从绞股蓝毛霉中提取具有细胞毒性的 Peptaibols。

IF 3.3 2区 生物学 Q2 CHEMISTRY, MEDICINAL Journal of Natural Products Pub Date : 2024-08-23 Epub Date: 2024-07-22 DOI:10.1021/acs.jnatprod.4c00590
Yun Seo Park, Eun-Sook Kim, Stephen T Deyrup, Jin Woo Lee, Sang Hee Shim
{"title":"从绞股蓝毛霉中提取具有细胞毒性的 Peptaibols。","authors":"Yun Seo Park, Eun-Sook Kim, Stephen T Deyrup, Jin Woo Lee, Sang Hee Shim","doi":"10.1021/acs.jnatprod.4c00590","DOIUrl":null,"url":null,"abstract":"<p><p>Five new lipopeptaibols (<b>1</b>-<b>5</b>) and eight new 19-residue peptaibols (<b>8</b>-<b>15</b>) along with two known lipopeptaibols, lipovelutibols C (<b>6</b>) and D (<b>7</b>) were isolated from <i>Trichoderma strigosum</i>. The planar structures of the newly discovered peptaibols (<b>1</b>-<b>5</b>, <b>8</b>-<b>15</b>) were elucidated using 1D and 2D NMR, and UPLC-MS/MS data. The absolute configurations for new peptaibols (<b>1</b>-<b>5</b>, <b>8</b>-<b>15</b>) were elucidated using the advanced Marfey's method and GITC (2,3,4,6-tetra-<i>O</i>-acetyl-β-d-glucopyranosyl isothiocyanate) derivatization. Through analysis of CD spectra, these peptabols were found to have right-handed helical conformations. While most of the new compounds were significantly more active than the positive control, <b>9</b>, <b>10</b>, <b>12</b>, and <b>15</b> containing Ser and Leu at positions 10 and 11, respectively, were the most cytotoxic against MDA-MB-231, SNU449, SKOV3, DU145, and HCT116 cancer cell lines, and the 19-residue peptaibols were generally more potent than lipopeptaibols.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"2081-2094"},"PeriodicalIF":3.3000,"publicationDate":"2024-08-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Cytotoxic Peptaibols from <i>Trichoderma strigosum</i>.\",\"authors\":\"Yun Seo Park, Eun-Sook Kim, Stephen T Deyrup, Jin Woo Lee, Sang Hee Shim\",\"doi\":\"10.1021/acs.jnatprod.4c00590\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>Five new lipopeptaibols (<b>1</b>-<b>5</b>) and eight new 19-residue peptaibols (<b>8</b>-<b>15</b>) along with two known lipopeptaibols, lipovelutibols C (<b>6</b>) and D (<b>7</b>) were isolated from <i>Trichoderma strigosum</i>. The planar structures of the newly discovered peptaibols (<b>1</b>-<b>5</b>, <b>8</b>-<b>15</b>) were elucidated using 1D and 2D NMR, and UPLC-MS/MS data. The absolute configurations for new peptaibols (<b>1</b>-<b>5</b>, <b>8</b>-<b>15</b>) were elucidated using the advanced Marfey's method and GITC (2,3,4,6-tetra-<i>O</i>-acetyl-β-d-glucopyranosyl isothiocyanate) derivatization. Through analysis of CD spectra, these peptabols were found to have right-handed helical conformations. While most of the new compounds were significantly more active than the positive control, <b>9</b>, <b>10</b>, <b>12</b>, and <b>15</b> containing Ser and Leu at positions 10 and 11, respectively, were the most cytotoxic against MDA-MB-231, SNU449, SKOV3, DU145, and HCT116 cancer cell lines, and the 19-residue peptaibols were generally more potent than lipopeptaibols.</p>\",\"PeriodicalId\":47,\"journal\":{\"name\":\"Journal of Natural Products \",\"volume\":\" \",\"pages\":\"2081-2094\"},\"PeriodicalIF\":3.3000,\"publicationDate\":\"2024-08-23\",\"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.4c00590\",\"RegionNum\":2,\"RegionCategory\":\"生物学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2024/7/22 0:00:00\",\"PubModel\":\"Epub\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, MEDICINAL\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Natural Products ","FirstCategoryId":"99","ListUrlMain":"https://doi.org/10.1021/acs.jnatprod.4c00590","RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/7/22 0:00:00","PubModel":"Epub","JCR":"Q2","JCRName":"CHEMISTRY, MEDICINAL","Score":null,"Total":0}
引用次数: 0

