Ahmed H Eissa, Helnan A Aboseada, Seif-Eldin N Ayyad
{"title":"红海软珊瑚中新的生物活性尤达斯曼型倍半萜类化合物。","authors":"Ahmed H Eissa, Helnan A Aboseada, Seif-Eldin N Ayyad","doi":"10.1002/cbdv.202502473","DOIUrl":null,"url":null,"abstract":"<p><p>Two previously unreported eudesmane-class sesquiterpenes, (4R*,5S*,6Z,10R*)-11-hydroperoxy-8-oxo-eudesm-6-en-5α-ol (1) and (4R*,5S*,6Z,10R*)-5-acetoxy-11-methoxy-8-oxo-eudesm-6-en (2), were obtained through fractionation of the CH<sub>2</sub>Cl<sub>2</sub>/MeOH (1:1) extract derived from the Red Sea-derived soft coral Nephthea sp., along with three known sesquiterpenes (3-5). The structural determination of the new compounds was achieved through comprehensive analysis of spectroscopic data, including one- and two-dimensional nuclear magnetic resonance techniques and high-resolution electrospray ionisation mass spectrometry measurements. The cytotoxic activities of the newly isolated compounds (1 and 2) were evaluated using the Sulforhodamine B assay against three human carcinoma cell lines: MCF-7, HT-29 and HepG2, with doxorubicin serving as the reference drug. Metabolite 2 showed moderate cytotoxicity towards MCF-7 and HT-29 cell lines, with IC<sub>50</sub> values of 51.5 ± 2.1 and 64.1 ± 1.9 µM, respectively, and weak activity against HepG2 (IC<sub>50</sub> = 71.3 ± 2.5 µM). In contrast, compound 1 displayed weak cytotoxic effects across all tested cell lines, with IC<sub>50</sub> values of 72.8 ± 2.3 µM (MCF-7), 85.4 ± 2.7 µM (HT-29) and 95.6 ± 3.2 µM (HepG2). These findings contribute to the chemical and biological characterisation of Nephthea sp. metabolites and support further exploration of eudesmane-type sesquiterpenes as potential anticancer agents.</p>","PeriodicalId":9878,"journal":{"name":"Chemistry & Biodiversity","volume":" ","pages":"e02473"},"PeriodicalIF":2.5000,"publicationDate":"2025-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"New Bioactive Eudesmane-type Sesquiterpenoids From the Red Sea Soft Coral Nephthea sp.\",\"authors\":\"Ahmed H Eissa, Helnan A Aboseada, Seif-Eldin N Ayyad\",\"doi\":\"10.1002/cbdv.202502473\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>Two previously unreported eudesmane-class sesquiterpenes, (4R*,5S*,6Z,10R*)-11-hydroperoxy-8-oxo-eudesm-6-en-5α-ol (1) and (4R*,5S*,6Z,10R*)-5-acetoxy-11-methoxy-8-oxo-eudesm-6-en (2), were obtained through fractionation of the CH<sub>2</sub>Cl<sub>2</sub>/MeOH (1:1) extract derived from the Red Sea-derived soft coral Nephthea sp., along with three known sesquiterpenes (3-5). The structural determination of the new compounds was achieved through comprehensive analysis of spectroscopic data, including one- and two-dimensional nuclear magnetic resonance techniques and high-resolution electrospray ionisation mass spectrometry measurements. The cytotoxic activities of the newly isolated compounds (1 and 2) were evaluated using the Sulforhodamine B assay against three human carcinoma cell lines: MCF-7, HT-29 and HepG2, with doxorubicin serving as the reference drug. Metabolite 2 showed moderate cytotoxicity towards MCF-7 and HT-29 cell lines, with IC<sub>50</sub> values of 51.5 ± 2.1 and 64.1 ± 1.9 µM, respectively, and weak activity against HepG2 (IC<sub>50</sub> = 71.3 ± 2.5 µM). In contrast, compound 1 displayed weak cytotoxic effects across all tested cell lines, with IC<sub>50</sub> values of 72.8 ± 2.3 µM (MCF-7), 85.4 ± 2.7 µM (HT-29) and 95.6 ± 3.2 µM (HepG2). These findings contribute to the chemical and biological characterisation of Nephthea sp. metabolites and support further exploration of eudesmane-type sesquiterpenes as potential anticancer agents.</p>\",\"PeriodicalId\":9878,\"journal\":{\"name\":\"Chemistry & Biodiversity\",\"volume\":\" \",\"pages\":\"e02473\"},\"PeriodicalIF\":2.5000,\"publicationDate\":\"2025-10-16\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Chemistry & Biodiversity\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1002/cbdv.202502473\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"BIOCHEMISTRY & MOLECULAR BIOLOGY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemistry & Biodiversity","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1002/cbdv.202502473","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}
New Bioactive Eudesmane-type Sesquiterpenoids From the Red Sea Soft Coral Nephthea sp.
Two previously unreported eudesmane-class sesquiterpenes, (4R*,5S*,6Z,10R*)-11-hydroperoxy-8-oxo-eudesm-6-en-5α-ol (1) and (4R*,5S*,6Z,10R*)-5-acetoxy-11-methoxy-8-oxo-eudesm-6-en (2), were obtained through fractionation of the CH2Cl2/MeOH (1:1) extract derived from the Red Sea-derived soft coral Nephthea sp., along with three known sesquiterpenes (3-5). The structural determination of the new compounds was achieved through comprehensive analysis of spectroscopic data, including one- and two-dimensional nuclear magnetic resonance techniques and high-resolution electrospray ionisation mass spectrometry measurements. The cytotoxic activities of the newly isolated compounds (1 and 2) were evaluated using the Sulforhodamine B assay against three human carcinoma cell lines: MCF-7, HT-29 and HepG2, with doxorubicin serving as the reference drug. Metabolite 2 showed moderate cytotoxicity towards MCF-7 and HT-29 cell lines, with IC50 values of 51.5 ± 2.1 and 64.1 ± 1.9 µM, respectively, and weak activity against HepG2 (IC50 = 71.3 ± 2.5 µM). In contrast, compound 1 displayed weak cytotoxic effects across all tested cell lines, with IC50 values of 72.8 ± 2.3 µM (MCF-7), 85.4 ± 2.7 µM (HT-29) and 95.6 ± 3.2 µM (HepG2). These findings contribute to the chemical and biological characterisation of Nephthea sp. metabolites and support further exploration of eudesmane-type sesquiterpenes as potential anticancer agents.
期刊介绍:
Chemistry & Biodiversity serves as a high-quality publishing forum covering a wide range of biorelevant topics for a truly international audience. This journal publishes both field-specific and interdisciplinary contributions on all aspects of biologically relevant chemistry research in the form of full-length original papers, short communications, invited reviews, and commentaries. It covers all research fields straddling the border between the chemical and biological sciences, with the ultimate goal of broadening our understanding of how nature works at a molecular level.
Since 2017, Chemistry & Biodiversity is published in an online-only format.