Xuetonglactones A-F: Highly Oxidized Lanostane and Cycloartane Triterpenoids From Roxb. Craib.

Journal: Frontiers in chemistry
Published Date: Jan 21, 2020

Abstract

Xuetonglactones A-F (-), six unreported highly oxidized lanostane- and cycloartane-type triterpenoids along with 22 known scaffolds (-) were isolated from the stems of (Roxb.) Craib. Compared with previous congeners, xuetonglactone A (), possesses an unprecedented 20,21-α-epoxide, and xuetonglactone D () features an unusual 19-α-hydroperoxyl moiety. The structures and the absolute configurations of the compounds were established by extensive one- and two-dimensional NMR, and electronic circular dichroism (ECD) spectroscopic analysis, with those of and confirmed by single-crystal X-ray diffraction technique. Compounds and exhibited inhibition of iNOS activity in LPS-induced macrophages with IC values of 22.0, and 17.0 μg/mL, respectively. While compounds , , , and showed potent cytotoxic activities against human cervical cancer cell lines (HeLa) with the IC values of 4.0, 5.8, 5.0, and 6.4 μM, and against human gastric cancer cells (BGC 823) with the IC values of 2.0, 5.0, 2.5, and 2.0 μM, respectively. Moreover, plausible biogenetic pathways of (-) were also proposed.

Authors

  • Nuzhat Shehla
    TCM and Ethnomedicine Innovation and Development International Laboratory, Academician Atta-ur-Rahman Belt and Road Traditional Medicine Research Center, School of Pharmacy, Hunan University of Chinese Medicine, Changsha, China.
  • Bin Li
    Department of Magnetic Resonance Imaging (MRI), Beijing Shijitan Hospital, Capital Medical University, Beijing, China.
  • Liang Cao
    Hunan Provincial Key Laboratory of Dong Medicine, Hunan University of Medicine, Huaihua, China.
  • Jianping Zhao
    National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, University of Mississippi, Oxford, MS, United States.
  • Yuqing Jian
    TCM and Ethnomedicine Innovation and Development International Laboratory, Academician Atta-ur-Rahman Belt and Road Traditional Medicine Research Center, School of Pharmacy, Hunan University of Chinese Medicine, Changsha, China.
  • Muhammad Daniyal
    TCM and Ethnomedicine Innovation and Development International Laboratory, Academician Atta-ur-Rahman Belt and Road Traditional Medicine Research Center, School of Pharmacy, Hunan University of Chinese Medicine, Changsha, China.
  • Atia-Tul Wahab
    Dr. Panjwani Center for Molecular Medicine and Drug Research, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, Pakistan.
  • Ikhlas A Khan
    National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, University of Mississippi, Oxford, MS, United States.
  • Duan-Fang Liao
    TCM and Ethnomedicine Innovation and Development International Laboratory, Academician Atta-ur-Rahman Belt and Road Traditional Medicine Research Center, School of Pharmacy, Hunan University of Chinese Medicine, Changsha, China.
  • Atta-Ur Rahman
    International Center for Chemical and Biological Sciences, H. E. J. Research Institute of Chemistry, University of Karachi, Karachi, Pakistan.
  • M Iqbal Choudhary
    TCM and Ethnomedicine Innovation and Development International Laboratory, Academician Atta-ur-Rahman Belt and Road Traditional Medicine Research Center, School of Pharmacy, Hunan University of Chinese Medicine, Changsha, China.
  • Wei Wang
    State Key Laboratory of Quality Research in Chinese Medicine, Institute of Chinese Medical Sciences, University of Macau, Macau 999078, China.

Keywords

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