Isolation, Synthesis And Structure Determination Of Cannabidiol Derivatives And Their Cytotoxic Activities

  • Nat Prod Res. 2021 Feb;35(3):471-480. doi: 10.1080/14786419.2019.1638381.
Yedukondalu Nalli  1  2 ,  Suraya Jan  2  3 ,  Gianluigi Lauro  4 ,  Javeed Ur Rasool  1  2 ,  Waseem I Lone  1  2 ,  Aminur R Sarkar  1 ,  Junaid Banday  1 ,  Giuseppe Bifulco  4 ,  Hartmut Laatsch  5 ,  Sajad H Syed  2  3 ,  Asif Ali  1  2
Affiliations
  • 1. Natural Product Chemistry Division, CSIR-Indian Institute of Integrative Medicine, Canal Road, Jammu-Tawi, J&K, 180001, India.
  • 2. Academy of Scientific and Innovative Research, New Delhi, India.
  • 3. Pharmacology Division, CSIR-Indian Institute of Integrative Medicine, Canal Road, Jammu, Sanatnagar Srinagar, 180001, India and 190005.
  • 4. Department of Pharmacy, University of Salerno, Via Giovanni Paolo II 132, Fisciano, 84084, Italy.
  • 5. Institute of Organic and Biomolecular Chemistry, University of Göttingen, Tammannstr. 2, Göttingen, D-37077, Germany.
PMID: 31282748 DOI: 10.1080/14786419.2019.1638381
Abstract

In a continuing effort to explore the structural diversity and pharmacological activities of natural products based scaffolds, herein, we report the isolation, synthesis, and structure determination of cannabidiol and its derivatives along with their cytotoxic activities. Treatment of cannabidiol (1) with acid catalyst POCl3 afforded a new derivative 6 along with six known molecules 2 - 5, 7 and, 8. The structure of 6 was elucidated by extensive spectroscopic analyses and DFT calculations of the NMR and ECD data. All the compounds (2 - 8) were evaluated for their cytotoxic potential against a panel of eight Cancer cell lines. Compounds 4, 5, 7, and 8 showed pronounced in vitro cytotoxic activity with IC50 values ranging from 5.6 to 60 μM. Out of the active molecules, compounds 4, and 7 were found to be comparable to that of the parent molecule 1 on the inhibition of almost all the tested Cancer cell lines.

Keywords
Cannabidiol; Cannabinoids; Cannabis sativa L.; Cytotoxic activities; Divergent synthesis.
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