• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利:CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法,用中文像聊天一样搜索,搜遍4000万医学文献。AI智能推荐,让科研检索更轻松。

立即免费搜索

文件翻译

保留排版,准确专业,支持PDF/Word/PPT等文件格式,支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述,25分钟生成高质量综述,智能提取关键信息,辅助科研写作。

立即免费体验

东海环康定 A-C:来自火山岛源海洋 sp 的新型细胞毒性重排安吉环酮

Donghaecyclinones A-C: New Cytotoxic Rearranged Angucyclinones from a Volcanic Island-Derived Marine sp.

机构信息

Natural Products Research Institute, College of Pharmacy, Seoul National University, Seoul 08826, Korea.

Department of Agricultural Biotechnology, College of Agriculture & Life Sciences, Seoul National University, Seoul 08826, Korea.

出版信息

Mar Drugs. 2020 Feb 18;18(2):121. doi: 10.3390/md18020121.

DOI:10.3390/md18020121
PMID:32085561
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7073551/
Abstract

Chemical profiling of the sp. strain SUD119, which was isolated from a marine sediment sample collected from a volcanic island in Korea, led to the discovery of three new metabolites: donghaecyclinones A-C (-). The structures of - were found to be rearranged, multicyclic, angucyclinone-class compounds according to nuclear magnetic resonance (NMR) and mass spectrometry (MS) analyses. The configurations of their stereogenic centers were successfully assigned using a combination of quantum mechanics-based computational methods for calculating the NMR shielding tensor (DP4 and CP3) as well as electronic circular dichroism (ECD) along with a modified version of Mosher's method. Donghaecyclinones A-C (-) displayed cytotoxicity against diverse human cancer cell lines (IC: 6.7-9.6 μM for ).

摘要

从韩国一座火山岛的海洋沉积物样本中分离到的 sp. 菌株 SUD119 的化学成分分析导致发现了三种新的代谢产物:donghaecyclinones A-C (-)。根据核磁共振 (NMR) 和质谱 (MS) 分析,- 的结构被发现是经过重排的、多环的、angucyclinone 类化合物。通过组合使用基于量子力学的计算方法来计算 NMR 屏蔽张量 (DP4 和 CP3) 以及电子圆二色性 (ECD),以及对 Mosher 方法的修改版本,成功地确定了它们的立体中心的构型。Donghaecyclinones A-C (-) 对多种人类癌细胞系显示出细胞毒性(IC:6.7-9.6 μM)。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/846b/7073551/0660e105f46c/marinedrugs-18-00121-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/846b/7073551/97b8ab00121b/marinedrugs-18-00121-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/846b/7073551/bb1d7e648fec/marinedrugs-18-00121-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/846b/7073551/9078ed363a3d/marinedrugs-18-00121-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/846b/7073551/6e51db81a300/marinedrugs-18-00121-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/846b/7073551/e2ee244ebf93/marinedrugs-18-00121-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/846b/7073551/0660e105f46c/marinedrugs-18-00121-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/846b/7073551/97b8ab00121b/marinedrugs-18-00121-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/846b/7073551/bb1d7e648fec/marinedrugs-18-00121-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/846b/7073551/9078ed363a3d/marinedrugs-18-00121-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/846b/7073551/6e51db81a300/marinedrugs-18-00121-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/846b/7073551/e2ee244ebf93/marinedrugs-18-00121-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/846b/7073551/0660e105f46c/marinedrugs-18-00121-g006.jpg

