Synthesis of Marine-Derived Bioactive Compounds

A special issue of Marine Drugs (ISSN 1660-3397).

Deadline for manuscript submissions: closed (30 November 2021) | Viewed by 2783

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Department of Chemistry and Biochemistry, Florida Atlantic University, Boca Raton, FL 33431, USA
Interests: synthesis of marine natural products
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Special Issue Information

Dear Colleagues,

The chemical complexity and diverse biological activities of marine natural products have been a source of inspiration and the challenges to chemists, and accessing these distinctive three-dimensional structures presents unique research opportunities that push the boundaries of organic chemistry. Natural Product synthesis both total and partial (semi-synthesis) provides confirmation of structure and allows the ability to carry-out structure-activity relationship (SAR) studies for lead optimization, together with providing a potential solution to the supply issue that has curtailed the development of many marine natural products. The aim of this Special Issue is to highlight the chemical and biological discoveries resulting from the total synthesis or semi-synthesis of marine-derived natural products. We invite scientists in the fields of chemistry, biochemistry, pharmacology, and toxicology to submit review papers or original articles where synthesis has contributed to the field of marine natural products drug discovery.

Dr. Lyndon West
Guest Editor

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Keywords

  • Marine natural product
  • Total synthesis
  • Biomimetic synthesis
  • Semi-synthesis
  • Chemical transformation
  • Structure-activity relationship
  • Lead optimization
  • Pharmacology

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Published Papers (1 paper)

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17 pages, 4618 KiB  
Article
Synthesis and Bioactivity of Ancorinoside B, a Marine Diglycosyl Tetramic Acid
by Kevin J. Soliga, Sofia I. Bär, Natalie Oberhuber, Haoxuan Zeng, Hedda Schrey and Rainer Schobert
Mar. Drugs 2021, 19(10), 583; https://doi.org/10.3390/md19100583 - 19 Oct 2021
Cited by 8 | Viewed by 2252
Abstract
The sponge metabolite ancorinoside B was prepared for the first time in 16 steps and 4% yield. It features a β-d-galactopyranosyl-(1→4)-β-d-glucuronic acid tethered to a d-aspartic acid-derived tetramic acid. Key steps were the synthesis of a fully protected [...] Read more.
The sponge metabolite ancorinoside B was prepared for the first time in 16 steps and 4% yield. It features a β-d-galactopyranosyl-(1→4)-β-d-glucuronic acid tethered to a d-aspartic acid-derived tetramic acid. Key steps were the synthesis of a fully protected d-lactose derived thioglycoside, its attachment to a C20-aldehyde spacer, functionalization of the latter with a terminal N-(β-ketoacyl)-d-aspartate, and a basic Dieckmann cyclization to close the pyrrolidin-2,4-dione ring with concomitant global deprotection. Ancorinoside B exhibited multiple biological effects of medicinal interest. It inhibited the secretion of the cancer metastasis-relevant matrix metalloproteinases MMP-2 and MMP-9, and also the growth of Staphylococcus aureus biofilms by ca 87% when applied at concentrations as low as 0.5 µg/mL. This concentration is far below its MIC of ca 67 µg/mL and thus unlikely to induce bacterial resistance. It also led to a 67% dispersion of preformed S. aureus biofilms when applied at a concentration of ca 2 µg/mL. Ancorinoside B might thus be an interesting candidate for the control of the general hospital, catheter, or joint protheses infections. Full article
(This article belongs to the Special Issue Synthesis of Marine-Derived Bioactive Compounds)
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