{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,11]],"date-time":"2026-04-11T07:01:57Z","timestamp":1775890917015,"version":"3.50.1"},"reference-count":29,"publisher":"Wiley","issue":"2","license":[{"start":{"date-parts":[[2026,2,26]],"date-time":"2026-02-26T00:00:00Z","timestamp":1772064000000},"content-version":"vor","delay-in-days":25,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2026,2,1]],"date-time":"2026-02-01T00:00:00Z","timestamp":1769904000000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"funder":[{"DOI":"10.13039\/501100003593","name":"Conselho Nacional de Desenvolvimento Cient\u00edfico e Tecnol\u00f3gico","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100003593","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001807","name":"Funda\u00e7\u00e3o de Amparo \u00e0 Pesquisa do Estado de S\u00e3o Paulo","doi-asserted-by":"publisher","award":["2024\/16243\u20104"],"award-info":[{"award-number":["2024\/16243\u20104"]}],"id":[{"id":"10.13039\/501100001807","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001807","name":"Funda\u00e7\u00e3o de Amparo \u00e0 Pesquisa do Estado de S\u00e3o Paulo","doi-asserted-by":"publisher","award":["2023\/07414\u20107"],"award-info":[{"award-number":["2023\/07414\u20107"]}],"id":[{"id":"10.13039\/501100001807","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001807","name":"Funda\u00e7\u00e3o de Amparo \u00e0 Pesquisa do Estado de S\u00e3o Paulo","doi-asserted-by":"publisher","award":["2025\/26427\u20108"],"award-info":[{"award-number":["2025\/26427\u20108"]}],"id":[{"id":"10.13039\/501100001807","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry &amp;amp; Biodiversity"],"published-print":{"date-parts":[[2026,2]]},"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>\n                    In the present work, the MeOH extract from roots of\n                    <jats:italic>Porcelia ponderosa<\/jats:italic>\n                    R.E. Fries (Annonaceae) was subjected to several chromatographic techniques to afford three chemically related amides:\n                    <jats:italic>N\u2010trans\u2010p<\/jats:italic>\n                    \u2010coumaroyltyramine (\n                    <jats:bold>1<\/jats:bold>\n                    ),\n                    <jats:italic>N<\/jats:italic>\n                    \u2010\n                    <jats:italic>trans<\/jats:italic>\n                    \u2010caffeoyltyramine (\n                    <jats:bold>2<\/jats:bold>\n                    ), and\n                    <jats:italic>N\u2010trans<\/jats:italic>\n                    \u2010feruloyltyramine (\n                    <jats:bold>3<\/jats:bold>\n                    ). Isolated compounds were characterized by NMR and MS spectral analysis. This is the first report of compounds\n                    <jats:bold>1\u20133<\/jats:bold>\n                    in\n                    <jats:italic>P. ponderosa<\/jats:italic>\n                    , while\n                    <jats:bold>1<\/jats:bold>\n                    is a previously unreported metabolite from the\n                    <jats:italic>Porcelia<\/jats:italic>\n                    genus. Previous studies reported the effects of amides\n                    <jats:bold>1\u20133<\/jats:bold>\n                    on the inhibition of sterol 14\u2010\u03b1\u2010demethylase (CYP51), a key enzyme in the life cycle of\n                    <jats:italic>Trypanosoma cruzi<\/jats:italic>\n                    , using an in silico approach. However, no experimental evidence was conducted to prove their effects against the parasite. Based on these data and isolation of amides\n                    <jats:bold>1\u20133<\/jats:bold>\n                    from roots of\n                    <jats:italic>P. ponderosa<\/jats:italic>\n                    , these compounds were tested in vitro against the intracellular amastigotes of\n                    <jats:italic>T. cruzi<\/jats:italic>\n                    . Compounds\n                    <jats:bold>1<\/jats:bold>\n                    and\n                    <jats:bold>2<\/jats:bold>\n                    , containing\n                    <jats:italic>p<\/jats:italic>\n                    \u2010coumaroyl and caffeic moieties, displayed potent activity with EC\n                    <jats:sub>50<\/jats:sub>\n                    values of 6.3 \u00b1 1.2 and 3.4 \u00b1 0.6 \u00b5M, respectively, a similar efficacy observed to the standard drug benznidazole (EC\n                    <jats:sub>50<\/jats:sub>\n                    of 5.5 \u00b1 2.2 \u00b5M). Otherwise, compound\n                    <jats:bold>3<\/jats:bold>\n                    , with a feruloyl moiety, showed moderate activity (EC\n                    <jats:sub>50<\/jats:sub>\n                    of 14.0 \u00b1 0.3 \u00b5M). These results indicated that\n                    <jats:italic>p<\/jats:italic>\n                    \u2010coumaric and caffeoyl moieties play an important role in the potency against amastigotes of\n                    <jats:italic>T. cruzi<\/jats:italic>\n                    . Otherwise, simplified derivatives of\n                    <jats:bold>1\u20133<\/jats:bold>\n                    such as\n                    <jats:italic>p<\/jats:italic>\n                    \u2010coumaric, caffeic and ferulic acids as well as tyramine, showed to be inactive against amastigotes (EC\n                    <jats:sub>50<\/jats:sub>\n                    &gt; 150 \u00b5M) reinforcing the importance of condensation of these free acids and tyramine for the efficacy of amides\n                    <jats:bold>1\u20133<\/jats:bold>\n                    . Considering the cytotoxicity against murine fibroblasts, compounds\n                    <jats:bold>1\u20133<\/jats:bold>\n                    displayed CC\n                    <jats:sub>50<\/jats:sub>\n                    values higher than 200 \u00b5M, and SI values higher than 31.7, 55.6, and 14.3, respectively. These findings highlight a safe profile and the antiparasitic potential of amides\n                    <jats:bold>1<\/jats:bold>\n                    and\n                    <jats:bold>2<\/jats:bold>\n                    , which could be used as promising hit compounds for the design of new drug candidates for Chagas disease.\n                  <\/jats:p>","DOI":"10.1002\/cbdv.202503258","type":"journal-article","created":{"date-parts":[[2026,3,8]],"date-time":"2026-03-08T12:44:29Z","timestamp":1772973869000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Amides from\n                    <i>Porcelia ponderosa<\/i>\n                    Roots Display Efficacy In Vitro Against Intracellular Amastigotes of\n                    <i>Trypanosoma cruzi<\/i>"],"prefix":"10.1002","volume":"23","author":[{"given":"Carlos Henrique T.","family":"Dos Santos","sequence":"first","affiliation":[{"name":"Center for Natural and Human Sciences Federal University of ABC Santo Andre S\u00e3o Paulo Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mariana B.","family":"Abiuzi","sequence":"additional","affiliation":[{"name":"Pathophysiology Laboratory Instituto Butantan  S\u00e3o Paulo S\u00e3o Paulo Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Beatriz A.","family":"De Andrade","sequence":"additional","affiliation":[{"name":"Pathophysiology Laboratory Instituto Butantan  S\u00e3o Paulo S\u00e3o Paulo Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Erica V. C.","family":"Levatti","sequence":"additional","affiliation":[{"name":"Pathophysiology Laboratory Instituto Butantan  S\u00e3o Paulo S\u00e3o Paulo Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mariana H.","family":"Chaves","sequence":"additional","affiliation":[{"name":"Department of Chemistry Federal University of Piaui  Teresina, Piau\u00ed Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Andre G.","family":"Tempone","sequence":"additional","affiliation":[{"name":"Pathophysiology Laboratory Instituto Butantan  S\u00e3o Paulo S\u00e3o Paulo Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1193-8374","authenticated-orcid":false,"given":"Jo\u00e3o Henrique G.","family":"Lago","sequence":"additional","affiliation":[{"name":"Center for Natural and Human Sciences Federal University of ABC Santo Andre S\u00e3o