相似文献

1
Donghaecyclinones A-C: New Cytotoxic Rearranged Angucyclinones from a Volcanic Island-Derived Marine sp.东海环康定 A-C:来自火山岛源海洋 sp 的新型细胞毒性重排安吉环酮
Mar Drugs. 2020 Feb 18;18(2):121. doi: 10.3390/md18020121.
2
Gephyyamycin and cysrabelomycin, two new angucyclinone derivatives from the sp. HN-A124.从 sp. HN-A124 中分离得到的两个新的蒽环酮衍生物:吉菲霉素和胱柔霉素。
Nat Prod Res. 2021 Jul;35(13):2117-2122. doi: 10.1080/14786419.2019.1660336. Epub 2019 Sep 6.
3
Rearranged and unrearranged angucyclinones from Indonesian Streptomyces spp.来自印度尼西亚链霉菌属的重排和未重排的安古环素类化合物
J Antibiot (Tokyo). 2008 Jul;61(7):449-56. doi: 10.1038/ja.2008.61.
4
Angucyclinones from an Indonesian Streptomyces sp.来自印度尼西亚链霉菌属的安古环素类化合物
J Nat Prod. 2008 Jan;71(1):61-5. doi: 10.1021/np0704102. Epub 2007 Dec 15.
5
Highly oxygenated angucycline from Streptomyces sp. KCB15JA014.来自链霉菌属KCB15JA014的高度氧化安古霉素。
J Antibiot (Tokyo). 2020 Dec;73(12):859-862. doi: 10.1038/s41429-020-0348-8. Epub 2020 Jul 10.
6
Angucycline Glycosides from an Intertidal Sediments Strain sp. and Their Cytotoxic Activity against Hepatoma Carcinoma Cells.来自潮间带沉积物菌株 sp. 的安卡环素糖苷及其对肝癌细胞的细胞毒性活性。
Mar Drugs. 2018 Nov 27;16(12):470. doi: 10.3390/md16120470.
7
Donghaesulfins A and B, Dimeric Benz[ a]anthracene Thioethers from Volcanic Island Derived Streptomyces sp.东海岸硫醚 A 和 B,来自火山岛衍生链霉菌的二聚苯并[a]蒽硫醚
Org Lett. 2019 May 17;21(10):3635-3639. doi: 10.1021/acs.orglett.9b01057. Epub 2019 Apr 29.
8
Tandocyclinones A and B, Ether Bridged -Glycosyl Benz[]anthracenes from an Intertidal Zone sp.环多西环素A和B,来自潮间带一种生物的醚桥连 - 糖基苯并[]蒽
Mar Drugs. 2023 Sep 21;21(9):500. doi: 10.3390/md21090500.
9
Grincamycins P-T: Rearranged Angucyclines from the Marine Sediment-Derived sp. CNZ-748 Inhibit Cell Lines of the Rare Cancer Pseudomyxoma Peritonei.格兰卡霉素 P-T:海洋沉积物来源的 sp. CNZ-748 产生的重排安卡环类化合物抑制罕见癌症腹膜假黏液瘤的细胞系。
J Nat Prod. 2021 May 28;84(5):1638-1648. doi: 10.1021/acs.jnatprod.1c00179. Epub 2021 Apr 26.
10
Angucyclines and Angucyclinones from Streptomyces sp. CB01913 Featuring C-Ring Cleavage and Expansion.来自链霉菌属菌株CB01913的安古环素类和安古环酮类化合物,具有C环裂解和扩展特征。
J Nat Prod. 2015 Oct 23;78(10):2471-80. doi: 10.1021/acs.jnatprod.5b00601. Epub 2015 Sep 3.

引用本文的文献

1
Diversity of secondary metabolites from marine Streptomyces with potential anti-tubercular activity: a review.具有潜在抗结核活性的海洋链霉菌次级代谢产物的多样性:综述
Arch Microbiol. 2025 Feb 17;207(3):64. doi: 10.1007/s00203-024-04233-8.
2
Bioactive Angucyclines/Angucyclinones Discovered from 1965 to 2023.1965年至2023年发现的生物活性安古环素/安古环酮类化合物
Mar Drugs. 2025 Jan 5;23(1):25. doi: 10.3390/md23010025.
3
Unravelling key enzymatic steps in C-ring cleavage during angucycline biosynthesis.解析安古霉素生物合成过程中C环裂解的关键酶促步骤。

