2-Pentenedioic acid derivatives from a soil-derived fungus Gongronella butleri

Akoné, Sergi Hervé; Rahn, Sebastian; Henrich, Birgit; Vardamides, Juliette Cathérine; Nkengfack, Augustin Ephrem; Lin, Wenhan; Lai, Daowan; Proksch, Peter

doi:10.1016/j.phytol.2014.09.001

Cited by 8 publications

(4 citation statements)

References 14 publications

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“…The α-hydro-carbon and C-8 with hydroxyl groups led to chiral centers. It had been reported in the literature that the alkane derivatives were found as enantiomers ( Akone et al, 2014 ).…”

Section: Resultsmentioning

confidence: 99%

Thiodiketopiperazines and Alkane Derivatives Produced by the Mangrove Sediment–Derived Fungus Penicillium ludwigii SCSIO 41408

et al. 2022

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A new trithiodiketopiperazine derivative, adametizine C (1), and five new alkane derivatives (7–11), were isolated from the mangrove sediment–derived fungus Penicillium ludwigii SCSIO 41408, together with five known dithiodiketopiperazine derivatives (2–6). Their structures were elucidated on the basis of spectroscopic analysis, and the absolute configuration of 1 was determined by X-ray crystallographic analysis. In a variety of bioactivity screening, 1–5 exhibited some selective antifungal or antibacterial activities. Compounds 1–3 showed cytotoxicity against prostate cancer cell line 22Rv1 with half maximal inhibitory concentration (IC50) values of 13.0–13.9 μM; moreover, 3 showed obvious activity against another prostate cancer PC-3 cells with an IC50 value of 5.1 μM. Further experiments revealed that 3 could significantly reduce PC-3 cells colony formation and induce apoptosis in a dose-dependent manner. Several compounds also exhibited obvious inhibitory activities of lipopolysaccharide–induced nuclear factor-κB with IC50 values range from 8.2 to 21.5 μM, and 1, 5, and 9 were further evaluated for their effects on receptor activator of NF-κB ligand (RANKL)-induced osteoclastogenesis. Adametizine C (1), with the strongest inhibitory activity against RANKL-induced osteoclast differentiation in bone marrow macrophage cells with 10 μM, was suggested to be the promising lead compound for the treatment of osteoclast-related diseases.

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“…The α-hydro-carbon and C-8 with hydroxyl groups led to chiral centers. It had been reported in the literature that the alkane derivatives were found as enantiomers ( Akone et al, 2014 ).…”

Section: Resultsmentioning

confidence: 99%

Thiodiketopiperazines and Alkane Derivatives Produced by the Mangrove Sediment–Derived Fungus Penicillium ludwigii SCSIO 41408

et al. 2022

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“…Notes : Species of Gongronella have mainly been isolated from soil ( Akone et al, 2014 ; Adamčík et al, 2015 ; Ariyawansa et al, 2015 ). Morphological characteristics of Gongronella species are diverse in shape, making it difficult to clearly delineate the species belonging to this genus.…”

Section: Resultsmentioning

confidence: 99%

Screening of Phosphate-Solubilizing Fungi From Air and Soil in Yunnan, China: Four Novel Species in Aspergillus, Gongronella, Penicillium, and Talaromyces

et al. 2020

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Phosphate-solubilizing fungi (PSF) play an important role in increasing the bioavailability of phosphorus in soils for plants. Thirteen fungal strains, one collected from air and 12 from soil, were screened and described here in detail. These fungal strains were tested for their ability to solubilize tricalcium phosphate (TCP) on both solid and liquid Pikovskaya (PVK) media in vitro . The airborne fungal strain KUMCC 18-0196 ( Aspergillus hydei sp. nov.) showed the most significant phosphate solubilizing activity on a solid PVK medium with the solubilization index (SI) (2.58 ± 0.04 cm) and the highest solubilized phosphates (1523.33 ± 47.87 μg/mL) on a liquid PVK medium. To the best of our knowledge, A. hydei sp. nov. is the first phosphate-solubilizing fungus reported from air. We also provide the identification especially for Aspergillus , Penicillium and Talaromyces , generally reported as PSF. It is important to not only screen for PSF but also identify species properly so that researchers have a clearer taxonomic picture for identifying potential taxa for future plant growth-promoting applications. Herein, A. hydei (section Nigri ), Gongronella hydei , Penicillium soli (section Lanata-Divaricata ) and Talaromyces yunnanensis (section Talaromyces ) are fully described and introduced as new to science. These four new species are identified based on both morphological characteristics and multigene phylogenetic analyses, including the genealogical concordance phylogenetic species recognition method where necessary. Penicillium austrosinense is considered to be a synonym of P. guaibinense.

