{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,21]],"date-time":"2026-08-21T13:10:13Z","timestamp":1787317813564,"version":"build-2736575974"},"reference-count":49,"publisher":"MDPI AG","issue":"10","license":[{"start":{"date-parts":[[2018,10,2]],"date-time":"2018-10-02T00:00:00Z","timestamp":1538438400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100003593","name":"Conselho Nacional de Desenvolvimento Cient\u00edfico e Tecnol\u00f3gico","doi-asserted-by":"publisher","award":["478661\/2010-0"],"award-info":[{"award-number":["478661\/2010-0"]}],"id":[{"id":"10.13039\/501100003593","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Genipa americana is a medicinal plant popularly known as \u201cjenipapo\u201d, which occurs in Brazil and belongs to the Rubiaceae family. It is a species widely distributed in the tropical Central and South America, especially in the Cerrado biome. Their leaves and fruits are used as food and popularly in folk medicine to treat anemias, as an antidiarrheal, and anti-syphilitic. Iridoids are the main secondary metabolites described from G. americana, but few studies have been conducted with their leaves. In this study, the aim was to chemical approach for identify the main compounds present at the extract of G. americana leaves. The powdered leaves were extracted by maceration with EtOH: water (70:30, v\/v), following liquid-liquid partition with petroleum ether, chloroform, ethyl acetate and n-butanol. A total of 13 compounds were identified. In addition three flavonoids were isolated from the ethyl acetate fraction: quercetin-3-O-robinoside (GAF 1), kaempferol-3-O-robinoside (GAF 2) and isorhamnetin-3-O-robinoside (GAF 3) and, from n-butanol fraction more two flavonoids were isolated, kaempferol-3-O-robinoside-7-O-rhamnoside (robinin) (GAF 4) and isorhamnetin-3-O-robinoside-7-rhamnoside (GAF 5). Chemical structures of these five flavonoids were elucidated using spectroscopic methods (MS, 1H and 13C-NMR 1D and 2D). These flavonoids glycosides were described for the first time in G. americana.<\/jats:p>","DOI":"10.3390\/molecules23102521","type":"journal-article","created":{"date-parts":[[2018,10,2]],"date-time":"2018-10-02T11:30:02Z","timestamp":1538479802000},"page":"2521","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":27,"title":["Isolation and Identification of the Five Novel Flavonoids from Genipa americana Leaves"],"prefix":"10.3390","volume":"23","author":[{"given":"Larissa","family":"Silva","sequence":"first","affiliation":[{"name":"Research Group on Bioactive Natural Products (PNBio), Laboratory of Pharmacognosy, Department of Pharmacy, Federal University of Rio Grande do Norte (UFRN), Natal 59010-180, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jovelina","family":"Alves","sequence":"additional","affiliation":[{"name":"Research Group on Bioactive Natural Products (PNBio), Laboratory of Pharmacognosy, Department of Pharmacy, Federal University of Rio Grande do Norte (UFRN), Natal 59010-180, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Emerson","family":"Da Silva Siqueira","sequence":"additional","affiliation":[{"name":"Research Group on Bioactive Natural Products (PNBio), Laboratory of Pharmacognosy, Department of Pharmacy, Federal University of Rio Grande do Norte (UFRN), Natal 59010-180, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Manoel","family":"De Souza Neto","sequence":"additional","affiliation":[{"name":"Research Group on Bioactive Natural Products (PNBio), Laboratory of Pharmacognosy, Department of Pharmacy, Federal University of Rio Grande do Norte (UFRN), Natal 59010-180, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5620-8095","authenticated-orcid":false,"given":"Lucas","family":"Abreu","sequence":"additional","affiliation":[{"name":"Multiuser Laboratory of Characterization and Analysis (LMCA), Federal University of Para\u00edba, Jo\u00e3o Pessoa 58051-900, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Josean","family":"Tavares","sequence":"additional","affiliation":[{"name":"Multiuser Laboratory of Characterization and Analysis (LMCA), Federal University of Para\u00edba, Jo\u00e3o Pessoa 58051-900, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dayanne","family":"Porto","sequence":"additional","affiliation":[{"name":"Laboratory of Quality Control of Medications (LCQMed), Department of Pharmacy, Federal University of Rio Grande do Norte (UFRN), Natal 59010-180, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8408-5886","authenticated-orcid":false,"given":"Leandro","family":"De Santis Ferreira","sequence":"additional","affiliation":[{"name":"Laboratory of Quality Control of Medications (LCQMed), Department of Pharmacy, Federal University of Rio Grande do Norte (UFRN), Natal 59010-180, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3576-5148","authenticated-orcid":false,"given":"Daniel","family":"Demarque","sequence":"additional","affiliation":[{"name":"Nucleus Research in Natural and Synthetic Products (NPPNS), Department of Physics and Chemistry, Faculty of Pharmaceutical Sciences of Ribeir\u00e3o Preto, University of S\u00e3o Paulo, S\u00e3o Paulo 14040-903, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8159-3658","authenticated-orcid":false,"given":"Norberto","family":"Lopes","sequence":"additional","affiliation":[{"name":"Nucleus Research in Natural and Synthetic Products (NPPNS), Department of Physics and Chemistry, Faculty of Pharmaceutical Sciences of Ribeir\u00e3o Preto, University of S\u00e3o Paulo, S\u00e3o Paulo 14040-903, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3434-2602","authenticated-orcid":false,"given":"C\u00edcero","family":"Arag\u00e3o","sequence":"additional","affiliation":[{"name":"Laboratory of Quality Control of Medications (LCQMed), Department of Pharmacy, Federal University of Rio Grande do Norte (UFRN), Natal 59010-180, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Silvana","family":"Zucolotto","sequence":"additional","affiliation":[{"name":"Research Group on Bioactive Natural Products (PNBio), Laboratory of Pharmacognosy, Department of Pharmacy, Federal University of Rio Grande do Norte (UFRN), Natal 59010-180, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2018,10,2]]},"reference":[{"key":"ref_1","unstructured":"Barbosa, M.R., Zappi, D., Taylor, C., Cabral, E., Jardim, J.G., Pereira, M.S., Cali\u00f3, M.F., Pessoa, M.C.R., Salas, R., and Souza, E.B. 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