Marine Drugs

Editorial

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2 pages, 178 KiB

Open AccessEditorial

Bioactive Compounds from Marine Sediment Derived Fungi

by Ekaterina A. Yurchenko

Mar. Drugs 2022, 20(4), 242; https://doi.org/10.3390/md20040242 - 30 Mar 2022

Cited by 2 | Viewed by 2110

Abstract

Marine sediment derived fungi are a very interesting source of biologically active compounds [...] Full article

(This article belongs to the Special Issue Bioactive Compounds from Marine Sediment Derived Fungi)

Research

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11 pages, 1805 KiB

Open AccessArticle

New Secondary Metabolites from the Marine-Derived Fungus Talaromyces mangshanicus BTBU20211089

by Kai Zhang, Xinwan Zhang, Rui Lin, Haijin Yang, Fuhang Song, Xiuli Xu and Long Wang

Mar. Drugs 2022, 20(2), 79; https://doi.org/10.3390/md20020079 - 18 Jan 2022

Cited by 18 | Viewed by 2361

Abstract

Seven new compounds, namely talaromanloid A (1), talaromydene (2), 10-hydroxy-8-demethyltalaromydine and 11-hydroxy-8-demethyltalaromydine (3 and 4), talaromylectone (5), and ditalaromylectones A and B (6 and 7), together with seven known compounds were identified from [...] Read more.

Seven new compounds, namely talaromanloid A (1), talaromydene (2), 10-hydroxy-8-demethyltalaromydine and 11-hydroxy-8-demethyltalaromydine (3 and 4), talaromylectone (5), and ditalaromylectones A and B (6 and 7), together with seven known compounds were identified from a marine-derived fungus, Talaromyces mangshanicus BTBU20211089, which was isolated from a sediment sample collected from the South China Sea. Their chemical structures were determined using spectroscopic data, including HRESIMS, 1D, and 2D NMR techniques. The absolute configurations of 1 and 2 were elucidated by comparing experimental and calculated ECD spectra. Compounds 1, 2, 6, and 7 are new compounds possessing a novel carbon skeleton. Compound 6 is a dimeric molecule of 3 and 9. Compound 7 shared a unique structure of the cyclized dimer of 3 and 4. All the compounds were tested for their bioactivities against Staphylococcus aureus, Escherichia coli, and Candida albicans. Full article

(This article belongs to the Special Issue Bioactive Compounds from Marine Sediment Derived Fungi)

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14 pages, 3352 KiB

Open AccessFeature PaperArticle

Six New Antimicrobial Metabolites from the Deep-Sea Sediment-Derived Fungus Aspergillus fumigatus SD-406

by Li-Hong Yan, Xiao-Ming Li, Lu-Ping Chi, Xin Li and Bin-Gui Wang

Mar. Drugs 2022, 20(1), 4; https://doi.org/10.3390/md20010004 - 21 Dec 2021

Cited by 15 | Viewed by 3826

Abstract

Six new metabolites, including a pair of inseparable mixtures of secofumitremorgins A (1a) and B (1b), which differed in the configuration of the nitrogen atom, 29-hydroxyfumiquinazoline C (6), 10R-15-methylpseurotin A (7), 1,4,23-trihydroxy-hopane-22,30-diol ( [...] Read more.

Six new metabolites, including a pair of inseparable mixtures of secofumitremorgins A (1a) and B (1b), which differed in the configuration of the nitrogen atom, 29-hydroxyfumiquinazoline C (6), 10R-15-methylpseurotin A (7), 1,4,23-trihydroxy-hopane-22,30-diol (10), and sphingofungin I (11), together with six known compounds (2–5 and 8–9), were isolated and identified from the deep-sea sediment-derived fungus Aspergillus fumigatus SD-406. Their structures were determined by detailed spectroscopic analysis of NMR and MS data, chiral HPLC analysis of the acidic hydrolysate, X-ray crystallographic analysis, J-based configuration analysis, and quantum chemical calculations of ECD, OR, and NMR (with DP4+ probability analysis). Among the compounds, 1a/1b represent a pair of novel scaffolds derived from indole diketopiperazine by cleavage of the amide bond following aromatization to give a pyridine ring. Compounds 1, 4, 6, 7, 10 and 11 showed inhibitory activities against pathogenic bacteria and plant pathogenic fungus, with MIC values ranging from 4 to 64 μg/mL. Full article

(This article belongs to the Special Issue Bioactive Compounds from Marine Sediment Derived Fungi)

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13 pages, 3164 KiB

Open AccessArticle

Discovery of GOT1 Inhibitors from a Marine-Derived Aspergillus terreus That Act against Pancreatic Ductal Adenocarcinoma

by Shan Yan, Changxing Qi, Wei Song, Qianqian Xu, Lianghu Gu, Weiguang Sun and Yonghui Zhang

Mar. Drugs 2021, 19(11), 588; https://doi.org/10.3390/md19110588 - 20 Oct 2021

Cited by 11 | Viewed by 2647

Abstract

Pancreatic ductal adenocarcinoma (PDAC) is a devastating digestive system carcinoma with high incidence and death rates. PDAC cells are dependent on the Gln metabolism, which can preferentially utilize glutamic oxaloacetate transaminase 1 (GOT1) to maintain the redox homeostasis of cancer cells. Therefore, small [...] Read more.

