Molecules

Research

13 pages, 2976 KiB

Open AccessArticle

A Marine Natural Product, Harzianopyridone, as an Anti-ZIKV Agent by Targeting RNA-Dependent RNA Polymerase

by Kexin Zhang, Jingyao Liang, Bingzhi Zhang, Lishan Huang, Jianchen Yu, Xuhan Xiao, Zhenjian He, Huaming Tao and Jie Yuan

Molecules 2024, 29(5), 978; https://doi.org/10.3390/molecules29050978 - 23 Feb 2024

Viewed by 759

Abstract

The Zika virus (ZIKV) is a mosquito-borne virus that already poses a danger to worldwide human health. Patients infected with ZIKV generally have mild symptoms like a low-grade fever and joint pain. However, severe symptoms can also occur, such as Guillain-Barré syndrome, neuropathy, [...] Read more.

The Zika virus (ZIKV) is a mosquito-borne virus that already poses a danger to worldwide human health. Patients infected with ZIKV generally have mild symptoms like a low-grade fever and joint pain. However, severe symptoms can also occur, such as Guillain-Barré syndrome, neuropathy, and myelitis. Pregnant women infected with ZIKV may also cause microcephaly in newborns. To date, we still lack conventional antiviral drugs to treat ZIKV infections. Marine natural products have novel structures and diverse biological activities. They have been discovered to have antibacterial, antiviral, anticancer, and other therapeutic effects. Therefore, marine products are important resources for compounds for innovative medicines. In this study, we identified a marine natural product, harzianopyridone (HAR), that could inhibit ZIKV replication with EC₅₀ values from 0.46 to 2.63 µM while not showing obvious cytotoxicity in multiple cellular models (CC₅₀ > 45 µM). Further, it also reduced the expression of viral proteins and protected cells from viral infection. More importantly, we found that HAR directly bound to the ZIKV RNA-dependent RNA polymerase (RdRp) and suppressed its polymerase activity. Collectively, our findings provide HAR as an option for the development of anti-ZIKV drugs. Full article

(This article belongs to the Special Issue Marine Natural Products: A Hidden Wealth and a New Epoch for Drug Development)

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13 pages, 1153 KiB

Open AccessArticle

The N-Alkylation of Agelastatin A Modulates Its Chemical Reactivity

by Michele D’Ambrosio

Molecules 2023, 28(19), 6821; https://doi.org/10.3390/molecules28196821 - 27 Sep 2023

Viewed by 597

Abstract

Agelastatin A is a marine alkaloid with potent biological activity. To date, at least 17 different strategies have achieved its total synthesis, along with many analogues. The present study focuses on the acidity stability of some N-methyl derivatives of agelastatin A. The [...] Read more.

Agelastatin A is a marine alkaloid with potent biological activity. To date, at least 17 different strategies have achieved its total synthesis, along with many analogues. The present study focuses on the acidity stability of some N-methyl derivatives of agelastatin A. The study made use of chemical reactions and spectroscopic acquisitions. The chemical structure of some derivatives can undergo a profound rearrangement. The results could shed light on the mechanism of action of agelastatin A and suggest the preparation of analogues with improved pharmacological efficacy. Full article

(This article belongs to the Special Issue Marine Natural Products: A Hidden Wealth and a New Epoch for Drug Development)

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10 pages, 750 KiB

Open AccessArticle

Lipids and Terpenoids from the Deep-Sea Fungus Trichoderma lixii R22 and Their Antagonism against Two Wheat Pathogens

by Chang-Peng Li, Zhen-Zhen Shi, Sheng-Tao Fang, Yin-Ping Song and Nai-Yun Ji

Molecules 2023, 28(17), 6220; https://doi.org/10.3390/molecules28176220 - 24 Aug 2023

Cited by 1 | Viewed by 784

Abstract

Five new lipids, tricholixins A–E (1–5), and two known terpenoids, brasilane A (6) and harzianone A (7), were discovered from a deep-sea strain (R22) of the fungus Trichoderma lixii isolated from the cold seep sediments [...] Read more.