摘要

从链霉菌(Trichoderma strigosum)中分离出了五种新的脂庚二醇(1-5)和八种新的 19 位元的脂庚二醇(8-15),以及两种已知的脂庚二醇,即脂藜芦醇 C(6)和 D(7)。利用 1D 和 2D NMR 以及 UPLC-MS/MS 数据阐明了新发现的七叶皂糖醇(1-5、8-15)的平面结构。采用先进的马菲法和 GITC(2,3,4,6-四-O-乙酰基-β-d-吡喃葡萄糖基异硫氰酸酯)衍生法阐明了新发现的庚二醇(1-5、8-15)的绝对构型。通过分析 CD 光谱,发现这些肽醇具有右手螺旋构象。虽然大多数新化合物的活性明显高于阳性对照,但分别在第 10 位和第 11 位含有 Ser 和 Leu 的 9、10、12 和 15 号化合物对 MDA-MB-231、SNU449、SKOV3、DU145 和 HCT116 癌细胞株的细胞毒性最强,而且 19 位元的肽多酚一般比脂肽多酚更有效。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

摘要图片

查看原文
分享 分享
微信好友 朋友圈 QQ好友 复制链接
本刊更多论文
Cytotoxic Peptaibols from Trichoderma strigosum.

Five new lipopeptaibols (1-5) and eight new 19-residue peptaibols (8-15) along with two known lipopeptaibols, lipovelutibols C (6) and D (7) were isolated from Trichoderma strigosum. The planar structures of the newly discovered peptaibols (1-5, 8-15) were elucidated using 1D and 2D NMR, and UPLC-MS/MS data. The absolute configurations for new peptaibols (1-5, 8-15) were elucidated using the advanced Marfey's method and GITC (2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl isothiocyanate) derivatization. Through analysis of CD spectra, these peptabols were found to have right-handed helical conformations. While most of the new compounds were significantly more active than the positive control, 9, 10, 12, and 15 containing Ser and Leu at positions 10 and 11, respectively, were the most cytotoxic against MDA-MB-231, SNU449, SKOV3, DU145, and HCT116 cancer cell lines, and the 19-residue peptaibols were generally more potent than lipopeptaibols.

求助全文
通过发布文献求助,成功后即可免费获取论文全文。 去求助
来源期刊
CiteScore
9.10
自引率
5.90%
发文量
294
审稿时长
2.3 months
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.
期刊最新文献
Discovery of Sporachelins by Genome Mining of a Micromonospora Strain. In Vitro Biological Target Screening and Colloidal Aggregation of Minor Cannabinoids. Tyrosinase Inhibitory Properties of Compounds Isolated from Artocarpus integer Roots. Discovery, Biosynthesis, Total Synthesis, and Biological Activities of Solanapyrones: [4 + 2] Cycloaddition-Derived Polyketides of Fungal Origin. Discovery of Chalcone Derivatives as Bifunctional Molecules with Anti-SARS-CoV-2 and Anti-inflammatory Activities.
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
现在去查看 取消
×
提示
确定
0
微信
客服QQ
Book学术公众号 扫码关注我们
反馈
×
意见反馈
请填写您的意见或建议
请填写您的手机或邮箱
已复制链接
已复制链接
快去分享给好友吧!
我知道了
×
扫码分享
扫码分享
Book学术官方微信
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术
文献互助 智能选刊 最新文献 互助须知 联系我们:info@booksci.cn
Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。
Copyright © 2023 Book学术 All rights reserved.
ghs 京公网安备 11010802042870号 京ICP备2023020795号-1