Marine Fungal Metabolites: Structures, Activities and Biosynthesis

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

Deadline for manuscript submissions: closed (31 October 2021) | Viewed by 42461

Special Issue Editors


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Guest Editor
Ocean College, Zhejiang University, Hangzhou 310058, China
Interests: marine natural product chemistry

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Guest Editor
Graduate School of Pharmaceutical Sciences, The university of Tokyo, Tokyo, Japan
Interests: biosynthesis of natural products (genome mining, engineered biosynthesis); enzyme biocatalysts (structure-based engineering, mechanistic studies)

Special Issue Information

Dear Colleagues,

Marine Fungi associated with marine alga, sponge, invertebrates, and sediments dwell in highly competitive environments. Most of them have evolved fungal-specific metabolic pathways to produce a diversified extent of metabolites ranging from antibiotics to mycotoxins that are traditionally termed secondary metabolites or natural products which have consistently delivered numerous lead structures for the pharmaceutical, agrochemical, and other life science applications. They are well-known to harbor an enormous biosynthetic potential. From an ecological point of view marine fungal secondary metabolites may be one of the key linkages to understand the interrelationships between fungi and the environment.

With the advent of new molecular biology tools and new methods for structural analysis, the landscape for the discovery and understanding of the structures, functions and biosynthesis of marine fungal secondary metabolites has changed dramatically during the last decade.

We invite submissions of manuscripts relevant to the structures, activities and biosynthesis of marine fungal natural products.

Prof. Dr. Bin Wu
Prof. Dr. Ikuro Abe
Guest Editors

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

  • Marine Fungi
  • Secondary metabolites
  • Structures
  • Biosynthesis
  • Bioactivity

Published Papers (15 papers)

