Ascochlorin derivatives from the leafhopper pathogenic fungus Microcera sp. BCC 17074

Isaka, Masahiko; Yangchum, Arunrat; Supothina, Sumalee; Laksanacharoen, Pattiyaa; Luangsa‐ard, J. Jennifer; Hywel‐Jones, Nigel L.

doi:10.1038/ja.2014.90

Cited by 11 publications

(13 citation statements)

References 22 publications

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“…Analogs of 3 and ilicicolinic acid D have been known to exhibit biological activities including antimicrobial and cytotoxic activities. To the best of our knowledge, as chlorinated phenolic sesquiterpenoids related with 3 , dihydroxyneogrifolic acid has been isolated from leafhopper pathogenic fungus Microcera sp., ilicicolins A, C, E and F from fungus Cylindrocladium ilicicola, and deacetylchloronectrin from Necrtia coccinea, too. The biosynthetic pathways of 1 , 2 , 4 , and 5 are derived from polyketides, which is different from the biosynthetic pathway of 3 that is derived from a farnesyl pyrophosphate and a gentisyl alcohol .…”

Section: Resultsmentioning

confidence: 99%

New Metabolites Produced by Cylindrocarpon sp. SY‐39 from a Driftwood

Suzuki

Yoshida

Koseki

et al. 2018

Chemistry & Biodiversity

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Four novel compounds, cylindropyrone A (1), 10'-hydroxyilicicolinic acid D (3), cylindrolactones A (4) and B (5), together with known dihydroinfectopyrone (2) were isolated from the culture of Cylindrocarpon sp. SY-39 from a driftwood. Their structures were elucidated using 1D- and 2D-NMR spectroscopy. Compound 3 showed antimicrobial activity against Staphylococcus aureus with MIC value of 5.0 μg/mL.

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Section: Resultsmentioning

confidence: 99%

New Metabolites Produced by Cylindrocarpon sp. SY‐39 from a Driftwood

Suzuki

Yoshida

Koseki

et al. 2018

Chemistry & Biodiversity

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“…LL-Z 1272ζ (34), LL-Z 1272δ (35) and LL-Z 1272ε (36), together with 1, 2 and 33, were isolated from Fusarium sp. LL-Z 1272 in 1969 (Fig.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

“…Subsequently, 12 and 13 were also found in Acremonium sp., Microcera sp. BCC 17 074, and A. sclerotigenum GXIMD 02 501 18 , 34 , 37 . Compound 12 exhibited stronger antitumor activity against the MCF-7 cell line (breast cancer) with an IC 50 value of 6.2 µg/mL, comparable to doxorubicin (IC 50 =8.6 µg/mL) 34 .…”

Section: Overviewmentioning

confidence: 99%

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Filamentous Fungi-Derived Orsellinic Acid-Sesquiterpene Meroterpenoids: Fungal Sources, Chemical Structures, Bioactivities, and Biosynthesis

Gao,

Zhou,

Zhang

et al. 2023

Planta Med

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Fungi-derived polyketide-terpenoid hybrids are important meroterpenoid natural products that possess diverse structure scaffolds with a broad spectrum of bioactivities. Herein, we focus on an ever-increasing group of meroterpenoids, orsellinic acid-sesquiterpene hybrids comprised of biosynthetic start unit orsellinic acid coupling to a farnesyl group or/and its modified cyclic products. The review entailed the search of China National Knowledge Infrastructure (CNKI), Web of Science, Science Direct, Google Scholar and PubMed databases up to June 2022. The key terms included "orsellinic acid", "sesquiterpene", ''ascochlorin'' ''ascofuranone'' and ''Ascochyta viciae'', which combined with the structures of ''ascochlorin'' and ''ascofuranone'' drawn by Reaxys and Scifinder databases. In our search, these orsellinic acid-sesquiterpene hybrids are mainly produced by filamentous fungi. Ascochlorin was the first compound reported in 1968 and isolated from filamentous fungus Ascochyta viciae (synonym: Acremonium egyptiacum; Acremonium sclerotigenum), to date, 71 molecules are discovered from various filamentous fungi inhabiting in a variety of ecological niches. As typical representatives of the hybrid molecules, the biosynthetic pathway of ascofuranone and ascochlorin are discussed. The group of meroterpenoid hybrids exhibited a broad arrange of bioactivities, as highlighted by targeting hDHODH (human dihydroorotate dehydrogenase) inhibition, antitrypanosomal and antimicrobial activities. This review summarizes the findings related to the structures, fungal sources, bioactivities and their biosynthesis from 1968 to June 2022.

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“…(18), Microcera sp. (19), and Nectria coccinea (20), and 1 from Paecilomyces variotii (21) and Verticillium hemipterigenum (22), indicating the broad distribution of the biosynthetic pathways. Compounds related to 1 and 2 are considered to be synthesized through the prenylation of orsellinic acid ( 3 ) and terminal cyclization via epoxidation (17, 18, 23) (Fig.…”

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confidence: 99%

Complete biosynthetic pathways of ascofuranone and ascochlorin in Acremonium egyptiacum

Araki

Awakawa

Matsuzaki

et al. 2019

Proc. Natl. Acad. Sci. U.S.A.

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Ascofuranone (AF) and ascochlorin (AC) are meroterpenoids produced by various filamentous fungi, includingAcremonium egyptiacum(synonym:Acremonium sclerotigenum), and exhibit diverse physiological activities. In particular, AF is a promising drug candidate against African trypanosomiasis and a potential anticancer lead compound. These compounds are supposedly biosynthesized through farnesylation of orsellinic acid, but the details have not been established. In this study, we present all of the reactions and responsible genes for AF and AC biosyntheses inA. egyptiacum, identified by heterologous expression, in vitro reconstruction, and gene deletion experiments with the aid of a genome-wide differential expression analysis. Both pathways share the common precursor, ilicicolin A epoxide, which is processed by the membrane-bound terpene cyclase (TPC) AscF in AC biosynthesis. AF biosynthesis branches from the precursor by hydroxylation at C-16 by the P450 monooxygenase AscH, followed by cyclization by a membrane-bound TPC AscI. All genes required for AC biosynthesis (ascABCDEFG) and a transcriptional factor (ascR) form a functional gene cluster, whereas those involved in the late steps of AF biosynthesis (ascHIJ) are present in another distantly located cluster. AF is therefore a rare example of fungal secondary metabolites requiring multilocus biosynthetic clusters, which are likely to be controlled by the single regulator, AscR. Finally, we achieved the selective production of AF inA. egyptiacumby genetically blocking the AC biosynthetic pathway; further manipulation of the strain will lead to the cost-effective mass production required for the clinical use of AF.

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Ascochlorin derivatives from the leafhopper pathogenic fungus Microcera sp. BCC 17074

Cited by 11 publications

References 22 publications

New Metabolites Produced by Cylindrocarpon sp. SY‐39 from a Driftwood

New Metabolites Produced by Cylindrocarpon sp. SY‐39 from a Driftwood

Filamentous Fungi-Derived Orsellinic Acid-Sesquiterpene Meroterpenoids: Fungal Sources, Chemical Structures, Bioactivities, and Biosynthesis

Complete biosynthetic pathways of ascofuranone and ascochlorin in Acremonium egyptiacum

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