本文引用的文献

1
Antitumor Activity of Ohmyungsamycin A through the Regulation of the Skp2-p27 Axis and MCM4 in Human Colorectal Cancer Cells.Ohmyungsamycin A 通过调控 Skp2-p27 轴和 MCM4 对人结直肠癌细胞的抗肿瘤活性。
J Nat Prod. 2020 Jan 24;83(1):118-126. doi: 10.1021/acs.jnatprod.9b00918. Epub 2020 Jan 2.
2
Characterization of the Ohmyungsamycin Biosynthetic Pathway and Generation of Derivatives with Improved Antituberculosis Activity.Ohmyungsamycin 生物合成途径的表征及具有改良抗结核活性的衍生物的生成。
Biomolecules. 2019 Oct 30;9(11):672. doi: 10.3390/biom9110672.
3
The optimal DFT approach in DP4 NMR structure analysis - pushing the limits of relative configuration elucidation.
Commun Chem. 2023 Dec 18;6(1):281. doi: 10.1038/s42004-023-01059-1.
4
Resistomycin Suppresses Prostate Cancer Cell Growth by Instigating Oxidative Stress, Mitochondrial Apoptosis, and Cell Cycle Arrest.利福平霉素通过引发氧化应激、线粒体凋亡和细胞周期停滞来抑制前列腺癌细胞生长。
Molecules. 2023 Nov 30;28(23):7871. doi: 10.3390/molecules28237871.
5
Cystargamides C and D, New Cyclic Lipopeptides From a Tidal Mudflat-Derived sp. JMS132.胱氨酸酰胺C和D,来自潮间带泥滩来源的新环脂肽,sp. JMS132。
Front Microbiol. 2022 May 13;13:904954. doi: 10.3389/fmicb.2022.904954. eCollection 2022.
6
Ligiamycins A and B, Decalin-Amino-Maleimides from the Co-Culture of sp. and sp. Isolated from the Marine Wharf Roach, .利加霉素 A 和 B,来源于 sp. 和 sp. 的共培养物的去甲氨基马来酰亚胺,它们分离自海洋码头蟑螂 。
Mar Drugs. 2022 Jan 18;20(2):83. doi: 10.3390/md20020083.
7
Novel Marine Secondary Metabolites Worthy of Development as Anticancer Agents: A Review.新型海洋次生代谢产物值得开发为抗癌药物:综述。
Molecules. 2021 Sep 23;26(19):5769. doi: 10.3390/molecules26195769.
8
Svalbamides A and B, Pyrrolidinone-Bearing Lipodipeptides from Arctic sp.斯瓦尔巴酰胺 A 和 B,来自北极的含有吡咯烷酮的脂肽
Mar Drugs. 2021 Apr 17;19(4):229. doi: 10.3390/md19040229.
在 DP4 NMR 结构分析中最优的 DFT 方法 - 推动相对构型阐明的极限。
Org Biomol Chem. 2019 Jun 28;17(24):5886-5890. doi: 10.1039/c9ob00840c. Epub 2019 May 31.
4
Donghaesulfins A and B, Dimeric Benz[ a]anthracene Thioethers from Volcanic Island Derived Streptomyces sp.东海岸硫醚 A 和 B,来自火山岛衍生链霉菌的二聚苯并[a]蒽硫醚
Org Lett. 2019 May 17;21(10):3635-3639. doi: 10.1021/acs.orglett.9b01057. Epub 2019 Apr 29.
5
Antibiotic angucycline derivatives from the deepsea-derived .深海来源的抗生素安莎环素衍生物。
Nat Prod Res. 2020 Dec;34(24):3444-3450. doi: 10.1080/14786419.2019.1577835. Epub 2019 Mar 5.
6
Lugdunomycin, an Angucycline-Derived Molecule with Unprecedented Chemical Architecture.芦竹霉素,一种具有空前化学结构的蒽环类衍生分子。
Angew Chem Int Ed Engl. 2019 Feb 25;58(9):2809-2814. doi: 10.1002/anie.201814581. Epub 2019 Jan 29.
7
Conformation-Enabled Total Syntheses of Ohmyungsamycins A and B and Structural Revision of Ohmyungsamycin B.构象赋活的噢麦孕素 A 和 B 的全合成及噢麦孕素 B 的结构修正。
Angew Chem Int Ed Engl. 2018 Mar 12;57(12):3069-3073. doi: 10.1002/anie.201711286. Epub 2018 Feb 21.
8
Ohmyungsamycins promote antimicrobial responses through autophagy activation via AMP-activated protein kinase pathway.哦美菌胺通过 AMP 激活的蛋白激酶通路诱导自噬激活来促进抗菌反应。
Sci Rep. 2017 Jun 13;7(1):3431. doi: 10.1038/s41598-017-03477-3.
9
QM-HiFSA-Aided Structure Determination of Succinilenes A-D, New Triene Polyols from a Marine-Derived Streptomyces sp.QM-HiFSA辅助的琥珀烯A-D的结构测定,来自海洋链霉菌属的新型三烯多元醇
Mar Drugs. 2017 Feb 14;15(2):38. doi: 10.3390/md15020038.
10
Angucycline antibiotics and its derivatives from marine-derived actinomycete Streptomyces sp. A6H.来自海洋放线菌链霉菌属A6H的安古霉素类抗生素及其衍生物。
Nat Prod Res. 2016 Nov;30(22):2551-2558. doi: 10.1080/14786419.2015.1120730. Epub 2016 Jan 4.