New naphthopyrones from marine-derived fungus <i>Aspergillus niger</i> 2HL-M-8 and their <i>in vitro</i> antiproliferative activity

Li, Dahong; Han, Tong; Guan, Liping; Bai, Jiao; Zhao, Nan; Li, Zhan‐Lin; Wu, Xin; Hua, Hui‐Ming

doi:10.1080/14786419.2015.1043553

Cited by 38 publications

(23 citation statements)

References 25 publications

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“…Recently, a growing number of Aspergillus spp. fungi, have been reported to produce novel bioactive compounds, such as butenolide derivatives as anti-inflammatory agents (Liu et al 2018), aurasperone H as anticancer (Li et al 2016), asperchondols A and B as antibacterials (Liu et al 2017), aspergivones A and B with anticancer and antibacterial activities (Ma et al 2017b), and aspochalasin B and D as antibacterials (Ratnaweera et al 2016). In this section, we discuss bioactive metabolites of Aspergillus spp., isolated from terrestrial environments, that shown antibacterial activities and could provide further cues for clinical trials.…”

Section: Antibacterial Metabolites From Terrestrial Aspergillus Sppmentioning

confidence: 99%

Overview on antibacterial metabolites from terrestrialAspergillusspp

Al-Fakih

Almaqtri

2019

Mycology

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Medicines developed from natural sources are a frequent target for the research and discovery of antimicrobial compounds. Discovering of penicillin in 1928 was a motive to explore of nature as a source of new antimicrobial agents. Fungi produce a diverse range of bioactive metabolites, making them rich source of different types of medicines. The purpose of this paper was to review studies on antibacterials from terrestrial Aspergillus published exclusively during 1942-2018, with emphasis on their antibacterial activities, structures, and mechanisms of action if present. According to the results from different studies in the world, large number of compounds and extracts showed different activities against different bacterial species, including Gram-positive and Gram-negative bacteria. The most prominent result was that of the compound CJ-17,665, isolated from A. ochraceus, showing good activity against multi-drug resistant Staphylococcus aureus, which is well-recognised to be one of the most important current public health problem. These findings may motivate scientists to undertake a project that may result in the development of novel antibacterial drugs from terrestrial-derived Aspergillus spp., although further toxicity assays (in vivo) must be performed before their application.

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Section: Antibacterial Metabolites From Terrestrial Aspergillus Sppmentioning

confidence: 99%

Overview on antibacterial metabolites from terrestrialAspergillusspp

Al-Fakih

Almaqtri

2019

Mycology

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“…Naphthopyrones are well-known to possess nonselective activities in biological systems and exhibit antimicrobial [28], cytotoxic [29], antimycobacterial [30], and antimalarial [31] independently from their antimicrobial activity. Conclusively, even though the mode of action of the pigmentosins remains to be studied, they constitute promising candidates for combination therapy with existing or novel antibiotics.…”

Section: Bioactivitiesmentioning

confidence: 99%

Pigmentosins from Gibellula sp. as antibiofilm agents and a new glycosylated asperfuran from Cordyceps javanica

Helaly¹,

Kuephadungphan²,

Phainuphong³

et al. 2019

Beilstein J. Org. Chem.

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In the course of our exploration of the Thai invertebrate-pathogenic fungi for biologically active metabolites, pigmentosin A (1) and a new bis(naphtho-α-pyrone) derivative, pigmentosin B (2), were isolated from the spider-associated fungus Gibellula sp. Furthermore, a new glycosylated asperfuran 3, together with one new (6) and two known (4 and 5) cyclodepsipeptides, was isolated from Cordyceps javanica. The pigmentosins 1 and 2 showed to be active against biofilm formation of Staphylococcus aureus DSM1104. The lack of toxicity toward the studied microorganism and cell lines of pigmentosin B (2), as well as the antimicrobial effect of pigmentosin A (1), made them good candidates for further development for use in combination therapy of infections involving biofilm-forming S. aureus. The structure elucidation and determination of the absolute configuration were accomplished using a combination of spectroscopy, including 1D and 2D NMR, HRMS, Mosher ester analysis, and comparison of calculated/experimental ECD spectra. A chemotaxonomic investigation of the secondary metabolite profiles using analytical HPLC coupled with diode array detection and mass spectrometry (HPLC–DAD–MS) revealed that the production of pigmentosin B (2) was apparently specific for Gibellula sp., while the glycoasperfuran 3 was specific for C. javanica.

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“…By comparing the spectroscopic data (HRESIMS, 1 H and 13 C NMR, Figures S9–S60) with those reported in the literature, the remaining nineteen known compounds ( 2 – 21 ) were identified as 2-benzyl-4 H -pyran-4-one ( 2 ) [11], asperpyrone D ( 3 ) [12], asperpyrone C ( 4 ) [13], aurosperone B ( 5 ) [14], fonsecinone B ( 6 ) [14], asperpyrone B ( 7 ) [15], dianhydro-aurasperone C ( 8 ) [12], isoaurasperone A ( 9 ) [15], aurasperone F ( 10 ) [16], fonsecinone D ( 11 ) [14], asperpyrone A ( 12 ) [12], fonsecinone A ( 13 ) [15], fonsecin ( 14 ) [14], TMC 256 A1 ( 15 ) [17], flavasperone ( 16 ) [14], carbonarone A ( 17 ) [18], pestalamide A ( 18 ) [19]. In addition, the p configuration of 12 was defined by ECD calculation at the B3LYP/6-311+G(d, p) level (Figure 2, Supplementary Materials, S34–S36).…”

Section: Resultsmentioning

confidence: 99%

“…Natural naphthopyrones have been previously reported for their anticancer potential [13,15,17]. Therefore, the present study evaluated the inhibitory effects of the isolated compounds on five human cancer cell lines (PANC-1, A549, MDA-MB-231, Caco-2, and SK-OV-3), and one human normal cell line (HL-7702) at a concentration of 50 µM.…”

Section: Resultsmentioning

confidence: 99%

Discovery of Natural Dimeric Naphthopyrones as Potential Cytotoxic Agents through ROS-Mediated Apoptotic Pathway

Guo

Shi

et al. 2019

Marine Drugs

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A study on the secondary metabolites of Aspergillus sp. XNM-4, which was derived from marine algae Leathesia nana (Chordariaceae), led to the identification of one previously undescribed (1) and seventeen known compounds (2−18). Their planar structures were established by extensive spectroscopic analyses, while the stereochemical assignments were defined by electronic circular dichroism (ECD) calculations. The biological activities of the compounds were assessed on five human cancer cell lines (PANC-1, A549, MDA-MB-231, Caco-2, and SK-OV-3), and one human normal cell line (HL-7702) using an MTT [3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl tetrazolium bromide] assay. Among them, the dimeric naphthopyrones 7, 10 and 12 exhibited potent cytotoxicity. Further mechanism studies showed that 12 induced apoptosis, arrested the cell cycle at the G0/G1 phase in the PANC-1 cells, caused morphological changes and generated ROS; and it induces PANC-1 cells apoptosis via ROS-mediated PI3K/Akt signaling pathway.

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New naphthopyrones from marine-derived fungus Aspergillus niger 2HL-M-8 and their in vitro antiproliferative activity

Cited by 38 publications

References 25 publications

Overview on antibacterial metabolites from terrestrialAspergillusspp

Overview on antibacterial metabolites from terrestrialAspergillusspp

Pigmentosins from Gibellula sp. as antibiofilm agents and a new glycosylated asperfuran from Cordyceps javanica

Discovery of Natural Dimeric Naphthopyrones as Potential Cytotoxic Agents through ROS-Mediated Apoptotic Pathway

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