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A new anthracene glycoside, asperflavin ribofuranoside (1), and the previously described polyketides, flavoglaucin (2), isodihydroauroglaucin (3), and citrinin (4) have been isolated from the marine-derived fungus Microsporum sp. The structure and absolute stereochemistry of a new compound (1) was assigned on the basis of physicochemical data. Compounds 1—3 exhibited a significant radical scavenging activity against 1,1-diphenyl-2-picrylhydrazyl (DPPH) with IC50 values of 14.2, 11.3, and 11.5 μM, respectively, which are more potent than the positive control, ascorbic acid (IC50, 20 μM). Compound 1 also showed a moderate antibacterial activity against the methicillin-resistant and multidrug-resistant Staphylococcus aureus (MRSA and MDRSA) with MIC value of 50 μg/ml.

radical scavenging activity, Microsporum sp., asperflavin ribofuranoside, flavoglaucin, isodihydroauroglaucin, citrinin

NCBI PubMed ID: 16755063
Publication DOI: 10.1248/cpb.54.882
Journal NLM ID: 0377775
Publisher: Pharmaceutical Society Of Japan
Correspondence: Sona BW
Institutions: Department of Chemistry, Pukyong National University, Busan, Korea, College of Dentistry, Pusan National University, Busan, Korea, Department of Chemistry, Dongeui University, Busan, Korea
Methods: 13C NMR, 1H NMR, methylation, NMR-2D, IR, GC-MS, sugar analysis, acid hydrolysis, HPLC, UV, extraction, antibacterial assay, radical scavenging assay, HR-FAB-MS, LR-FAB-MS

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

Cultivation of the fungal strain Eurotium cristatum EN-220, an endophyte obtained from the marine alga Sargassum thunbergii, resulted in the isolation of one new anthraquinone glycoside, 3-O-(α-D-ribofuranosyl)questinol (1) and one new orsellinic acid ester, cristatumside A (2), together with three known aromatic glycosides, 3-O-(α-D-ribofuranosyl)questin (3), isotorachrysone 6-O-α-D-ribofuranoside (4), and asperflavin ribofuranoside (5), as well as three anthraquinone derivatives, asperflavin (6), eurorubrin (7), and (+)-variecolorquinone A (8). The structures of these compounds were determined by extensive analysis of their spectroscopic data, as well as by their comparison with those in the literature. Each of the isolated compounds was evaluated for its antimicrobial activity and brine shrimp lethality.

analysis, anthraquinone glycoside, Eurotium cristatum

Publication DOI: 10.1002/hlca.201300358
Journal NLM ID: 2985094R
Publisher: Verlag Helvetica Chimica Acta
Correspondence: Wang BG
Institutions: Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Qingdao, China, College of Chemistry & Pharmacy, Qingdao Agricultural University, Qingdao, China
Methods: 13C NMR, 1H NMR, TLC, HPLC, extraction, optical rotation measurement, CC, cell growth, HR-ESI-MS, DEPT, COSY, VLC