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Keywords = asperpyrone

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10 pages, 962 KB  
Article
Aromatic Polyketides from a Symbiotic Strain Aspergillus fumigatus D and Characterization of Their Biosynthetic Gene D8.t287
by Yi Hua, Rui Pan, Xuelian Bai, Bin Wei, Jianwei Chen, Hong Wang and Huawei Zhang
Mar. Drugs 2020, 18(6), 324; https://doi.org/10.3390/md18060324 - 20 Jun 2020
Cited by 15 | Viewed by 5791
Abstract
The chemical investigation of one symbiotic strain, Aspergillus fumigatus D, from the coastal plant Edgeworthia chrysantha Lindl led to the isolation of eight compounds (1–8), which were respectively identified as rubrofusarin B (1), alternariol 9-O-methyl [...] Read more.
The chemical investigation of one symbiotic strain, Aspergillus fumigatus D, from the coastal plant Edgeworthia chrysantha Lindl led to the isolation of eight compounds (1–8), which were respectively identified as rubrofusarin B (1), alternariol 9-O-methyl ether (2), fonsecinone D (3), asperpyrone A (4), asperpyrone D (5), fonsecinone B (6), fonsecinone A (7), and aurasperone A (8) by a combination of spectroscopic methods (1D NMR and ESI-MS) as well as by comparison with the literature data. An antimicrobial assay showed that these aromatic polyketides exhibited no remarkable inhibitory effect on Escherichia coli, Staphyloccocus aureus and Candida albicans. The genomic feature of strain D was analyzed, as well as its biosynthetic gene clusters, using antibiotics and Secondary Metabolite Analysis Shell 5.1.2 (antiSMASH). Plausible biosynthetic pathways for dimeric naphtho-γ-pyrones 3–8 were first proposed in this work. A non-reducing polyketide synthase (PKS) gene D8.t287 responsible for the biosynthesis of these aromatic polyketides 1–8 was identified and characterized by target gene knockout experiment and UPLC-MS analysis. Full article
(This article belongs to the Special Issue Aromatic Marine Natural Products: Chemistry and Bioactivity)
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15 pages, 1532 KB  
Article
Naphtho-Gamma-Pyrones Produced by Aspergillus tubingensis G131: New Source of Natural Nontoxic Antioxidants
by Quentin Carboué, Marc Maresca, Gaëtan Herbette, Sevastianos Roussos, Rayhane Hamrouni and Isabelle Bombarda
Biomolecules 2020, 10(1), 29; https://doi.org/10.3390/biom10010029 - 24 Dec 2019
Cited by 16 | Viewed by 4164
Abstract
Seven naphtho-gamma-pyrones (NγPs), including asperpyrone E, aurasperone A, dianhydroaurasperone C, fonsecin, fonsecinone A, fonsecin B, and ustilaginoidin A, were isolated from Aspergillus tubingensis G131, a non-toxigenic strain. The radical scavenging activity of these NγPs was evaluated using ABTS assay. The Trolox equivalent antioxidant [...] Read more.
Seven naphtho-gamma-pyrones (NγPs), including asperpyrone E, aurasperone A, dianhydroaurasperone C, fonsecin, fonsecinone A, fonsecin B, and ustilaginoidin A, were isolated from Aspergillus tubingensis G131, a non-toxigenic strain. The radical scavenging activity of these NγPs was evaluated using ABTS assay. The Trolox equivalent antioxidant capacity on the seven isolated NγPs ranged from 2.4 to 14.6 μmol L−1. The toxicity and ability of the NγPs to prevent H2O2-mediated cell death were evaluated using normal/not cancerous cells (CHO cells). This cell-based assay showed that NγPs: (1) Are not toxic or weakly toxic towards cells and (2) are able to protect cells from oxidant injuries with an IC50 on H2O2-mediated cell death ranging from 2.25 to 1800 μmol mL−1. Our data show that A. tubingensis G131 strain is able to produce various NγPs possessing strong antioxidant activities and low toxicities, making this strain a good candidate for antioxidant applications in food and cosmetic industries. Full article
(This article belongs to the Special Issue 2019 Feature Papers by Biomolecules’ Editorial Board Members)
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8 pages, 3331 KB  
Article
Asperpyrone-Type Bis-Naphtho-γ-Pyrones with COX-2–Inhibitory Activities from Marine-Derived Fungus Aspergillus niger
by Wei Fang, Xiuping Lin, Jianjiao Wang, Yonghong Liu, Huaming Tao and Xuefeng Zhou
Molecules 2016, 21(7), 941; https://doi.org/10.3390/molecules21070941 - 20 Jul 2016
Cited by 28 | Viewed by 8325
Abstract
Bis-naphtho-γ-pyrones (BNPs) are an important group of aromatic polyketides derived from fungi, and asperpyrone-type BNPs are produced primarily by Aspergillus species. The fungal strain Aspergillus niger SCSIO Jcsw6F30, isolated from a marine alga, Sargassum sp., and identified according to its morphological traits and [...] Read more.
Bis-naphtho-γ-pyrones (BNPs) are an important group of aromatic polyketides derived from fungi, and asperpyrone-type BNPs are produced primarily by Aspergillus species. The fungal strain Aspergillus niger SCSIO Jcsw6F30, isolated from a marine alga, Sargassum sp., and identified according to its morphological traits and the internal transcribed spacer (ITS) region sequence, was studied for BNPs secondary metabolisms. After HPLC/MS analysis of crude extract of the fermentation broth, 11 asperpyrone-type BNPs were obtained directly and quickly by chromatographic separation in the extract, and those isolated asperpyrone-type BNPs were structurally identified by NMR and MS analyses. All of the BNPs showed weak cytotoxicities against 10 human tumor cells (IC50 > 30 μM). However, three of them, aurasperone F (3), aurasperone C (6) and asperpyrone A (8), exhibited obvious COX-2–inhibitory activities, with the IC50 values being 11.1, 4.2, and 6.4 μM, respectively. This is the first time the COX-2–inhibitory activities of BNPs have been reported. Full article
(This article belongs to the Special Issue Natural Products and Inflammation)
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20 pages, 286 KB  
Review
Bis-naphtho-γ-pyrones from Fungi and Their Bioactivities
by Shiqiong Lu, Jin Tian, Weibo Sun, Jiajia Meng, Xiaohan Wang, Xiaoxiang Fu, Ali Wang, Daowan Lai, Yang Liu and Ligang Zhou
Molecules 2014, 19(6), 7169-7188; https://doi.org/10.3390/molecules19067169 - 30 May 2014
Cited by 64 | Viewed by 11949
Abstract
Bis-naphtho-γ-pyrones are an important group of aromatic polyketides derived from fungi. They have a variety of biological activities including cytotoxic, antitumor, antimicrobial, tyrosine kinase and HIV-1 integrase inhibition properties, demonstrating their potential applications in medicine and agriculture. At least 59 bis-naphtho-γ-pyrones from fungi [...] Read more.
Bis-naphtho-γ-pyrones are an important group of aromatic polyketides derived from fungi. They have a variety of biological activities including cytotoxic, antitumor, antimicrobial, tyrosine kinase and HIV-1 integrase inhibition properties, demonstrating their potential applications in medicine and agriculture. At least 59 bis-naphtho-γ-pyrones from fungi have been reported in the past few decades. This mini-review aims to briefly summarize their occurrence, biosynthesis, and structure, as well as their biological activities. Some considerations regarding to synthesis, production, and medicinal and agricultural applications of bis-naphtho-γ-pyrones are also discussed. Full article
(This article belongs to the Section Natural Products Chemistry)
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