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Marine Drugs
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Chemical Modification of Marine Natural Products
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Chemical Modification of Marine Natural Products

A special issue of Marine Drugs (ISSN 1660-3397). This special issue belongs to the section "Synthesis and Medicinal Chemistry of Marine Natural Products".

Deadline for manuscript submissions: closed (3 July 2020) | Viewed by 23471

Special Issue Editor

Prof. Dr. Joanne Harvey

E-Mail Website
Guest Editor
Victoria University of Wellington, Wellington, New Zealand
Interests: natural product synthesis; nature-inspired drug discovery; design and synthesis of natural product analogues; reaction mechanism
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Marine natural products are a source of great inspiration for chemical and medicinal studies, due to the diversity and complexity of their structures and their potent biological activity. Through semi-synthetic derivatisation of such natural compounds and the de novo synthesis of analogues, chemists can add value to the existing repertoire of chemicals and explore structure–activity relationships. Both goals enable the discovery of exciting new drugs from marine natural products.

This Special Issue seeks to bring together articles and reviews covering semi-synthetic modifications of marine natural products, the design and synthesis of analogues, and the biological evaluation of the resulting compounds. Submissions from scientists in the fields of chemistry, chemical biology, biochemistry, and pharmacology are most cordially invited.

Dr. Joanne Harvey
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 submissions that pass pre-check are 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 2900 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

  • semi-synthesis
  • derivative
  • analogs
  • synthesis
  • bioactive
  • marine natural products

Published Papers (6 papers)

