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Daphnepedunins G and H, anti-HIV macrocyclic 3,4-seco-daphnane orthoesters from Daphne pedunculata

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Abstract

Daphnepedunins G (1) and H (2) with unusual macrocyclic 3,4-seco-daphnane orthoester structure were isolated from Daphne pedunculata. Their structures were determined by physicochemical and spectroscopic analyses combined with synthetic methods, including methyl esterification, derivatization reaction using a chiral anisotropic agent, and biomimetic conversion. Compounds 1 and 2 along with their methyl esters 1a and 2a were evaluated for anti-HIV activity, among which 1a and 2a exhibited potent activity with IC50 values of 1.08 and 1.17 μM, respectively.

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Acknowledgements

The investigation was supported by the Japan Society for the Promotion of Science KAKENHI 21K06619 (W. L.). This work was also supported by the United States National Institute of Allergy and Infectious Diseases (NIAID) R01 AI165473 (C. H. C.). We appreciate the editing of the manuscript by Ms. Jessica Bronchick at the Duke University School of Medicine.

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Authors and Affiliations

  1. Faculty of Pharmaceutical Sciences, Toho University, Miyama 2-2-1, Funabashi, Chiba, 274-8510, Japan

    Lingjian Tan, Kouharu Otsuki, Mi Zhang, Takashi Kikuchi & Wei Li

  2. School of Traditional Chinese Materia Medica, Key Laboratory of Innovative Traditional Chinese Medicine for Major Chronic Diseases of Liaoning Province, Key Laboratory for TCM Material Basis Study and Innovative Drug Development of Shenyang City, Shenyang Pharmaceutical University, Shenyang, 110016, People’s Republic of China

    Di Zhou & Ning Li

  3. Surgical Sciences, Department of Surgery, Duke University Medical Center, Durham, NC, 27710, USA

    Li Huang & Chin-Ho Chen

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  1. Lingjian Tan
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Correspondence to Kouharu Otsuki or Wei Li.

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Tan, L., Otsuki, K., Zhang, M. et al. Daphnepedunins G and H, anti-HIV macrocyclic 3,4-seco-daphnane orthoesters from Daphne pedunculata. J Nat Med 78, 114–122 (2024). https://doi.org/10.1007/s11418-023-01750-6

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