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Five new compounds, including a benzopyran ribonic glycoside, daldiniside A (1), two isocoumarin ribonic glycosides, daldinisides B (2) and C (3), and two alkaloids, 1-(3-indolyl)-2R,3-dihydroxypropan-1-one (4) and 3-ethyl-2, 5-pyrazinedipropanoic acid (5), along with five known compounds (6-10), were isolated from the EtOAc extract of the marine-associated fungus, Daldinia eschscholzii. Their structures were elucidated by extensive physicochemical and spectroscopic properties, besides comparison with literature data. The absolute configurations of compounds 1-3 were corroborated by chemical transformation, GC analysis and X-ray crystallographic analysis. Meanwhile, the absolute configuration of compound 4 and the planar structure of compound 6 were also determined based on the X-ray diffraction analysis. The cytotoxicity of compounds 1-10, antifungal and anti-HIV activities of compounds 1-5 and the in vitro assay for glucose consumption of compounds 1-3 were done in the anti-diabetic model, whereas none showed obvious activity.

hydrolysis, secondary metabolites, marine-associated fungus, Daldinia eschscholzii, GC analysis, X-ray diffraction analysis

NCBI PubMed ID: 25419997
Publication DOI: 10.3390/md12115563
Journal NLM ID: 101213729
Publisher: Basel, Switzerland: Molecular Diversity Preservation International
Correspondence: Wang JP ; Zhang YH ; Hu ZX ; Xue YB ; Bi XB ; Luo ZW ; Yao GM ; Zhang JW ; Li XN
Institutions: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, China, Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan, China, Tongji Hospital Affiliated to Tongji Medical College, Huazhong University of Science and Technology, Wuhan, China
Methods: 13C NMR, 1H NMR, X-ray, HPLC, UV, HR-ESI-MS, cytotoxicity assay, HMBC, COSY, NOESY, antifungal activity assay, FT-IR, TFA hydrolysis, GС

References to other databases: GenDB:KF030724 and GenDB:KF030725
Structural formula & atomic coordinates
Sweet-II 3D model
Show glycosyltransferases

Background: Natural products acquire vast and intriguing structural diversity and have been recognized as a tremendously diverse source of new lead compounds. Numerous bioactive secondary metabolites are present in the form of glycosylated molecules in which the sugar parts are normally associated with the interaction along with molecular recognition of the cellular target. Scope and approach: The presence of sugar entities are crucial as well as in some cases necessary, for therapeutic effects. Establishing novel and potent glycosylated secondary metabolites has formed a main goal in the natural product field from fungi and bacteria. These compounds possess a diverse range of sugar units. Key findings and conclusions: Fungi is considered one of the important sources for approved drugs with a diverse range of mode of action. The sugar part in numerous pharmacologically active natural products enhances bioavailability, biological potential, reduce toxicity, and improve stability. The vast majority of glyocosides showed antimicrobial effects, cytotoxic, antiviral and antiinflammatory effects. Notably, numerous fungal glycosides presented in this review illustrate significant antimicrobial effects towards various microorganisms especially against plant pathogens. The antimicrobial effects of these fungal glycosides indicate that these metabolites could be employed as natural preservatives in food in order to abolish or control the growth of pathogenic and spoilage microorganisms.

glycoside, antimicrobial, fungi, food preservative, secondary metabolites

Publication DOI: 10.1016/j.tifs.2021.02.029
Journal NLM ID: 9426004
Publisher: Cambridge, UK: Elsevier Trends Journals
Correspondence: Hussain H ; Hussain H ; Xiao J ; Xiao J
Institutions: Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Halle (Saale), Germany, Institute of the Chemistry of Plant Substances of the Academy Sciences of Uzbekistan, Tashkent, Uzbekistan, School of Pharmaceutical Sciences and Key Laboratory for Applied Technology of Sophisticated Analytical Instruments of Shandong Province, Shandong Analysis and Test Center, Qilu University of Technology (Shandong Academy of Sciences), Jinan, China, Department Materials Engineering, National University of Sciences and Technology (NUST) H12, Islamabad, Pakistan, Department of Chemistry and Polymer Science, University of Stellenbosch, Matieland, South Africa, Key Laboratory of Coarse Cereal Processing, Ministry of Agriculture and Rural Affairs, Chengdu University, Chengdu, China, Nutrition and Bromatology Group, Department of Analytical Chemistry and Food Science, Faculty of Food Science and Technology, University of Vigo - Ourense Campus, Ourense, Spain

Ribosylation is a significant modification conferring new complex and broadened cellular roles of compounds, but small organic molecules are rarely ribosylated. Here, we report the 3-O- and 4′-O-α-ribosylation of resveratrol, a phytoalexin that is exogenous to the fungus Daldinia eschscholzii IFB-TL01. The ribosylation is mechanistically due to the resveratrol-activated expression of the silent or less active fungal genes governing the ribosylation of non-fungal phytophenols. The resveratrol-induced ribosylation is also characterized by an increased expression of ribosyltransferases in concert with a rare ribosylating reaction using nicotinamide mononucleotide (NMN) as a ribose donor. The ribosylation-reduced toxicity of resveratrol to D. eschscholzii, along with the involvement of at least two p-glycoproteins in the glycosylation, suggests that such a glycosylation process may be a general strategy for the fungal detoxification of phenolic chemicals. The findings present an updated view of the ribosylation of small molecules, and provide direct chemogenetic evidence that will aid understanding of how phytophenols such as resveratrol function differently in the plant, microbial and animal kingdoms

resveratrol, ribosylation, Daldinia eschscholzii IFB-TL01

Publication DOI: 10.1039/c4ra12851f
Journal NLM ID: 101581657
Publisher: Cambridge, UK: Royal Society of Chemistry
Correspondence: Tan RX ; Jiao RH
Institutions: State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, Shanghai, China, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, China
Methods: 13C NMR, 1H NMR, gel filtration, NMR-2D, PCR, DNA techniques, ESI-MS, HPLC, UV, extraction, LC-MS, CC, cell growth, evaporation