Pancreatic ductal adenocarcinoma (PDAC) is a devastating digestive system carcinoma with high incidence and death rates. PDAC cells are dependent on the Gln metabolism, which can preferentially utilize glutamic oxaloacetate transaminase 1 (GOT1) to maintain the redox homeostasis of cancer cells. Therefore, small molecule inhibitors targeting GOT1 can be used as a new strategy for developing cancer therapies. In this study, 18 butyrolactone derivatives (1–18) were isolated from a marine-derived Aspergillus terreus, and asperteretone B (5), aspulvinone H (AH, 6), and (+)-3′,3′-di-(dimethylallyl)-butyrolactone II (12) were discovered to possess significant GOT1-inhibitory activities in vitro, with IC₅₀ values of (19.16 ± 0.15), (5.91 ± 0.04), and (26.38 ± 0.1) µM, respectively. Significantly, the molecular mechanism of the crystal structure of GOT1–AH was elucidated, wherein AH and the cofactor pyrido-aldehyde 5-phosphate competitively bound to the active sites of GOT1. More importantly, although the crystal structure of GOT1 has been discovered, the complex structure of GOT1 and its inhibitors has never been obtained, and the crystal structure of GOT1–AH is the first reported complex structure of GOT1/inhibitor. Further in vitro biological study indicated that AH could suppress glutamine metabolism, making PDAC cells sensitive to oxidative stress and inhibiting cell proliferation. More significantly, AH exhibited potent in vivo antitumor activity in an SW1990-cell-induced xenograft model. These findings suggest that AH could be considered as a promising lead molecule for the development of anti-PDAC agents. Full article

(This article belongs to the Special Issue Bioactive Compounds from Marine Sediment Derived Fungi)

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13 pages, 4059 KiB

Open AccessArticle

Marine Fungal Cerebroside Flavuside B Protects HaCaT Keratinocytes against Staphylococcus aureus Induced Damage

by Ekaterina A. Chingizova, Ekaterina S. Menchinskaya, Artur R. Chingizov, Evgeny A. Pislyagin, Elena V. Girich, Anton N. Yurchenko, Irina V. Guzhova, Valery V. Mikhailov, Dmitry L. Aminin and Ekaterina A. Yurchenko

Mar. Drugs 2021, 19(10), 553; https://doi.org/10.3390/md19100553 - 29 Sep 2021

Cited by 6 | Viewed by 2818

Abstract

Cerebrosides are glycosylated sphingolipids, and in mammals they contribute to the pro-/anti-inflammatory properties and innate antimicrobial activity of the skin and mucosal surfaces. Staphylococcus aureus infection can develop, not only from minor scratches of the skin, but this pathogen can also actively promote [...] Read more.

Cerebrosides are glycosylated sphingolipids, and in mammals they contribute to the pro-/anti-inflammatory properties and innate antimicrobial activity of the skin and mucosal surfaces. Staphylococcus aureus infection can develop, not only from minor scratches of the skin, but this pathogen can also actively promote epithelial breach. The effect of cerebroside flavuside B from marine sediment-derived fungus Penicillium islandicum (Aniva Bay, the Sea of Okhotsk) on viability, apoptosis, total caspase activity, and cell cycle in human epidermal keratinocytes HaCaT line co-cultivated with S. aureus, as well as influence of flavuside B on LPS-treated HaCaT cells were studied. Influence of flavuside B on bacterial growth and biofilm formation of S. aureus and its effect on the enzymatic activity of sortase A was also investigated. It was found S. aureus co-cultivated with keratinocytes induces caspase-depended apoptosis and cell death, arrest cell cycle in the G0/G1 phase, and increases in cellular immune inflammation. Cerebroside flavuside B has demonstrated its antimicrobial and anti-inflammatory properties, substantially eliminating all the negative consequences caused by co-cultivation of keratinocytes with S. aureus or bacterial LPS. The dual action of flavuside B may be highly effective in the treatment of bacterial skin lesions and will be studied in the future in in vivo experiments. Full article

