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Discovery and Biosynthesis of Fungal Natural Products

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A special issue of Journal of Fungi (ISSN 2309-608X).

Deadline for manuscript submissions: closed (31 January 2023) | Viewed by 14818

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Special Issue Editors

Prof. Dr. Wenbing Yin

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Guest Editor

State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences, Beijing, China
Interests: fungal secondary metabolites; combinatorial biosynthesis; genome mining; new tools or techniques; biological and ecological function of fungal natural product
Special Issues, Collections and Topics in MDPI journals

Prof. Dr. Shu-Ming Li

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Guest Editor

Institut für Pharmazeutische Biologie und Biotechnologie, Philipps-Universität Marburg, Marburg, Germany
Interests: biosynthesis of microbial natural products; prenylated metabolites and prenyltransferases; polyketide synthases; enzyme catalysts; genetic manipulation in ascomycetes and actinomyces

Prof. Dr. Xiaolong Yang

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Guest Editor

School of Pharmaceutical Sciences, South-Central Minzu University, Wuhan, China
Interests: fungal natural products; biosynthesis or combinatorial biosynthesis; novel enzymes or catalytic mechanism; natural product (total) synthesis; biological function of natural or semisynthetic products
Special Issues, Collections and Topics in MDPI journals

Dr. Lin Chen

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Guest Editor

Institute of Nano-Structured Functional Materials, Huanghe Science and Technology College, Zhengzhou, China
Interests: microbial chemistry; phytochemistry; structural modifications

Special Issue Information

Dear Colleagues,

As an important source of natural products, fungi play a special role in medicine, food, brewing and other fields, and also play an irreplaceable role in biology and ecology. With the higher needs of human beings in the field of health, more and more new methods and techniques have been applied to the discovery of natural products with novel structures and significant biological activities. However, the current methods are still unable to meet the pace of rapid development of human society. We need to continue to develop new research methods and explore biological functional active molecules beneficial to human health under the premise of following the laws of nature. Benefit from the abundant resources and powerful genetic manipulation space of fungi, humans will make great achievements in the field of natural products of fungi.

Prof. Dr. Wenbing Yin
Prof. Dr. Shu-Ming Li
Prof. Dr. Xiaolong Yang
Dr. Lin Chen
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. Journal of Fungi 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 2600 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

secondary metabolites
fungal natural products
heterologous expression
biosynthesis
combinatorial biosynthesis
novel enzymes
new techniques

Published Papers (7 papers)

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Research

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11 pages, 2096 KiB

Open AccessArticle

Phaeosphaeridiols A–C: Three New Compounds from Undescribed Phaeosphaeriaceae sp. SGSF723

by Lu Si, Yao Liu, Tingting Du, Wei Meng and Lijian Xu

J. Fungi 2022, 8(11), 1190; https://doi.org/10.3390/jof8111190 - 11 Nov 2022

Viewed by 1057

Abstract

Fungi in forest litter are diverse as decomposers but natural products from these fungi are rarely investigated, especially for their antimicrobial activities against crop diseases. In this study, fungal isolate SGSF723 with antimicrobial activities was cultured. A multi-gene phylogenetic analysis showed SGSF723 was an undescribed species in the family Phaeosphaeriaceae. By bio-guided assay, three new compounds (Phaeosphaeridiols A–C) and two known compounds were purified from the ethyl acetate extract. The structures of Phaeosphaeridiols A–C were elucidated as 2-(2′-butenyl)-5 (3″-pentene)-1,3-benzenediol (1), 2-(2′-butenyl)-5-(3″S,4″S-pentane diol)-1,3-benzenediol (2), and 3-(4′-(2″-butenyl)-3′,5′-benzenediol phenol)-2-acrylic acid (3) by 2D NMR, HRESIMS, and Mosher’s method. Phaeosphaeridiols A–C exhibited moderate or weak antimicrobial activities against plant pathogens by 96-well plate and spore germination assays. Full article

(This article belongs to the Special Issue Discovery and Biosynthesis of Fungal Natural Products)

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13 pages, 2955 KiB

Open AccessArticle

Induction of Secondary Metabolite Biosynthesis by Deleting the Histone Deacetylase HdaA in the Marine-Derived Fungus Aspergillus terreus RA2905

by Yao-Yao Zheng, Zhong-Lian Ma, Jing-Shuai Wu, Chang-Lun Shao, Guang-Shan Yao and Chang-Yun Wang

