Marine-Derived Macrolides 1990–2020: An Overview of Chemical and Biological Diversity

Macrolides are a significant family of natural products with diverse structures and bioactivities. Considerable effort has been made in recent decades to isolate additional macrolides and characterize their chemical and bioactive properties. The majority of macrolides are obtained from marine organisms, including sponges, marine microorganisms and zooplankton, cnidarians, mollusks, red algae, bryozoans, and tunicates. Sponges, fungi and dinoflagellates are the main producers of macrolides. Marine macrolides possess a wide range of bioactive properties including cytotoxic, antibacterial, antifungal, antimitotic, antiviral, and other activities. Cytotoxicity is their most significant property, highlighting that marine macrolides still encompass many potential antitumor drug leads. This extensive review details the chemical and biological diversity of 505 macrolides derived from marine organisms which have been reported from 1990 to 2020.

Synthetic efforts on the road to marine natural products bearing 4-O-2,3,4,6-tetrasubstituted THPs: an update

A review covering the synthetic efforts directed to miyakolide, polycavernoside A, lasonolide A, clavosolide A and madeirolide A. They belong to the unique families of marine macrolides bearing 4-O-2,3,4,6 tetrasubstituted THPs.

Gibbosolide A, a highly functionalized 20-membered macrolide with a terminal cis-fused 2-methylhexahydro-2H-furo[3,2-b]pyran motif: insights into late-stage cyclization of marine macrolides

A sailboat-shaped 20-membered macrolide, named gibbosolide A, featuring a rare cis-fused 2-methylhexahydro-2H-furo[3,2-b]pyran motif, was obtained from the South China Sea dinoflagellate, Amphidinium gibbosum. Its planar structure and absolute configuration, containing...

Marine Macrolides with Antibacterial and/or Antifungal Activity

Currently, the increasing resistance of microorganisms to antibiotics is a serious problem. Marine organisms are the source of thousands of substances, which also have antibacterial and antifungal effects. Among them, marine macrolides are significant. In this review, the antibacterial and/or antifungal activities of 34 groups of marine macrolides are presented. Exemplary groups are chalcomycins, curvulides, halichondramides, lobophorins, macrolactins, modiolides, scytophycins, spongistatins, or zearalanones. In the paper, 74 antibiotics or their analog sets, among which 29 with antifungal activity, 25 that are antibacterial, and 20 that are both antifungal and antibacterial are summarized. Also, 36 macrolides or their sets are produced by bacteria, 18 by fungi, ten by sponges, seven by algae, two by porifera, and one by nudibranch. Moreover, the chemical structures of representatives from each of the 34 groups of these antibiotics are presented. To summarize, marine organisms are rich in natural macrolides. Some of these may be used in the future in the treatment of bacterial and fungal infections. Marine macrolides can also be potential drugs applicable against pathogens resistant to currently known antibiotics.

Generation of Molecular Shape Diverstiy. From Privileged Scaffolds to Diverted Total Synthesis

Molecular shape is a presentation of a molecule’s three-dimensional structure and its volume of space and surface electrostatic potential map collectively define the function, e. g. as a modulator or probe to biological targets. Molecular shape diversity for compound libraries with multiple scaffolds (rich skeletal diversity) is recognized as a prerequisite for discovering broad bioactivity. Established strategies and methodologies for diversity-oriented synthesis (DOS) are useful for generating molecular shape diversity by synthesizing natural product-like compounds. On the other hand, diverted total synthesis (DTS) offers natural products and analogues with a higher degree of structural diversity and complexity. Examples of DOS of privileged heterocycles and DTS of amphidinolide T marine macrolides from the author’s laboratories are illustrated.