\/jats:p>\n                  <\/jats:sec>","DOI":"10.1002\/rcm.8705","type":"journal-article","created":{"date-parts":[[2019,12,17]],"date-time":"2019-12-17T02:19:17Z","timestamp":1576549157000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":10,"title":["Characterization of 3\u2010aminospirostane alkaloids from roots of\n                    <scp>\n                      <i>Solanum paniculatum<\/i>\n                    <\/scp>\n                    L. with hepatoprotective activity"],"prefix":"10.1002","volume":"34","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-6694-8644","authenticated-orcid":false,"given":"Matheus Coutinho","family":"Gazolla","sequence":"first","affiliation":[{"name":"N\u00facleo de Pesquisa em Produtos Naturais e Sint\u00e9ticos, Departamento de Ci\u00eancias BioMoleculares, Faculdade de Ci\u00eancias Farmac\u00eauticas de Ribeir\u00e3o Preto Universidade de S\u00e3o Paulo  14040\u2010903 Ribeir\u00e3o Preto SP Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Lucas Maciel Mauriz","family":"Marques","sequence":"additional","affiliation":[{"name":"N\u00facleo de Pesquisa em Produtos Naturais e Sint\u00e9ticos, Departamento de Ci\u00eancias BioMoleculares, Faculdade de Ci\u00eancias Farmac\u00eauticas de Ribeir\u00e3o Preto Universidade de S\u00e3o Paulo  14040\u2010903 Ribeir\u00e3o Preto SP Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mariana Gama","family":"e Silva","sequence":"additional","affiliation":[{"name":"N\u00facleo de Estudos e Pesquisa de Plantas Medicinais Universidade Federal do Vale do S\u00e3o Francisco  56304\u2010205 Petrolina PE Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Maria Ta\u00eds Moura Fontes","family":"Ara\u00fajo","sequence":"additional","affiliation":[{"name":"N\u00facleo de Estudos e Pesquisa de Plantas Medicinais Universidade Federal do Vale do S\u00e3o Francisco  56304\u2010205 Petrolina PE Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Rosemairy Luciane","family":"Mendes","sequence":"additional","affiliation":[{"name":"N\u00facleo de Estudos e Pesquisa de Plantas Medicinais Universidade Federal do Vale do S\u00e3o Francisco  56304\u2010205 Petrolina PE Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0867-1357","authenticated-orcid":false,"given":"Jackson Roberto Guedes","family":"da Silva Almeida","sequence":"additional","affiliation":[{"name":"N\u00facleo de Estudos e Pesquisa de Plantas Medicinais Universidade Federal do Vale do S\u00e3o Francisco  56304\u2010205 Petrolina PE Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ricardo","family":"Vessecchi","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica, Faculdade de Filosofia, Ci\u00eancias e Letras de Ribeir\u00e3o Preto Universidade de S\u00e3o Paulo  14040\u2010901 Ribeir\u00e3o Preto SP Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8159-3658","authenticated-orcid":false,"given":"Norberto Peporine","family":"Lopes","sequence":"additional","affiliation":[{"name":"N\u00facleo de Pesquisa em Produtos Naturais e Sint\u00e9ticos, Departamento de Ci\u00eancias BioMoleculares, Faculdade de Ci\u00eancias Farmac\u00eauticas de Ribeir\u00e3o Preto Universidade de S\u00e3o Paulo  14040\u2010903 Ribeir\u00e3o Preto SP Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2020,2,11]]},"reference":[{"issue":"1","key":"e_1_2_7_2_1","first-page":"58","article-title":"Toxicological, antidiarrheal and spasmolytic activities of Solanum paniculatum","volume":"82","author":"Clementino\u2010Neto J","year":"2016","journal-title":"Planta Med"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jep.2013.02.030"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bjp.2016.02.003"},{"key":"e_1_2_7_5_1","unstructured":"daSa\u00fade M..RENISUS \u2013 Rela\u00e7\u00e3o Nacional de Plantas Medicinais de Interesse ao SUS2009.http:\/\/portalarquivos2.saude.gov.br\/images\/pdf\/2017\/junho\/06\/renisus.pdf. 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