基于系统发育的方法从海洋蓝藻 cf. 珍珠藻中分离乙基 Tumonoate A。
Phylogeny-guided isolation of ethyl tumonoate A from the marine cyanobacterium cf. Oscillatoria margaritifera.
机构信息
Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California, San Diego, La Jolla, California 92093, USA.
出版信息
J Nat Prod. 2011 Aug 26;74(8):1737-43. doi: 10.1021/np200236c. Epub 2011 Jul 13.
Abstract
The evolutionary relationships of cyanobacteria, as inferred by their SSU (16S) rRNA genes, were used as predictors of their potential to produce varied secondary metabolites. The evolutionary relatedness in geographically distant cyanobacterial specimens was then used as a guide for the detection and isolation of new variations of predicted molecules. This phylogeny-guided isolation approach for new secondary metabolites was tested in its capacity to direct the search for specific classes of new natural products from Curaçao marine cyanobacteria. As a result, we discovered ethyl tumonoate A (1), a new tumonoic acid derivative with anti-inflammatory activity and inhibitory activity of calcium oscillations in neocortical neurons.
摘要
根据蓝藻的 SSU（16S）rRNA 基因推断其进化关系，可作为其产生不同次生代谢产物的潜力的预测因子。然后，利用地理上遥远的蓝藻标本的进化相关性来指导预测分子的新变体的检测和分离。这种基于系统发育的新型次生代谢产物分离方法用于指导从库拉索海洋蓝藻中寻找特定类别的新型天然产物。结果，我们发现了乙基 Tumonoate A（1），这是一种新型的 Tumonoic 酸衍生物，具有抗炎活性和新皮质神经元钙震荡的抑制活性。
相似文献
1
Phylogeny-guided isolation of ethyl tumonoate A from the marine cyanobacterium cf. Oscillatoria margaritifera.
J Nat Prod. 2011 Aug 26;74(8):1737-43. doi: 10.1021/np200236c. Epub 2011 Jul 13.
2
Cytotoxic veraguamides, alkynyl bromide-containing cyclic depsipeptides from the marine cyanobacterium cf. Oscillatoria margaritifera.
J Nat Prod. 2011 May 27;74(5):928-36. doi: 10.1021/np200077f. Epub 2011 Apr 13.
3
Coibacins A-D, antileishmanial marine cyanobacterial polyketides with intriguing biosynthetic origins.
Org Lett. 2012 Aug 3;14(15):3878-81. doi: 10.1021/ol301607q. Epub 2012 Jul 13.
4
Dihydroanatoxin-a Is Biosynthesized from Proline in Cylindrospermum stagnale PCC 7417: Isotopic Incorporation Experiments and Mass Spectrometry Analysis.
J Nat Prod. 2016 Jul 22;79(7):1775-82. doi: 10.1021/acs.jnatprod.6b00189. Epub 2016 Jun 24.
5
Targeted Discovery of Amantamide B, an Ion Channel Modulating Nonapeptide from a South China Sea Cyanobacterium.
J Nat Prod. 2022 Mar 25;85(3):493-500. doi: 10.1021/acs.jnatprod.1c00983. Epub 2022 Jan 5.
6
Phylogenetic relationships of nonaxenic filamentous cyanobacterial strains based on 16S rRNA sequence analysis.
J Mol Evol. 1996 Feb;42(2):194-200. doi: 10.1007/BF02198845.
7
MS/MS-Based Molecular Networking Approach for the Detection of Aplysiatoxin-Related Compounds in Environmental Marine Cyanobacteria.
Mar Drugs. 2018 Dec 13;16(12):505. doi: 10.3390/md16120505.
8
Viridamides A and B, lipodepsipeptides with antiprotozoal activity from the marine cyanobacterium Oscillatoria nigro-viridis.
J Nat Prod. 2008 Sep;71(9):1544-50. doi: 10.1021/np800110e. Epub 2008 Aug 21.
9
Biosynthesis of Anatoxins in Cyanobacteria: Identification of the Carboxy-anatoxins as the Penultimate Biosynthetic Intermediates.
J Nat Prod. 2020 Jan 24;83(1):142-151. doi: 10.1021/acs.jnatprod.9b01121. Epub 2020 Jan 3.
10
Natural products chemistry and taxonomy of the marine cyanobacterium Blennothrix cantharidosmum.
J Nat Prod. 2008 Sep;71(9):1530-7. doi: 10.1021/np800088a. Epub 2008 Aug 13.
引用本文的文献
1
Analysis of metabolomics and transcriptomics data to assess interactions in microalgal co-culture of Skeletonema marinoi and Prymnesium parvum.
PLoS One. 2025 Jul 28;20(7):e0329115. doi: 10.1371/journal.pone.0329115. eCollection 2025.
