New furanoid metabolites fromRhizoctonia solani

D'silva, T. D. J.; Herrett, Richard A.

doi:10.1007/bf02286886

Cited by 4 publications

(6 citation statements)

References 8 publications

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“…First, HMF 2 can be converted to 5 alongside 1. [14] Minor component HAF 3, a known natural product, [15] is untested as a fuel constituent, but its similar chemical nature to 5 and 6 suggest it will incorporate cleanly into biofuel blends based mainly on the latter compounds. Levulinic acid 4 is a versatile chemical intermediate that appears on NREL's top 12 list of value-added chemicals from biomass, [16] and furfural 7 is a chemical commodity produced globally as a feedstock for resin manufacture and as precursor to a range of specialty chemicals, including fuel additives.…”

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confidence: 99%

Towards the Efficient, Total Glycan Utilization of Biomass

2009

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[a] Currently, automotive fuel production from biomass on any meaningful scale is limited in practice to the fermentative processing of starch hydrolysates or sucrose to ethanol. Although cellulosic ethanol and biodiesel are gaining momentum as reasonable alternatives to agriculturally derived ethanol, [1] they do not at present make a significant impression on the alternative fuel landscape. The principal issue in the case of cellulosic ethanol is first and foremost the difficult and expensive derivation of fermentable sugars from lignocellulosic biomass. Beyond this, there are also the limitations inherent in the fermentation process in terms of rate, efficiency, and the cost of isolating pure ethanol from a dilute aqueous solution.[2] Finally, ethanol is volatile, toxic, hydrophilic, potentially corrosive to engine components, [3] and of relatively low energy content compared to gasoline or diesel fuel.The disincentives associated with both agriculturally derived biofuels and cellulosic ethanol have driven innovation in the area of alternative energy. In particular, work by Dumesic and coworkers on the reductive stripping of sugars and sugar condensation products to hydrocarbons has figured centrally in this field of endeavor.[4] Huber and coworkers have also described the pyrolysis of biomass in the presence of catalysts to give a range of aromatic hydrocarbons in good yield. [5] Most recently, Binder and Raines have shown that corn stover can be processed to 5-hydroxymethylfurural (HMF) in a medium loaded with 10 mol % CrCl 3 , 10 mol % HCl, and 60 wt % 1-ethyl-3-methyl-imidazolium chloride ([EMIM]Cl) in an N,N-dimethylacetamide-LiCl solution to give 48 % yield of HMF alongside 34 % furfural (by HPLC analysis). Appending a catalytic reduction step to this process gave 2,5-dimethylfuran, a potential biofuel, in 9 % isolated yield. [6] In an earlier communication, we reported that glucose, sucrose, and microcrystalline cellulose could be converted into a mixture of 5-(chloromethyl)furfural (CMF; 1), 5-(hydroxymethyl) furfural (HMF; 2), 2-(2-hydroxyacetyl)furan (HAF; 3), and levulinic acid (LA; 4) in combined yields of up to 90 % by simple reaction with an aqueous HCl-LiCl solution.[7] The major product, CMF 1, accounts for about 80 % of the material isolated, and could be converted into 5-(ethoxymethyl)furfural (EMF; 5) by simple mixing with ethanol. EMF, a liquid with a boiling point of 235 8C, is already being commercially developed as a promising diesel fuel additive.[8] Alternatively, hydrogenolysis of the halogen in 1 gave 5-methylfurfural (MF; 6), boiling point 187 8C, which we consider to be a particularly attractive biofuel candidate, since only 2 g of H 2 are required for the synthesis of 110 g of 6, as opposed to 46 g of ethanol in the synthesis of 154 g of 5.Hemicellulose is the second-most-abundant organic material in nature, representing 25-35 % of lignocellulose by mass.[9] In mainstream ethanol production, this vast resource goes unutilized, because conventional yeasts cannot ferment C 5 su...

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confidence: 99%

Towards the Efficient, Total Glycan Utilization of Biomass

2009

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“…( Mast and Pace, 1938 ; Jorgensen, 1956 ). Additionally, compound 2 isolated from Rhizoctonia solani could inhibit seed germination that have also been reported ( D’Silva and Herrett, 1971 ). Previous report suggested that furan organic compounds are of bacteriostatic and fungistatic effect on diverse microorganisms ( Vijayakumar and Thirunanasambandham, 2021 ; Steglińska et al, 2022 ).…”

Section: Resultsmentioning

confidence: 78%

“…Previous report suggested that furan organic compounds are of bacteriostatic and fungistatic effect on diverse microorganisms ( Vijayakumar and Thirunanasambandham, 2021 ; Steglińska et al, 2022 ). Besides, previous studies had confirmed that microbes could produce different secondary metabolites under different culture conditions ( D’Silva and Herrett, 1971 ; Portela et al, 2022 ). In this research, GS2 was cultured on rice media, whether compounds 1 – 5 or other potential secondary metabolites are capable of promoting seed germination that could be produced under symbiotic condition or on different media deserved to be investigated in future research.…”

