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Phytochemical profiling and bioactivity evaluation of CBD- and THC-enriched Cannabis sativa extracts: In vitro and in silico investigation of antioxidant and anti-inflammatory effects Cover

Phytochemical profiling and bioactivity evaluation of CBD- and THC-enriched Cannabis sativa extracts: In vitro and in silico investigation of antioxidant and anti-inflammatory effects

Open Access
|Dec 2024

Figures & Tables

Figure 1

GC-MS chromatogram of chloroformic extract Cannabis sativa L. enriched in CBD.
GC-MS chromatogram of chloroformic extract Cannabis sativa L. enriched in CBD.

Figure 2

GC-MS chromatogram of hexanic extract of Cannabis sativa L. enriched in THC.
GC-MS chromatogram of hexanic extract of Cannabis sativa L. enriched in THC.

Figure 3

HPLC-DAD chromatogram of chloroformic extract of Cannabis sativa L. enriched in CBD.
HPLC-DAD chromatogram of chloroformic extract of Cannabis sativa L. enriched in CBD.

Figure 4

HPLC-DAD chromatogram of hexanic extract of Cannabis sativa L. enriched in THC.
HPLC-DAD chromatogram of hexanic extract of Cannabis sativa L. enriched in THC.

Figure 5

The structure of identified compounds in HEX-THC and CHL-CBD extracts: (a) l-ascorbic acid, (b) gallic acid, (c) catechin hydrate, (d) p-coumaric acid, (e) quercetin, and (f) rosmarinic acid.
The structure of identified compounds in HEX-THC and CHL-CBD extracts: (a) l-ascorbic acid, (b) gallic acid, (c) catechin hydrate, (d) p-coumaric acid, (e) quercetin, and (f) rosmarinic acid.

Figure 6

IC50 values for inhibiting albumin denaturation, data are expressed as mean value ± SD, n = 3, **p < 0.01.
IC50 values for inhibiting albumin denaturation, data are expressed as mean value ± SD, n = 3, **p < 0.01.

Figure 7

Effect of HEX-THC, CHL-CBD, and aspirin on inhibition of hemolysis in heat induced test.
Effect of HEX-THC, CHL-CBD, and aspirin on inhibition of hemolysis in heat induced test.

Figure 8

Effect of HEX-THC, CHL-CBD, and indomethacin on inhibition of hemolysis hypotonicity-induced test.
Effect of HEX-THC, CHL-CBD, and indomethacin on inhibition of hemolysis hypotonicity-induced test.

Figure 9

Interaction of NF-κB (5LDE) target protein with the quercetin (a) showing 3D amino acid interactive view along with H-Bond surface and 2D amino acid interactive view.
Interaction of NF-κB (5LDE) target protein with the quercetin (a) showing 3D amino acid interactive view along with H-Bond surface and 2D amino acid interactive view.

Figure 10

Interaction of COX-1 (1EQG) target protein with the quercetin (b) showing 3D amino acid interactive view along with H-Bond surface and 2D amino acid interactive view.
Interaction of COX-1 (1EQG) target protein with the quercetin (b) showing 3D amino acid interactive view along with H-Bond surface and 2D amino acid interactive view.

Figure 11

Interaction of COX-1 (1EQG) target protein with the co-crystallized ligand (c) showing 3D amino acid interactive view along with H-Bond surface and 2D amino acid interactive view.
Interaction of COX-1 (1EQG) target protein with the co-crystallized ligand (c) showing 3D amino acid interactive view along with H-Bond surface and 2D amino acid interactive view.

Figure 12

Interaction of COX-2 (1CX2) target protein with the Quercetin (d) showing 3D amino acid interactive view along with H-Bond surface and 2D amino acid interactive view.
Interaction of COX-2 (1CX2) target protein with the Quercetin (d) showing 3D amino acid interactive view along with H-Bond surface and 2D amino acid interactive view.

Figure 13

Interaction of COX-2 (1CX2) target protein with the co-crystallized ligand (e) showing a 3D amino acid interactive view along with H-Bond surface and 2D amino acid interactive view.
Interaction of COX-2 (1CX2) target protein with the co-crystallized ligand (e) showing a 3D amino acid interactive view along with H-Bond surface and 2D amino acid interactive view.

