Secondary Metabolites from Marine Molluscs: Chemistry, Biosynthesis, Synthesis and Bioactivity

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

Deadline for manuscript submissions: closed (31 August 2019) | Viewed by 10396

Special Issue Editor


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Guest Editor
Institute of Biomolecular Chemistry, National Research Council, Pozzuoli, Italy
Interests: natural products chemistry; bioactive metabolites; structural characterization; NMR; mass spectrometry; lipidomics
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Special Issue Information

Dear Colleagues,

The phylum Mollusca embraces a high diversity of species, which turned out to be of great interest to natural products chemists. Chemical studies unveiled a variety of unique scaffolds inspiring leading drugs currently in clinical trials. Thus, extending investigation on unexplored species is expected to reveal novel molecular architectures. Beyond the chemistry and pharmacological potential of molluscan metabolites, their crucial role in regulating chemo-ecological interactions has also been addressed. The majority of these molecules are obtained from food sources, but they can be biosynthesized de novo, or derived from symbiotic microorganisms.

This Special Issue is open to contributions covering all aspects of chemistry, chemical ecology and pharmacological potential of secondary metabolites from molluscs; papers are welcome reporting on: i) the discovery of novel bioactive compounds and their molecular targets; ii) the origin and the biosynthetic pathways by which these metabolites are produced; iii) their chemo-ecological role; iv) the synthetic strategies designed to overcome the supply issue for the metabolites themselves and to provide derivatives with improved potency.

Dr. Adele Cutignano
Guest Editor

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Keywords

  • Secondary metabolites
  • Molluscs
  • Biosynthesis
  • Synthesis
  • Structural elucidation
  • Biological activity
  • Chemo-ecological study

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Published Papers (2 papers)

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Research

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14 pages, 1535 KiB  
Article
Amphilectene Diterpene Isonitriles and Formamido Derivatives from the Hainan Nudibranch Phyllidia Coelestis
by Marianna Carbone, Maria Letizia Ciavatta, Emiliano Manzo, Xiao-Lu Li, Ernesto Mollo, I Wayan Mudianta, Yue-Wei Guo and Margherita Gavagnin
Mar. Drugs 2019, 17(11), 603; https://doi.org/10.3390/md17110603 - 24 Oct 2019
Cited by 7 | Viewed by 3177
Abstract
Terpene content of two distinct collections of the nudibranch Phyllidia coelestis from the South China Sea has been chemically analyzed. A series of amphilectene diterpenes, most likely of dietary origin, with isocyano and formamido functionalities have been isolated from both collections and spectroscopically [...] Read more.
Terpene content of two distinct collections of the nudibranch Phyllidia coelestis from the South China Sea has been chemically analyzed. A series of amphilectene diterpenes, most likely of dietary origin, with isocyano and formamido functionalities have been isolated from both collections and spectroscopically characterized by an exhaustive nuclear magnetic resonance (NMR) analysis. Interestingly, the structural architecture of compounds 57 and 9 with both 8,13-cis and 12,13-cis ring junctions is unprecedented in the amphilectene skeleton. Metabolite 3, which was the most abundant in the nudibranch’s mantle, has been shown to deter feeding by a generalist predator, supporting its involvement in chemical defense. Full article
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Review

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38 pages, 4661 KiB  
Review
Terpenoids in Marine Heterobranch Molluscs
by Conxita Avila
Mar. Drugs 2020, 18(3), 162; https://doi.org/10.3390/md18030162 - 14 Mar 2020
Cited by 29 | Viewed by 6265
Abstract
Heterobranch molluscs are rich in natural products. As other marine organisms, these gastropods are still quite unexplored, but they provide a stunning arsenal of compounds with interesting activities. Among their natural products, terpenoids are particularly abundant and diverse, including monoterpenoids, sesquiterpenoids, diterpenoids, sesterterpenoids, [...] Read more.
Heterobranch molluscs are rich in natural products. As other marine organisms, these gastropods are still quite unexplored, but they provide a stunning arsenal of compounds with interesting activities. Among their natural products, terpenoids are particularly abundant and diverse, including monoterpenoids, sesquiterpenoids, diterpenoids, sesterterpenoids, triterpenoids, tetraterpenoids, and steroids. This review evaluates the different kinds of terpenoids found in heterobranchs and reports on their bioactivity. It includes more than 330 metabolites isolated from ca. 70 species of heterobranchs. The monoterpenoids reported may be linear or monocyclic, while sesquiterpenoids may include linear, monocyclic, bicyclic, or tricyclic molecules. Diterpenoids in heterobranchs may include linear, monocyclic, bicyclic, tricyclic, or tetracyclic compounds. Sesterterpenoids, instead, are linear, bicyclic, or tetracyclic. Triterpenoids, tetraterpenoids, and steroids are not as abundant as the previously mentioned types. Within heterobranch molluscs, no terpenoids have been described in this period in tylodinoideans, cephalaspideans, or pteropods, and most terpenoids have been found in nudibranchs, anaspideans, and sacoglossans, with very few compounds in pleurobranchoideans and pulmonates. Monoterpenoids are present mostly in anaspidea, and less abundant in sacoglossa. Nudibranchs are especially rich in sesquiterpenes, which are also present in anaspidea, and in less numbers in sacoglossa and pulmonata. Diterpenoids are also very abundant in nudibranchs, present also in anaspidea, and scarce in pleurobranchoidea, sacoglossa, and pulmonata. Sesterterpenoids are only found in nudibranchia, while triterpenoids, carotenoids, and steroids are only reported for nudibranchia, pleurobranchoidea, and anaspidea. Many of these compounds are obtained from their diet, while others are biotransformed, or de novo biosynthesized by the molluscs. Overall, a huge variety of structures is found, indicating that chemodiversity correlates to the amazing biodiversity of this fascinating group of molluscs. Full article
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