{"title":"基于分子网络从海洋海绵 Phakellia fusca 中发现环七肽 phakefusins A-E。","authors":"","doi":"10.1016/j.phytochem.2024.114248","DOIUrl":null,"url":null,"abstract":"<div><p>Guided by a probe-based molecular networking strategy, five undescribed cycloheptapeptides, phakefusins A−E (<strong>1</strong>−<strong>5</strong>), were isolated from the marine sponge <em>Phakellia fusca</em>. Compounds <strong>1</strong> and <strong>2</strong> contain the nonproteinogenic amino acid residues of dioxindolyalanine (Dioia) and <em>β</em>-3-oxindolylalanine (Oia), respectively. Compound <strong>3</strong> possesses a unique methionine sulfoxide, whereas compound <strong>5</strong> includes a glutamic acid ethyl ester unit. Their structures were elucidated through NMR spectroscopy, HR-MS/MS analysis, and the advanced Marfey's method. By synthesizing the (<em>S</em>, <em>S/R</em>)-Oia standard through tryptophan oxidation, we determined the configuration of this amino acid in compound <strong>2</strong> using the advanced Marfey's method. These cycloheptapeptides were evaluated for their antitumor, antibacterial, and antioxidant activities. Compound <strong>1</strong> showed moderate cytotoxicity against MCF-7 and PC9 cells, with IC<sub>50</sub> values of 6.8 and 9.6 μM, respectively, while compounds <strong>2</strong>−<strong>5</strong> demonstrated potential antioxidant effects by upregulating HO-1, NQO1, and SOD2 levels, as well as inducing Nrf2 activation.</p></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2000,"publicationDate":"2024-08-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Discovery of cycloheptapeptides phakefusins A−E from the marine sponge Phakellia fusca based on molecular networking\",\"authors\":\"\",\"doi\":\"10.1016/j.phytochem.2024.114248\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>Guided by a probe-based molecular networking strategy, five undescribed cycloheptapeptides, phakefusins A−E (<strong>1</strong>−<strong>5</strong>), were isolated from the marine sponge <em>Phakellia fusca</em>. Compounds <strong>1</strong> and <strong>2</strong> contain the nonproteinogenic amino acid residues of dioxindolyalanine (Dioia) and <em>β</em>-3-oxindolylalanine (Oia), respectively. Compound <strong>3</strong> possesses a unique methionine sulfoxide, whereas compound <strong>5</strong> includes a glutamic acid ethyl ester unit. Their structures were elucidated through NMR spectroscopy, HR-MS/MS analysis, and the advanced Marfey's method. By synthesizing the (<em>S</em>, <em>S/R</em>)-Oia standard through tryptophan oxidation, we determined the configuration of this amino acid in compound <strong>2</strong> using the advanced Marfey's method. These cycloheptapeptides were evaluated for their antitumor, antibacterial, and antioxidant activities. Compound <strong>1</strong> showed moderate cytotoxicity against MCF-7 and PC9 cells, with IC<sub>50</sub> values of 6.8 and 9.6 μM, respectively, while compounds <strong>2</strong>−<strong>5</strong> demonstrated potential antioxidant effects by upregulating HO-1, NQO1, and SOD2 levels, as well as inducing Nrf2 activation.</p></div>\",\"PeriodicalId\":20170,\"journal\":{\"name\":\"Phytochemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":3.2000,\"publicationDate\":\"2024-08-26\",\"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/S0031942224002851\",\"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/S0031942224002851","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}
Discovery of cycloheptapeptides phakefusins A−E from the marine sponge Phakellia fusca based on molecular networking
Guided by a probe-based molecular networking strategy, five undescribed cycloheptapeptides, phakefusins A−E (1−5), were isolated from the marine sponge Phakellia fusca. Compounds 1 and 2 contain the nonproteinogenic amino acid residues of dioxindolyalanine (Dioia) and β-3-oxindolylalanine (Oia), respectively. Compound 3 possesses a unique methionine sulfoxide, whereas compound 5 includes a glutamic acid ethyl ester unit. Their structures were elucidated through NMR spectroscopy, HR-MS/MS analysis, and the advanced Marfey's method. By synthesizing the (S, S/R)-Oia standard through tryptophan oxidation, we determined the configuration of this amino acid in compound 2 using the advanced Marfey's method. These cycloheptapeptides were evaluated for their antitumor, antibacterial, and antioxidant activities. Compound 1 showed moderate cytotoxicity against MCF-7 and PC9 cells, with IC50 values of 6.8 and 9.6 μM, respectively, while compounds 2−5 demonstrated potential antioxidant effects by upregulating HO-1, NQO1, and SOD2 levels, as well as inducing Nrf2 activation.
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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