Armillariols A to C from the culture broth of Armillaria sp.

Kobori, Hajime; Sekiya, Atsushi; Yasuda, Nobuhiro; Noguchi, Keiichi; Suzuki, Tomohiro; Choi, Jae-Hoon; Hirai, Hirofumi; Kawagishi, Hirokazu

doi:10.1016/j.tetlet.2013.07.131

Cited by 12 publications

(10 citation statements)

References 15 publications

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“…This was corroborated by the 13 C-NMR and DEPT data, which displayed nine resonances for four sp 2 quaternary carbons (δ C 172.7, 163.1, 160.0, 142.8), two sp 2 methines (δ C 121.3 and 108.8), two sp 3 methylenes (δ C 32.0 and 23.8) and one methoxyl group (δ C 52.0). These observations, in combination with 2D NMR signals (the 1 H- 1 H COSY cross-peak of H-3′/H-4′ and HMBC cross-peaks of H-3′/C-2′ and H-4′/C-5′), were consistent with the assumption that 1 possessed a ring and a carbonyl-conjugated diene (C-1, δ C 160.0; C-2′, δ C 142.8; C-3′, δ C/H 121.3/7.10; C-4′, δ C/H 108.8/6.21; C-5′, δ C 163.1), indicating 2-furan-carboxylic acid unit in the structure [ 11 ]. The 1 H- 1 H COSY correlation of H 2 -1′′/H 2 -2′′ and HMBC correlations from H 2 -1′′ (δ H 3.04) to C-2′′ (δ C 32.0) and C-3′′ (δ C 172.7); from H 2 -2′′ (δ H 2.71) to C-1′′ (δ C 23.8) and C-3′′; as well as from H 3 -4′′ (3.68) to C-3′′ consisted of the methyl propionate moiety.…”

Section: Resultsmentioning

confidence: 99%

New Furan Derivatives from a Mangrove-Derived Endophytic Fungus Coriolopsis sp. J5

et al. 2017

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Six new furan derivatives, named 5-(3-methoxy-3-oxopropyl)-furan-2-carboxylic acid (1), 1-(5-(2-hydroxypropanoyl)-furan-2-yl)-pentan-3-one (2), 2-hydroxy-1-(5-(1-hydroxypentyl)-furan-2-yl)-propan-1-one (3), 1-(5-(1,2-dihydroxypropyl)-furan-2-yl)-pentan-1-one (4), 5-(1-hydroxypent-4-en-1-yl)-furan-2-carboxylic acid (5) and 5-(3-hydroxypentyl)-furan-2-carboxylic acid (6), together with two new natural products, named 5-(1-hydroxypentyl)-furan-2-carboxylic acid (7) and (E)-5-(2-carboxyvinyl)-furan-2-carboxylic acid (8), were isolated from the solid rice fermentation of endophytic fungus Coriolopsis sp. J5, which was derived from mangrove plant Ceriops tagal. Their structures were unambiguously elucidated based on 1D and 2D NMR spectroscopy, and by HRESIMS measurements, as well as by comparison with the literature.

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Section: Resultsmentioning

confidence: 99%

New Furan Derivatives from a Mangrove-Derived Endophytic Fungus Coriolopsis sp. J5

et al. 2017

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“…The furan compound 5-(hydroxymethyl)furan-3-carboxylic acid was identified for the first time as a natural product in cultures of Polyporus ciliatus [20], and afterwards reported from other fungi (Table 1). Although furan derivatives are not an extensive class of fungal compounds [35], over the past few years the literature concerning these natural products has been enriched by new reports [36,37,38,39,40]. According to their biosynthetic origin, the structure of natural furan derivatives shows the presence of furan rings substituted in position 2 and 5 [35].…”

Section: Discussionmentioning

confidence: 99%

The Issue of Misidentification of Kojic Acid with Flufuran in Aspergillus flavus

et al. 2019

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In the course of investigations on the complex phenomenon of bee decline, Aspergillus flavus was isolated from the haemocoel of worker bees. Observations on the metabolomic profile of this strain showed kojic acid to be the dominant product in cultures on Czapek-Dox broth. However, an accurate review of papers documenting secondary metabolite production in A. flavus also showed that an isomer of kojic acid, identified as 5-(hydroxymethyl)-furan-3-carboxylic acid and named flufuran is reported from this species. The spectroscopic data of kojic acid were almost identical to those reported in the literature for flufuran. This motivated a comparative study of commercial kojic acid and 5-(hydroxymethyl)-furan-3-carboxylic acid, highlighting some differences, for example in the 13C-NMR and UV spectra for the two compounds, indicating that misidentification of the kojic acid as 5-(hydroxymethyl)-furan-3-carboxylic acid has occurred in the past.

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“…For example, the work carried out by Donnelly, Hutchinson, Coveney, and Yonemitsu (1990), Donnelly, Konishi, Dunne, and Cremin (1997), as well as by Kobory et al. (2013), has indicated a direct relationship between sesquiterpene aryl esters produced by this fungus and pathogenicity. However, some researchers, as Guillaumin, Mercier, and Dubos (1982), consider that these toxins (in contrast to the case of Rosellinia necatrix ; Guillaumin et al, 1982; Tourvieille de Labrouhe, 1983) do not play a major role in the disease.…”

Section: Discussionmentioning

confidence: 97%

Production of β‐glucosidases by European Armillaria species

et al. 2020

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Species of the genus Armillaria (Fr.:Fr.) Staude are widely distributed Basidiomycota belonging to the Agaricomycetes, and most are potential root-rot pathogens with a broad host range. Using interfertility tests, Korhonen (1978) separated European Armillaria within the annulate mellea complex into five biological groups later described as five biological species based on different ecological and physiological criteria. These species include Armillaria mellea (Vahl.:Fr.) Kummer, Armillaria ostoyae (Romagnesi) Herink, Armillaria gallica Marxmuller & Romagnesi, Armillaria borealis Marxmuller & Korhonen and Armillaria cepistipes Velenossky. In addition, two exannulate species include Armillaria ectypa (Fr.) Lamoure, found in peat bogs as a saprophyte, and Armillaria tabescens (Scop.:Fr) Emel, a forest species commonly found in southern Europe, usually considered as a saprotroph, but at least once reported in Europe as a weak parasite (Tsopelas & Tjamos, 1997). Armillaria mellea attacks vineyards, orchard trees and deciduous trees, but can also infect young conifers. Armillaria ostoyae is regarded as a parasite of coniferous trees, while A. gallica, A. borealis and A. cepistipes are all three generally considered as saprophytes (

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Armillariols A to C from the culture broth of Armillaria sp.

Abstract: Three novel compounds were isolated from the culture broth of Armillaria sp.. Their structures were elucidated mainly by spectroscopic data analyses. All the compounds regulated hypocotyl and root growth of lettuce.

Cited by 12 publications

References 15 publications

New Furan Derivatives from a Mangrove-Derived Endophytic Fungus Coriolopsis sp. J5

New Furan Derivatives from a Mangrove-Derived Endophytic Fungus Coriolopsis sp. J5

The Issue of Misidentification of Kojic Acid with Flufuran in Aspergillus flavus

Production of β‐glucosidases by European Armillaria species

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