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Research

Jump to: Review

13 pages, 1962 KiB  
Article
Antiplatelet and Antithrombotic Effects of Isaridin E Isolated from the Marine-Derived Fungus via Downregulating the PI3K/Akt Signaling Pathway
by Ni Pan, Zi-Cheng Li, Zhi-Hong Li, Sen-Hua Chen, Ming-Hua Jiang, Han-Yan Yang, Yao-Sheng Liu, Rui Hu, Yu-Wei Zeng, Le-Hui Dai, Lan Liu and Guan-Lei Wang
Mar. Drugs 2022, 20(1), 23; https://doi.org/10.3390/md20010023 - 24 Dec 2021
Cited by 3 | Viewed by 2718
Abstract
Isaridin E, a cyclodepsipeptide isolated from the marine-derived fungus Amphichorda felina (syn. Beauveria felina) SYSU-MS7908, has been demonstrated to possess anti-inflammatory and insecticidal activities. Here, we first found that isaridin E concentration-dependently inhibited ADP-induced platelet aggregation, activation, and secretion in vitro, but [...] Read more.
Isaridin E, a cyclodepsipeptide isolated from the marine-derived fungus Amphichorda felina (syn. Beauveria felina) SYSU-MS7908, has been demonstrated to possess anti-inflammatory and insecticidal activities. Here, we first found that isaridin E concentration-dependently inhibited ADP-induced platelet aggregation, activation, and secretion in vitro, but did not affect collagen- or thrombin-induced platelet aggregation. Furthermore, isaridin E dose-dependently reduced thrombosis formation in an FeCl3-induced mouse carotid model without increasing the bleeding time. Mechanistically, isaridin E significantly decreased the ADP-mediated phosphorylation of PI3K and Akt. In conclusion, these results suggest that isaridin E exerts potent antithrombotic effects in vivo without increasing the risk of bleeding, which may be due to its important role in inhibiting ADP-induced platelet activation, secretion and aggregation via the PI3K/Akt pathways. Full article
(This article belongs to the Special Issue Marine Fungal Metabolites: Structures, Activities and Biosynthesis)
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8 pages, 671 KiB  
Communication
Targeted Isolation of a Cytotoxic Cyclic Hexadepsipeptide from the Mesophotic Zone Sponge-Associated Fungus Cymostachys sp. NBUF082
by Ye Yuan, Te Li, Tingting Wang, C. Benjamin Naman, Jing Ye, Xingxin Wu, J. Enrico H. Lazaro, Xiaojun Yan and Shan He
Mar. Drugs 2021, 19(10), 565; https://doi.org/10.3390/md19100565 - 11 Oct 2021
Cited by 4 | Viewed by 1930
Abstract
LC-MS/MS-based molecular networking facilitated the targeted isolation of a new cyclic hexadepsipeptide, cymodepsipeptide (1), and two known analogues, RF–2691A (2) and RF–2691B (3), from the fungus Cymostachys sp. NBUF082 that was derived from a mesophotic zone Aaptos [...] Read more.
LC-MS/MS-based molecular networking facilitated the targeted isolation of a new cyclic hexadepsipeptide, cymodepsipeptide (1), and two known analogues, RF–2691A (2) and RF–2691B (3), from the fungus Cymostachys sp. NBUF082 that was derived from a mesophotic zone Aaptos sponge collected near Apo Island. The constitution and configuration of 1 was elucidated through 1D and 2D NMR-spectroscopy, high resolution mass-spectrometry, and chemical degradations including Marfey’s analysis and chiral HPLC. It was observed that 1 was moderately cytotoxic against CCRF-CEM human acute lymphocytic leukemia cells in vitro with the IC50 value of 9.2 ± 1.1 μM. Full article
(This article belongs to the Special Issue Marine Fungal Metabolites: Structures, Activities and Biosynthesis)
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15 pages, 2972 KiB  
Article
Comparative Metabolomics Reveals Fungal Conversion of Co-Existing Bacterial Metabolites within a Synthetic Aspergillus-Streptomyces Community
by Yutong Shi, Yihan Ma, Jihua Wei, Yichao Ge, Wei Jiang, Shan He, Xiaodan Wu, Xiaoqin Zhang and Bin Wu
Mar. Drugs 2021, 19(9), 526; https://doi.org/10.3390/md19090526 - 19 Sep 2021
Cited by 9 | Viewed by 2468
Abstract
In nature, secondary metabolites have been proven to be the essential communication media between co-occurring microorganisms and to influence their relationship with each other. In this study, we conducted a metabolomics survey of the secondary metabolites of an artificial co-culture related to a [...] Read more.