J. Fungi 2022, 8(10), 1024; https://doi.org/10.3390/jof8101024 - 28 Sep 2022

Cited by 3 | Viewed by 1653

Abstract

Aspergillus terreus is well-known for its ability to biosynthesize valuable pharmaceuticals as well as structurally unique secondary metabolites. However, numerous promising cryptic secondary metabolites in this strain regulated by silent gene clusters remain unidentified. In this study, to further explore the secondary metabolite potential of A. terreus, the essential histone deacetylase hdaA gene was deleted in the marine-derived A. terreus RA2905. The results showed that HdaA plays a vital and negative regulatory role in both conidiation and secondary metabolism. Loss of HdaA in A. terreus RA2905 not only resulted in the improvement in butyrolactone production, but also activated the biosynthesis of new azaphilone derivatives. After scaled fermentation, two new azaphilones, asperterilones A and B (1 and 2), were isolated from ΔhdaA mutant. The planar structures of compounds 1 and 2 were undoubtedly characterized by NMR spectroscopy and mass spectrometry analysis. Their absolute configurations were assigned by circular dichroism spectra analysis and proposed biosynthesis pathway. Compounds 1 and 2 displayed moderate anti-Candida activities with the MIC values ranging from 18.0 to 47.9 μM, and compound 1 exhibited significant cytotoxic activity against human breast cancer cell line MDA-MB-231. This study provides novel evidence that hdaA plays essential and global roles in repressing secondary metabolite gene expression in fungi, and its deletion represents an efficient strategy to mine new compounds from A. terreus and other available marine-derived fungi. Full article

(This article belongs to the Special Issue Discovery and Biosynthesis of Fungal Natural Products)

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13 pages, 2477 KiB

Open AccessArticle

Characterization of a NRPS-like Protein from Pestalotiopsis fici for Aldehyde Generation

by Yuanyuan Li, Peng-Lin Wei, Huomiao Ran, Jie Fan and Wen-Bing Yin

J. Fungi 2022, 8(10), 1001; https://doi.org/10.3390/jof8101001 - 23 Sep 2022

Cited by 1 | Viewed by 1854

Abstract

Nonribosomal peptide synthetase (NRPS)-like enzymes containing A-T-R domain architecture are also known as carboxylate reductases (CARs) for aldehyde generation. To identify new members of CARs, we established a virtual library containing 84 fungal CARs distributed in seven distinct clades by genome mining and phylogenetic analysis. Nine CARs, including PnlA from Pestalotiopsis fici and eight known CARs, were clustered in clade VI and proposed to catalyze the reduction of nonreducing polyketide synthase (NR-PKS)-derived aryl carboxylic acids. The recombinant protein PnlA was overproduced and purified to apparent homogeneity from Saccharomyces cerevisiae. In vitro enzyme assays of PnlA with 28 different benzoic acid derivatives (1–28) revealed the corresponding aldehyde formation in 14 cases (1–14). Comparison of conversion yields indicated the high preference of PnlA toward 3,5-dimethylorsellinic acid (DMOA, 4) and vanillic acid (10). A specificity-conferring code Q355 in PnlA was postulated by sequence alignment with the known CARs in clade VI. Our study provides an updated virtual library of fungal CAR enzymes and expands the biocatalytic selectivity of CARs. Full article

(This article belongs to the Special Issue Discovery and Biosynthesis of Fungal Natural Products)

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17 pages, 3106 KiB

Open AccessArticle

Purification and Characterization of a Novel α-L-Rhamnosidase from Papiliotrema laurentii ZJU-L07 and Its Application in Production of Icariin from Epimedin C

by Hanghang Lou, Xiayu Liu, Siyu Liu and Qihe Chen

J. Fungi 2022, 8(6), 644; https://doi.org/10.3390/jof8060644 - 20 Jun 2022

Cited by 5 | Viewed by 1836

Abstract

Icariin is the most effective bioactive compound in Herba Epimedii. To enhance the content of icariin in the epimedium water extract, a novel strain, Papiliotrema laurentii ZJU-L07, producing an intracellular α-L-rhamnosidase was isolated from the soil and mutagenized. The specific activity of α-L-rhamnosidase was 29.89 U·mg⁻¹ through purification, and the molecular mass of the enzyme was 100 kDa, as assayed by SDS-PAGE. The characterization of the purified enzyme was determined. The optimal temperature and pH were 55 °C and 7.0, respectively. The enzyme was stable in the pH range 5.5–9.0 for 2 h over 80% and the temperature range 30–40 °C for 2 h more than 70%. The enzyme activity was inhibited by Ca²⁺, Fe²⁺, Cu²⁺, and Mg²⁺, especially Fe²⁺. The kinetic parameters of K_m and V_max were 1.38 mM and 24.64 μmol·mg⁻¹·min⁻¹ using pNPR as the substrate, respectively. When epimedin C was used as a nature substrate to determine the kinetic parameters of α-L-rhamnosidase, the values of K_m and V_max were 3.28 mM and 0.01 μmol·mg⁻¹·min⁻¹, respectively. The conditions of enzymatic hydrolysis were optimized through single factor experiments and response surface methodology. The icariin yield increased from 61% to over 83% after optimization. The enzymatic hydrolysis method could be used for the industrialized production of icariin. At the same time, this enzyme could also cleave the α-1,2 glycosidic linkage between glucoside and rhamnoside in naringin and neohesperidin, which could be applicable in other biotechnological processes. Full article

