Halogenated cladosporols produced by the sodium halide-supplemented fermentation of the plant-associated fungus Cladosporium sp. TMPU1621

Yamazaki, Hiroyuki; Yagi, Akiho; Akaishi, Masanari; Kirikoshi, Ryota; Takahashi, Ohgi; Abe, Tatsuki; Chiba, Satomi; Takahashi, Kenta; Iwakura, Natsuki; Namikoshi, Michio; Uchida, Ryuji

doi:10.1016/j.tetlet.2018.03.082

Cited by 12 publications

(14 citation statements)

References 10 publications

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“…Typically, they are connected through the polymerization of the benzene ring of one α-naphthalone derivative with the benzene ring of another α-naphthalone derivative or the benzene ring of one α-naphthalone derivative with the cyclohexanone ring of another α-naphthalone derivative. The biological activities of α -naphthalenone dimer derivatives include anticancer, antimicrobial, and so on [ 26 , 27 , 28 , 29 , 30 , 31 , 32 ]. Two novel α -naphthalenone dimer derivatives were isolated and identified during the study of secondary metabolites of Neohelicosporium griseum .…”

Section: Discussionmentioning

confidence: 99%

Neogrisphenol A, a Potential Ovarian Cancer Inhibitor from a New Record Fungus Neohelicosporium griseum

Zhang

Yang

et al. 2023

Metabolites

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From the rice fermentation product of a new record fungus, Neohelicosporium griseum, two new polyketides, neogrisphenol A (1) and neogrisphenol B (2), one new isochroman-1-one, (S)-6-hydroxy-7-methoxy-3,5-dimethylisochroman-1-one (3), and four known compounds (4–7) were isolated. Their structures were determined using 1D- and 2D-NMR, mass spectrometry, and chemical calculations. The C-3~C-2′ polymerization mode between the two α-naphthalenone derivative moieties is uncommon in compounds 1 and 2. Meanwhile, compounds 1–2 and 5 exhibited antibacterial activity against Bacillus subtilis, Clostridium perfringens, Staphylococcus aureus, and Staphylococcus aureus, with MIC values ranging between 16 and 31 µg/mL. In addition, compound 5 showed antifungal activity against Sclerotinia sclerotiorum and Phytophthora nicotianae var. nicotianae, with respective IC50 values of 88.14 ± 2.21 µg/mL and 52.36 ± 1.38 µg/mL. Compound 1 showed significant cytotoxicity against A2780, PC-3, and MBA-MD-231 cell lines with respective IC50 values of 3.20, 10.68, and 16.30 µM, and the cytotoxicity against A2780 cells was even higher than that of cisplatin (CDDP). With an IC50 value of 10.13 µM, compound 2 also exhibited cytotoxicity against A2780. The in vitro results showed that compound 1 inhibited A2780 cell proliferation, induced apoptosis, and arrested the cell cycle at the S-phase in a concentration-dependent manner.

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Section: Discussionmentioning

confidence: 99%

Neogrisphenol A, a Potential Ovarian Cancer Inhibitor from a New Record Fungus Neohelicosporium griseum

Zhang

Yang

et al. 2023

Metabolites

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“…Compounds 2 and 3 and two other cladosporols (including compound 1) were isolated from Cladosporium tenuissimum in an investigation of the biocontrol mechanisms of this hyperparasite of the rust fungus Uromyces appendiculatus (44). The stereochemical configurations of compound 2 and, by inference, compounds 1 and 3, were revised in 2017, and each was shown to have modest antibacterial activity against the bacteria Escherichia coli, Micrococcus luteus, Vibrio harveyi (62), and methicillin-resistant Staphylococcus aureus (MRSA) (45). Compound 1 has also attracted considerable interest as a peroxisome proliferator-activated receptor ␥ (PPAR␥)-mediated inhibitor of cancer cell proliferation (see reference 63 and references therein).…”

Section: Discussionmentioning

confidence: 99%

An In Vitro Pipeline for Screening and Selection of Citrus-Associated Microbiota with Potential Anti-“ Candidatus Liberibacter asiaticus” Properties

