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Secondary Metabolites and PI3K Inhibitory Activity of Colletotrichum gloeosporioides, a Fungal Endophyte of Uncaria rhynchophylla

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Abstract

In the present study, nine compounds (1–9) were isolated from Colletotrichum gloeosporioides (an endophytic fungus from Uncaria rhynchophylla) which was cultured in wheat bran medium. Their structures were elucidated as 4-Epi-14-hydroxy-10, 23-dihydro-24, 25-dehydroaflavinine (1), 10, 23-Dihydro-24,25 -dehydro-21–oxoaflavinine (2), Ergosterol (3), Ergosterol peroxide (4), Mellein (5), 4, 5-dihydroblumenol A (6), Colletotrichine A (7), Cyclo(L-leucyl-L-leucyl) (8), and Brevianamide F (9) based on NMR spectral data, as well as comparing with previous literature data. This is the first report about the isolation of compounds 1–2, 6, and 8–9 from Colletotrichum genus. All compounds were tested for their phosphoinositide 3-kinase (PI3Kα) inhibitory activity. Compounds 8 and 9 showed potent PI3K α inhibitory activity with IC50 values of 38.1 and 4.8 µM, respectively, while the other compounds showed very weak activity at a concentration of 20 µg/mL.

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References

  1. Sun Z-L, Zhang M, Zhang J-F, Feng J (2011) Antifungal and cytotoxic activities of the secondary metabolites from endophytic fungus Massrison sp. Phytomedicine 18(10):859–862

    Article  CAS  PubMed  Google Scholar 

  2. Zhang H-W, Song Y-C, Tan R-X (2006) Biology and chemistry of endophytes. Nat Prod Rep 23(5):753–771

    Article  CAS  PubMed  Google Scholar 

  3. Wei B, Yang Z-D, Chen X-W, Zhou S-Y, Yu H-T, Sun J-Y, Yao X-J, Wang Y-G, Xue H-Y (2016) Colletotrilactam A-D, novel lactams from Colletotrichum gloeosporioides GT-7, a fungal endophyte of Uncaria rhynchophylla. Fitoterapia 113:158–163

    Article  CAS  PubMed  Google Scholar 

  4. Chen X-W, Yang Z-D, Sun J-H, Song T-T, Zhu B-Y, Zhao J-W (2018) Colletotrichine A, a new sesquiterpenoid from Colletotrichum gloeosporioides GT-7, a fungal endophyte of Uncaria rhynchophylla. Nat Prod Res 32(8):880–884

    Article  CAS  PubMed  Google Scholar 

  5. Liu Y, Li X-M, Meng L-H, Jiang W-L, Xu G-M, Huang C-G, Wang B-G (2015) Bisthiodiketopiperazines and acorane sesquiterpenes produced by the marine-derived fungus Penicillium adametzioides AS-53 on different culture media. J Nat Prod 78(6):1294–1299

    Article  CAS  PubMed  Google Scholar 

  6. Yamazaki H, Rotinsulu H, Narita R, Takahashi R, Namikoshi M (2015) Induced production of halogenated epidithiodiketopiperazines by a marine-derived Trichoderma cf. brevicompactum with sodium halides. J Nat Prod 78(10):2319–2321

    Article  CAS  PubMed  Google Scholar 

  7. Stephens L, Williams R, Hawkins P (2005) Phosphoinositide 3-kinases as drug targets in cancer. Curr Opin Pharmacol 5(4):357–365

    Article  CAS  PubMed  Google Scholar 

  8. Wu C-J, Zhao J-L, Zhou Z-X, Lei D-U, Liu B-B, Sun T-M (2014) Research progress of selective PI3K inhibitors. Central South Pharm 12(4):305–310

    CAS  Google Scholar 

  9. Han F, Lin S, Liu P, Liu X, Tao J, Deng X, Yi C, Xu H (2015) Discovery of a novel series of thienopyrimidine as highly potent and selective PI3K inhibitors. ACS Med Chem Lett 6(4):434–438

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  10. Tepaske MR, Gloer JB, Wicklow DT, Dowd PF (1989) Three new aflavinines from the sclerotia of Aspergillus tubingensis. Tetrahedron 45(16):4961–4968

    Article  CAS  Google Scholar 

  11. Zhang Y, Mills GL, Nair MG (2002) Cyclooxygenase inhibitory and antioxidant compounds from the mycelia of the edible mushroom Grifola frondosa. J Agric Food Chem 50(26):7581–7585

    Article  CAS  PubMed  Google Scholar 

  12. Sun H-F, Zhao J, Zhao J, Xun X-I, Qin C-H, Xu A-L, Xia Y (2013) Preliminary study on separation and purification of endophytic microorganism from water hyacinth and metabolic product fromEichhornia crassipes fungus. J Qingdao Technol Univ 34(6):44–48

    CAS  Google Scholar 

  13. Wang J-Y, Wang G-P, Zhang Y-L, Zheng B-Q, Zhang C-L, Wang L-W (2014) Isolation and identification of an endophytic fungus Pezicula sp. in Forsythia viridissima and its secondary metabolites. World J Microbiol Biotechnol 30:2639–2644

