Antimicrobial Marine Natural Products and Their Potential Applications

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

Deadline for manuscript submissions: closed (15 March 2022) | Viewed by 15629

Special Issue Editor


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Guest Editor
Collegel of Pharmacy, Yeungnam University, Gyeongsan-si, Republic of Korea
Interests: natural product chemistry; natural product isolation; natural product drug discovery; chromatography; bioactivity; extraction; NMR structure elucidation; phytochemical analysis; high-performance liquid chromatography; mass spectrometry
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Special Issue Information

Dear Colleagues,

The discovery of antimicrobial agents is a major research focus of marine natural products chemistry. The increasing prevalence of drug-resistant pathogens is a global threat to public health, resulting in a high demand for new antimicrobials agents. Recently, multidisciplinary research related to natural products has resulted in new application possibilities of antimicrobial agents in a great number of fields, such as agriculture, food industry, and manufacturing, in addition to new drug development.

This Special Issue aims to integrate original research articles on the discovery of new antimicrobial natural products derived from marine organisms and the new antimicrobial potential of previously reported marine natural products, as well as various applications of marine derived antimicrobial agents in drug development, medical manufacturing, and other fields.

Prof. Dr. Hyukjae Choi
Guest Editor

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Keywords

  • Marine natural products
  • Antimicrobial
  • Antifungal
  • Antibiotics
  • Inhibitor of microbial biofilm formation
  • Quorum sensing inhibitor
  • Marine microorganisms
  • Pharmaceutical application
  • Isolation
  • Structure elucidation

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Published Papers (5 papers)