Blacutt

Ginnan

Dang

et al. 2020

Appl Environ Microbiol

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Huanglongbing (HLB) is a destructive citrus disease that is lethal to all commercial citrus plants, making it the most serious citrus disease and one of the most serious plant diseases. Because of the severity of HLB and the paucity of effective control measures, we structured this study to encompass the entirety of the citrus microbiome and the chemistries associated with that microbial community. We describe the spatial niche diversity of bacteria and fungi associated with citrus roots, stems, and leaves using traditional microbial culturing integrated with culture-independent methods. Using the culturable sector of the citrus microbiome, we created a microbial repository using a high-throughput bulk culturing and microbial identification pipeline. We integrated an in vitro agar diffusion inhibition bioassay into our culturing pipeline that queried the repository for antimicrobial activity against Liberibacter crescens, a culturable surrogate for the nonculturable “Candidatus Liberibacter asiaticus” bacterium associated with HLB. We identified microbes with robust inhibitory activity against L. crescens that include the fungi Cladosporium cladosporioides and Epicoccum nigrum and bacterial species of Pantoea, Bacillus, and Curtobacterium. Purified bioactive natural products with anti-“Ca. Liberibacter asiaticus” activity were identified from the fungus C. cladosporioides. Bioassay-guided fractionation of an organic extract of C. cladosporioides yielded the natural products cladosporols A, C, and D as the active agents against L. crescens. This work serves as a foundation for unraveling the complex chemistries associated with the citrus microbiome to begin to understand the functional roles of members of the microbiome, with the long-term goal of developing anti-“Ca. Liberibacter asiaticus” bioinoculants that thrive in the citrus holosystem. IMPORTANCE Globally, citrus is threatened by huanglongbing (HLB), and the lack of effective control measures is a major concern of farmers, markets, and consumers. There is compelling evidence that plant health is a function of the activities of the plant's associated microbiome. Using Liberibacter crescens, a culturable surrogate for the unculturable HLB-associated bacterium “Candidatus Liberibacter asiaticus,” we tested the hypothesis that members of the citrus microbiome produce potential anti-“Ca. Liberibacter asiaticus” natural products with potential anti-“Ca. Liberibacter asiaticus” activity. A subset of isolates obtained from the microbiome inhibited L. crescens growth in an agar diffusion inhibition assay. Further fractionation experiments linked the inhibitory activity of the fungus Cladosporium cladosporioides to the fungus-produced natural products cladosporols A, C, and D, demonstrating dose-dependent antagonism to L. crescens.

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“…From the above achievements, we were further interested in halogenated natural products that exhibit significant biological activity. Therefore, we attempted fermentation study with a focus on fungal strains to efficiently produce halogencontaining metabolites [149][150][151][152][153][154][155].…”

Section: Efficient Production Of Halogenated Metabolites By Fungal Strainsmentioning

confidence: 99%

“…TMPU1621 isolated from the leaves of Okinawan Achyranthes aspera var. rubrofusca was identified as the second producer with the productivity of organohalides [155]. The TMPU1621 strain produced a series of cladosporol derivatives [168][169][170], including a chlorinated congener under freshwater medium conditions, and the supplementation of 3.0% NaCl into the medium increased the production of chlorinated cladosporol.…”

Section: Efficient Production Of Halogenated Metabolites By Fungal Strainsmentioning

confidence: 99%

Exploration of marine natural resources in Indonesia and development of efficient strategies for the production of microbial halogenated metabolites

Yamazaki

2021

J Nat Med

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Nature is a prolific source of organic products with diverse scaffolds and biological activities. The process of natural product discovery has gradually become more challenging, and advances in novel strategic approaches are essential to evolve natural product chemistry. Our focus has been on surveying untouched marine resources and fermentation to enhance microbial productive performance. The first topic is the screening of marine natural products isolated from Indonesian marine organisms for new types of bioactive compounds, such as antineoplastics, antimycobacterium substances, and inhibitors of protein tyrosine phosphatase 1B, sterol O-acyl-transferase, and bone morphogenetic protein-induced osteoblastic differentiation. The unique biological properties of marine organohalides are discussed herein and attempts to efficiently produce fungal halogenated metabolites are documented. This review presents an overview of our recent work accomplishments based on the MONOTORI study. Graphic abstract

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Halogenated cladosporols produced by the sodium halide-supplemented fermentation of the plant-associated fungus Cladosporium sp. TMPU1621

Cited by 12 publications

References 10 publications

Neogrisphenol A, a Potential Ovarian Cancer Inhibitor from a New Record Fungus Neohelicosporium griseum

Neogrisphenol A, a Potential Ovarian Cancer Inhibitor from a New Record Fungus Neohelicosporium griseum

An In Vitro Pipeline for Screening and Selection of Citrus-Associated Microbiota with Potential Anti-“ Candidatus Liberibacter asiaticus” Properties

Exploration of marine natural resources in Indonesia and development of efficient strategies for the production of microbial halogenated metabolites

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