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Special Issue "Synthetic and Biosynthetic Approaches to Marine Natural Products"

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

Deadline for manuscript submissions: 31 July 2019

Special Issue Editor

Guest Editor
Prof. Dr. Asunción Barbero

Deparment of Organic Chemistry, Universidad de Valladolid | UVA, Spain
Website | E-Mail

Special Issue Information

Dear Colleagues,

The ocean is the natural habitat for abundant multicellular plants or animals, and unicelular bacteria. These organisms are excellent producers of secondary metabolites with important biological properties. The interesting chemical structures and properties of these marine natural products have attracted the attention of the scientific community, which has made great efforts in the synthesis and biosynthesis of these types of compounds. As Guest Editor of this Special Issue of Marine Drugs, I invite you to provide papers and review articles describing synthetic or biosynthetic approaches to marine natural products. Manuscripts describing total or partial synthesis of marine drugs, as well as analogues, are most welcome.

Prof. Dr. Asunción Barbero
Guest Editor

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All papers will be peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Marine Drugs is an international peer-reviewed open access monthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2000 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • marine natural products
  • total synthesis
  • synthesis of analogs
  • biosynthesis

Published Papers (5 papers)

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Research

Open AccessArticle
Short Chain Fatty Acid Biosynthesis in Microalgae Synechococcus sp. PCC 7942
Mar. Drugs 2019, 17(5), 255; https://doi.org/10.3390/md17050255
Received: 19 April 2019 / Accepted: 25 April 2019 / Published: 28 April 2019
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Abstract
Short chain fatty acids (SCFAs) are valued as a functional material in cosmetics. Cyanobacteria can accumulate SCFAs under some conditions, the related mechanism is unclear. Two potential genes Synpcc7942_0537 (fabB/F) and Synpcc7942_1455 (fabH) in Synechococcus sp. PCC 7942 have [...] Read more.
Short chain fatty acids (SCFAs) are valued as a functional material in cosmetics. Cyanobacteria can accumulate SCFAs under some conditions, the related mechanism is unclear. Two potential genes Synpcc7942_0537 (fabB/F) and Synpcc7942_1455 (fabH) in Synechococcus sp. PCC 7942 have homology with fabB/F and fabH encoding β-ketoacyl ACP synthases (I/II/III) in plants. Therefore, effects of culture time and cerulenin on SCFAs accumulation, expression levels and functions of these two potential genes were studied. The results showed Synechococcus sp. PCC 7942 accumulated high SCFAs (C12 + C14) in early growth stage (day 4) and at 7.5g/L cerulenin concentration, reaching to 2.44% and 2.84% of the total fatty acids respectively, where fabB/F expression was down-regulated. Fatty acid composition analysis showed C14 increased by 65.19% and 130% respectively, when fabB/F and fabH were antisense expressed. C14 increased by 10.79% (fab(B/F)) and 6.47% (fabH) under mutation conditions, while C8 increased by six times in fab(B/F) mutant strain. These results suggested fabB/F is involved in fatty acid elongation (C <18) and the elongation of cis-16:1 to cis-18:1 fatty acid in Synechococcus sp. PCC 7942, while fabH was involved in elongation of fatty acid synthesis, which were further confirmed in complementary experiments of E. coli. The research could provide the scientific basis for the breeding of SCFA-rich microalgae species. Full article
(This article belongs to the Special Issue Synthetic and Biosynthetic Approaches to Marine Natural Products)
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Open AccessArticle
A General Strategy for the Stereoselective Synthesis of the Furanosesquiterpenes Structurally Related to Pallescensins 1–2
Mar. Drugs 2019, 17(4), 245; https://doi.org/10.3390/md17040245
Received: 22 March 2019 / Revised: 16 April 2019 / Accepted: 23 April 2019 / Published: 25 April 2019
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Abstract
Here, we describe a general stereoselective synthesis of the marine furanosesquiterpenes structurally related to pallescensins 1–2. The stereoisomeric forms of the pallescensin 1, pallescensin 2, and dihydropallescensin 2 were obtained in high chemical and isomeric purity, whereas isomicrocionin-3 was synthesized for the first [...] Read more.
Here, we describe a general stereoselective synthesis of the marine furanosesquiterpenes structurally related to pallescensins 1–2. The stereoisomeric forms of the pallescensin 1, pallescensin 2, and dihydropallescensin 2 were obtained in high chemical and isomeric purity, whereas isomicrocionin-3 was synthesized for the first time. The sesquiterpene framework was built up by means of the coupling of the C10 cyclogeranyl moiety with the C5 3-(methylene)furan moiety. The key steps of our synthetic procedure are the stereoselective synthesis of four cyclogeraniol isomers, their conversion into the corresponding cyclogeranylsulfonylbenzene derivatives, their alkylation with 3-(chloromethyl)furan, and the final reductive cleavage of the phenylsulfonyl functional group to afford the whole sesquiterpene framework. The enantioselective synthesis of the α-, 3,4-dehydro-γ- and γ-cyclogeraniol isomers was performed using both a lipase-mediated resolution procedure and different regioselective chemical transformations. Full article
(This article belongs to the Special Issue Synthetic and Biosynthetic Approaches to Marine Natural Products)
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Open AccessArticle
Synthesis of Polysubstituted Tetrahydropyrans by Stereoselective Hydroalkoxylation of Silyl Alkenols: En Route to Tetrahydropyranyl Marine Analogues
Mar. Drugs 2018, 16(11), 421; https://doi.org/10.3390/md16110421
Received: 9 September 2018 / Revised: 19 October 2018 / Accepted: 25 October 2018 / Published: 1 November 2018
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Abstract
Tetrahydropyrans are abundantly found in marine natural products. The interesting biological properties of these compounds and their analogues make necessary the development of convenient procedures for their synthesis. In this paper, an atom economy access to tetrahydropyrans by intramolecular acid-mediated cyclization of silylated [...] Read more.
Tetrahydropyrans are abundantly found in marine natural products. The interesting biological properties of these compounds and their analogues make necessary the development of convenient procedures for their synthesis. In this paper, an atom economy access to tetrahydropyrans by intramolecular acid-mediated cyclization of silylated alkenols is described. p-TsOH has shown to be an efficient reagent to yield highly substituted tetrahydropyrans. Moreover, excellent diastereoselectivities are obtained both for unsubstituted and alkylsubstituted vinylsilyl alcohols. The methodology herein developed may potentially be applied to the synthesis of marine drugs derivatives. Full article
(This article belongs to the Special Issue Synthetic and Biosynthetic Approaches to Marine Natural Products)
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Graphical abstract

