Ahmed H Eissa, Asmaa M Abdel-Tawab, El Sayed A E Hamed, Fawzia Z El-Ablack, Seif-Eldin N Ayyad
{"title":"来自红海软珊瑚Litophyton mollis的新型多羟基类固醇的细胞毒性评价(Macfadyen, 1936)。","authors":"Ahmed H Eissa, Asmaa M Abdel-Tawab, El Sayed A E Hamed, Fawzia Z El-Ablack, Seif-Eldin N Ayyad","doi":"10.1080/14786419.2023.2284259","DOIUrl":null,"url":null,"abstract":"<p><p>An efficient column chromatography of the CH<sub>2</sub>Cl<sub>2</sub>/MeOH crude extract from the soft coral <i>Litophyton mollis</i> (Macfadyen, 1936) yielded seven steroids, including five 4α-methylated steroids (<b>1-5</b>) and two 19-oxygenated steroids (<b>6-7</b>). Notably, both compounds <b>3</b> and <b>7</b> are new, identified as (22<i>E</i>)-4α,24-dimethyl-5α-cholesta-22,24(28)-dien-3β,8β-diol (<b>3</b>) and (22<i>E</i>,24<i>R</i>)-7β-acetoxy-24-methyl-cholesta-5,22-dien-3β,19-diol (<b>7</b>). The chemical structures and relative configurations were elucidated through comprehensive spectroscopic analyses, including 1D and 2D NMR, as well as HRESIMS analysis. The cytotoxicity of metabolites <b>1-7</b> was evaluated against three cancer cell lines: MCF-7, HepG2, and NCI-1299. Remarkably, metabolites <b>6</b> and <b>7</b> exhibited strong cytotoxic activity against MCF-7, with IC<sub>50</sub> values of 8.6 and 8.4 μM, respectively, while also showing moderate effects against NCI-1299, with IC<sub>50</sub> values of 15.7 and 15.1 μM, respectively. Additionally, steroids <b>4</b> and <b>5</b> displayed weak cytotoxicity against all three cell lines, with IC<sub>50</sub> values in the ranges of 34.7-37.5 and 30.8-46.3 μM, respectively.</p>","PeriodicalId":18990,"journal":{"name":"Natural Product Research","volume":" ","pages":"4390-4398"},"PeriodicalIF":1.9000,"publicationDate":"2024-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Cytotoxic evaluation of new polyhydroxylated steroids from the Red Sea soft coral <i>Litophyton mollis</i> (Macfadyen, 1936).\",\"authors\":\"Ahmed H Eissa, Asmaa M Abdel-Tawab, El Sayed A E Hamed, Fawzia Z El-Ablack, Seif-Eldin N Ayyad\",\"doi\":\"10.1080/14786419.2023.2284259\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>An efficient column chromatography of the CH<sub>2</sub>Cl<sub>2</sub>/MeOH crude extract from the soft coral <i>Litophyton mollis</i> (Macfadyen, 1936) yielded seven steroids, including five 4α-methylated steroids (<b>1-5</b>) and two 19-oxygenated steroids (<b>6-7</b>). Notably, both compounds <b>3</b> and <b>7</b> are new, identified as (22<i>E</i>)-4α,24-dimethyl-5α-cholesta-22,24(28)-dien-3β,8β-diol (<b>3</b>) and (22<i>E</i>,24<i>R</i>)-7β-acetoxy-24-methyl-cholesta-5,22-dien-3β,19-diol (<b>7</b>). The chemical structures and relative configurations were elucidated through comprehensive spectroscopic analyses, including 1D and 2D NMR, as well as HRESIMS analysis. The cytotoxicity of metabolites <b>1-7</b> was evaluated against three cancer cell lines: MCF-7, HepG2, and NCI-1299. Remarkably, metabolites <b>6</b> and <b>7</b> exhibited strong cytotoxic activity against MCF-7, with IC<sub>50</sub> values of 8.6 and 8.4 μM, respectively, while also showing moderate effects against NCI-1299, with IC<sub>50</sub> values of 15.7 and 15.1 μM, respectively. Additionally, steroids <b>4</b> and <b>5</b> displayed weak cytotoxicity against all three cell lines, with IC<sub>50</sub> values in the ranges of 34.7-37.5 and 30.8-46.3 μM, respectively.</p>\",\"PeriodicalId\":18990,\"journal\":{\"name\":\"Natural Product Research\",\"volume\":\" \",\"pages\":\"4390-4398\"},\"PeriodicalIF\":1.9000,\"publicationDate\":\"2024-12-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Natural Product Research\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1080/14786419.2023.2284259\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2023/11/19 0:00:00\",\"PubModel\":\"Epub\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, APPLIED\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Natural Product Research","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1080/14786419.2023.2284259","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2023/11/19 0:00:00","PubModel":"Epub","JCR":"Q3","JCRName":"CHEMISTRY, APPLIED","Score":null,"Total":0}
Cytotoxic evaluation of new polyhydroxylated steroids from the Red Sea soft coral Litophyton mollis (Macfadyen, 1936).
An efficient column chromatography of the CH2Cl2/MeOH crude extract from the soft coral Litophyton mollis (Macfadyen, 1936) yielded seven steroids, including five 4α-methylated steroids (1-5) and two 19-oxygenated steroids (6-7). Notably, both compounds 3 and 7 are new, identified as (22E)-4α,24-dimethyl-5α-cholesta-22,24(28)-dien-3β,8β-diol (3) and (22E,24R)-7β-acetoxy-24-methyl-cholesta-5,22-dien-3β,19-diol (7). The chemical structures and relative configurations were elucidated through comprehensive spectroscopic analyses, including 1D and 2D NMR, as well as HRESIMS analysis. The cytotoxicity of metabolites 1-7 was evaluated against three cancer cell lines: MCF-7, HepG2, and NCI-1299. Remarkably, metabolites 6 and 7 exhibited strong cytotoxic activity against MCF-7, with IC50 values of 8.6 and 8.4 μM, respectively, while also showing moderate effects against NCI-1299, with IC50 values of 15.7 and 15.1 μM, respectively. Additionally, steroids 4 and 5 displayed weak cytotoxicity against all three cell lines, with IC50 values in the ranges of 34.7-37.5 and 30.8-46.3 μM, respectively.
期刊介绍：
The aim of Natural Product Research is to publish important contributions in the field of natural product chemistry. The journal covers all aspects of research in the chemistry and biochemistry of naturally occurring compounds.
The communications include coverage of work on natural substances of land and sea and of plants, microbes and animals. Discussions of structure elucidation, synthesis and experimental biosynthesis of natural products as well as developments of methods in these areas are welcomed in the journal. Finally, research papers in fields on the chemistry-biology boundary, eg. fermentation chemistry, plant tissue culture investigations etc., are accepted into the journal.
Natural Product Research issues will be subtitled either ""Part A - Synthesis and Structure"" or ""Part B - Bioactive Natural Products"". for details on this , see the forthcoming articles section.
All manuscript submissions are subject to initial appraisal by the Editor, and, if found suitable for further consideration, to peer review by independent, anonymous expert referees. All peer review is single blind and submission is online via ScholarOne Manuscripts.
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