Table 4.
Plant Part | Extraction Method (Solvent) | Bioactive Metabolites |
Biological Activity | Results | Reference |
---|---|---|---|---|---|
Seed | Ultrasound-assisted extraction (methanol–water 80:20) |
Polyphenols |
Antioxidant—DPPH Standard: (not used) |
Inhibition activity = 74 ± 1% at 500 µL/mL |
[83] |
Seed | Maceration (ethanol–water 95:05) |
Cannabinoids and polyphenols |
Antioxidant—DPPH Standard: Ascorbic acid (IC50 = 0.012 ± 0.002 mg/mL) |
IC50 = 14.39 ± 2.27 mg/mL | [155] |
Seed | Maceration (ethanol–water 95:05) |
Cannabinoids and polyphenols |
Antioxidant—metal ion chelating assay Standard: EDTA (CC50 = 0.15 ± 0.002 mg/mL) |
CC50 = 1.92 ± 1.05 mg/mL | [155] |
Seed | Maceration (ethanol–water 95:05) |
Cannabinoids and polyphenols |
Antioxidant—lipid peroxidation inhibition Standard: α-tocopherol (IPC50 = 0.045 ± 0.002 mg/mL) |
IPC50 = 92.68 ± 30.77 mg/mL | [155] |
Seed | Maceration (ethanol–water 75:25) |
Lignanamides |
Antioxidant—DPPH Standard: Quercetin (IC50 = 25.5 µm) |
Cannabisin M (IC50 = 69.5 µm) Cannabisin N and O (IC50 = ND) 3,3′-demethyl-heliotropamide (IC50 = 39.3 µm) |
[156] |
Seed | Maceration (ethanol–water 75:25) |
Lignanamides |
Antioxidant—ORAC Standard: Quercetin (IC50 = 0.40 µm) |
Cannabisin M (IC50 = 6.61 µm) Cannabisin N and O (IC50 = ND) 3,3′-demethyl-heliotropamide (IC50 = 0.56 µm) |
[156] |
Seed | Maceration (ethanol–water 75:25) |
Lignanamides |
Antioxidant—ABTS Standard: Quercetin (IC50 = 9.19 µm) |
Cannabisin M (IC50 = 74.70 µm) 3,3′-demethyl-heliotropamide (IC50 = 16.41 µm) |
[156] |
Seed oil | Acid/alkali extraction | Proteins |
Antioxidant—DPPH Standard: (not used) |
Alkali soluble proteins: - inhibition value = 73.33% after ht enzyme hydrolysis. Acid soluble proteins: - inhibition value = 68.67% after ht enzyme hydrolysis. |
[157] |
Seed flour | Ultrasound-assisted extraction (methanol–water 80:20) |
Polyphenols |
Antioxidant—DPPH Standard: (not used) |
Inhibition activity = 67 ± 1% at 500 µL/mL | [83] |
Seed oil | Ultrasound-assisted extraction (methanol–water 80:20) |
Polyphenols |
Antioxidant—DPPH Standard: (not used) |
Inhibition activity = 22 ± 2% at 500 µL/mL | [112] |
Seed | Maceration (ethanol–water 80:20) |
Polyphenols |
Antibacterial (against Staphylococcus aureus, Escherichia coli, Salmonella typhimurium, Enterobacter aerogenes and Enterococcus faecalis) Standard: Gentamycin and vancomycin (MIC < 0.05 mg/mL) |
All bacterial strains showed MIC values superior to 1 mg/mL | [158] |
Seed | Maceration (ethanol–water 95:05) |
Cannabinoids and polyphenols |
Antibacterial (against Staphylococcus aureus) Standard: Erythromycin (ID = 26.67 ± 1.15 mm) |
Inhibition diameter = 1.00 mm | [155] |
Seed | Maceration (ethanol–water 80:20) |
Polyphenols |
Antibacterial (against Lactobacillus paracasei, Lactobacillus reuteri, Lactobacillus brevis, Lactobacillus plantarum, Bifidobacterium bifidum, Bifidobacterium longum and Bifidobacterium breve) Standard: Gentamycin and vancomycin (MIC < 0.05 mg/mL) |
All bacterial strains showed MIC values superior to 1 mg/mL | [158] |
Seed | Maceration (ethanol–water 95:05) |
Terpenoid,
