Journal of Integrative Agriculture ›› 2016, Vol. 15 ›› Issue (4): 832-839.DOI: 10.1016/S2095-3119(15)61145-5

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Isolation, identification, derivatization and phytotoxic activity of secondary metabolites produced by Cladosporium oxysporum DH14, a locust-associated fungus

LU Yi-hui1, LI Shuai1, SHAO Ming-wei1, XIAO Xiao-hui1, KONG Li-chun1, JIANG Dong-hua1, ZHANG Ying-lao1, 2   

  1. 1 College of Chemistry and Life Sciences, Zhejiang Normal University, Jinhua 321004, P.R.China
    2 State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing 210093, P.R.China
  • 收稿日期:2015-04-07 出版日期:2016-04-01 发布日期:2016-04-07
  • 通讯作者: ZHANG Ying-lao, Tel/Fax: +86-579-82282269, E-mail: ylzhang@zjnu.cn
  • 基金资助:

    This work was co-financed by the National Natural Science Foundation of China (NSFC) (21002092 and 21272215) and  the Open Project of State Key Laboratory of Pharmaceutical Biotechnology in Nanjing University, China (KF-GN-201411).

Isolation, identification, derivatization and phytotoxic activity of secondary metabolites produced by Cladosporium oxysporum DH14, a locust-associated fungus

LU Yi-hui1, LI Shuai1, SHAO Ming-wei1, XIAO Xiao-hui1, KONG Li-chun1, JIANG Dong-hua1, ZHANG Ying-lao1, 2   

  1. 1 College of Chemistry and Life Sciences, Zhejiang Normal University, Jinhua 321004, P.R.China
    2 State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing 210093, P.R.China
  • Received:2015-04-07 Online:2016-04-01 Published:2016-04-07
  • Contact: ZHANG Ying-lao, Tel/Fax: +86-579-82282269, E-mail: ylzhang@zjnu.cn
  • Supported by:

    This work was co-financed by the National Natural Science Foundation of China (NSFC) (21002092 and 21272215) and the Open Project of State Key Laboratory of Pharmaceutical Biotechnology in Nanjing University, China (KF-GN-201411).

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摘要： Three main phytotoxic compounds including lunatoic acid A (1), 5Z-7-oxozeaenol (2) and zeaenol (3) were isolated from the fermentation broth of Cladosporium oxysporum DH14, a fungus residing in the locust (Oxya chinensis ) gut.  Two additional derivative compounds, compound 1a and 1b, were synthesized by methylation and chlorination of compound 1, respectively.  The structures of such compounds were identified on the basis of spectroscopic analysis and by comparison of the corresponding data to those previously reported in the literature.  Compounds 1–3 exhibited significantly phytotoxic activities against the radicle growth of Amaranthus retroflexus L. with the 50% inhibitory concentrations (IC50 values) of 4.51, 4.80 and 8.16 μg mL–1, respectively, which is comparable to that positive control 2,4-dichlorophenoxyacetic acid (IC50=1.95 μg mL–1).  Furthermore, the compound 1 showed selective phytotoxic activity with the inhibition rate of less than 22% against the crops of Brassica rapa L., Sorghum durra, Brassica campestris L., Capsicum annucm and Raphanus sativus L. under the concentration of 100 μg mL–1.  Both derivatives of compound 1 had moderate phytotoxic activity against the radicle growth of A. retroflexus L.  The findings of our present study suggest that these compounds provide new promising candidates for the potential management strategies of weeds.

关键词: Oxya chinensis ,  phytotoxic activity ,  Cladosporium oxysporum ,  phytotoxic metabolites ,  derivatization

Abstract: Three main phytotoxic compounds including lunatoic acid A (1), 5Z-7-oxozeaenol (2) and zeaenol (3) were isolated from the fermentation broth of Cladosporium oxysporum DH14, a fungus residing in the locust (Oxya chinensis ) gut.  Two additional derivative compounds, compound 1a and 1b, were synthesized by methylation and chlorination of compound 1, respectively.  The structures of such compounds were identified on the basis of spectroscopic analysis and by comparison of the corresponding data to those previously reported in the literature.  Compounds 1–3 exhibited significantly phytotoxic activities against the radicle growth of Amaranthus retroflexus L. with the 50% inhibitory concentrations (IC50 values) of 4.51, 4.80 and 8.16 μg mL–1, respectively, which is comparable to that positive control 2,4-dichlorophenoxyacetic acid (IC50=1.95 μg mL–1).  Furthermore, the compound 1 showed selective phytotoxic activity with the inhibition rate of less than 22% against the crops of Brassica rapa L., Sorghum durra, Brassica campestris L., Capsicum annucm and Raphanus sativus L. under the concentration of 100 μg mL–1.  Both derivatives of compound 1 had moderate phytotoxic activity against the radicle growth of A. retroflexus L.  The findings of our present study suggest that these compounds provide new promising candidates for the potential management strategies of weeds.

Key words: Oxya chinensis ,  phytotoxic activity ,  Cladosporium oxysporum ,  phytotoxic metabolites ,  derivatization