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Research

14 pages, 1249 KiB  
Article
Chemistry of Renieramycins. Part 19: Semi-Syntheses of 22-O-Amino Ester and Hydroquinone 5-O-Amino Ester Derivatives of Renieramycin M and Their Cytotoxicity against Non-Small-Cell Lung Cancer Cell Lines
by Supakarn Chamni, Natchanun Sirimangkalakitti, Pithi Chanvorachote, Khanit Suwanborirux and Naoki Saito
Mar. Drugs 2020, 18(8), 418; https://doi.org/10.3390/md18080418 - 10 Aug 2020
Cited by 12 | Viewed by 2990
Abstract
Two new series of synthetic renieramycins including 22-O-amino ester and hydroquinone 5-O-amino ester derivatives of renieramycin M were semi-synthesized and evaluated for their cytotoxicity against the metastatic non-small-cell lung cancer H292 and H460 cell lines. Interestingly, the series of [...] Read more.
Two new series of synthetic renieramycins including 22-O-amino ester and hydroquinone 5-O-amino ester derivatives of renieramycin M were semi-synthesized and evaluated for their cytotoxicity against the metastatic non-small-cell lung cancer H292 and H460 cell lines. Interestingly, the series of 22-O-amino ester derivatives displayed a potent cytotoxic activity greater than the hydroquinone derivatives. The most cytotoxic derivative of the series was the 22-O-(N-Boc-l-glycine) ester of renieramycin M (5a: IC50 3.56 nM), which showed 7-fold higher potency than renieramycin M (IC50 24.56 nM) and 61-fold more than jorunnamycin A (IC50 217.43 nM) against H292 cells. In addition, 5a exhibited a significantly higher cytotoxic activity than doxorubicin (ca. 100 times). The new semi-synthetic renieramycin derivatives will be further studied and developed as potential cytotoxic agents for non-small-cell lung cancer treatment. Full article
(This article belongs to the Special Issue Chemical Modification of Marine Natural Products)
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38 pages, 5584 KiB  
Article
Screening for Small Molecule Modulators of Trypanosoma brucei Hsp70 Chaperone Activity Based upon Alcyonarian Coral-Derived Natural Products
by Sarah K. Andreassend, Stephen J. Bentley, Gregory L. Blatch, Aileen Boshoff and Robert A. Keyzers
Mar. Drugs 2020, 18(2), 81; https://doi.org/10.3390/md18020081 - 27 Jan 2020
Cited by 5 | Viewed by 3346
Abstract
The Trypanosoma brucei Hsp70/J-protein machinery plays an essential role in survival, differentiation, and pathogenesis of the protozoan parasite, and is an emerging target against African Trypanosomiasis. This study evaluated a set of small molecules, inspired by the malonganenones and nuttingins, as modulators of [...] Read more.
The Trypanosoma brucei Hsp70/J-protein machinery plays an essential role in survival, differentiation, and pathogenesis of the protozoan parasite, and is an emerging target against African Trypanosomiasis. This study evaluated a set of small molecules, inspired by the malonganenones and nuttingins, as modulators of the chaperone activity of the cytosolic heat inducible T. brucei Hsp70 and constitutive TbHsp70.4 proteins. The compounds were assessed for cytotoxicity on both the bloodstream form of T. b. brucei parasites and a mammalian cell line. The compounds were then investigated for their modulatory effect on the aggregation suppression and ATPase activities of the TbHsp70 proteins. A structure–activity relationship for the malonganenone-class of alkaloids is proposed based upon these results. Full article
(This article belongs to the Special Issue Chemical Modification of Marine Natural Products)
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15 pages, 1293 KiB  
Article
Isolation and Structure-Activity Relationship of Subergorgic Acid and Synthesis of Its Derivatives as Antifouling Agent
by Jun Zhang, Wei Ling, Zhiqiang Yang, Yan Liang, Linyan Zhang, Can Guo, Kailing Wang, Balian Zhong, Shihai Xu and Ying Xu
Mar. Drugs 2019, 17(2), 101; https://doi.org/10.3390/md17020101 - 6 Feb 2019
Cited by 14 | Viewed by 5080
Abstract
In this study, as part of our continuous search for environmentally-friendly antifoulants from natural resources, subergorgic acid (SA) was identified from the gorgonian coral Subergorgia suberosa, demonstrating non-toxic, significant inhibitory effects (EC50 1.25 μg/mL, LC50 > 25 μg/mL) against the [...] Read more.
In this study, as part of our continuous search for environmentally-friendly antifoulants from natural resources, subergorgic acid (SA) was identified from the gorgonian coral Subergorgia suberosa, demonstrating non-toxic, significant inhibitory effects (EC50 1.25 μg/mL, LC50 > 25 μg/mL) against the settlement of Balanus amphitrite. To further explore the bioactive functional groups of SA and synthesize more potent antifouling compounds based on the lead SA, the structure-activity relationships of SA were studied, followed by rational design and synthesis of two series of SA derivatives (one being benzyl esters of SA and another being SA derivatives containing methylene chains of various lengths). Our results indicated that (1) both the double bond and ketone carbonyl are essential elements responsible for the antifouling effect of SA, while the acid group is not absolutely necessary for maintaining the antifouling effect; (2) all benzyl esters of SA displayed good antifouling effects (EC50 ranged from 0.30 to 2.50 μg/mL) with the most potent compound being 5 (EC50 0.30 μg/mL, LC50 > 25 μg/mL), which was over four-fold more potent than SA; and (3) the introduction of a methylene chain into SA reduces the antifouling potency while the length of the methylene chain may differently influence the antifouling effect, depending on the functional group at the opposite site of the methylene chain. Not only has this study successfully revealed the bioactive functional groups of SA, contributing to the mechanism of SA against the settlement of B. amphitrite, but it has also resulted in the identification of a more potent compound 5, which might represent a non-toxic, high-efficiency antifoulant. Full article