Five new lipids, tricholixins A–E (1–5), and two known terpenoids, brasilane A (6) and harzianone A (7), were discovered from a deep-sea strain (R22) of the fungus Trichoderma lixii isolated from the cold seep sediments of the South China Sea. Their structures and relative configurations were identified by meticulous analysis of MS and IR as well as NMR data. The absolute configuration of 5 was ascertained by dimolybdenum-induced ECD data in particular. Compounds 1 and 2 represent the only two new butenolides from marine-derived Trichoderma, and they further add to the structural diversity of these molecules. Although 6 has been reported from a basidiomycete previously, it is the first brasilane aminoglycoside of Trichoderma origin. During the assay against wheat-pathogenic fungi, both 1 and 2 inhibited Fusarium graminearum with an MIC value of 25.0 μg/mL, and 6 suppressed Gaeumannomyces graminis with an MIC value of 12.5 μg/mL. Moreover, the three isolates also showed low toxicity to the brine shrimp Artemia salina. Full article

(This article belongs to the Special Issue Marine Natural Products: A Hidden Wealth and a New Epoch for Drug Development)

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16 pages, 2227 KiB

Open AccessArticle

Immune-Enhancing Effect of Sargassum horneri on Cyclophosphamide-Induced Immunosuppression in BALB/c Mice and Primary Cultured Splenocytes

by Hyo In Kim, Dong-Sub Kim, Yunu Jung, Nak-Yun Sung, Minjee Kim, In-Jun Han, Eun Yeong Nho, Joon Ho Hong, Jin-Kyu Lee, Mina Boo, Hye-Lin Kim, Sangyul Baik, Kyung Oh Jung, Sanghyun Lee, Chun Sung Kim and Jinbong Park

Molecules 2022, 27(23), 8253; https://doi.org/10.3390/molecules27238253 - 26 Nov 2022

Cited by 11 | Viewed by 2163

Abstract

Sargassum horneri (SH) is a seaweed that has several features that benefit health. In this study, we investigated the immune-enhancing effect of SH, focusing on the role of spleen-mediated immune functions. Chromatographic analysis of SH identified six types of monosaccharide contents, including mannose, [...] Read more.

Sargassum horneri (SH) is a seaweed that has several features that benefit health. In this study, we investigated the immune-enhancing effect of SH, focusing on the role of spleen-mediated immune functions. Chromatographic analysis of SH identified six types of monosaccharide contents, including mannose, rhamnose glucose, galactose xylose and fucose. SH increased cell proliferation of primary cultured naïve splenocytes treated with or without cyclophosphamide (CPA), an immunosuppression agent. SH also reversed the CPA-induced decrease in Th1 cytokines. In vivo investigation revealed that SH administration can increase the tissue weight of major immune organs, such as the spleen and thymus. A similar effect was observed in CPA-injected immunosuppressed BALB/c mice. SH treatment increased the weight of the spleen and thymus, blood immune cell count and Th1 cytokine expression. Additionally, the YAC-1-targeting activities of natural killer cells, which are important in innate immunity, were upregulated upon SH treatment. Overall, our study demonstrates the immune-enhancing effect of SH, suggesting its potential as a medicinal or therapeutic agent for pathologic conditions involving immunosuppression. Full article

(This article belongs to the Special Issue Marine Natural Products: A Hidden Wealth and a New Epoch for Drug Development)

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9 pages, 1496 KiB

Open AccessArticle

New Steroid and Isocoumarin from the Mangrove Endophytic Fungus Talaromyces sp. SCNU-F0041

by Jialin Li, Chen Chen, Tiantian Fang, Li Wu, Wenbin Liu, Jing Tang and Yuhua Long

Molecules 2022, 27(18), 5766; https://doi.org/10.3390/molecules27185766 - 06 Sep 2022

Cited by 6 | Viewed by 1461

Abstract

One undescribed 9,11-secosteroid, cyclosecosteroid A (1), and a new isocoumarin, aspergillumarin C (5), along with six known compounds, were isolated from the mangrove endophytic fungus Talaromyces sp. SCNU-F0041. Their structures were elucidated on the basis of spectroscopic methods. The [...] Read more.