Paulo Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2026,2,26]]},"reference":[{"key":"e_1_2_9_2_1","doi-asserted-by":"publisher","DOI":"10.1093\/bmb\/ldp046"},{"key":"e_1_2_9_3_1","doi-asserted-by":"publisher","DOI":"10.1186\/s40249\u2010020\u20100630\u20109"},{"key":"e_1_2_9_4_1","doi-asserted-by":"publisher","DOI":"10.1016\/S1473\u20103099(22)00064\u20100"},{"key":"e_1_2_9_5_1","doi-asserted-by":"publisher","DOI":"10.1371\/journal.pntd.0006859"},{"key":"e_1_2_9_6_1","doi-asserted-by":"publisher","DOI":"10.5334\/gh.1150"},{"key":"e_1_2_9_7_1","doi-asserted-by":"publisher","DOI":"10.3389\/fmicb.2025.1539629"},{"key":"e_1_2_9_8_1","doi-asserted-by":"publisher","DOI":"10.1191\/0960327106het653oa"},{"key":"e_1_2_9_9_1","doi-asserted-by":"publisher","DOI":"10.1080\/10286020.2011.570265"},{"key":"e_1_2_9_10_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules27113462"},{"key":"e_1_2_9_11_1","first-page":"447","article-title":"Antileishmanial Acetylene Fatty Acid and Acetogenins From Seeds of Porcelia macrocarpa","volume":"32","author":"Brito I. A.","year":"2021","journal-title":"Journal of the Brazilian Chemical Society"},{"key":"e_1_2_9_12_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.phytochem.2024.114360"},{"key":"e_1_2_9_13_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41598\u2010023\u201037520\u20103"},{"key":"e_1_2_9_14_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules20058168"},{"key":"e_1_2_9_15_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jnatprod.8b00890"},{"key":"e_1_2_9_16_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2018.03.025"},{"key":"e_1_2_9_17_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.phymed.2024.156045"},{"key":"e_1_2_9_18_1","doi-asserted-by":"publisher","DOI":"10.1007\/s40203-025-00312-w"},{"key":"e_1_2_9_19_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0031\u20109422(97)00364\u20106"},{"key":"e_1_2_9_20_1","doi-asserted-by":"publisher","DOI":"10.1016\/0031\u20109422(88)80189\u20104"},{"key":"e_1_2_9_21_1","doi-asserted-by":"publisher","DOI":"10.1016\/0031\u20109422(80)85081\u20103"},{"key":"e_1_2_9_22_1","doi-asserted-by":"publisher","DOI":"10.1021\/np0401260"},{"key":"e_1_2_9_23_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules25153533"},{"key":"e_1_2_9_24_1","first-page":"844","article-title":"Constituents of Dendrobium devonianum and Their Antioxidant Activity","volume":"38","author":"Zhang A. L.","year":"2013","journal-title":"Zhongguo Zhong Yao Za Zhi"},{"key":"e_1_2_9_25_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.biopha.2017.07.013"},{"key":"e_1_2_9_26_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules190811366"},{"key":"e_1_2_9_27_1","doi-asserted-by":"publisher","DOI":"10.1177\/1934578X1100600623"},{"key":"e_1_2_9_28_1","doi-asserted-by":"publisher","DOI":"10.1038\/nrd4683"},{"key":"e_1_2_9_29_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jnatprod.0c01303"},{"key":"e_1_2_9_30_1","doi-asserted-by":"publisher","DOI":"10.1002\/cbdv.202403109"}],"container-title":["Chemistry &amp; Biodiversity"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cbdv.202503258","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/cbdv.202503258","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cbdv.202503258","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,4,11]],"date-time":"2026-04-11T06:33:44Z","timestamp":1775889224000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/cbdv.202503258"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,2]]},"references-count":29,"journal-issue":{"issue":"2","published-print":{"date-parts":[[2026,2]]}},"alternative-id":["10.1002\/cbdv.202503258"],"URL":"https:\/\/doi.org\/10.1002\/cbdv.202503258","archive":["Portico"],"relation":{},"ISSN":["1612-1872","1612-1880"],"issn-type":[{"value":"1612-1872","type":"print"},{"value":"1612-1880","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,2]]},"assertion":[{"value":"2025-10-03","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-02-09","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-02-26","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e03258"}}