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A series of six isopimarane-type diterpene glycosides, along with an eremophilane-type sesquiterpene, i.e., elaeicolasides A-C (1-3, resp.), 16-(α-D-mannopyranosyloxy)isopimar-7-en-19-oic acid (4), hymatoxin K (5), hymatoxin L (6), and elaeicolalactone (7), were isolated from the AcOEt extract of the fermented broth of Stilbohypoxylon elaeicola YMJ173. Among these, 1-3 and 7 are new compounds based on their spectroscopic data and sugar composition analysis. The effects of 1-7 on the inhibition of nitric oxide (NO) production in lipopolysaccharide (LPS)-activated murine macrophage RAW264.7 cells were evaluated. All these compounds inhibited NO production, detected as nitrite in the culture medium, in activated macrophages without any cytotoxicity at a concentration of 100 μM. Among these compounds, 2 showed a significant activity with the average maximum inhibition (E(max)) and median inhibitory concentration (IC(50)) values of 93.3±0.5% and 79.3±0.4 μM, respectively.

NCBI PubMed ID: 22253110
Publication DOI: 10.1002/cbdv.201100025
Journal NLM ID: 101197449
Publisher: Verlag Helvetica Chimica Acta
Correspondence: thlee@tmu.edu.tw
Institutions: Institute of Plant and Microbial Biology, Academia Sinica, Taipei, Taiwan, Graduate Institute of Pharmacognosy, Taipei Medical University, Taipei, Taiwan, L5 Research Center, China Medical University Hospital, Taichung, Taiwan, School of Pharmacy, Taipei Medical University, Taipei, Taiwan, Genomics Research Center, Academia Sin, Taipei, Taiwan
Methods: 13C NMR, 1H NMR, IR, TLC, ESI-MS, acid hydrolysis, UV, HPAEC-PAD, extraction, optical rotation measurement, CC, RP-HPLC, cell growth, HR-ESI-MS, determination of NO production, cell viability assay, evaporation

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

Seven undescribed isopimarane diterpene glycosides hypoxylonoids A-G, along with five known analogues were obtained from the fungus Xylaria hypoxylon. The structures and absolute configurations of hypoxylonoids A-G were confirmed by extensive spectroscopic and single-crystal X-ray diffraction analyses. Among these compounds, the γ-lactone moiety formed between C-19 and C-6 of hypoxylonoid A; the 1,2-methyl shift of Me-18 of hypoxylonoids B and E; and the decarboxylation of C-19 of hypoxylonoid E, make them outstanding from the isopimarane family. Single crystal X-ray diffraction analyses of hypoxylonoids A, C, F, and 15-hydroxy-16-α-D-mannopyranosyloxyisopimar-7-en-19-oic acid was performed to determine their absolute structural configuration.

Xylariaceae, Isopimarane diterpene glycosides, X-ray diffraction analyses, Xylaria hypoxylon

NCBI PubMed ID: 33316595
Publication DOI: 10.1016/j.phytochem.2020.112613
Journal NLM ID: 0151434
Publisher: Elsevier
Correspondence: C. Chen ; Y. Zhang
Institutions: Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, Tongji Medical College, Huazhong University of Science and Technology, Wuhan, 430030, Hubei Province, China, State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650204, Yunnan Province, China
Methods: 13C NMR, 1H NMR, NMR-2D, X-ray, TLC, GC, FTIR, HPLC, extraction, optical rotation measurement, fermentation, HR-ESI-MS, antibacterial assay, cytotoxicity assay, NO production, enzyme inhibition assay