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Planta Med 2016; 82(05): 414-417
DOI: 10.1055/s-0035-1558331
Biological and Pharmacological Activity
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Antiviral and Cytotoxic Isocoumarin Derivatives from an Endophytic Fungus Aspergillus oryzae

Min Zhou
1   Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan Minzu University, Kunming, P. R. China
2   School of Ethnic Medicine, Yunnan Minzu University, Kunming, P. R. China
3   Technology Center, China Tobacco Yunnan Industry Company (Ltd.), Kunming, P. R. China
,
Kun Zhou
1   Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan Minzu University, Kunming, P. R. China
2   School of Ethnic Medicine, Yunnan Minzu University, Kunming, P. R. China
,
Pei He
3   Technology Center, China Tobacco Yunnan Industry Company (Ltd.), Kunming, P. R. China
,
Kun-Miao Wang
3   Technology Center, China Tobacco Yunnan Industry Company (Ltd.), Kunming, P. R. China
,
Rui-Zhi Zhu
3   Technology Center, China Tobacco Yunnan Industry Company (Ltd.), Kunming, P. R. China
,
Yue-De Wang
1   Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan Minzu University, Kunming, P. R. China
2   School of Ethnic Medicine, Yunnan Minzu University, Kunming, P. R. China
,
Wei Dong
1   Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan Minzu University, Kunming, P. R. China
2   School of Ethnic Medicine, Yunnan Minzu University, Kunming, P. R. China
,
Gan-Peng Li
1   Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan Minzu University, Kunming, P. R. China
2   School of Ethnic Medicine, Yunnan Minzu University, Kunming, P. R. China
,
Hai-Ying Yang
1   Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan Minzu University, Kunming, P. R. China
,
Yan-Qing Ye
1   Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan Minzu University, Kunming, P. R. China
,
Gang Du
1   Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan Minzu University, Kunming, P. R. China
2   School of Ethnic Medicine, Yunnan Minzu University, Kunming, P. R. China
,
Xue-Mei Li
3   Technology Center, China Tobacco Yunnan Industry Company (Ltd.), Kunming, P. R. China
,
Qiu-Fen Hu
1   Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan Minzu University, Kunming, P. R. China
2   School of Ethnic Medicine, Yunnan Minzu University, Kunming, P. R. China
› Author Affiliations
Further Information

Publication History

received 14 September 2015
revised 03 November 2015

accepted 09 November 2015

Publication Date:
29 January 2016 (online)

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Abstract

Oryzaeins A–D (1-4), four new isocoumarin derivatives, along with five known ones (5-9) were isolated from solid cultures of an endophytic fungus Aspergillus oryzae. Their structures were elucidated by detailed spectroscopic analysis and by comparison with reported data of related derivatives. Among them, compounds 1 and 2 represent the first examples of isocoumarins possessing an unusual 2-oxopropyl group and a rare 3-hydroxypropyl group. Compounds 1 and 2 displayed moderate anti-tobacco mosaic virus activities with inhibition rates of 28.4 % and 30.6 %, respectively, at the concentration of 20 µM. The new compounds showed moderate inhibitory activities against several human tumor cell lines with IC50 values in the range of 2.8–8.8 µM.

Supporting information available online at http://www.thieme-connect.de/products

Key words

Aspergillus oryzae - Trichocomaceae - isocoumarin derivatives - anti-tobacco mosaic virus activity - cytotoxicity

Supporting Information

 

  • References

  • 1 Sanchez JF, Somoza AD, Keller NP, Wang CC. Advances in Aspergillus secondary metabolite research in the post-genomic era. Nat Prod Rep 2012; 29: 351-371
    CrossrefPubMedSearch in Google Scholar
  • 2 Zhou YM, Debbab A, Mándi A, Wray V, Schulz B, Müller WEG, Kassack M, Lin WH, Kurtán T, Proksch P, Aly AH. Alkaloids from the sponge-associated fungus Aspergillus sp. Eur J Org Chem 2013; 32: 894-906
    PubMedSearch in Google Scholar
  • 3 Zhou M, Miao MM, Du G, Li XN, Shang SZ, Zhao W, Liu ZH, Yang GY, Che CT, Hu QF, Gao XM. Aspeverin, Aspergillines A–E, highly oxygenated hexacyclic indole-tetrahydrofuran-tetramic acid derivatives from Aspergillus versicolor . Org Lett 2014; 16: 5016-5019
    CrossrefPubMedSearch in Google Scholar
  • 4 Rokas A. The effect of domestication on the fungal proteome. Trends Genet 2009; 25: 60-63
    CrossrefPubMedSearch in Google Scholar
  • 5 Wang H, Liu L, Guo YX, Dong YS, Zhang DJ, Xiu ZL. Biotransformation of piceid in Polygonum cuspidatum to resveratrol by Aspergillus oryzae . Appl Microbiol Biotechnol 2007; 75: 763-768
    CrossrefPubMedSearch in Google Scholar
  • 6 Qiao MF, Ji NY, Liu XH, Li K, Zhu QM, Xue QZ. Indoloditerpenes from an algicolous isolate of Aspergillus oryzae . Bioorg Med Chem Lett 2010; 20: 5677-5680
    CrossrefPubMedSearch in Google Scholar
  • 7 Shang SZ, Xu WX, Li L, Tang JG, Zhao W, Lei P, Miao MM, Sun HD, Pu JX, Chen YK, Yang GY. Antiviral isocoumarins from the roots and stems of Nicotiana tabacum . Phytochem Lett 2015; 11: 53-56
    CrossrefPubMedSearch in Google Scholar
  • 8 Ye YQ, Xia CF, Yang JX, Yang YC, Gao XM, Du G, Yang HY, Li YK, Hu QF. Isocoumarins from the back of Lindera caudate . Heterocycles 2014; 89: 2365-2374
    PubMedSearch in Google Scholar
  • 9 Zhou M, Lou J, Li YK, Wang YD, Zhou K, Ji BK, Dong W, Gao XM, Du G, Hu QF. Versicolols A and B, two new prenylated isocoumarins from endophytic fungus Aspergillus versicolor and their cytotoxic activity. Arch Pharm Res advance online publication 07.03.2015;
    PubMedSearch in Google Scholar
  • 10 Li RX, Chen SX, Niu SB, Guo LD, Yin J, Che YS. Exserolides A–F, new isocoumarin derivatives from the plant endophytic fungus Exserohilum sp. Fitoterapia 2014; 96: 88-94
    CrossrefPubMedSearch in Google Scholar
  • 11 Zhou M, Du G, Yang HY, Xia CF, Yang JX, Li XN, Ye YQ, Gao XM, Du G, Hu QF. Antiviral butyrolactones from the endophytic fungus Aspergillus versicolor . Planta Med 2015; 81: 235-240
    Thieme ConnectPubMedSearch in Google Scholar
  • 12 Reed LJ, Muench H. A simple method of estimating fifty percent endpoints. Am J Epidemiol 1938; 27: 493-497
    PubMedSearch in Google Scholar