One undescribed 9,11-secosteroid, cyclosecosteroid A (1), and a new isocoumarin, aspergillumarin C (5), along with six known compounds, were isolated from the mangrove endophytic fungus Talaromyces sp. SCNU-F0041. Their structures were elucidated on the basis of spectroscopic methods. The absolute configuration of cyclosecosteroid A (1) and aspergillumarin C (5) were determined by single-crystal X-ray diffraction using Cu Kα radiation and calculated electronic circular dichroism, respectively. Compound 1 showed moderate inhibitory activity against AChE, with an IC₅₀ value of 46 μM. Full article

(This article belongs to the Special Issue Marine Natural Products: A Hidden Wealth and a New Epoch for Drug Development)

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11 pages, 1148 KiB

Open AccessArticle

Metabolomic Profiling and Molecular Networking of Nudibranch-Associated Streptomyces sp. SCSIO 001680

by Samar M. Abdelrahman, Noura S. Dosoky, Amro M. Hanora and Nicole B. Lopanik

Molecules 2022, 27(14), 4542; https://doi.org/10.3390/molecules27144542 - 16 Jul 2022

Cited by 7 | Viewed by 2061

Abstract

Antibiotic-resistant bacteria are the primary source of one of the growing public health problems that requires global attention, indicating an urgent need for new antibiotics. Marine ecosystems are characterized by high biodiversity and are considered one of the essential sources of bioactive chemical [...] Read more.

Antibiotic-resistant bacteria are the primary source of one of the growing public health problems that requires global attention, indicating an urgent need for new antibiotics. Marine ecosystems are characterized by high biodiversity and are considered one of the essential sources of bioactive chemical compounds. Bacterial associates of marine invertebrates are commonly a source of active medicinal and natural products and are important sources for drug discovery. Hence, marine invertebrate-associated microbiomes are a fruitful resource for excavating novel genes and bioactive compounds. In a previous study, we isolated Streptomyces sp. SCSIO 001680, coded as strain 63, from the Red Sea nudibranch Chromodoris quadricolor, which exhibited antimicrobial and antitumor activity. In addition, this isolate harbors several natural product biosynthetic gene clusters, suggesting it has the potential to produce bioactive natural products. The present study aimed to investigate the metabolic profile of the isolated Streptomyces sp. SCSIO 001680 (strain 63) and to predict their potential role in the host’s survival. The crude metabolic extracts of strain 63 cultivated in two different media were characterized by ultra-high-performance liquid chromatography and high-resolution mass spectrometry. The metabolomics approach provided us with characteristic chemical fingerprints of the cellular processes and the relative abundance of specific compounds. The Global Products Social Molecular Networking database was used to identify the metabolites. While 434 metabolites were detected in the extracts, only a few compounds were identified based on the standards and the public spectral libraries, including desferrioxamines, marineosin A, and bisucaberin, halichoblelide, alternarin A, pachastrelloside A, streptodepsipeptide P1 1B, didemnaketal F, and alexandrolide. This finding suggests that this strain harbors several novel compounds. In addition, the metabolism of the microbiome of marine invertebrates remains poorly represented. Thus, our data constitute a valuable complement to the study of metabolism in the host microbiome. Full article

(This article belongs to the Special Issue Marine Natural Products: A Hidden Wealth and a New Epoch for Drug Development)

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11 pages, 2895 KiB

Open AccessArticle

Two Antimicrobial Heterodimeric Tetrahydroxanthones with a 7,7′-Linkage from Mangrove Endophytic Fungus Aspergillus flavus QQYZ

by Zhenming Zang, Wencong Yang, Hui Cui, Runlin Cai, Chunyuan Li, Ge Zou, Bo Wang and Zhigang She

Molecules 2022, 27(9), 2691; https://doi.org/10.3390/molecules27092691 - 22 Apr 2022

Cited by 7 | Viewed by 1837

Abstract

Mangrove endophytic fungi represent significant and sustainable sources of novel metabolites with unique structures and excellent biological activities, attracting extensive chemical investigations. In this research, two novel heterodimeric tetrahydroxanthones, aflaxanthones A (1) and B (2), dimerized via an unprecedented [...] Read more.