(This article belongs to the Special Issue Bioactive Compounds from Marine Sediment Derived Fungi)

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15 pages, 3373 KiB

Open AccessFeature PaperArticle

Structurally Diverse Polycyclic Salicylaldehyde Derivative Enantiomers from a Marine-Derived Fungus Eurotium sp. SCSIO F452

by Wei-Mao Zhong, Xiao-Yi Wei, Yu-Chan Chen, Qi Zeng, Jun-Feng Wang, Xue-Feng Shi, Xin-Peng Tian, Wei-Min Zhang, Fa-Zuo Wang and Si Zhang

Mar. Drugs 2021, 19(10), 543; https://doi.org/10.3390/md19100543 - 26 Sep 2021

Cited by 6 | Viewed by 2692

Abstract

To enlarge the chemical diversity of Eurotium sp. SCSIO F452, a talented marine-derived fungus, we further investigated its chemical constituents from a large-scale fermentation with modified culture. Four pairs of new salicylaldehyde derivative enantiomers, euroticins F-I (1–4), as well [...] Read more.

To enlarge the chemical diversity of Eurotium sp. SCSIO F452, a talented marine-derived fungus, we further investigated its chemical constituents from a large-scale fermentation with modified culture. Four pairs of new salicylaldehyde derivative enantiomers, euroticins F-I (1–4), as well as a known one eurotirumin (5) were isolated and characterized. Compound 1 features an unprecedented constructed 6/6/6/5 tetracyclic structures, while 2 and 3 represent two new types of 6/6/5 scaffolds. Their structures were established by comprehensive spectroscopic analyses, X-ray diffraction, ¹³C NMR, and electronic circular dichroism calculations. Selected compounds showed significant inhibitory activity against α-glucosidase and moderate cytotoxic activities against SF-268, MCF-7, HepG2, and A549 cell lines. Full article

(This article belongs to the Special Issue Bioactive Compounds from Marine Sediment Derived Fungi)

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18 pages, 2544 KiB

Open AccessArticle

Neuroprotective Metabolites from Vietnamese Marine Derived Fungi of Aspergillus and Penicillium Genera

by Elena V. Girich, Anton N. Yurchenko, Olga F. Smetanina, Phan Thi Hoai Trinh, Ngo Thi Duy Ngoc, Mikhail V. Pivkin, Roman S. Popov, Evgeny A. Pislyagin, Ekaterina S. Menchinskaya, Ekaterina A. Chingizova, Shamil S. Afiyatullov and Ekaterina A. Yurchenko

Mar. Drugs 2020, 18(12), 608; https://doi.org/10.3390/md18120608 - 30 Nov 2020

Cited by 22 | Viewed by 3681

Abstract

Low molecular weight secondary metabolites of marine fungi Aspergillus flocculosus, Aspergillus terreus and Penicillium sp. from Van Phong and Nha Trang Bays (Vietnam) were studied and a number of polyketides, bis-indole quinones and terpenoids were isolated. The structures of the isolated compounds [...] Read more.

Low molecular weight secondary metabolites of marine fungi Aspergillus flocculosus, Aspergillus terreus and Penicillium sp. from Van Phong and Nha Trang Bays (Vietnam) were studied and a number of polyketides, bis-indole quinones and terpenoids were isolated. The structures of the isolated compounds were determined by 1D and 2D NMR and HR-ESI-MS techniques. Stereochemistry of some compounds was established based on ECD data. A chemical structure of asterriquinone F (6) was thoroughly described for the first time. Anthraquinone (13) was firstly obtained from a natural source. Neuroprotective influences of the isolated compounds against 6-OHDA, paraquat and rotenone toxicity were investigated. 4-Hydroxyscytalone (1), 4-hydroxy-6-dehydroxyscytalone (2) and demethylcitreoviranol (3) have shown significant increasing of paraquat- and rotenone-treated Neuro-2a cell viability and anti-ROS activity. Full article

(This article belongs to the Special Issue Bioactive Compounds from Marine Sediment Derived Fungi)

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10 pages, 763 KiB

Open AccessArticle

Hatsusamides A and B: Two New Metabolites Produced by the Deep-Sea-Derived Fungal Strain Penicillium steckii FKJ-0213

by Hirotaka Matsuo, Rei Hokari, Aki Ishiyama, Masato Iwatsuki, Mayuka Higo, Kenichi Nonaka, Yuriko Nagano, Yōko Takahashi, Satoshi Ōmura and Takuji Nakashima

Mar. Drugs 2020, 18(10), 513; https://doi.org/10.3390/md18100513 - 12 Oct 2020

Cited by 13 | Viewed by 3322

Abstract

Two new nitrogen-containing metabolites, designated hatsusamide A (1) and B (2), were isolated from a culture broth of Penicilliumsteckii FKJ-0213 together with the known compounds tanzawaic acid B (3) and trichodermamide C (4) by [...] Read more.