In nature, secondary metabolites have been proven to be the essential communication media between co-occurring microorganisms and to influence their relationship with each other. In this study, we conducted a metabolomics survey of the secondary metabolites of an artificial co-culture related to a hydrothermal vent fungal–bacterial community comprising Aspergillus sclerotiorum and Streptomyces and their reciprocal relationship. The fungal strain was found to increase the secretion of notoamides and the compound cyclo(Pro-Trp) produced by the actinomycetes strain was discovered to be the responsible molecule. This led to the hypothesis that the fungi transformed cyclo(Pro-Trp) synthesized by the actinomycetes as the biosynthetic precursors of notoamides in the chemical communication. Further analysis showed Streptomyces sp. WU20 was efficient in transforming amino acids into cyclo(Pro-Trp) and adding tryptophan as well as proline into the chemical communication enhanced the induction of the notoamide accumulation. Thus, we propose that the microbial transformation during the synthetic metabolically-mediated chemical communication might be a promising means of speeding up the discovery of novel bioactive molecules. The objective of this research was to clarify the mechanism of microbial transformation for the chemical communication. Besides, this research also highlights the utility of mass spectrometry-based metabolomics as an effective tool in the direct biochemical analysis of community metabolites. Full article
(This article belongs to the Special Issue Marine Fungal Metabolites: Structures, Activities and Biosynthesis)
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19 pages, 2226 KiB  
Article
New Antiproliferative Compounds against Glioma Cells from the Marine-Sourced Fungus Penicillium sp. ZZ1750
by Kuo Yong, Sidra Kaleem, Bin Wu and Zhizhen Zhang
Mar. Drugs 2021, 19(9), 483; https://doi.org/10.3390/md19090483 - 26 Aug 2021
Cited by 8 | Viewed by 2356
Abstract
Seven novel compounds, namely peniresorcinosides A–E (15), penidifarnesylin A (6), and penipyridinone A (7), together with the 11 known ones 817, were isolated from a culture of the marine-associated fungus Penicillium sp. [...] Read more.
Seven novel compounds, namely peniresorcinosides A–E (15), penidifarnesylin A (6), and penipyridinone A (7), together with the 11 known ones 817, were isolated from a culture of the marine-associated fungus Penicillium sp. ZZ1750 in rice medium. The structures of the new compounds were established based on their high-resolution electrospray ionization mass spectroscopy (HRESIMS) data, extensive nuclear magnetic resonance (NMR) spectroscopic analyses, chemical degradation, Mosher’s method, 13C-NMR calculations, electronic circular dichroism (ECD) calculations, and single crystal X-ray diffraction. Peniresorcinosides A (1) and B (2) are rare glycosylated alkylresorcinols and exhibited potent antiglioma activity, with IC50 values of 4.0 and 5.6 µM for U87MG cells and 14.1 and 9.8 µM for U251 cells, respectively. Full article
(This article belongs to the Special Issue Marine Fungal Metabolites: Structures, Activities and Biosynthesis)
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15 pages, 3137 KiB  
Article
New Drimane Sesquiterpenes and Polyketides from Marine-Derived Fungus Penicillium sp. TW58-16 and Their Anti-Inflammatory and α-Glucosidase Inhibitory Effects
by Xiaoshuang Gou, Danmei Tian, Jihua Wei, Yihan Ma, Yixue Zhang, Mei Chen, Wenjuan Ding, Bin Wu and Jinshan Tang
Mar. Drugs 2021, 19(8), 416; https://doi.org/10.3390/md19080416 - 26 Jul 2021
Cited by 13 | Viewed by 2714
Abstract
Marine fungi-derived natural products represent an excellent reservoir for the discovery of novel lead compounds with biological activities. Here, we report the identification of two new drimane sesquiterpenes (1 and 2) and six new polyketides (38), together [...] Read more.
Marine fungi-derived natural products represent an excellent reservoir for the discovery of novel lead compounds with biological activities. Here, we report the identification of two new drimane sesquiterpenes (1 and 2) and six new polyketides (38), together with 10 known compounds (918), from a marine-derived fungus Penicillium sp. TW58-16. The planar structures of these compounds were elucidated by extensive 1D and 2D NMR, which was supported by HR-ESI-MS data. The absolute configurations of these compounds were determined by experimental and calculated electronic circular dichroism (ECD), and their optical rotations compared with those reported. Evaluation of the anti-inflammatory activity of compounds 118 revealed that compound 5 significantly inhibited the release of nitric oxide (NO) induced by lipopolysaccharide (LPS) in RAW264.7 cells, correlating with the inhibition of expression of inducible nitric oxide synthase (iNOS). In addition, we revealed that compounds 1, 36, 14, 16, and 18 showed strong α-glucosidase inhibitory effects with inhibition rates of 35.4%, 73.2%, 55.6%, 74.4%, 32.0%, 36.9%, 88.0%, and 91.1%, respectively, which were comparable with or even better than that of the positive control, acarbose. Together, our results illustrate the potential of discovering new marine-based therapeutic agents against inflammation and diabetes mellitus. Full article
(This article belongs to the Special Issue Marine Fungal Metabolites: Structures, Activities and Biosynthesis)