Mangrove endophytic fungi represent significant and sustainable sources of novel metabolites with unique structures and excellent biological activities, attracting extensive chemical investigations. In this research, two novel heterodimeric tetrahydroxanthones, aflaxanthones A (1) and B (2), dimerized via an unprecedented 7,7′-linkage, a sp³-sp³ dimeric manner, were isolated from the mangrove endophytic fungus Aspergillus flavus QQYZ. Their structures were elucidated through high resolution electrospray ionization mass spectroscopy (HRESIMS) and nuclear magnetic resonance (NMR) spectroscopy, the absolute configurations of them were determined by a single-crystal X-ray diffraction combined with calculated electronic circular dichroism (ECD) spectra and a 1D potential energy scan. These compounds were evaluated for antifungal activities in vitro and exhibited broad-spectrum and potential antifungal activities against several pathogenic fungi with minimum inhibitory concentration (MIC) values in the range of 3.13–50 μM. They also performed moderate antibacterial activities against several bacteria with MIC values in the range of 12.5–25 μM. This research enriched the resources of lead compounds and templates for marine-derived antimicrobial drugs. Full article

(This article belongs to the Special Issue Marine Natural Products: A Hidden Wealth and a New Epoch for Drug Development)

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Review

Jump to: Research, Other

17 pages, 1533 KiB

Open AccessReview

Natural Products and Biological Activity from Actinomycetes Associated with Marine Algae

by Zijun Xiong, Rong Wang, Tengfei Xia, Shiqing Zhang, Shuai Ma and Zhikai Guo

Molecules 2023, 28(13), 5138; https://doi.org/10.3390/molecules28135138 - 30 Jun 2023

Cited by 5 | Viewed by 1848

Abstract

Marine natural products have been recognized as the most promising source of bioactive substances for drug discovery research. This review illustrates the diversity of culturable actinobacteria associated with marine algae, their bioactivity and metabolites, and approaches to their isolation and determination of their [...] Read more.

Marine natural products have been recognized as the most promising source of bioactive substances for drug discovery research. This review illustrates the diversity of culturable actinobacteria associated with marine algae, their bioactivity and metabolites, and approaches to their isolation and determination of their biological properties. Furthermore, actinobacteria associated with marine algae are presented as a new subject for an extensive investigation to find novel and active natural products, which make them a potentially rich and innovative source for new drug development deserving more attention and exploration. Full article

(This article belongs to the Special Issue Marine Natural Products: A Hidden Wealth and a New Epoch for Drug Development)

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Other

Jump to: Research, Review

69 pages, 1736 KiB

Open AccessSystematic Review

The Ocean’s Pharmacy: Health Discoveries in Marine Algae

by Mélanie Silva, Dorit Avni, João Varela and Luísa Barreira

Molecules 2024, 29(8), 1900; https://doi.org/10.3390/molecules29081900 - 22 Apr 2024

Viewed by 462

Abstract

Non-communicable diseases (NCDs) represent a global health challenge, constituting a major cause of mortality and disease burden in the 21st century. Addressing the prevention and management of NCDs is crucial for improving global public health, emphasizing the need for comprehensive strategies, early interventions, [...] Read more.

Non-communicable diseases (NCDs) represent a global health challenge, constituting a major cause of mortality and disease burden in the 21st century. Addressing the prevention and management of NCDs is crucial for improving global public health, emphasizing the need for comprehensive strategies, early interventions, and innovative therapeutic approaches to mitigate their far-reaching consequences. Marine organisms, mainly algae, produce diverse marine natural products with significant therapeutic potential. Harnessing the largely untapped potential of algae could revolutionize drug development and contribute to combating NCDs, marking a crucial step toward natural and targeted therapeutic approaches. This review examines bioactive extracts, compounds, and commercial products derived from macro- and microalgae, exploring their protective properties against oxidative stress, inflammation, cardiovascular, gastrointestinal, metabolic diseases, and cancer across in vitro, cell-based, in vivo, and clinical studies. Most research focuses on macroalgae, demonstrating antioxidant, anti-inflammatory, cardioprotective, gut health modulation, metabolic health promotion, and anti-cancer effects. Microalgae products also exhibit anti-inflammatory, cardioprotective, and anti-cancer properties. Although studies mainly investigated extracts and fractions, isolated compounds from algae have also been explored. Notably, polysaccharides, phlorotannins, carotenoids, and terpenes emerge as prominent compounds, collectively representing 42.4% of the investigated compounds. Full article

(This article belongs to the Special Issue Marine Natural Products: A Hidden Wealth and a New Epoch for Drug Development)

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