(This article belongs to the Special Issue Chemical Modification of Marine Natural Products)
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8 pages, 3104 KiB  
Article
Structural Revision of Wentiquinone C and Related Congeners from Anthraquinones to Xanthones Using Chemical Derivatization and NMR Analysis
by Xin Li, Xiao-Ming Li and Bin-Gui Wang
Mar. Drugs 2019, 17(1), 8; https://doi.org/10.3390/md17010008 - 24 Dec 2018
Cited by 5 | Viewed by 3873
Abstract
Wentiquinone C, which was previously isolated from the marine brown alga-derived endophytic fungus Aspergillus wentii EN-48, was found to be a potent antioxidant against α,α-diphenyl-picrylhydrazyl (DPPH) radical. The structure of wentiquinone C was originally assigned as an anthraquinone derivative (1,10-dihydroxy-3-(hydroxymethyl)-8-methoxydibenzo [b, [...] Read more.
Wentiquinone C, which was previously isolated from the marine brown alga-derived endophytic fungus Aspergillus wentii EN-48, was found to be a potent antioxidant against α,α-diphenyl-picrylhydrazyl (DPPH) radical. The structure of wentiquinone C was originally assigned as an anthraquinone derivative (1,10-dihydroxy-3-(hydroxymethyl)-8-methoxydibenzo [b,e]oxepine-6,11-dione, 1) by 1D and 2D NMR experiments. However, the minor differences of the chemical shifts between xanthones and anthraquinones were queried, leading to the structure of 1 to be revised as a xanthone analog (8-hydroxy-6-(hydroxymethyl)-3-methoxy-9-oxo-9H-xanthene-1-carboxylic acid, 2) on the basis of a methylation and subsequent NMR measurements, and was confirmed by X-ray crystallographic analysis. The method established in this paper could be applied to the structural re-examination or revision for some of the reported seco-anthraquinone derivatives. Full article
(This article belongs to the Special Issue Chemical Modification of Marine Natural Products)
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17 pages, 1777 KiB  
Article
Asymmetric Synthesis and Cytotoxicity Evaluation of Right-Half Models of Antitumor Renieramycin Marine Natural Products
by Takehiro Matsubara, Masashi Yokoya, Natchanun Sirimangkalakitti and Naoki Saito
Mar. Drugs 2019, 17(1), 3; https://doi.org/10.3390/md17010003 - 20 Dec 2018
Cited by 10 | Viewed by 3434
Abstract
A general protocol for the asymmetric synthesis of 3-N-arylmethylated right-half model compounds of renieramycins was developed, which enabled structure–activity relationship (SAR) study of several 3-N-arylmethyl derivatives. The most active compound (6a) showed significant cytotoxic activity against human [...] Read more.
A general protocol for the asymmetric synthesis of 3-N-arylmethylated right-half model compounds of renieramycins was developed, which enabled structure–activity relationship (SAR) study of several 3-N-arylmethyl derivatives. The most active compound (6a) showed significant cytotoxic activity against human prostate cancer DU145 and colorectal cancer HCT116 cell lines (IC50 = 11.9, and 12.5 nM, respectively). Full article
(This article belongs to the Special Issue Chemical Modification of Marine Natural Products)
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20 pages, 3910 KiB  
Article
Preparation of the Sodium Alginate-g-(Polyacrylic Acid-co-Allyltrimethylammonium Chloride) Polyampholytic Superabsorbent Polymer and Its Dye Adsorption Property
by Shuxian Tang, Ying Zhao, Haitao Wang, Yuqiao Wang, Hexiang Zhu, Yu Chen, Shusen Chen, Shaohua Jin, Ziming Yang, Puwang Li and Sidong Li
Mar. Drugs 2018, 16(12), 476; https://doi.org/10.3390/md16120476 - 29 Nov 2018
Cited by 16 | Viewed by 4268
Abstract
A polyampholytic superabsorbent polymer (PASAP), sodium alginate-g-(polyacrylic acid-co-allyltrimethylammonium chloride) (SA-g-(PAA-co-PTM)), was prepared by free-radical graft copolymerization and characterized. The polymer exhibited pH-dependent swelling behaviors with extremely high swelling ratios, and was saline tolerant. The dye adsorption properties of SA-g-(PAA-co-PTM) were investigated using methylene [...] Read more.
A polyampholytic superabsorbent polymer (PASAP), sodium alginate-g-(polyacrylic acid-co-allyltrimethylammonium chloride) (SA-g-(PAA-co-PTM)), was prepared by free-radical graft copolymerization and characterized. The polymer exhibited pH-dependent swelling behaviors with extremely high swelling ratios, and was saline tolerant. The dye adsorption properties of SA-g-(PAA-co-PTM) were investigated using methylene blue (MB) as a cationic dye model. It was found that its dye adsorption capacity was significantly affected by the TM content in PASAP and pH of dye solution. The dye adsorption kinetics and isotherm obey the pseudo-second-order kinetic model and the Langmuir isotherm model, respectively, and the adsorption process is chemisorption in nature. In addition, SA-g-(PAA-co-PTM) exhibited high MB adsorption capacities in a wide pH range and reusability in at least five adsorption-desorption cycles, indicating its great application potentials as the adsorbent for dye removals from effluents. Full article
(This article belongs to the Special Issue Chemical Modification of Marine Natural Products)
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