Section: Resultsmentioning

confidence: 92%

Furanoids from the Gymnadenia conopsea (Orchidaceae) seed germination supporting fungus Ceratobasidium sp. (GS2)

et al. 2022

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Five furanoids including a new analog (S)-1,4-di(furan-2-yl)-2-hydroxybutane-1,4-dione (1) together with four known ones, rhizosolaniol (2), 5-hydroxymethylfurfural (3), 2-furoic acid (4) and (2-furyl) oxoacetamide (5), were isolated from the fungal strain Ceratobasidium sp. (GS2) inducing seed germination of the endangered medicinal plant Gymnadenia conopsea of Orchidaceae. The structure of new furanoid 1 was determined mainly based on HR-ESI-MS and NMR spectral data. Modified Mosher’s reactions were used to establish the stereochemistry of the hydroxyl group in 1, which was not stable in Mosher’s reagents and transformed into four analogs 6–9. These degraded products (6–9) were elucidated based on UPLC-Q-TOF-MS/MS analysis, and compound 8 was further isolated from the degraded mixture and its structure was characterized through NMR experiments. Therefore, the absolute configuration of compound 1 was determined by electronic circular dichroism combined with quantum-chemical calculations adopting time-dependent density functional theory. Compounds (1–5), and 8 showed weak antioxidant activities, and compounds (2–4) displayed phytotoxicity on punctured detached green foxtail leaves. In addition, compounds 3 and 4 strongly showed inhibition activities on the seed germination of G. conopsea. This was the first chemical investigation of the symbiotic fungus of G. conopsea.

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“…Among the above twenty-six compounds, compounds 1 and 2 are two rare di-furfural derivatives, compound 1 represents a previously undescribed one featuring a furanolac- tone ring, and compound 2 has been reported previously only from Rhizoctonia solani, [39] and processed Polygonatum cyrtonema Hua., [8] with anti-inflammatory potential by inhibiting NO release in LPS-induced RAW264. [14,26,[33][34][35][36] As reported to date, tuberostemonoxonine (3), [37,38] didehydrotuberostemonine A (4), [10] stilbostemin B 3'-β-D-glucopyranoside (8), [14] and rutin (11) [39] have been isolated only from S. tuberosa among the three species [S. tuberosa Lour., S. sessilifolia (Miq.) Miq., and S. japonica (Blume) Miq.…”

Section: Resultsmentioning

confidence: 99%

“…Among the above twenty‐six compounds, compounds 1 and 2 are two rare di‐furfural derivatives, compound 1 represents a previously undescribed one featuring a furanolactone ring, and compound 2 has been reported previously only from Rhizoctonia solani , [39] and processed Polygonatum cyrtonema Hua., [8] with anti‐inflammatory potential by inhibiting NO release in LPS‐induced RAW264.7 cells (IC 50 35.4 μ M). The known compounds 2 , 5 – 6 , 9 , and 15 – 16 were isolated from Stemona plants for the first time, revealing the chemical diversity of Stemona plants, while the simple phenolic compounds 19 – 26 have been reported to be widespread in plants of the genus Stemonae [14,26,33–36] .…”

Section: Resultsmentioning

confidence: 99%

Furfural Derivatives and Phenolic Constituents in Stemona tuberosa Lour

He,

Li,

Yang

et al. 2023

Chemistry & Biodiversity

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Chemical investigation on the water‐soluble constituents of Stemona tuberosa Lour. resulted in the isolation of a previously undescribed furfural derivative namely (S)‐5‐((R)‐Hydroxy(5‐(hydroxymethyl)furan‐2‐yl)methyl)‐5‐methylfuran‐2(5H)‐one and twenty‐five known compounds from the water decoction of the dried root tubers. Their structures were determined by analysis of the extensive spectroscopic data, including 1D/2D NMR, HRESIMS, and ORD, as well as the ECD simulation and comparison. Most of them were phenolic and among them, four compounds were isolated from Stemona plants for the first time. This study uncovers diverse constituents from water decoction of S. tuberosa dedicated for its quality control and allows for the exploitation of chemical markers with potential significance for discrimination of Stemona plants.

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New furanoid metabolites fromRhizoctonia solani

Cited by 4 publications

References 8 publications

Towards the Efficient, Total Glycan Utilization of Biomass

Towards the Efficient, Total Glycan Utilization of Biomass

Furanoids from the Gymnadenia conopsea (Orchidaceae) seed germination supporting fungus Ceratobasidium sp. (GS2)

Furfural Derivatives and Phenolic Constituents in Stemona tuberosa Lour

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