    Article  CAS  PubMed  Google Scholar 

  14. González AG, Guillermo JA, Ravelo AG, Jimenez IA, Gupta MP (1994) 4,5-Dihydroblumenol A, a New Nor-isoprenoid from Perrottetia multiflora. J Nat Prod 57(3):400–402

    Article  Google Scholar 

  15. Hensens OD, Goetz MA, Liesch JM, Zink DL, Raghoobar SL, Helms GL, Singh SB (1995) Isolation and structure of flutimide, a novel endonuclease inhibitor of influenza virus. Tetrahedron Lett 36(12):2005–2008

    Article  CAS  Google Scholar 

  16. Kobayashi M, Aoki S, Gato K, Matsunami K, Kurosu M, Kitagawa I (1994) Marine natural products. XXXIV. Trisindoline, a new antibiotic indole trimer, produced by a bacterium of Vibrio sp. separated from the marine sponge Hyrtios altum. Chem Pharm Bull 42(12):2449–2451

    Article  CAS  PubMed  Google Scholar 

  17. Alberdi-Cedeño J, Ibargoitia ML, Guillén MD (2017) Bioactive compounds detected for the first time in corn oil: cyclic dipeptides and other nitrogenated compounds. J Food Compos Anal 62:197–204

    Article  CAS  Google Scholar 

  18. Jing S-S, Wang Y, Li X-J, Li X, Zhao W-S, Zhou B, Zhao C-C, Huang L-Q, Gao W-Y (2017) Phytochemical and chemotaxonomic studies on Dioscorea collettii. Biochem Syst Ecol 71:10–15

    Article  CAS  Google Scholar 

  19. Li S-Q, Yang Y-B, Yang X-Q, Jiang Y, Li Z-J, Li X-Z, Chen X, Li Q-L, Qin S-H, Ding Z-T (2016) Two new cyclic tetrapeptides of Streptomyces rutgersensis T009 isolated from Elaphodus davidianus excrement. Helv Chim Acta 99(3):210–214

    Article  CAS  Google Scholar 

  20. Huang H, She Z, Lin Y, Vrijmoed L, Lin W (2007) Cyclic peptides from an endophytic fungus obtained from a mangrove leaf (Kandelia candel). J Nat Prod 70(11):1696–1699

    Article  CAS  PubMed  Google Scholar 

  21. Leyton Y, Borquez J, Darias J, Cueto M, Díaz-Marrero A, Riquelme C (2012) Diketopiperazines produced by an Bacillus species inhibits Vibrio parahaemolyticus. J Aquacult Res Dev 3(4):1–10. https://doi.org/10.4172/2155-9546.1000144

    Article  CAS  Google Scholar 

  22. Furukawa T, Akutagawa T, Funatani H, Uchida T, Hotta Y, Niwa M, Takaya Y (2012) Cyclic dipeptides exhibit potency for scavenging radicals. Bioorg Med Chem 20(6):2002–2009

    Article  CAS  PubMed  Google Scholar 

  23. Deng L, Wang R, Wang G, Liu M, Liao Z, Liao G, Chen M (2018) Roseosporol A, the first isolation of a novel sesquiterpenoid from Streptomyces roseosporus. Nat Prod Res 11:1–6

    Article  Google Scholar 

  24. Wen H, Liu X, Zhang Q, Deng Y, Zang Y, Wang J, Liu J, Zhou Q, Hu L, Zhu H (2018) Three new indole diketopiperazine alkaloids from Aspergillus ochraceus. Chem Biodivers 15(4):e1700550

    Article  CAS  PubMed  Google Scholar 

  25. Wang X, Li J, Yu S, Ye L, Feng M, Li J (2017) Peniproline A, a new 1-phenylamino-2-pyrrolidone metabolite from the endophytic fungus Penicillium decumbens CP-4. Nat Prod Res 31(15):1772–1777

    Article  CAS  PubMed  Google Scholar 

  26. El-Gendy BE-DM, Rateb ME (2015) Antibacterial activity of diketopiperazines isolated from a marine fungus using t-butoxycarbonyl group as a simple tool for purification. Bioorg Med Chem Lett 25(16):3125–3128

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. School of Life Science and Engineering, Lanzhou University of Technology, 287 Lan Gong Pin Road, Qi Li He Block, Lanzhou, 730050, Gansu Province, People’s Republic of China

    Zhong-Duo Yang, Zhi-Jie Li, Jun-Wen Zhao, Jian-Hui Sun, Li-Jun Yang & Zong-Mei Shu

  2. The Provincial Education Key Laboratory of Screening, Evaluation and Advanced Processing of Traditional Chinese Medicine and Tibetan Medicine, School of Life Science and Engineering, Lanzhou University of Technology, Lanzhou, 730050, People’s Republic of China

    Zong-Mei Shu

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  1. Zhong-Duo Yang
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Yang, ZD., Li, ZJ., Zhao, JW. et al. Secondary Metabolites and PI3K Inhibitory Activity of Colletotrichum gloeosporioides, a Fungal Endophyte of Uncaria rhynchophylla. Curr Microbiol 76, 904–908 (2019). https://doi.org/10.1007/s00284-019-01707-7

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  • DOI: https://doi.org/10.1007/s00284-019-01707-7

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