ArticleChemistry (Weinheim an der Bergstrasse, Germany)2016
Discovery, Total Synthesis and Key Structural Elements for the Immunosuppressive Activity of Cocosolide, a Symmetrical Glycosylated Macrolide Dimer from Marine Cyanobacteria.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed, 33 citations in OpenAlex.
- Chemical diversity of cyanobacterial natural products.Natural product reports · 2025Review
- Cyclopropane-Containing Specialized Metabolites from the Marine Cyanobacterium cf.Molecules (Basel, Switzerland) · 2023Article
- Cyanobacteria-From the Oceans to the Potential Biotechnological and Biomedical Applications.Marine drugs · 2021Review
- Review
- Advanced Methods for Studying Structure and Interactions of Macrolide Antibiotics.International journal of molecular sciences · 2020Review
- Total Synthesis of Clavosolide A via Asymmetric Alcohol-Mediated Carbonyl Allylation: Beyond Protecting Groups or Chiral Auxiliaries in Polyketide Construction.Angewandte Chemie (International ed. in English) · 2019Article
- Inhibition of T Cell Receptor Activation by Semi-Synthetic Sesquiterpene Lactone Derivatives and Molecular Modeling of Their Interaction with Glutathione and Tyrosine Kinase ZAP-70.Molecules (Basel, Switzerland) · 2019Article
- Glycosylated Natural Products From Marine Microbes.Frontiers in chemistry · 2019Review
- Total Synthesis of Endolides A and B.Synlett : accounts and rapid communications in synthetic organic chemistry · 2019Article
- Total Synthesis of Asperphenins A and B.Organic letters · 2018Article
- A Review Study on Macrolides Isolated from Cyanobacteria.Marine drugs · 2017Review
Corrections and comments
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Authors and funding
11 authors at 5 institutions in 2 countries.
Funding
Abstract
A new dimeric macrolide xylopyranoside, cocosolide (1), was isolated from the marine cyanobacterium preliminarily identified as Symploca sp. from Guam. The structure was determined by a combination of NMR spectroscopy, HRMS, X-ray diffraction studies and Mosher's analysis of the base hydrolysis product. Its carbon skeleton closely resembles that of clavosolides A-D isolated from the sponge Myriastra clavosa, for which no bioactivity is known. We performed the first total synthesis of cocosolide (1) along with its [α,α]-anomer (26) and macrocyclic core (28), thus leading to the confirmation of the structure of natural 1. The convergent synthesis featured Wadsworth-Emmons cyclopropanation, Sakurai annulation, Yamaguchi macrocyclization/dimerization reaction, α-selective glycosidation and β-selective glycosidation. Compounds 1 and 26 potently inhibited IL-2 production in both T-cell receptor dependent and independent manners. Full activity requires the presence of the sugar moiety as well as the intact dimeric structure. Cocosolide also suppressed the proliferation of anti-CD3-stimulated T-cells in a dose-dependent manner.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.