2
Chemical diversity of cyanobacterial natural products.
Nat Prod Rep. 2025 Jan 22;42(1):6-49. doi: 10.1039/d4np00040d.
3
The Neuroprotective Role of Cyanobacteria with Focus on the Anti-Inflammatory and Antioxidant Potential: Current Status and Perspectives.
Molecules. 2024 Oct 10;29(20):4799. doi: 10.3390/molecules29204799.
4
A Review of the Antimicrobial Properties of Cyanobacterial Natural Products.
Molecules. 2023 Oct 17;28(20):7127. doi: 10.3390/molecules28207127.
5
Cyanobacteria: A Promising Source of Antifungal Metabolites.
Mar Drugs. 2023 Jun 14;21(6):359. doi: 10.3390/md21060359.
6
Gut and Gill-Associated Microbiota of the Flatfish European Plaice (): Diversity, Metabolome and Bioactivity against Human and Aquaculture Pathogens.
Mar Drugs. 2022 Sep 9;20(9):573. doi: 10.3390/md20090573.
7
Anti-lung cancer properties of cyanobacterial bioactive compounds.
Arch Microbiol. 2022 Sep 5;204(10):603. doi: 10.1007/s00203-022-03194-0.
8
Anti-inflammatory Activity of Bioactive Compounds from Microalgae and Cyanobacteria by Focusing on the Mechanisms of Action.
Mol Biol Rep. 2020 Aug;47(8):6193-6205. doi: 10.1007/s11033-020-05562-9. Epub 2020 Jun 15.
9
Uncovering Potential Applications of Cyanobacteria and Algal Metabolites in Biology, Agriculture and Medicine: Current Status and Future Prospects.
Front Microbiol. 2017 Apr 25;8:515. doi: 10.3389/fmicb.2017.00515. eCollection 2017.
10
Lyngbyabellins K-N from Two Palmyra Atoll Collections of the Marine Cyanobacterium .
European J Org Chem. 2012 Sep 1;2012(27):5141-5150. doi: 10.1002/ejoc.201200691. Epub 2012 Aug 14.
本文引用的文献
1
Genomic insights into the physiology and ecology of the marine filamentous cyanobacterium Lyngbya majuscula.
Proc Natl Acad Sci U S A. 2011 May 24;108(21):8815-20. doi: 10.1073/pnas.1101137108. Epub 2011 May 9.
2
Underestimated biodiversity as a major explanation for the perceived rich secondary metabolite capacity of the cyanobacterial genus Lyngbya.
Environ Microbiol. 2011 Jun;13(6):1601-10. doi: 10.1111/j.1462-2920.2011.02472.x. Epub 2011 Apr 7.
3
Evolved diversification of a modular natural product pathway: apratoxins F and G, two cytotoxic cyclic depsipeptides from a Palmyra collection of Lyngbya bouillonii.
Chembiochem. 2010 Jul 5;11(10):1458-66. doi: 10.1002/cbic.201000070.
4
The cylindrospermopsin gene cluster of Aphanizomenon sp. strain 10E6: organization and recombination.
Microbiology (Reading). 2010 Aug;156(Pt 8):2438-2451. doi: 10.1099/mic.0.036988-0. Epub 2010 Apr 29.
5
Palmyramide A, a cyclic depsipeptide from a Palmyra Atoll collection of the marine cyanobacterium Lyngbya majuscula.
J Nat Prod. 2010 Mar 26;73(3):393-8. doi: 10.1021/np900428h.
6
Phylogenetic and chemical diversity of three chemotypes of bloom-forming lyngbya species (Cyanobacteria: Oscillatoriales) from reefs of southeastern Florida.
Appl Environ Microbiol. 2009 May;75(9):2879-88. doi: 10.1128/AEM.02656-08. Epub 2009 Mar 6.
7
Viridamides A and B, lipodepsipeptides with antiprotozoal activity from the marine cyanobacterium Oscillatoria nigro-viridis.
J Nat Prod. 2008 Sep;71(9):1544-50. doi: 10.1021/np800110e. Epub 2008 Aug 21.
8
Natural products chemistry and taxonomy of the marine cyanobacterium Blennothrix cantharidosmum.
J Nat Prod. 2008 Sep;71(9):1530-7. doi: 10.1021/np800088a. Epub 2008 Aug 13.
9
Biosynthetic origin of natural products isolated from marine microorganism-invertebrate assemblages.
Proc Natl Acad Sci U S A. 2008 Mar 25;105(12):4587-94. doi: 10.1073/pnas.0709851105. Epub 2008 Feb 4.
10
Bioactive natural products from marine cyanobacteria for drug discovery.
Phytochemistry. 2007 Apr;68(7):954-79. doi: 10.1016/j.phytochem.2007.01.012. Epub 2007 Mar 2.
Zotero 插件