{"title":"从 Vernonia amygdalina Delile 树枝中提取的高含氧抗疟和非溶血性 Δ7,9(11) 柱头甾烷类固醇","authors":"","doi":"10.1016/j.phytochem.2024.114286","DOIUrl":null,"url":null,"abstract":"<div><p>Chemical investigations of a methanolic extract of the twigs of <em>Vernonia amygdalina</em> Delile (Asteraceae) resulted in the isolation and identification of three previously undescribed highly oxygenated Δ<sup>7,9(11)</sup> stigmastane-type steroids namely vernonins U–W (<strong>1</strong>−<strong>3</strong>) along with six known compounds (<strong>4</strong>−<strong>9</strong>). The structural characterization of all the isolated compounds has been conducted via comprehensive 1D and 2D-NMR spectroscopy as well as HRMS. The seven steroidal derivatives <strong>1</strong>−<strong>7</strong> were evaluated for their antiplasmodial activity against the chloroquine-resistant strain <em>P. falciparum</em> Dd2 (<em>Pf</em>Dd2) and their hemolytic effect on human red blood cells (RBCs). Vernonins U (<strong>1</strong>), A (<strong>4</strong>) and stigmasterol-3-<em>O</em>-<em>β</em>-<span>d</span>-glucopyranoside (<strong>7</strong>) showed the highest activity with IC<sub>50</sub> values of (5.47 ± 0.01) μg/mL, (6.02 ± 0.13) μg/mL and (6.34 ± 0.80) μg/mL, respectively, against <em>Pf</em>Dd2, while vernonin W (<strong>3</strong>) showed moderate activity of (21.20 ± 0.40) μg/mL. None of the tested compounds displayed hemolytic effects on human RBCs up to 100 μg/mL indicating their safety. These results enrich the known chemistry of <em>V. amygdalina</em> and support its use in folk medicine for the treatment of malaria. This encourages further research towards new antiplasmodial drug candidates from this plant.</p></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2000,"publicationDate":"2024-09-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Highly oxygenated antiplasmodial and non-hemolytic Δ7,9(11) stigmastane-type steroids from the twigs of Vernonia amygdalina Delile\",\"authors\":\"\",\"doi\":\"10.1016/j.phytochem.2024.114286\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>Chemical investigations of a methanolic extract of the twigs of <em>Vernonia amygdalina</em> Delile (Asteraceae) resulted in the isolation and identification of three previously undescribed highly oxygenated Δ<sup>7,9(11)</sup> stigmastane-type steroids namely vernonins U–W (<strong>1</strong>−<strong>3</strong>) along with six known compounds (<strong>4</strong>−<strong>9</strong>). The structural characterization of all the isolated compounds has been conducted via comprehensive 1D and 2D-NMR spectroscopy as well as HRMS. The seven steroidal derivatives <strong>1</strong>−<strong>7</strong> were evaluated for their antiplasmodial activity against the chloroquine-resistant strain <em>P. falciparum</em> Dd2 (<em>Pf</em>Dd2) and their hemolytic effect on human red blood cells (RBCs). Vernonins U (<strong>1</strong>), A (<strong>4</strong>) and stigmasterol-3-<em>O</em>-<em>β</em>-<span>d</span>-glucopyranoside (<strong>7</strong>) showed the highest activity with IC<sub>50</sub> values of (5.47 ± 0.01) μg/mL, (6.02 ± 0.13) μg/mL and (6.34 ± 0.80) μg/mL, respectively, against <em>Pf</em>Dd2, while vernonin W (<strong>3</strong>) showed moderate activity of (21.20 ± 0.40) μg/mL. None of the tested compounds displayed hemolytic effects on human RBCs up to 100 μg/mL indicating their safety. These results enrich the known chemistry of <em>V. amygdalina</em> and support its use in folk medicine for the treatment of malaria. This encourages further research towards new antiplasmodial drug candidates from this plant.</p></div>\",\"PeriodicalId\":20170,\"journal\":{\"name\":\"Phytochemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":3.2000,\"publicationDate\":\"2024-09-11\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Phytochemistry\",\"FirstCategoryId\":\"99\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0031942224003236\",\"RegionNum\":2,\"RegionCategory\":\"生物学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"BIOCHEMISTRY & MOLECULAR BIOLOGY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Phytochemistry","FirstCategoryId":"99","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0031942224003236","RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}
Highly oxygenated antiplasmodial and non-hemolytic Δ7,9(11) stigmastane-type steroids from the twigs of Vernonia amygdalina Delile
Chemical investigations of a methanolic extract of the twigs of Vernonia amygdalina Delile (Asteraceae) resulted in the isolation and identification of three previously undescribed highly oxygenated Δ7,9(11) stigmastane-type steroids namely vernonins U–W (1−3) along with six known compounds (4−9). The structural characterization of all the isolated compounds has been conducted via comprehensive 1D and 2D-NMR spectroscopy as well as HRMS. The seven steroidal derivatives 1−7 were evaluated for their antiplasmodial activity against the chloroquine-resistant strain P. falciparum Dd2 (PfDd2) and their hemolytic effect on human red blood cells (RBCs). Vernonins U (1), A (4) and stigmasterol-3-O-β-d-glucopyranoside (7) showed the highest activity with IC50 values of (5.47 ± 0.01) μg/mL, (6.02 ± 0.13) μg/mL and (6.34 ± 0.80) μg/mL, respectively, against PfDd2, while vernonin W (3) showed moderate activity of (21.20 ± 0.40) μg/mL. None of the tested compounds displayed hemolytic effects on human RBCs up to 100 μg/mL indicating their safety. These results enrich the known chemistry of V. amygdalina and support its use in folk medicine for the treatment of malaria. This encourages further research towards new antiplasmodial drug candidates from this plant.
期刊介绍：
Phytochemistry is a leading international journal publishing studies of plant chemistry, biochemistry, molecular biology and genetics, structure and bioactivities of phytochemicals, including ''-omics'' and bioinformatics/computational biology approaches. Phytochemistry is a primary source for papers dealing with phytochemicals, especially reports concerning their biosynthesis, regulation, and biological properties both in planta and as bioactive principles. Articles are published online as soon as possible as Articles-in-Press and in 12 volumes per year. Occasional topic-focussed special issues are published composed of papers from invited authors.
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