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Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Org. Chem. 2020, 85, 16, 10806-10812
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Bungsteroid A: One Unusual C34 Pentacyclic Steroid Analogue from Zanthoxylum bungeanum Maxim

  • Xian-Hua Meng
    Xian-Hua Meng
    CAS Key Laboratory of Chemistry of Northwestern Plant Resources and Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences (CAS), Lanzhou 730000, People’s Republic of China
    More by Xian-Hua Meng
    • , 
  • Tian Chai
    Tian Chai
    CAS Key Laboratory of Chemistry of Northwestern Plant Resources and Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences (CAS), Lanzhou 730000, People’s Republic of China
    More by Tian Chai
    • , 
  • Yan-Ping Shi
    Yan-Ping Shi
    CAS Key Laboratory of Chemistry of Northwestern Plant Resources and Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences (CAS), Lanzhou 730000, People’s Republic of China
    More by Yan-Ping Shi
    Orcidhttp://orcid.org/0000-0001-6517-9556
    • , and 
  • Jun-Li Yang*
    Jun-Li Yang
    CAS Key Laboratory of Chemistry of Northwestern Plant Resources and Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences (CAS), Lanzhou 730000, People’s Republic of China
    *Email: [email protected]
    More by Jun-Li Yang
    Orcidhttp://orcid.org/0000-0001-7199-0214
Cite this: J. Org. Chem. 2020, 85, 16, 10806–10812
Publication Date (Web):July 24, 2020
https://doi.org/10.1021/acs.joc.0c01312
Copyright © 2020 American Chemical Society
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Abstract

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Bungsteroid A (1), possessing an unreported carbon skeleton, was isolated from the pericarps of Zanthoxylum bungeanum Maxim. It represents the first carbon skeleton of a C34 steroid analogue featuring a unique 6/6/6/6/5-fused pentacyclic skeleton, which has been determined by spectroscopic methods, quantum-chemical 13C NMR, ECD calculations, and calculations of optical rotations. Bungsteroid A showed the antiproliferative effects against HepG2, MCF-7, and HeLa cell lines with the IC50 values of 56.3 ± 1.1, 64.2 ± 0.9, and 74.2 ± 1.3 μM, respectively.

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The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.joc.0c01312.

  • Experimental section and raw spectroscopic data including HRESIMS, IR, UV, CD, and NMR spectra for compound 1 (PDF)

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Cited By

This article is cited by 3 publications.

  1. Tian Chai, Xian-Hua Meng, Cheng-Bo Wang, Kai Wang, Li-Mei Ma, Yan-Ping Shi, Jun-Li Yang. Narjatamolide, an Unusual Homoguaiane Sesquiterpene Lactone from Nardostachys jatamansi. The Journal of Organic Chemistry 2020, Article ASAP.
  2. Yan Sun, Qing-Hong Zeng, Hui-Qiang Lu, Fan-Cheng Meng, Yong Shen, Wei-You Zeng, Hao Chi, Yu-Qiang Zhou, Min Chen. Two new lignans from Zanthoxylum armatum. Natural Product Research 2020, 12 , 1-6. https://doi.org/10.1080/14786419.2020.1855646
  3. Robert A. Hill, Andrew Sutherland. Hot off the Press. Natural Product Reports 2020, 37 (10) , 1294-1299. https://doi.org/10.1039/D0NP90037K

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