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Planta Med 2022; 88(05): 389-397
DOI: 10.1055/a-1468-3781
Natural Product Chemistry and Analytical Studies
Original Papers

Microbial Biotransformation of Cannabidiol (CBD) from Cannabis sativa

Safwat A. Ahmed
1   Department of Pharmacognosy, Faculty of Pharmacy, Suez Canal University, Ismailia, Egypt
,
Amany K. Ibrahim
1   Department of Pharmacognosy, Faculty of Pharmacy, Suez Canal University, Ismailia, Egypt
,
Mohamed M. Radwan
2   National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, School of Pharmacy, University of Mississippi, University, MS, USA
3   Department of Pharmacognosy, Faculty of Pharmacy, University of Alexandria, Alexandria, Egypt
,
Desmond Slade
2   National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, School of Pharmacy, University of Mississippi, University, MS, USA
,
Suman Chandra
2   National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, School of Pharmacy, University of Mississippi, University, MS, USA
,
Ikhlas A. Khan
2   National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, School of Pharmacy, University of Mississippi, University, MS, USA
4   Department of Biomolecular Sciences, School of Pharmacy, University of Mississippi, University, MS, USA
,
Mahmoud A. ElSohly
2   National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, School of Pharmacy, University of Mississippi, University, MS, USA
5   Department of Pharmaceutics and Drug Delivery, School of Pharmacy, University of Mississippi, University, MS, USA
› Author AffiliationsSupported by: National Institute on Drug Abuse N01DA-15-7793
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Abstract

Microbial biotransformation of cannabidiol was assessed using 31 different microorganisms. Only Mucor ramannianus (ATCC 9628), Beauveria bassiana (ATCC 7195), and Absidia glauca (ATCC 22 752) were able to metabolize cannabidiol. M. ramannianus (ATCC 9628) yielded five metabolites, namely, 7,4″β-dihydroxycannabidiol (1), 6β,4″β-dihydroxycannabidiol (2), 6β,2″β-dihydroxycannabidiol (3), 6β,3″α-dihydroxycannabidiol (4), and 6β,7,4″β-trihydroxycannabidiol (5). B. bassiana (ATCC 7195) metabolized cannabidiol to afford six metabolites identified as 7,3″-dihydroxycannabidivarin (6), 7-hydroxycannabidivarin-3″-carboxylic acid (7), 3″-hydroxycannabidivarin (8), 4″β-hydroxycannabidiol (9), and cannabidivarin-3″-carboxylic acid (10) along with compound 1. Incubation of cannabidiol with A. glauca (ATCC 22 752) yielded three metabolites, 6α,3″-dihyroxycannabidivarin (11), 6β,3″-dihyroxycannabidivarin (12), and compound 6. All compounds were evaluated for their antimicrobial and antiprotozoal activity.

Key words

cannabidiol - biotransformation - metabolites - antimicrobial - Cannabis sativa - Cannabaceae

Supporting Information

    NMR spectra of the isolated metabolites and Δδ values for the MTPA derivatives of metabolites 1 – 5, 9, 11, and 12 are available as Supporting Information.

  • Supporting Information


Publication History

Received: 20 July 2020

Accepted after revision: 26 March 2021

Article published online:
26 April 2021

© 2021. Thieme. All rights reserved.

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