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18 pages, 6169 KiB  
Article
Anti-Cancer and Anti-Inflammatory Activities of Three New Chromone Derivatives from the Marine-Derived Penicillium citrinum
by Yi-Cheng Chu, Chun-Hao Chang, Hsiang-Ruei Liao, Shu-Ling Fu and Jih-Jung Chen
Mar. Drugs 2021, 19(8), 408; https://doi.org/10.3390/md19080408 - 23 Jul 2021
Cited by 14 | Viewed by 2654
Abstract
Three new and uncommon chromone analogs, epiremisporine F (1), epiremisporine G (2), and epiremisporine H (3), were isolated from marine-origin Penicillium citrinum. Among the isolated compounds, compounds 23 remarkably suppressed fMLP-induced superoxide anion generation [...] Read more.
Three new and uncommon chromone analogs, epiremisporine F (1), epiremisporine G (2), and epiremisporine H (3), were isolated from marine-origin Penicillium citrinum. Among the isolated compounds, compounds 23 remarkably suppressed fMLP-induced superoxide anion generation by human neutrophils, with IC50 values of 31.68 ± 2.53, and 33.52 ± 0.42 μM, respectively. Compound 3 exhibited cytotoxic activities against human colon carcinoma (HT-29) and non-small lung cancer cell (A549) with IC50 values of 21.17 ± 4.89 and 31.43 ± 3.01 μM, respectively, and Western blot assay confirmed that compound 3 obviously induced apoptosis of HT-29 cells, via Bcl-2, Bax, and caspase 3 signaling cascades. Full article
(This article belongs to the Special Issue Marine Fungal Metabolites: Structures, Activities and Biosynthesis)
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12 pages, 1994 KiB  
Article
Isolation, Structural Characterization and Antidiabetic Activity of New Diketopiperazine Alkaloids from Mangrove Endophytic Fungus Aspergillus sp. 16-5c
by Geting Ye, Cuiying Huang, Jialin Li, Tao Chen, Jing Tang, Wenbin Liu and Yuhua Long
Mar. Drugs 2021, 19(7), 402; https://doi.org/10.3390/md19070402 - 20 Jul 2021
Cited by 26 | Viewed by 4080
Abstract
Six new DIKETOPIPERAZINE alkaloids aspergiamides A–F (16), together with ten known alkaloids (716), were isolated from the mangrove endophytic fungus Aspergillus sp. 16-5c. The structures of the new compounds were elucidated based on 1D/2D NMR [...] Read more.
Six new DIKETOPIPERAZINE alkaloids aspergiamides A–F (16), together with ten known alkaloids (716), were isolated from the mangrove endophytic fungus Aspergillus sp. 16-5c. The structures of the new compounds were elucidated based on 1D/2D NMR spectroscopic and HR-ESIMS data analyses. The absolute configurations of aspergiamides A-F were established based on the experimental and calculated ECD data. All the compounds were evaluated for the antidiabetic activity against α-glucosidase and PTP1B enzyme. The bioassay results disclosed compounds 1 and 9 exhibited significant α-glucosidase inhibitory with IC50 values of 18.2 and 7.6 μM, respectively; compounds 3, 10, 11, and 15 exhibited moderate α-glucosidase inhibition with IC50 values ranging from 40.7 to 83.9 μM; while no compounds showed obvious PTP1B enzyme inhibition activity. Full article
(This article belongs to the Special Issue Marine Fungal Metabolites: Structures, Activities and Biosynthesis)
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8 pages, 1346 KiB  
Article
Furobenzotropolones A, B and 3-Hydroxyepicoccone B with Antioxidative Activity from Mangrove Endophytic Fungus Epicoccum nigrum MLY-3
by Ge Zou, Qi Tan, Yan Chen, Wencong Yang, Zhenming Zang, Hongming Jiang, Shenyu Chen, Bo Wang and Zhigang She
Mar. Drugs 2021, 19(7), 395; https://doi.org/10.3390/md19070395 - 14 Jul 2021
Cited by 7 | Viewed by 2289
Abstract
Three new metabolites, furobenzotropolones A, B (12) with unusual benzene and dihydrofuran moieties and 3-hydroxyepicoccone B (3), together with seven known compounds (410) were obtained from the endophytic fungus Epicoccum nigrum MLY-3 isolated [...] Read more.
Three new metabolites, furobenzotropolones A, B (12) with unusual benzene and dihydrofuran moieties and 3-hydroxyepicoccone B (3), together with seven known compounds (410) were obtained from the endophytic fungus Epicoccum nigrum MLY-3 isolated from the fresh leaf of mangrove plant Bruguiear gymnorrhiza collected from Zhuhai. Their structures were assigned by the analysis of UV, IR, NMR, and mass spectroscopic data. Compound 1 was further confirmed by single-crystal X-ray diffraction experiment using Cu Kα radiation. In antioxidant activities in vitro, compounds 2, 3, 5, and 8 showed promising DPPH· scavenging activity with IC50 values ranging from 14.7 to 29.3 µM. Compounds 2, 3, 5, 7, and 8 exhibited promising potent activity in scavenging ABTS· with IC50 values in the range of 18–29.2 µM, which was stronger than that of the positive control ascorbic acid (IC50 = 33.6 ± 0.8 µM). Full article