Two new nitrogen-containing metabolites, designated hatsusamide A (1) and B (2), were isolated from a culture broth of Penicilliumsteckii FKJ-0213 together with the known compounds tanzawaic acid B (3) and trichodermamide C (4) by physicochemical (PC) screening. The structures of 1 and 2 were determined as a tanzawaic acid B-trichodermamide C hybrid structure and a new analog of aspergillazines, respectively. The absolute configuration of 1 was determined by comparing the values of tanzawaic acid B and trichodermamide C in the literatures, such as ¹H-nuclear magnetic resonance (¹H-NMR) data and optical rotation, after hydrolysis of 1. Compounds 1–4 were evaluated for cytotoxicity and anti-malarial activities. Compounds 1 and 3 exhibited weak anti-malarial activity at half-maximal inhibitory concentration (IC₅₀) values of 27.2 and 78.5 µM against the K1 strain, and 27.9 and 79.2 µM against the FCR3 strain of Plasmodium falciparum, respectively. Furthermore, 1 exhibited cytotoxicity against HeLa S3, A549, Panc1, HT29 and H1299 cells, with IC₅₀ values of 15.0, 13.7, 12.9, 6.8, and 18.7 μM, respectively. Full article

(This article belongs to the Special Issue Bioactive Compounds from Marine Sediment Derived Fungi)

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13 pages, 3201 KiB

Open AccessArticle

Bioactive Metabolites from the Deep-Sea-Derived Fungus Diaporthe longicolla FS429

by Zhaoming Liu, Yuchan Chen, Saini Li, Qinglin Wang, Caiyun Hu, Hongxin Liu and Weimin Zhang

Mar. Drugs 2020, 18(8), 381; https://doi.org/10.3390/md18080381 - 23 Jul 2020

Cited by 8 | Viewed by 3263

Abstract

The chemical investigation of a methanol extract of the deep-sea-derived fungus Diaporthe longicolla FS429 led to the isolation of two novel diterpenoids longidiacids A and B (1 and 2), two new polyketides (3 and 4), two new cytochalasin analogues [...] Read more.

The chemical investigation of a methanol extract of the deep-sea-derived fungus Diaporthe longicolla FS429 led to the isolation of two novel diterpenoids longidiacids A and B (1 and 2), two new polyketides (3 and 4), two new cytochalasin analogues longichalasins A and B (6 and 8) and three known analogues 5, 7, 9. Their structures were elucidated through comprehensive spectroscopic analysis, while the absolute configurations were established by the comparison of the experimental and quantum chemical calculated ECD spectra. The structure of compound 7 was confirmed through X-ray diffraction for the first time. In the bioassays compound 8 exhibited antiproliferative effects against SF-268, with an IC₅₀ value of 16.44 μM. Moreover, compounds 1 and 8 were detected to inhibit 35.4% and 53.5% of enzyme activity of Mycobacterium tuberculosis protein tyrosine phosphatase B (MptpB) at a concentration of 50 μM. Full article

(This article belongs to the Special Issue Bioactive Compounds from Marine Sediment Derived Fungi)

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Review

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38 pages, 3575 KiB

Open AccessReview

Metabolites of Marine Sediment-Derived Fungi: Actual Trends of Biological Activity Studies

by Anton N. Yurchenko, Elena V. Girich and Ekaterina A. Yurchenko

Mar. Drugs 2021, 19(2), 88; https://doi.org/10.3390/md19020088 - 4 Feb 2021

Cited by 21 | Viewed by 4247

Abstract

Marine sediments are characterized by intense degradation of sedimenting organic matter in the water column and near surface sediments, combined with characteristically low temperatures and elevated pressures. Fungi are less represented in the microbial communities of sediments than bacteria and archaea and their [...] Read more.

Marine sediments are characterized by intense degradation of sedimenting organic matter in the water column and near surface sediments, combined with characteristically low temperatures and elevated pressures. Fungi are less represented in the microbial communities of sediments than bacteria and archaea and their relationships are competitive. This results in wide variety of secondary metabolites produced by marine sediment-derived fungi both for environmental adaptation and for interspecies interactions. Earlier marine fungal metabolites were investigated mainly for their antibacterial and antifungal activities, but now also as anticancer and cytoprotective drug candidates. This review aims to describe low-molecular-weight secondary metabolites of marine sediment-derived fungi in the context of their biological activity and covers research articles published between January 2016 and November 2020. Full article

(This article belongs to the Special Issue Bioactive Compounds from Marine Sediment Derived Fungi)

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