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Bioactive ambuic acid congeners from endophytic fungus Pestalotiopsis trachicarpicola SC-J551

The Journal of Antibiotics volume 77, pages 21–29 (2024)Cite this article

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Abstract

New ambuic acid derivatives, pestallic acids R–V (1−5), together with ambuic acid (6), were isolated from the endophytic fungus Pestalotiopsis trachicarpicola SC-J551 derived from the fern Blechnum orientale L., of which compound 2, being racemic, was separated to two optically pure enantiomers (+)-2 and (−)-2. The structures including absolute configurations of these new compounds were elucidated by extensive spectroscopic analysis and theoretical simulations of their ECD spectra and 13C NMR chemical shifts. Compounds 1 and 3 exhibited cytotoxicity against human carcinoma A549, HeLa, HepG2, and MCF-7 cells (IC50: 3.6–12.5 μM) and compound 3 was also active against Staphylococcus aureus and MRSA (MIC = 20 μg ml−1). Compound (±)-2 showed inhibitory activity against LPS-induced NO release (IC50 = 21.1 μM) and t-BHP-induced ROS production (IC50 = 8.5 μM) in RAW264.7 macrophages.

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Acknowledgements

We thank Mr. Yunfei Yuan, South China Botanical Garden, Chinese Academy of Sciences, for NMR spectroscopic measurements and Ms. Aijun Sun, South China Sea Institute of Oceanology, Chinese Academy of Sciences, for HRESIMS measurements. This work was supported by NSFC grants (Nos. 82073732 and 81872773). Electronic supplementary information (ESI) available on The Journal of Antibiotics website (http://www.nature.com/ja). Computational details, NMR spectra and HR-ESIMS of 1‒5, and HPLC chromatograms of 1‒6 (PDF).

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Authors and Affiliations

  1. Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences, Xingke Road 723, Tianhe District, Guangzhou, 510650, People’s Republic of China

    Fanyu Dong, Zhiming Jiang, Ping Wu, Fangfang Duan, Jinghua Xue, Haibo Tan & Xiaoyi Wei

  2. School of Life Sciences, University of Chinese Academy of Sciences, Yuquanlu 19A, Beijing, 100049, People’s Republic of China

    Fanyu Dong & Zhiming Jiang

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Correspondence to Ping Wu or Xiaoyi Wei.

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Dong, F., Jiang, Z., Wu, P. et al. Bioactive ambuic acid congeners from endophytic fungus Pestalotiopsis trachicarpicola SC-J551. J Antibiot 77, 21–29 (2024). https://doi.org/10.1038/s41429-023-00674-3

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