Figure 14

Interaction of lipoxygenase (3V99) target protein with the quercetin (f) showing 3D amino acid interactive view along with H-Bond surface and 2D amino acid interactive view.
Interaction of lipoxygenase (3V99) target protein with the quercetin (f) showing 3D amino acid interactive view along with H-Bond surface and 2D amino acid interactive view.

Figure 15

Interaction of lipoxygenase (3V99) target protein with the co-crystallized ligand (g) showing a 3D amino acid interactive view along with H-Bond surface and 2D amino acid interactive view.
Interaction of lipoxygenase (3V99) target protein with the co-crystallized ligand (g) showing a 3D amino acid interactive view along with H-Bond surface and 2D amino acid interactive view.

Content of TPCs, TFCs, FC and TTCs of Cannabis extracts

TPC (mg GAE/g DWE)TFC (mg QE/g DW)FC (mg QE/g DW)TTC (mg CE/g DW)
CHL-CBD130 ± 2.5a 6 ± 1.2a 0.9 ± 0.2a 0.46 ± 0.09a
HEX-THC175 ± 4b 14 ± 1.5b 2.2 ± 0.4b 0.51 ± 0.08a

Cannabinoid profile of Cannabis sativa L_ extracts and their percentage area

Molecular weightMolecular structureRetention timeArea %
HEX-THC (%)CHL -CBD (%)
CBD314 22.86<147.38
THC314 23.9189.87<1

Identified compounds in cannabis sativa L_ HEX-THC and CHL-CBD extracts using HPLC-DAD

Pick numberRetention timeCompoundArea %
HEX-THCCHL-CBD
13.35 l-ascorbic acid2.20.5
25.45Gallic acid2.11.9
38.50Catechin hydrate10.8
414.68 P-coumaric acid47.2
530.38Quercetin3029.1
631.60Rosmarinic acid0.10.4

Membrane stabilizing effect of HEX-THC and CHL-CBD on hypotonicity‑induced hemolysis test and heat‑induced hemolysis test

IC50 heat-induced test (μg/mL)IC50 hypotonicity-induced test (μg/mL)
CHL-CBD301.55 ± 8.43a 469.58 ± 27.01a
HEX-THC185.94 ± 8.81b 264.51 ± 41.18b
Aspirin100.73 ± 4.60c
Indomethacin121.63 ± 6.75c

Antioxidant potential of Cannabis sativa L_ extracts was assessed using DPPH, ABTS, TAC and FRAP assays

DPPH (IC50 μg/mL)ABTS (IC50 μg/mL)TAC μg AAE/g DWEFRAP (EC50 μg/mL)
CHL-CBD45 ± 2.7a 65 ± 5a 88 ± 3a 33 ± 2a
HEX-THC32 ± 43b 47 ± 4.1b 108 ± 4b 26 ± 1.9b
BHT14.1 ± 1c
Ascorbic acid12.34c 55.4c

Interacting amino acids, types of interactions, and binding affinity of ligands with various target proteins

Ligands (from GC-MS and HPLC)NF-κBCOX-1COX-2Lipoxygenase
5LDE1EQG1CX23V99
Co-crystallized ligand−7.6−9.2−6.0
CBD−4.6−6.9−7.7−7.4
THC−5.2−7.3−8.7−7.8
l-ascorbic acid−4.0−6.1−6.2−5.8
Gallic acid−3.7−6.6−6.7−6.3
(+)-catechin hydrate−4.8−7.1−8.4−8.0
P-coumaric acid−4.5−6.2−7.0−6.4
Quercetin−5.6−8.9−9.6−8.6
Rosmarinic acid−3.7−6.8−9.2−7.4
Language: English
Submitted on: Sep 21, 2024
Accepted on: Nov 6, 2024
Published on: Dec 16, 2024
Published by: Sciendo
In partnership with: Paradigm Publishing Services

© 2024 Rafik El-Mernissi, Naoual El Menyiy, Aziz Zouhri, Yahya El-Mernissi, Fedoua Diai, Farhan Siddique, Fakhreldeen Dabiellil, Khalid S. Almaary, Hassan Amhamdi, Oualid Abboussi, Lhoussain Hajji, published by Sciendo
This work is licensed under the Creative Commons Attribution 4.0 License.