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“…BF-0343 Fuji Cemetery, Shizuoka, Japan Inhibited BMP-induced ALP activity [ 150 ] 479 Ilyoresorcy A Ilyonectria sp. sb65 Hunan Province, China Inhibition of ConA-induced T-cell proliferation (481*, 482*); Immunosuppressive effects toward the LPS-induced B-cell proliferation (484*, 485*, 488*) [ 151 ] 480* Atrop-ilyoresorcy A 481*, 482, 483*, 484*, 485, 486, 487*, 488–490 Ilyoresorcys B-K Other compounds 491*, 492–493 Prenylterphenyllins A-C Aspergillus taichungensis ZHN-7-07 - Cytotoxicity [ 152 ] 494* 4”-dehydro-3-hydroxyterphenyllin 495, 496*, 497 Prenylcandidusins A-C 498 4-hydroxy-3-(3-methyoxy-3-methylbutyl)-benzoic acid Curvularia inaequalis strain.HS-FG-257 Heilongjiang Province, China - [ 153 ] 499 ( Z )-2-(5-hydroxyhexyl)pent-2-enedioic acid Gongronella butleri Forest at Koukoue, Cameroon - [ 154 ] 500 ( Z )-2-hexylpent-2-enedioic acid 501 ( Z )-2-(5-oxohexyl)pent-2-enedioic acid 502 ( Z )-oct-2-ene-1,3,8-tricarboxylic acid 503 ( Z )-2-(7-hydroxyoctyl)pent-2-enedioic acid 504 ( Z )-2-(3-methoxy-3-oxo...…”

Section: Concluding Remarks and Discussionmentioning

confidence: 99%

“…The isolated compounds feature a 2-pentenedioic acid core structure substituted by a 2-alkyl chain that has even number of carbon atoms (C 6 , C 8 , and C 10 ) with or without an oxygenated substituent. 154 Peniciketals A-C 507 – 509 ( Figure 8A ), three new spiroketals with a benzo-fused 2.8-dioxabicyclo[3.3.1]nonane moiety, were isolated from the saline soil-derived fungus Penicillium raistrichii . 155 Masaphy et al report on the purification and characterization of a novel anticandidal echinocandin – MIG0310 510 ( Figure 8A ) from Fusarium brachygibbosum strain MS-R1 and the elucidation of its molecular structure.…”

Section: Structure Types Of New Compounds Derived From Soil Fungimentioning

confidence: 99%

The Novel Compounds with Biological Activity Derived from Soil Fungi in the Past Decade

Zhang¹,

Li²,

Fan³

et al. 2022

DDDT

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The secondary metabolites isolated from soil fungi have received more and more attention, especially new compounds that exhibited good biological activities. In this review, a total of 546 new compounds are included in the relevant literature since 2011. The new compounds are isolated from soil fungi, We divided these compounds into seven categories, including alkaloids, terpenoids, steroids, ketones, phenylpropanoids, quinones, esters, lactones, etc. In addition, the biological activities and structure–activity relationships of these compounds have also been fully discussed. The activities of these compounds are roughly divided into eight categories, including anticancer activity, antimicrobial activity, anti-inflammatory activity, antioxidant activity, antiviral activity, antimalarial activity, immunosuppressive activity and other activities. Since natural products are an important source of new drugs, this review may have a positive guiding effect on drug screening.

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2-Pentenedioic acid derivatives from a soil-derived fungus Gongronella butleri

Cited by 8 publications

References 14 publications

Thiodiketopiperazines and Alkane Derivatives Produced by the Mangrove Sediment–Derived Fungus Penicillium ludwigii SCSIO 41408

Thiodiketopiperazines and Alkane Derivatives Produced by the Mangrove Sediment–Derived Fungus Penicillium ludwigii SCSIO 41408

Screening of Phosphate-Solubilizing Fungi From Air and Soil in Yunnan, China: Four Novel Species in Aspergillus, Gongronella, Penicillium, and Talaromyces

The Novel Compounds with Biological Activity Derived from Soil Fungi in the Past Decade

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