(This article belongs to the Special Issue Marine Fungal Metabolites: Structures, Activities and Biosynthesis)
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13 pages, 1904 KiB  
Article
New Diterpenoids and Isocoumarin Derivatives from the Mangrove-Derived Fungus Hypoxylon sp.
by Bolin Hou, Sushi Liu, Ruiyun Huo, Yueqian Li, Jinwei Ren, Wenzhao Wang, Tao Wei, Xuejun Jiang, Wenbing Yin, Hongwei Liu, Ling Liu and Erwei Li
Mar. Drugs 2021, 19(7), 362; https://doi.org/10.3390/md19070362 - 24 Jun 2021
Cited by 15 | Viewed by 2182
Abstract
Two new diterpenoids, hypoxyterpoids A (1) and B (2), and four new isocoumarin derivatives, hypoxymarins A–D (47), together, with seven known metabolites (3 and 813) were obtained from the crude extract [...] Read more.
Two new diterpenoids, hypoxyterpoids A (1) and B (2), and four new isocoumarin derivatives, hypoxymarins A–D (47), together, with seven known metabolites (3 and 813) were obtained from the crude extract of the mangrove-derived fungus Hypoxylon sp. The structures of the new compounds were elucidated on the basis of 1- and 2-dimensional (1D/2D) nuclear magnetic resonance (NMR) spectroscopic and mass spectrometric analysis. The absolute configurations of compounds 1, 2, 4, 5, and 7 were determined by comparison of experimental and calculated electronic circular dichroism (ECD) spectra, and the absolute configurations of C-4′ in 6 and C-9 in 7 were determined by [Rh2(OCOCF3)4]-induced ECD spectra. Compound 1 showed moderate α-glucosidase inhibitory activities with IC50 values of 741.5 ± 2.83 μM. Compounds 6 and 11 exhibited DPPH scavenging activities with IC50 values of 15.36 ± 0.24 and 3.69 ± 0.07 μM, respectively. Full article
(This article belongs to the Special Issue Marine Fungal Metabolites: Structures, Activities and Biosynthesis)
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11 pages, 1493 KiB  
Article
Fusarins G–L with Inhibition of NO in RAW264.7 from Marine-Derived Fungus Fusarium solani 7227
by Guangyuan Luo, Li Zheng, Qilin Wu, Senhua Chen, Jing Li and Lan Liu
Mar. Drugs 2021, 19(6), 305; https://doi.org/10.3390/md19060305 - 25 May 2021
Cited by 2 | Viewed by 2096
Abstract
Six new fusarin derivatives, fusarins G–L (16), together with five known compounds (511) were isolated from the marine-derived fungus Fusarium solani 7227. The structures of the new compounds were elucidated by means of comprehensive spectroscopic [...] Read more.
Six new fusarin derivatives, fusarins G–L (16), together with five known compounds (511) were isolated from the marine-derived fungus Fusarium solani 7227. The structures of the new compounds were elucidated by means of comprehensive spectroscopic methods (1D and 2D NMR, HRESIMS, ECD, and ORC) and X-ray crystallography. Compounds 511 exhibited potent anti-inflammatory activity by inhibiting the production of NO in RAW264.7 cells activated by lipopolysaccharide, with IC50 values ranging from 3.6 to 32.2 μM. The structure–activity relationships of the fusarins are discussed herein. Full article
(This article belongs to the Special Issue Marine Fungal Metabolites: Structures, Activities and Biosynthesis)
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9 pages, 1288 KiB  
Article
New Andrastin-Type Meroterpenoids from the Marine-Derived Fungus Penicillium sp.
by Jinwei Ren, Ruiyun Huo, Gaoran Liu and Ling Liu
Mar. Drugs 2021, 19(4), 189; https://doi.org/10.3390/md19040189 - 27 Mar 2021
Cited by 19 | Viewed by 2269
Abstract
Three new andrastin-type meroterpenoids penimeroterpenoids A–C (13) together with two known analogs (4 and 5) were isolated from the cultures of the marine-derived Penicillium species (sp.). The structures of the new compounds were elucidated on the basis [...] Read more.
Three new andrastin-type meroterpenoids penimeroterpenoids A–C (13) together with two known analogs (4 and 5) were isolated from the cultures of the marine-derived Penicillium species (sp.). The structures of the new compounds were elucidated on the basis of 1- and 2-dimensional (1D/2D) Nuclear Magnetic Resonance (NMR) spectroscopic and mass spectrometric analysis. The absolute configurations of 13 were determined by comparison of experimental and calculated electronic circular dichroism (ECD) spectra. Compound 1 showed moderate cytotoxicity against A549, HCT116, and SW480 cell lines. Full article
(This article belongs to the Special Issue Marine Fungal Metabolites: Structures, Activities and Biosynthesis)
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9 pages, 1268 KiB  
Communication
Cytotoxic Polyketide Metabolites from a Marine Mesophotic Zone Chalinidae Sponge-Associated Fungus Pleosporales sp. NBUF144
by Jing Zhou, Hairong Zhang, Jing Ye, Xingxin Wu, Weiyi Wang, Houwen Lin, Xiaojun Yan, J. Enrico H. Lazaro, Tingting Wang, C. Benjamin Naman and Shan He
Mar. Drugs 2021, 19(4), 186; https://doi.org/10.3390/md19040186 - 26 Mar 2021
