{"title":"Isolation of Antiplasmodial Oxazoles and Isoflavonoids from the Roots of <i>Oxytropis trichophysa</i> and Total Synthesis of Oxazole-type Alkaloids.","authors":"Buyanmandakh Buyankhishig, Toshihiro Murata, Koichi Narita, Chinbat Delgermaa, Yoshifumi Nishikawa, Nanang R Ariefta, Baasandorj Gantumur, Tseesuren Byambajav, Yoshinobu Ishikawa, Bekh-Ochir Davaapurev, Kenroh Sasaki, Javzan Batkhuu","doi":"10.1021/acs.jnatprod.4c01254","DOIUrl":null,"url":null,"abstract":"<p><p>A chemical examination of a root extract of <i>Oxytropis trichophysa</i> led to the isolation and identification of 23 compounds, including oxazole-type alkaloids and isoflavonoid derivatives. Notably, three oxazole-type alkaloids (<b>1</b>, <b>2</b>, and <b>3</b>) and two isoflavonoid derivatives (<b>7</b> and <b>10</b>) were obtained from a natural source for the first time. In addition, <i>O. trichophysa</i> derived 2,5-diphenyloxazoles and their derivatives were synthesized. Despite their potential activity, the antiplasmodial activities of naturally occurring 2,5-diphenyloxazoles and certain isoflavonoids remain unexplored. Therefore, the antiplasmodial activities of both the naturally occurring and synthesized compounds were evaluated against <i>Plasmodium falciparum</i> strain 3D7. Among the tested compounds, three naturally occurring oxazole-type alkaloids (<b>1</b>, <b>5</b>, and <b>6</b>), one synthesized alkaloid (<b>34</b>), and two isoflavonoid derivatives (<b>13</b> and <b>15</b>) demonstrated significant inhibitory effects, with half-maximal inhibitory concentration (IC<sub>50</sub>) values ranging from 3.1 to 6.2 μM and selective indices between 0.9 and 18.8. Compound <b>1</b> showed the most potent inhibitory activity, with an IC<sub>50</sub> of 3.1 μM, while its cytotoxic concentration 50% value against human foreskin fibroblasts was found to be 8.5 μM. The oxazole-type alkaloids and isoflavonoids isolated from this plant provide valuable insights into its chemical composition and may help elucidate the antiplasmodial properties of <i>O</i>. <i>trichophysa</i>.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":""},"PeriodicalIF":3.3000,"publicationDate":"2025-01-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Natural Products ","FirstCategoryId":"99","ListUrlMain":"https://doi.org/10.1021/acs.jnatprod.4c01254","RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MEDICINAL","Score":null,"Total":0}
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Abstract
A chemical examination of a root extract of Oxytropis trichophysa led to the isolation and identification of 23 compounds, including oxazole-type alkaloids and isoflavonoid derivatives. Notably, three oxazole-type alkaloids (1, 2, and 3) and two isoflavonoid derivatives (7 and 10) were obtained from a natural source for the first time. In addition, O. trichophysa derived 2,5-diphenyloxazoles and their derivatives were synthesized. Despite their potential activity, the antiplasmodial activities of naturally occurring 2,5-diphenyloxazoles and certain isoflavonoids remain unexplored. Therefore, the antiplasmodial activities of both the naturally occurring and synthesized compounds were evaluated against Plasmodium falciparum strain 3D7. Among the tested compounds, three naturally occurring oxazole-type alkaloids (1, 5, and 6), one synthesized alkaloid (34), and two isoflavonoid derivatives (13 and 15) demonstrated significant inhibitory effects, with half-maximal inhibitory concentration (IC50) values ranging from 3.1 to 6.2 μM and selective indices between 0.9 and 18.8. Compound 1 showed the most potent inhibitory activity, with an IC50 of 3.1 μM, while its cytotoxic concentration 50% value against human foreskin fibroblasts was found to be 8.5 μM. The oxazole-type alkaloids and isoflavonoids isolated from this plant provide valuable insights into its chemical composition and may help elucidate the antiplasmodial properties of O. trichophysa.
期刊介绍：
The Journal of Natural Products invites and publishes papers that make substantial and scholarly contributions to the area of natural products research. Contributions may relate to the chemistry and/or biochemistry of naturally occurring compounds or the biology of living systems from which they are obtained.
Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin.
When new compounds are reported, manuscripts describing their biological activity are much preferred.
Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin.
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