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Research

20 pages, 4741 KiB  
Article
Lulworthinone: In Vitro Mode of Action Investigation of an Antibacterial Dimeric Naphthopyrone Isolated from a Marine Fungus
by Eric Juskewitz, Ekaterina Mishchenko, Vishesh K. Dubey, Marte Jenssen, Martin Jakubec, Philip Rainsford, Johan Isaksson, Jeanette H. Andersen and Johanna U. Ericson
Mar. Drugs 2022, 20(5), 277; https://doi.org/10.3390/md20050277 - 21 Apr 2022
Cited by 3 | Viewed by 2961
Abstract
Treatment options for infections caused by antimicrobial-resistant bacteria are rendered ineffective, and drug alternatives are needed—either from new chemical classes or drugs with new modes of action. Historically, natural products have been important contributors to drug discovery. In a recent study, the dimeric [...] Read more.
Treatment options for infections caused by antimicrobial-resistant bacteria are rendered ineffective, and drug alternatives are needed—either from new chemical classes or drugs with new modes of action. Historically, natural products have been important contributors to drug discovery. In a recent study, the dimeric naphthopyrone lulworthinone produced by an obligate marine fungus in the family Lulworthiaceae was discovered. The observed potent antibacterial activity against Gram-positive bacteria, including several clinical methicillin-resistant Staphylococcus aureus (MRSA) isolates, prompted this follow-up mode of action investigation. This paper aimed to characterize the antibacterial mode of action (MOA) of lulworthinone by combining in vitro assays, NMR experiments and microscopy. The results point to a MOA targeting the bacterial membrane, leading to improper cell division. Treatment with lulworthinone induced an upregulation of genes responding to cell envelope stress in Bacillus subtilis. Analysis of the membrane integrity and membrane potential indicated that lulworthinone targets the bacterial membrane without destroying it. This was supported by NMR experiments using artificial lipid bilayers. Fluorescence microscopy revealed that lulworthinone affects cell morphology and impedes the localization of the cell division protein FtsZ. Surface plasmon resonance and dynamic light scattering assays showed that this activity is linked with the compound‘s ability to form colloidal aggregates. Antibacterial agents acting at cell membranes are of special interest, as the development of bacterial resistance to such compounds is deemed more difficult to occur. Full article
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13 pages, 1227 KiB  
Article
Antibacterial Meroterpenoids, Merochlorins G–J from the Marine Bacterium Streptomyces sp.
by Min-Ji Ryu, Prima F. Hillman, Jihye Lee, Sunghoon Hwang, Eun-Young Lee, Sun-Shin Cha, Inho Yang, Dong-Chan Oh, Sang-Jip Nam and William Fenical
Mar. Drugs 2021, 19(11), 618; https://doi.org/10.3390/md19110618 - 30 Oct 2021
Cited by 11 | Viewed by 2892
Abstract
Four new chlorinated meroterpenoids, merochlorins G−J (14), and 10, a dihydronaphthalenedione precursor, along with known merochlorins A (5) and C−F (69), were obtained from cultivation of the bacterium strain Streptomyces sp. CNH-189, [...] Read more.
Four new chlorinated meroterpenoids, merochlorins G−J (14), and 10, a dihydronaphthalenedione precursor, along with known merochlorins A (5) and C−F (69), were obtained from cultivation of the bacterium strain Streptomyces sp. CNH-189, which was isolated from marine sediment. The planar structures of compounds 14 and 10 were elucidated by interpretation of MS, UV, and NMR spectroscopic data. The relative configurations of compounds 14 were determined via analysis of nuclear Overhauser effect (NOE) spectroscopic data, after which their absolute configurations were established by comparing the experimental electronic circular dichroism (ECD) spectra of compounds 14 to those of previously reported possible enantiomer models and DP4 calculations. Compound 3 displayed strong antibacterial activities against Bacillus subtilis, Kocuria rhizophila, and Staphylococcus aureus, with MIC values of 1, 2, and 2 μg/mL, respectively, whereas compound 1 exhibited weak antibacterial effects on these three strains, with a 16−32 μg/mL MIC value range. Full article
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11 pages, 1133 KiB  
Article
Anti-Mycoplasma Activity of Bacilotetrins C–E, Cyclic Lipodepsipeptides from the Marine-Derived Bacillus subtilis and Structure Revision of Bacilotetrins A and B
by Hwa-Sun Lee and Hee Jae Shin
Mar. Drugs 2021, 19(10), 528; https://doi.org/10.3390/md19100528 - 22 Sep 2021
Cited by 6 | Viewed by 2250
Abstract
Mycoplasma hyorhinis most commonly causes polyserositis and arthritis in swine and is a common contaminant during the cell culture in the laboratory. In our continuing research for diverse bioactive compounds from Bacillus subtilis 109GGC020, we discovered uncommon cyclic lipotetrapeptides showing inhibitory activities against [...] Read more.
Mycoplasma hyorhinis most commonly causes polyserositis and arthritis in swine and is a common contaminant during the cell culture in the laboratory. In our continuing research for diverse bioactive compounds from Bacillus subtilis 109GGC020, we discovered uncommon cyclic lipotetrapeptides showing inhibitory activities against M. hyorhinis with similar structures to previously reported bacilotetrins A and B. Bacilotetrins C–E (13), new cyclic lipodepsipeptides, were isolated from the EtOAc extract obtained from the fermentation of marine-derived Bacillus subtilis isolated from a marine sponge sample collected from the Gageo reef, Republic of Korea. The structures of 13, consisting of three leucine residues, one glutamic acid, and a β-hydroxy fatty acid, were elucidated by detailed analysis of 1D, 2D NMR, and HR-ESIMS data. The absolute configurations of the amino acids and β-hydroxy fatty acid were established by advanced Marfey’s method and Mosher’s method, respectively. The localization of L- and D-amino acids within the compounds was determined by retention time comparison of each purchased dipeptide standard to the partial hydrolysate products using LC-MS. Compounds 13 exhibited anti-mycoplasma activity, with an MIC value of 31 μg/mL, twofold stronger than that of the positive control, BioMycoX®. Detailed analysis and comparison of the spectroscopic data between bacilotetrins A (4) and B (5) and 13 led us to revise the structures of 4 and 5. Full article
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11 pages, 1211 KiB  
Article
Antibacterial Bicyclic Fatty Acids from a Korean Colonial Tunicate Didemnum sp.
by Hiyoung Kim, Tae Gu Lee, Inho Yang, Weihong Wang, Jungwook Chin, Jusung Lee, Boon Jo Rho, Hyukjae Choi, Sang-Jip Nam, Dongyup Hahn and Heonjoong Kang
Mar. Drugs 2021, 19(9), 521; https://doi.org/10.3390/md19090521 - 16 Sep 2021
Cited by 1 | Viewed by 2719
Abstract
Five new bicyclic carboxylic acids were obtained by antibacterial activity-guided isolation from a Korean colonial tunicate Didemnum sp. Their structures were elucidated by the interpretation of NMR, MS and CD spectroscopic data. They all belong to the class of aplidic acids. Three of [...] Read more.
Five new bicyclic carboxylic acids were obtained by antibacterial activity-guided isolation from a Korean colonial tunicate Didemnum sp. Their structures were elucidated by the interpretation of NMR, MS and CD spectroscopic data. They all belong to the class of aplidic acids. Three of them were amide derivatives (13), and the other two were dicarboxylic derivatives (4 and 5). The absolute configurations were determined by a bisignate pattern of CD spectroscopy, which revealed that the absolute configurations of amides were opposite to those of dicarboxylates at every stereogenic centers. Compound 2 exhibited the most potent antibacterial activity (MIC, 2 μg/mL). Full article
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14 pages, 2138 KiB  
Article
A Broad-Specificity Chitinase from Penicillium oxalicum k10 Exhibits Antifungal Activity and Biodegradation Properties of Chitin
by Xing-Huan Xie, Xin Fu, Xing-Yu Yan, Wen-Fang Peng and Li-Xin Kang
Mar. Drugs 2021, 19(7), 356; https://doi.org/10.3390/md19070356 - 23 Jun 2021
Cited by 31 | Viewed by 3591
Abstract
Penicillium oxalicum k10 isolated from soil revealed the hydrolyzing ability of shrimp chitin and antifungal activity against Sclerotinia sclerotiorum. The k10 chitinase was produced from a powder chitin-containing medium and purified by ammonium sulfate precipitation and column chromatography. The purified chitinase showed maximal [...] Read more.
Penicillium oxalicum k10 isolated from soil revealed the hydrolyzing ability of shrimp chitin and antifungal activity against Sclerotinia sclerotiorum. The k10 chitinase was produced from a powder chitin-containing medium and purified by ammonium sulfate precipitation and column chromatography. The purified chitinase showed maximal activity toward colloidal chitin at pH 5 and 40 °C. The enzymatic activity was enhanced by potassium and zinc, and it was inhibited by silver, iron, and copper. The chitinase could convert colloidal chitin to N-acetylglucosamine (GlcNAc), (GlcNAc)2, and (GlcNAc)3, showing that this enzyme had endocleavage and exocleavage activities. In addition, the chitinase prevented the mycelial growth of the phytopathogenic fungi S. sclerotiorum and Mucor circinelloides. These results indicate that k10 is a potential candidate for producing chitinase that could be useful for generating chitooligosaccharides from chitinous waste and functions as a fungicide. Full article
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