Open AccessArticle
Asymmetric Synthesis of the C15–C32 Fragment of Alotamide and Determination of the Relative Stereochemistry
Mar. Drugs 2018, 16(11), 414; https://doi.org/10.3390/md16110414
Received: 15 October 2018 / Revised: 24 October 2018 / Accepted: 24 October 2018 / Published: 30 October 2018
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Abstract
Alotamide is a cyclic depsipetide isolated from a marine cyanobacterium and possesses a unique activation of calcium influx in murine cerebrocortical neurons (EC50 4.18 µM). Due to its limited source, the three stereocenters (C19, C28, and C30) in its polyketide fragment remain [...] Read more.
Alotamide is a cyclic depsipetide isolated from a marine cyanobacterium and possesses a unique activation of calcium influx in murine cerebrocortical neurons (EC50 4.18 µM). Due to its limited source, the three stereocenters (C19, C28, and C30) in its polyketide fragment remain undetermined. In this study, the first asymmetric synthesis of its polyketide fragment was achieved. Four relative possible diastereomers were constructed with a boron-mediated enantioselective aldol reaction and Julia–Kocienski olefination as the key steps. Comparison of 13C NMR spectra revealed the relative structure of fragment C15–C32 of alotamide. Full article
(This article belongs to the Special Issue Synthetic and Biosynthetic Approaches to Marine Natural Products)
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Graphical abstract

Open AccessArticle
Smenamide A Analogues. Synthesis and Biological Activity on Multiple Myeloma Cells
Mar. Drugs 2018, 16(6), 206; https://doi.org/10.3390/md16060206
Received: 29 May 2018 / Revised: 5 June 2018 / Accepted: 10 June 2018 / Published: 13 June 2018
Cited by 2 | PDF Full-text (4586 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Smenamides are an intriguing class of peptide/polyketide molecules of marine origin showing antiproliferative activity against lung cancer Calu-1 cells at nanomolar concentrations through a clear pro-apoptotic mechanism. To probe the role of the activity-determining structural features, the 16-epi-analogue of smenamide A [...] Read more.
Smenamides are an intriguing class of peptide/polyketide molecules of marine origin showing antiproliferative activity against lung cancer Calu-1 cells at nanomolar concentrations through a clear pro-apoptotic mechanism. To probe the role of the activity-determining structural features, the 16-epi-analogue of smenamide A and eight simplified analogues in the 16-epi series were prepared using a flexible synthetic route. The synthetic analogues were tested on multiple myeloma (MM) cell lines showing that the configuration at C-16 slightly affects the activity, since the 16-epi-derivative is still active at nanomolar concentrations. Interestingly, it was found that the truncated compound 8, mainly composed of the pyrrolinone terminus, was not active, while compound 13, essentially lacking the pyrrolinone moiety, was 1000-fold less active than the intact substance and was the most active among all the synthesized compounds. Full article
(This article belongs to the Special Issue Synthetic and Biosynthetic Approaches to Marine Natural Products)
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Graphical abstract

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