phytocannabinoids and unsaturated fatty acids |
Cytotoxicity—SRB assay Standard: (not used) |
Percentages of human skin fibroblast viability 66.12 ± 7.63% at 1 mg/mL | [155] |
Seed | Maceration (ethanol–water 95:05) |
Terpenoids and flavonoids |
Antiproliferative—SRB assay Standard: Doxorubicin (IC50 = 0.0042 ± 0.0025 mg/mL) |
On hepg2 cell lines: IC50 = 12.07 ± 1.18 mg/mL |
[155] |
Seed oil | Ultrasound-assisted extraction (methanol–water 80:20) |
Polyphenols |
Antiproliferative Standard: (not used) |
Reduction in caco-2 and ht-29 cell viability to less than 40% from 150 mg/mL | [83] |
Seed | Maceration (ethanol–water 95:05) |
Terpenoids and flavonoids |
Anti-tyrosinase Standard: Kojic acid (IC50 = 0.005 ± 0.004 mg/mL) |
IC50 = 0.07 ± 0.06 mg/mL | [155] |
Seed | Maceration (ethanol–water 75:25) |
Lignanamides |
Acetyl choline esterase inhibition Standard: Galantamine (IC50 = 2.76 μm) |
Cannabisin M, N and O (IC50 = nd) 3,3′-demethyl-heliotropamide (IC50 = 46.2 µm) |
[156] |
Leaf | Maceration (ethanol–water 95:05) |
Cannabinoids and
polyphenols |
Antioxidant—DPPH Standard: Ascorbic acid (IC50 = 0.012 ± 0.002 mg/mL) |
IC50 = 2.73 ± 0.422 mg/mL | [155] |
Leaf | Maceration (ethanol–water 95:05) |
Cannabinoids and
polyphenols |
Antioxidant—Metal ion chelating assay Standard: EDTA (CC50 = 0.15 ± 0.002 mg/mL) |
CC50 = 0.93 ± 0.20 mg/mL | [155] |
Leaf | Maceration (ethanol–water 95:05) |
Cannabinoids and
polyphenols |
Antioxidant—Lipid peroxidation inhibition Standard: α-tocopherol (IPC50 = 0.045 ± 0.002 mg/mL) |
IPC50 = 246.32 ± 69.38 mg/mL | [155] |
Leaf | Ultrasound-assisted extraction (ethanol–water 80:20) |
Polyphenols and
flavonoids |
Antioxidant—DPPH Standard: (not used) |
Inhibition activity of 40% at 1000 µg/mL | [87] |
Leaf | Maceration (acetone) |
ND |
Antibacterial Standard: Ampicillin (ID = 17.3 to 19.6 mm) |
Inhibition diameters: Escherichia coli = 24.7 ± 1.5 mm Staphylococcus aureus = 19.6 ± 2.1 mm Pseudomonas aeruginosa = 19.0 ± 2.6 mm |
[159] |
Leaf | Maceration (chloroform) |
ND |
Antibacterial Standard: Ampicillin (ID = 17.3 to 19.6 mm) |
Inhibition diameters: Escherichia coli = 23.0 ± 2.0 mm Staphylococcus aureus = 18.6 ± 2.08 mm Pseudomonas aeruginosa = 22.3 ± 1.52 mm |
[159] |
Leaf | Maceration (ethanol–water 60:40) |
ND |
Antibacterial Standard: Ampicillin (ID = 17.3 to 19.6 mm) |
Inhibition diameters: Escherichia coli = 19.3 ± 1.2 mm Staphylococcus aureus = 18.6 ± 3.05 mm |
[159] |
Leaf | Maceration (ethanol–water 95:05) |
Polyphenols, flavones and polyholozides |
Antibacterial (against Staphylococcus mutans) Standard: Erythromycin (ID = 23 mm) |
Inhibition diameter: 1.33 ± 0.58 mm | [155] |
Leaf | Maceration (acetone) |
ND |
Antifungal Standard: (not used) |
Inhibition diameters: Aspergillus niger = 21.3 ± 2 mm Fusarium spp. = 20 ± 2.64 mm |
[159] |
Leaf | Maceration (chloroform) |
ND |
Antifungal Standard: (not used) |
Inhibition diameters: Aspergillus niger = 20.6 ± 1.5 mm Fusarium spp. = 18.3 ± 1.52 mm |
[159] |
Leaf | Maceration (ethanol–water 60:40) |
ND |
Antifungal Standard: (not used) |
Inhibition diameters: Aspergillus niger = 23 ± 2 mm Fusarium spp. = 21.3 ± 3.21 mm |
