ArticleThe Journal of organic chemistry2010
Mutremdamide A and koshikamides C-H, peptide inhibitors of HIV-1 entry from different Theonella species.
Article in The Journal of organic chemistry, 2010. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 22 papers.
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Who cites it
22 citing papers in PubMed, 67 citations in OpenAlex.
- Discovery, biosynthesis, and bioactivities of peptidic natural products from marine sponges and sponge-associated bacteria.Natural product reports · 2025Review
- Chemical and biological diversity of new natural products from marine sponges: a review (2009-2018).Marine life science & technology · 2022Review
- Therapeutic Potential of Marine Bioactive Peptides against Human Immunodeficiency Virus: Recent Evidence, Challenges, and Future Trends.Marine drugs · 2022Review
- Marine Cyclic Peptides: Antimicrobial Activity and Synthetic Strategies.Marine drugs · 2022Review
- The Immune System of Marine Organisms as Source for Drugs against Infectious Diseases.Marine drugs · 2022Review
- Antiviral Peptides (AVPs) of Marine Origin as Propitious Therapeutic Drug Candidates for the Treatment of Human Viruses.Molecules (Basel, Switzerland) · 2022Review
- Leucinostatins fromJournal of natural products · 2020Article
- Therapeutic Properties and Biological Benefits of Marine-Derived Anticancer Peptides.International journal of molecular sciences · 2018Review
- Marine Natural Peptides: Determination of Absolute Configuration Using Liquid Chromatography Methods and Evaluation of Bioactivities.Molecules (Basel, Switzerland) · 2018Review
- Marine natural product peptides with therapeutic potential: Chemistry, biosynthesis, and pharmacology.Biochimica et biophysica acta. General subjects · 2018Review
- Peptides, Peptidomimetics, and Polypeptides from Marine Sources: A Wealth of Natural Sources for Pharmaceutical Applications.Marine drugs · 2017Review
- Antiviral activity of animal venom peptides and related compounds.The journal of venomous animals and toxins including tropical diseases · 2017Review
- The Pharmacological Potential of Non-ribosomal Peptides from Marine Sponge and Tunicates.Frontiers in pharmacology · 2016Review
- Marine peptides and their anti-infective activities.Marine drugs · 2015Review
- α,β-Dehydroamino acids in naturally occurring peptides.Amino acids · 2015Review
- New cyclic cystine bridged peptides from the sponge Suberites waedoensis.Marine drugs · 2014Article
- Configurational assignments of conformationally restricted bis-monoterpene hydroquinones: utility in exploration of endangered plants.Biochimica et biophysica acta · 2013Article
- Synthesis of N-methylated cyclic peptides.Nature protocols · 2012Article
- Identification of the protease inhibitor miraziridine A in the Red sea sponge Theonella swinhoei.Pharmacognosy research · 2012Article
- Natural products from the Lithistida: a review of the literature since 2000.Marine drugs · 2011Review
Corrections and comments
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Authors and funding
9 authors at 5 institutions in 4 countries.
Funding
Abstract
A new sulfated cyclic depsipeptide, termed mutremdamide A, and six new highly N-methylated peptides, termed koshikamides C-H, were isolated from different deep-water specimens of Theonella swinhoei and Theonella cupola. Their structures were determined using extensive 2D NMR, ESI, or CDESI and QTOF-MS/MS experiments and absolute configurations established by quantum mechanical calculations, advanced Marfey's method, and chiral HPLC. Mutremdamide A displays a rare 2-amino-3-(2-hydroxyphenyl)propanoic acid and a new N(delta)-carbamoyl-beta-sulfated asparagine. Koshikamides C-E are linear undecapeptides, and koshikamides F-H are 17-residue depsipeptides containing a 10-residue macrolactone. Koshikamides F and G differ from B and H in part by the presence of the conjugated unit 2-(3-amino-5-oxopyrrolidin-2-ylidene)propanoic acid. Cyclic koshikamides F and H inhibited HIV-1 entry at low micromolar concentrations while their linear counterparts were inactive. The Theonella collections studied here are distinguished by co-occurrence of mutremdamide A, koshikamides, and theonellamides, the combination of which appears to define a new Theonella chemotype that can be found in deeper waters.
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Registered trials
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