Cited by 6 | Viewed by 2663
Abstract
Two new polyketide natural products, globosuxanthone F (1), and 2′-hydroxy bisdechlorogeodin (2), were isolated from the fungus Pleosporales sp. NBUF144, which was derived from a 62 m deep Chalinidae family sponge together with four known metabolites, 3,4-dihydroglobosuxanthone A ( [...] Read more.
Two new polyketide natural products, globosuxanthone F (1), and 2′-hydroxy bisdechlorogeodin (2), were isolated from the fungus Pleosporales sp. NBUF144, which was derived from a 62 m deep Chalinidae family sponge together with four known metabolites, 3,4-dihydroglobosuxanthone A (3), 8-hydroxy-3-methylxanthone-1-carboxylate (4), crosphaeropsone C (5), and 4-megastigmen-3,9-dione (6). The structures of these compounds were elucidated on the basis of extensive spectroscopic analysis, including 1D and 2D NMR and high-resolution electrospray ionization mass spectra (HRESIMS) data. The absolute configuration of 1 was further established by single-crystal X-ray diffraction studies. Compounds 1-5 were evaluated for cytotoxicity towards CCRF-CEM human acute lymphatic leukemia cells, and it was found that 1 had an IC50 value of 0.46 µM. Full article
(This article belongs to the Special Issue Marine Fungal Metabolites: Structures, Activities and Biosynthesis)
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9 pages, 3180 KiB  
Article
New Polyketides from the Antarctic Fungus Pseudogymnoascus sp. HSX2#-11
by Ting Shi, Yan-Yan Yu, Jia-Jia Dai, Yi-Ting Zhang, Wen-Peng Hu, Li Zheng and Da-Yong Shi
Mar. Drugs 2021, 19(3), 168; https://doi.org/10.3390/md19030168 - 22 Mar 2021
Cited by 16 | Viewed by 2902
Abstract
The species Pseudogymnoascus is known as a psychrophilic pathogenic fungus with a ubiquitous distribution in Antarctica. Meanwhile, the study of its secondary metabolites is infrequent. Systematic research of the metabolites of the fungus Pseudogymnoascus sp. HSX2#-11, guided by the method of molecular networking, [...] Read more.
The species Pseudogymnoascus is known as a psychrophilic pathogenic fungus with a ubiquitous distribution in Antarctica. Meanwhile, the study of its secondary metabolites is infrequent. Systematic research of the metabolites of the fungus Pseudogymnoascus sp. HSX2#-11, guided by the method of molecular networking, led to the isolation of one novel polyketide, pseudophenone A (1), along with six known analogs (27). The structure of the new compound was elucidated by extensive spectroscopic investigation and single-crystal X-ray diffraction. Pseudophenone A (1) is a dimer of diphenyl ketone and diphenyl ether, and there is only one analog of 1 to the best of our knowledge. Compounds 1 and 2 exhibited antibacterial activities against a panel of strains. This is the first time to use molecular networking to study the metabolic profiles of Antarctica fungi. Full article
(This article belongs to the Special Issue Marine Fungal Metabolites: Structures, Activities and Biosynthesis)
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11 pages, 1741 KiB  
Article
Bioactive Indole Diketopiperazine Alkaloids from the Marine Endophytic Fungus Aspergillus sp. YJ191021
by Jin Yang, Lizhi Gong, Miaomiao Guo, Yu Jiang, Yi Ding, Zhijie Wang, Xiujuan Xin and Faliang An
Mar. Drugs 2021, 19(3), 157; https://doi.org/10.3390/md19030157 - 17 Mar 2021
Cited by 20 | Viewed by 3090
Abstract
Six new prenylated indole diketopiperazine alkaloids, asperthrins A–F (16), along with eight known analogues (714), were isolated from the marine-derived endophytic fungus Aspergillus sp. YJ191021. Their planar structures and absolute configurations were elucidated by HR-ESI-MS, [...] Read more.
Six new prenylated indole diketopiperazine alkaloids, asperthrins A–F (16), along with eight known analogues (714), were isolated from the marine-derived endophytic fungus Aspergillus sp. YJ191021. Their planar structures and absolute configurations were elucidated by HR-ESI-MS, 1D/2D NMR data, and time-dependent density functional theory (TDDFT)/ECD calculation. The isolated compounds were assayed for their inhibition against three agricultural pathogenic fungi, four fish pathogenic bacteria, and two agricultural pathogenic bacteria. Compound 1 exhibited moderate antifungal and antibacterial activities against Vibrioanguillarum, Xanthomonas oryzae pv. Oryzicola, and Rhizoctoniasolani with minimal inhibitory concentration (MIC) values of 8, 12.5, and 25 μg/mL, respectively. Furthermore, 1 displayed notable anti-inflammatory activity with IC50 value of 1.46 ± 0.21 μM in Propionibacteriumacnes induced human monocyte cell line (THP-1). Full article
(This article belongs to the Special Issue Marine Fungal Metabolites: Structures, Activities and Biosynthesis)
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Review