[159] |
Leaf | Maceration (water) |
ND |
Antifungal Standard: (not used) |
Inhibition diameters: Aspergillus niger = 21 ± 2.6 mm Fusarium spp. = 24.3 ± 3.51 mm |
[159] |
Leaf | Maceration (ethanol–water 95:05) |
Polyphenols, flavones and polyholozides |
Cytotoxicity—SRB assay Standard: (not used) |
Percentages of human skin fibroblast viability 73.02 ± 3.57% at 1 mg/mL | [155] |
Leaf | Ultrasound-assisted extraction (ethanol–water 80:20) |
Polyphenols and flavonoids |
Cytotoxicity Standard: (not used) |
Viability of: HaCaT keratinocytes cells with 120% at 100 g/mL. BJ fibroblasts cells with 188% at 500 µg/mL. |
[87] |
Leaf | Maceration (ethanol–water 95:05) |
Polyphenols, flavones and polyholozides |
Antiproliferative—SRB assay Standard: Doxorubicin (IC50 = 0.0042 to 0.0274 mg/mL) |
On hepg2 cell lines: IC50 = 13.17 ± 1.53mg/mL On kb cell lines: IC50 = 5.16 ± 1.66 mg/mL |
[155] |
Leaf | Maceration (ethanol–water 95:05) |
Terpenoids and flavonoids |
Anti-tyrosinase Standard: Kojic acid (IC50 = 0.005 ± 0.004 mg/mL) |
IC50 = 0.049 ± 0.02 mg/mL | [155] |
Leaf | Ultrasound-assisted extraction (ethanol–water 80:20) |
Cannabinoids |
Anti-elastase Standard (not used) |
Inhibition value of 30% at 1000 µg/mL | [87] |
Leaf | Ultrasound-assisted extraction (ethanol–water 80:20) |
Cannabinoids |
Anti-collagenase Standard: (not used) |
Inhibition value of 80% at 1000 µg/mL | [87] |
Leaf | Maceration (chloroform) |
Cannabinoids (THC, CBD and CBN) |
Anticoagulant Standard: (not used) |
Inhibition values at 1 mg/mL: THC = 34.87% (IC50 = 1.79 mg/mL) CBN = 7.3% (IC50 = high value) |
[160] |
Flowers | Maceration (acetone–water 50:50) |
Polyphenols |
Antifungal (against Aspergillus favus) |
Total inhibition at > 0.225 mg of DM/mL of medium | [161] |
Flowers | Maceration (acetone–water 50:50) |
Polyphenols |
Anti-aflatoxigenic Standard: (not used) |
Reduction in fungal growth by 36% at 7.2 mg DM/mL of medium | [161] |
Inflorescences | Hydrodistillation (essential oil) |
Terpenes |
Insecticidal Standard: (not used) |
Lethal concentration of LC50: Anopheles stephensi = 73.50 to 78.80 ppm for larvae. Anopheles gambiae = 20.13 to 67.19 ppm for pupae. |
[162] |
Inflorescences | Hydrodistillation (essential oil) |
Terpenes |
Cytotoxicity Standard: (not used) |
IC50 values of: HaCaT cells = 2.23 ± 0.09 mg/mL Nhf a12 cells = 3.71 ± 0.2 mg/mL |
[162] |
Aerial parts | Hydrodistillation (essential oil + aromatic water) |
Terpenes and polyphenols |
Antioxidant—DPPH Standard: (not used) |
Inhibition activity: Essential oil = 5.6 mg TE/g sample Aromatic water = 40 mg TE/g sample. |
[94] |
Aerial parts | Hydrodistillation (essential oil) |
Terpenes |
Antioxidant—DPPH Standard: Quercetin (IC50 = 1.1 ± 0.0 µg/mL) |
IC50 = 1.6 ± 0.1 mg/mL | [163] |
Aerial parts | Hydrodistillation (essential oil + aromatic water) |
Terpenes and polyphenols |
Antioxidant—FRAP Standard: (not used) |
Inhibition activity: Essential oil = 57 mg TE/g sample Aromatic water = 83 mg TE/g sample. |
[94] |
Aerial parts | Hydrodistillation (essential oil + aromatic water) |
Terpenes and polyphenols |
