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Hispidulones A and B, two new phenalenone analogs from desert plant endophytic fungus Chaetosphaeronema hispidulum

The Journal of Antibiotics volume 73, pages 56–59 (2020)Cite this article

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Abstract

Two new phenalenone analogs hispidulones A (1) and B (2) were isolated from the specially bioenvironmental desert plant endophytic fungus Chaetosphaeronema hispidulum. The structure of these two compounds were elucidated by extensive spectra analysis including HR-ESI-MS, NMR (1H, 13C, 1H–1H COSY, HSQC, and HMBC), CD, and electronic circular dichroism (ECD) combined with quantum-chemical calculations adopting time-dependent density functional theory (TDDFT) approaches. The W long-ranged 1H–1H COSY and HMBC correlations are very important in the structural elucidation of these two compounds. Hispidulone A (1) possesses a cyclohexa-2,5-dien-1-one moiety, whereas hispidulone B (2) contains a hemiacetal OCH3 group, which are very rare in the structures of phenalenone analogs. According to structural features of these two compounds together considering the literature, the possible biosynthetic pathway of 1 and 2 was postulated. Hispidulone B (2) displayed cytotoxic activities against three cancer cell lines A549, Huh7, and HeLa with IC50 values of 2.71 ± 0.08, 22.93 ± 1.61, and 23.94 ± 0.33 μM.

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Acknowledgements

We acknowledge financial support from CAMS Initiative for Innovative Medicine (2017-I2M-4-004 for GD), the National Key Research and Development Program of China “Research and Development of Comprehensive Technologies on Chemical Fertilizer and Pesticide Reduction and Synergism” (2017YFD0201402 for GD), the National Major Increase or Decrease Project-Construction of the Sustainable Utilization Capacity of Famous Traditional Chinese Medicine Resources (2060302 for JQ), and the Open Funding Project of the State Key Laboratory of Bioactive Substance and Function of Natural Medicines (GTZK201903 for BS).

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Authors and Affiliations

  1. Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine, Ministry of Education, Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences and Peking Union Medical College, 100193, Beijing, China

    Xiaoyan Zhang, Xiangmei Tan, Yuanyuan Li, Yanduo Wang, Meng Yu & Gang Ding

  2. College of Plant Sciences, Jilin University, 130062, Changchun, China

    Jianchun Qing

  3. Institute of Microbiology, Chinese Academy of Sciences, 100090, Beijing, China

    Bingda Sun

  4. School of Biological Medicine, Beijing City University, 100083, Beijing, China

    Shubin Niu

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  1. Xiaoyan Zhang
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Correspondence to Gang Ding.

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Zhang, X., Tan, X., Li, Y. et al. Hispidulones A and B, two new phenalenone analogs from desert plant endophytic fungus Chaetosphaeronema hispidulum. J Antibiot 73, 56–59 (2020). https://doi.org/10.1038/s41429-019-0247-z

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