2. Academic Validation
  3. Cyclopiazonic acid type indole alkaloids from Nicotiana tabacum-derived fungus Aspergillus versicolor and their anti-tobacco mosaic virus activities

Cyclopiazonic acid type indole alkaloids from Nicotiana tabacum-derived fungus Aspergillus versicolor and their anti-tobacco mosaic virus activities

  • Phytochemistry. 2022 Jun;198:113137. doi: 10.1016/j.phytochem.2022.113137.
Guang-Yu Yang 1,  Jia-Meng Dai 2,  Qi-Li Mi 2,  Zhen-Jie Li 2,  Xue-Mei Li 2,  Jian-Duo Zhang 2,  Jin Wang 2,  Yin-Ke Li 1,  Wei-Guang Wang 3,  Min Zhou 4,  Qiu-Fen Hu 5
Affiliations

Affiliations

  • 1 Yunnan Key Laboratory of Tobacco Chemistry, China Tobacco Yunnan Industrial Co., Ltd, Kunming, 650231, PR China; Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission and Ministry of Education and Key Laboratory of Natural Products Synthetic Biology of Ethnic Medicinal Endophytes, State Ethnic Affairs Commission, Yunnan Minzu University, Kunming, 650031, China.
  • 2 Yunnan Key Laboratory of Tobacco Chemistry, China Tobacco Yunnan Industrial Co., Ltd, Kunming, 650231, PR China.
  • 3 Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission and Ministry of Education and Key Laboratory of Natural Products Synthetic Biology of Ethnic Medicinal Endophytes, State Ethnic Affairs Commission, Yunnan Minzu University, Kunming, 650031, China.
  • 4 Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission and Ministry of Education and Key Laboratory of Natural Products Synthetic Biology of Ethnic Medicinal Endophytes, State Ethnic Affairs Commission, Yunnan Minzu University, Kunming, 650031, China. Electronic address: zhouminynun@163.com.
  • 5 Yunnan Key Laboratory of Tobacco Chemistry, China Tobacco Yunnan Industrial Co., Ltd, Kunming, 650231, PR China; Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission and Ministry of Education and Key Laboratory of Natural Products Synthetic Biology of Ethnic Medicinal Endophytes, State Ethnic Affairs Commission, Yunnan Minzu University, Kunming, 650031, China. Electronic address: huqiufena@aliyun.com.
PMID: 35240133 DOI: 10.1016/j.phytochem.2022.113137
Abstract

Indole Alkaloids have attracted widespread attention of chemists and biologists. Therefore, the aim of this study is to screen more bioactivities Indole Alkaloids from the Microorganisms. In this study, five undescribed CPA-type Indole Alkaloids, aspergillines F-J, and three known CPA-type Indole Alkaloids, aspergilline A, aspergilline C, and cyclopiamide E, were obtained from the Nicotiana tabacum-derived fungus Aspergillus versicolor. Notably, aspergillines F and G represent the first examples of Indole Alkaloids with a benzo[cd]indol-2(1H)-one skeleton, and aspergilline J is also the firstly obtained Indole Alkaloids bearing a N-1-(2-(1H-imidazole-5-yl)ethyl) moiety. Aspergillines F-J and cyclopiamide E were tested for their anti-TMV activities, and the results revealed that aspergillines G and J exhibited obvious anti-TMV activities with inhibition rates of 41.2 and 56.8% at the concentration of 20 μM, respectively. These rates are high than that of positive control (with inhibition rate of 32.5%). In addition, the molecular docking studies for the isolated CPA-type Indole Alkaloids may also reveal that the benzo[cd]indol-2(1H)-one substructure is the fundamental for anti-TMV activity and the oxygen-containing substituent groups at C-19 also increases the inhibitory activity. This study of structure-activity relationship is helpful to find new anti-TMV activity inhibitors.

Keywords

Anti-TMV activities; Aspergillus versicolor; CPA-Type indole alkaloids; Family Trichocomaceae; Nicotiana tabacum derived Fungus.

Figures
Products
  • Cat. No.
    Product Name
    Description
    Target
    Research Area
  • HY-152259
    TMV Inhibitor
    TMV