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67 pages, 12362 KiB  
Review
Marine-Derived Macrolides 1990–2020: An Overview of Chemical and Biological Diversity
by Hairong Zhang, Jiabin Zou, Xiaoxue Yan, Junlong Chen, Xiujiao Cao, Jialing Wu, Yinghui Liu and Tingting Wang
Mar. Drugs 2021, 19(4), 180; https://doi.org/10.3390/md19040180 - 25 Mar 2021
Cited by 31 | Viewed by 4353
Abstract
Macrolides are a significant family of natural products with diverse structures and bioactivities. Considerable effort has been made in recent decades to isolate additional macrolides and characterize their chemical and bioactive properties. The majority of macrolides are obtained from marine organisms, including sponges, [...] Read more.
Macrolides are a significant family of natural products with diverse structures and bioactivities. Considerable effort has been made in recent decades to isolate additional macrolides and characterize their chemical and bioactive properties. The majority of macrolides are obtained from marine organisms, including sponges, marine microorganisms and zooplankton, cnidarians, mollusks, red algae, bryozoans, and tunicates. Sponges, fungi and dinoflagellates are the main producers of macrolides. Marine macrolides possess a wide range of bioactive properties including cytotoxic, antibacterial, antifungal, antimitotic, antiviral, and other activities. Cytotoxicity is their most significant property, highlighting that marine macrolides still encompass many potential antitumor drug leads. This extensive review details the chemical and biological diversity of 505 macrolides derived from marine organisms which have been reported from 1990 to 2020. Full article
(This article belongs to the Special Issue Marine Fungal Metabolites: Structures, Activities and Biosynthesis)
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