Volume 1 Issue 1
Sep.  2021
Turn off MathJax
Article Contents
Sen-Feng Sun, Shao Zhu, Hai-Yan Cao, Yun-Bao Liu, Shi-Shan Yu. Tridepsides from the endophytic fungus colletotrichum gloeosporioides associated with a toxic medicinal plant tylophora ovata[J]. Frigid Zone Medicine, 2021, 1(1): 45-51. doi: 10.2478/fzm-2021-0006
Citation: Sen-Feng Sun, Shao Zhu, Hai-Yan Cao, Yun-Bao Liu, Shi-Shan Yu. Tridepsides from the endophytic fungus colletotrichum gloeosporioides associated with a toxic medicinal plant tylophora ovata[J]. Frigid Zone Medicine, 2021, 1(1): 45-51. doi: 10.2478/fzm-2021-0006

Tridepsides from the endophytic fungus colletotrichum gloeosporioides associated with a toxic medicinal plant tylophora ovata

doi: 10.2478/fzm-2021-0006
More Information
  •   Introduction  Bioactive secondary metabolites from the microbes living in frigid, toxic or other extreme environments are emerging as a new medicinal resource. Here, we report the discovery of new antidiabetic and anti-inflammatory compounds with novel structures from endophytic fungi hosted toxic medicinal plant.  Methods  The endophytic fungus isolated from toxic plants was fermented and extracted. The obtained extracts were purified with preparative HPLC to yield pure compounds. The purified compounds were examined by PTP1b inhibition and NO inhibition assays to evaluate their bioactivities.  Results  One new tridepsides (Compound 1), one new benzeneacetic acid derivative (Compound 3) and five known compounds (Compounds 2 and 4-7) were isolated from the ethyl acetate extract of Colletotrichum gloeosporioides, an endophytic fungus obtained from a toxic medicinal plant Tylophora ovata. Their structures were determined by spectroscopic data (1D and 2D NMR, HRESIMS) analyses. Compound 2 showed significant inhibitory activity against PTP1b with an IC50 value of 0.84 μM. Compounds 2 and 3 exhibited moderate inhibitory activities against the NO (nitric oxide) release in LPS-induced RAW 264.7 cells at 10 μM with percent inhibition of 39% and 33%, respectively.  Conclusion  The Compound 2 has potent PTP1b inhibitory effect indicating its antidiabetic potential and thus might be considered a lead compound for antidiabetic drug development.

     