(This article belongs to the Special Issue Discovery and Biosynthesis of Fungal Natural Products)

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9 pages, 1399 KiB

Open AccessArticle

Biosynthesis of Xylariolide D in Penicillium crustosum Implies a Chain Branching Reaction Catalyzed by a Highly Reducing Polyketide Synthase

by Sina A. Stierle and Shu-Ming Li

J. Fungi 2022, 8(5), 493; https://doi.org/10.3390/jof8050493 - 9 May 2022

Cited by 1 | Viewed by 3109

Abstract

Fungi are important sources for the discovery of natural products. During the last decades, technological progress and the increasing number of sequenced genomes facilitated the exploration of new secondary metabolites. Among those, polyketides represent a structurally diverse group with manifold biological activities. In this study, we successfully used genome mining and genetic manipulation for functional proof of a polyketide biosynthetic gene cluster from the filamentous fungus Penicillium crustosum. Gene activation in the native host and heterologous expression in Aspergillus nidulans led to the identification of the xil cluster, being responsible for the formation of the 6-methyl-2-pyrone derivative xylariolide D. Feeding with ¹³C-labeled precursors supported the hypothesis of chain branching during the backbone formation catalyzed by a highly reducing fungal polyketide synthase. A cytochrome P450-catalyzed hydroxylation converts the PKS product to the final metabolite. This proved that just two enzymes are required for the biosynthesis of xylariolide D. Full article

(This article belongs to the Special Issue Discovery and Biosynthesis of Fungal Natural Products)

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Review

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32 pages, 860 KiB

Open AccessReview

Lichen Depsides and Tridepsides: Progress in Pharmacological Approaches

by Isabel Ureña-Vacas, Elena González-Burgos, Pradeep Kumar Divakar and María Pilar Gómez-Serranillos

J. Fungi 2023, 9(1), 116; https://doi.org/10.3390/jof9010116 - 14 Jan 2023

Cited by 5 | Viewed by 2033

Abstract

Depsides and tridepsides are secondary metabolites found in lichens. In the last 10 years, there has been a growing interest in the pharmacological activity of these compounds. This review aims to discuss the research findings related to the biological effects and mechanisms of action of lichen depsides and tridepsides. The most studied compound is atranorin, followed by gyrophoric acid, diffractaic acid, and lecanoric acid. Antioxidant, cytotoxic, and antimicrobial activities are among the most investigated activities, mainly in in vitro studies, with occasional in silico and in vivo studies. Clinical trials have not been conducted using depsides and tridepsides. Therefore, future research should focus on conducting more in vivo work and clinical trials, as well as on evaluating the other activities. Moreover, despite the significant increase in research work on the pharmacology of depsides and tridepsides, there are many of these compounds which have yet to be investigated (e.g., hiascic acid, lassalic acid, ovoic acid, crustinic acid, and hypothamnolic acid). Full article

(This article belongs to the Special Issue Discovery and Biosynthesis of Fungal Natural Products)

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15 pages, 5379 KiB

Open AccessReview

Research Progress on Fungal Sesterterpenoids Biosynthesis

by Ping Zhang, Jianzhao Qi, Yingce Duan, Jin-ming Gao and Chengwei Liu

J. Fungi 2022, 8(10), 1080; https://doi.org/10.3390/jof8101080 - 14 Oct 2022

Cited by 6 | Viewed by 1906

Abstract

Sesterterpenes are 25-carbon terpenoids formed by the cyclization of dimethyl allyl diphosphate (DMAPP) and isopentenyl diphosphate (IPP) as structural units by sesterterpenes synthases. Some (not all) sesterterpenoids are modified by cytochrome P450s (CYP450s), resulting in more intricate structures. These compounds have significant physiological activities and pharmacological effects in anti-inflammatory, antibacterial, antitumour, and hypolipidemic communities. Despite being a rare class of terpenoids, sesterterpenoids derived from fungi show a wide range of structural variations. The discovered fungal sesterterpenoid synthases are composed of C-terminal prenyltransferase (PT) and N-terminal terpene synthase (TS) domains, which were given the name PTTSs. PTTSs have the capacities to catalyze chain lengthening and cyclization concurrently. This review summarizes all 52 fungal PTTSs synthases and their biosynthetic pathways involving 100 sesterterpenoids since the discovery of the first PTTSs synthase from fungi in 2013. Full article

(This article belongs to the Special Issue Discovery and Biosynthesis of Fungal Natural Products)

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