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A new aromatic polyketide glycoside, indigotide A (1), was isolated from the culture broth of the entomopathogenic fungus, Cordyceps indigotica, along with known cyclic depsipeptides, destruxins A, A2, B, B2 and E (3–7), and a polyketide, NG-393 (8). Repeated treatment of the C. indigotica culture broth with 5-azacytidine, a DNA methyltransferase inhibitor, led to the isolation of another new aromatic polyketide glycoside, indigotide B (2).

polyketides, secondary metabolites, entomopathogenic fungi, DNA methyltransferase inhibitor, epigenetics

Publication DOI: 10.1016/j.tetlet.2011.10.013
Journal NLM ID: 2984819R
Publisher: Elsevier
Correspondence: tasai@m.tohoku.ac.jp
Institutions: Graduate School of Pharmaceutical Sciences, Tohoku University, Sendai, Japan, Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan, Graduate Institute of Integrated Medicine, College of Chinese Medicine, China Medical University, Taichung, Taiwan, Tohoku Pharmaceutical University, Sendai, Japan
Methods: 13C NMR, 1H NMR, acid hydrolysis, optical rotation measurement, CC, RP-HPLC, LC, COSY, HR-FAB-MS, HREI-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 Cordyceps indigotica, an entomopathogenic fungus, in the presence of suberoyl bis-hydroxamic acid (an HDAC inhibitor) greatly activated its polyketide synthesis apparatus to afford six novel aromatic polyketides, indigotides C-F (1-4), 13-hydroxyindigotide A (5), and 8-O-methylindigotide B (6). The structures of these compounds were determined by NMR spectroscopic analyses. Among the compounds, indigotides C-E (1-3) possessed unprecedented dimeric polyketide frameworks possibly generated via a [4 + 2] cycloaddition or Michael type reaction.

polyketide, Cordyceps, histone deacetylase inhibitor, hydroxamic acid, suberoyl bis-hydroxamic acid

NCBI PubMed ID: 22480311
Publication DOI: 10.1021/ol3005062
Journal NLM ID: 100890393
Publisher: American Chemical Society
Correspondence: tasai@m.tohoku.ac.jp
Institutions: Graduate School of Pharmaceutical Sciences, Tohoku University, Sendai, Japan
Methods: 13C NMR, 1H NMR, IR, DNA techniques, TLC, acid hydrolysis, MS, HPLC, UV, extraction, optical rotation measurement, CD, CC, cell growth, COSY, HR-EI-MS