  • loading
  • [1]
    Liu Y B, Ding G Z, Li Y, et al. Structures and absolute configurations of penicillactones A–C from an endophytic microorganism, penicillium dangeardii pitt. Org. Lett, 2013; 15: 5206-5209. doi: 10.1021/ol4023485
    [2]
    Liu Y B, Li Y, Qu J, et al. Eremophilane sesquiterpenes and polyketones produced by an endophytic guignardia fungus from the toxic plant gelsemium elegans. J. Nat. Prod, 2015; 78: 2149-2154. doi: 10.1021/np5009027
    [3]
    Liu J Y, Zhao X, Liang X X, et al. Dothiorelone derivatives from an endophyte diaporthe pseudomangiferaea inhibit the activation of human lung fibroblasts MRC-5 cells. Fitoterapia, 2018; 127: 7-14. doi: 10.1016/j.fitote.2018.04.009
    [4]
    Liu Y B, Li Y, Liu Z, et al. Sesquiterpenes from the endophyte glomerella cingulata. J. Nat. Prod, 2017; 80: 2609-2614. doi: 10.1021/acs.jnatprod.7b00054
    [5]
    Liu Z, Zhao J Y, Sun S F, et al. Sesquiterpenes from an endophytic aspergillus flavus. J. Nat. Prod, 2019; 82: 1063-1071. doi: 10.1021/acs.jnatprod.8b01084
    [6]
    Zou W X, Meng J C, Lu H, et al. Metabolities of colletorichum gloeosrioides, an endophytic fungus in Artemisia mongolica, J. Nat. Prod, 2000; 63: 1529-1530. doi: 10.1021/np000204t
    [7]
    Bang S, Lee C, Kim S, et al. Neuroprotective glycosylated cyclic lipodepsipeptides, Colletotrichamides A-E, from a halophyte-associated fungus, Colletotrichu-m gloeosporioides JS419. J. Org. Chem, 2019; 84: 10999-11006. doi: 10.1021/acs.joc.9b01511
    [8]
    Luo Y P, Zheng C J, Chen G Y, et al. Three new polyketides from a mangrove-derived fungus Colletotrichum gloeosporioides. J. Antibiot, 2019; 72: 513-517. doi: 10.1038/s41429-019-0178-8
    [9]
    Yang Z D, Li Z J, Zhao J W, et al. Secondary metabolites and PI3K inhibitory activity of Colletotrichum gloeosporioides, a fungal endophyte of Uncaria rhynchophylla. Curr. Microbiol, 2019; 76: 904-908. doi: 10.1007/s00284-019-01707-7
    [10]
    Pamela N K, Sergi H A, Armelle T T, et al. Augustin, Colletotrin: a sesquiterpene lactone from the endophytic fungus Colletotrichum gloeosporioides associated with Trichilia monadelpha. J. Chem. Sci, 2017; 72: 697-703. http://www.degruyter.com/view/j/znb.2017.72.issue-10/znb-2017-0058/znb-2017-0058.xml?format=INT
    [11]
    Vanessa M C, Maria L Z, Ioanis H L, et al. Antifungal compounds produced by Colletotrichum gloeosporioides, an endophytic fungus from Michelia champac. Molecules, 2014; 19: 19243-19252. doi: 10.3390/molecules191119243
    [12]
    Inacio M L, Silva G H, Teles H L, et al. Antifungal metabolites from Colletotrichum gloeosporioides, an endophytic fungus in Cryptocarya mandioccana Nees (Lauraceae). Biochem. Syst. Ecol, 2006; 34: 822-824. doi: 10.1016/j.bse.2006.06.007
    [13]
    Liu H X, Tan H B, Chen Y C, et al. Secondary metabolites from the colletotrichum gloeosporioides A12, an endophytic fungus derived from Aquilaria sinensis. Nat. Prod. Rep, 2018; 32: 2360-2365. doi: 10.1080/14786419.2017.1410810
    [14]
    Andre A, Wojtowicz N, Toure K, et al. New acorane sesquiterpenes isolated from the endophytic fungus Colletotrichum gloeosporioides SNB-GSS07. Tetrahedron. Lett, 2017; 58: 1269-1272. doi: 10.1016/j.tetlet.2017.02.024
    [15]
    Chen X W, Yang Z D, Sun J H, et al. Colletotrichine A, a new sesquiterpenoid from Colletotrichum gloeosporioides GT-7, a fungal endophyte of Uncaria rhynchophylla. Nat. Prod. Rep, 2018; 32: 880-884. doi: 10.1080/14786419.2017.1365071
    [16]
    Li Y, Wei W, Wang R L, et al. Colletolides A and B, two new γ-butyrolactone derivatives from the endophytic fungus Colletotrichum gloeosporioide. Phytochem. Lett, 2019; 33: 90-93. doi: 10.1016/j.phytol.2019.08.004
    [17]
    Zhao J Y, Wang X J, Liu Z, et al. Nonadride and spirocyclic anhydride derivatives from the plant endophytic fungus Talaromyces purpurogenus. J. Nat. Prod, 2019; 82: 2953-2962. doi: 10.1021/acs.jnatprod.9b00210
    [18]
    Huneck S, Porzel A, Schmidt J, et al. A tridepside from Umbilicaria crustulosa. Phytochemistry, 1993; 32: 475-477. doi: 10.1016/S0031-9422(00)95022-2
    [19]
    Zou W X, Meng J C, Lu H, et al. Metabolites of colletotrichum gloeosporioides, an endophytic fungus in artemisia mongolica. J. Nat. Prod, 2000; 63: 1529-1530. doi: 10.1021/np000204t
    [20]
    Gao T, Cao F, Yu H, et al. Secondary metabolites from the marine fungus Aspergillus sydowii. Chem. Nat. Compd, 2017; 53: 1204-1207. doi: 10.1007/s10600-017-2241-7
    [21]
    Pedras M S, Yu Y, Liu J, et al. Metabolites produced by the phytopathogenic fungus Rhizoctonia solani: isolation, chemical structure determination, syntheses and bioactivity. Ztschrift. für Naturforschung, 2005; 60: 9-10. http://www.degruyter.com/dg/viewarticle.fullcontentlink:pdfeventlink/$002fj$002fznc.2005.60.issue-9-10$002fznc-2005-9-1010$002fznc-2005-9-1010.pdf/znc-2005-9-1010.pdf?t:ac=j$002fznc.2005.60.issue-9-10$002fznc-2005-9-1010$002fznc-2005-9-1010.xml
    [22]
    Gubiani J R, Teles H L, Silva G H, et al. Cyclo-(TRP-PHE) diketopiperazines from the endophytic fungus Aspergillus versicolor isolated from Piper aduncum. Quim. Nova, 2017; 40: 138-142. http://quimicanova.sbq.org.br/audiencia_pdf.asp?aid2=6521&nomeArquivo=AR20160256.pdf
    [23]
    Evidente A, Iacobellis N S, Sisto A. Isolation of indole-3-acetic acid methyl ester, a metabolite of indole-3-acetic acid from Pseudomonas amygdali. Experientia, 1993; 49: 182-183. doi: 10.1007/BF01989428
    [24]
    Zucconi L, Canini F, Temporiti M E, et al. Extracellular Enzymes and Bioactive Compounds from Antarctic Terrestrial Fungi for Bioprospecting. Int. J. Env. Res. Pub. He, 2020; 17: 6459. doi: 10.3390/ijerph17186459
    [25]
    Eleftheriou P, Geronikaki A, Petrou A. PTP1b Inhibition, A Promising Approach for the Treatment of Diabetes Type Ⅱ. Curr. Top. Med. Chem, 2019; 19: 246-263. doi: 10.2174/1568026619666190201152153
    [26]
    Sharma B, Xing L X, Yang F, et al. Recent advance on PTP1B inhibitors and their biomedical applications. Eur. J. Med. Chem, 2020; 199: 112376. doi: 10.1016/j.ejmech.2020.112376
  • 加载中

Catalog

    通讯作者: 陈斌, bchen63@163.com
    • 1. 

      沈阳化工大学材料科学与工程学院 沈阳 110142

    1. 本站搜索
    2. 百度学术搜索
    3. 万方数据库搜索
    4. CNKI搜索

    Figures(3)  / Tables(3)

    Article Metrics

    Article views (364) PDF downloads(5) Cited by()
    Proportional views
    Related

    /

    DownLoad:  Full-Size Img  PowerPoint
    Return
    Return