Antioxidant—metal chelating activity Standard: (not used) |
Inhibition activity: Essential oil = 19.3 mg EDTAE/g sample Aromatic water = 3.8 mg mg EDTAE/g DW |
[94] |
Aerial parts | Hydrodistillation (essential oil + aromatic water) |
Terpenes and polyphenols |
Antioxidant—phosphomolybdenum Standard: (not used) |
Inhibition activity: Essential oil = 35.1 mmol TE/g of oil Aromatic water = 1.4 mmol TE/g DW |
[94] |
Aerial parts | Hydrodistillation (essential oil) |
Terpenes |
Antioxidant—reducing power assay Standard: Quercetin (EC50 = 2.3 ± 0.1 µg/mL) |
EC50 = 1.8 ± 0.2 mg/mL | [163] |
Aerial parts | Hydrodistillation (essential oil) |
Terpenes |
Antioxidant—β-carotene/linoleic acid Standard: Quercetin (EC50 = 0.9 ± 0.0 µg/mL) |
EC50 = 0.9 ± 0.1 mg/mL | [163] |
Aerial parts | Hydrodistillation (essential oil + aromatic water) |
Terpenes and polyphenols |
Antioxidant—CUPRAC Standard: (not used) |
Inhibition activity: Essential oil = 141 mg TE/g sample Aromatic water = 109 mg TE/g sample. |
[94] |
Aerial parts | Hydrodistillation (essential oil) |
Terpenes and polyphenols |
Antibacterial (against Helicobacter pylori strains) Standard: Naringenin (MIC and MBC = 8–32 µg/mL) |
MIC = 8–64 µg/mL MBC = 8–32 µg/mL |
[94] |
Aerial parts | Hydrodistillation (essential oil) |
Terpenes and polyphenols |
Antibacterial (against Staphylococcus aureus) Standard: (not used) |
MIC = 8 mg/mL MBC = 16 mg/mL MBEC = 16–24 mg/mL |
[94] |
Aerial parts | Hydrodistillation (essential oil) |
Terpenes |
Antibacterial Standard: Ciprofloxacin (MIC = 0.015–1.00 mm) |
Micrococcus luteus and Staphylococcus aureus: MIC = 4.7 mg/mL Bacillus subtilis, Escherichia coli and Pseudomonas aeruginosa: MIC = 1.2 mg/mL |
[163] |
Aerial parts | Hydrodistillation (essential oil) |
Terpenes |
Antifungal Standard: Fluconazole (MIC = 1.00 mm) |
Candida albicans, Candida glabrata, Candida krusei and Candida parapsilosis: MIC = 9.5 mg/mL |
[163] |
Aerial parts | Hydrodistillation (essential oil) |
Terpenes and polyphenols |
Antifungal (against Candida spp. and Malassezia spp.) Standard: (not used) |
MIC value > 12,460 µg/mL | [94] |
Aerial parts | Hydrodistillation (essential oil + aromatic water) |
Terpenes and polyphenols |
Cytotoxicity Standard: Doxorubicin (IC50 = 3.1–23.3 µg/mL) |
Inhibition activity of 50%: IC50 (mda-mb-468) = 53.0 µg/mL IC50 (caco-2) = 28.7 µg/mL IC50 (mz-cha-1) = 22.3 µg/mL |
[94] |
Aerial parts | Hydrodistillation (essential oil + aromatic water) |
Terpenes and polyphenols |
Antidiabetic Standard: (not used) |
α-amylase inhibition: Essential oil = nd Aromatic water = 0.10 mmol ACAE/g extract α-glucosidase inhibition: Essential oil = 3.77 mmol ACAE/g oil Aromatic water = 0.17 mmol ACAE/g extract |
[94] |
Aerial parts | Hydrodistillation (essential oil + aromatic water) |
Terpenes and polyphenols |
Acetyl- and butyryl-choline esterase inhibition Standard: (not used) |
Acetyl-choline esterase inhibition: Essential oil = nd Aromatic water = 2.56 mg GALAE/g extract Butyryl-choline esterase inhibition: Essential oil = 3.4 mg GALAE/g oil Aromatic water = 3.48 mg GALAE/g extract |
[94] |
Aerial parts | Hydrodistillation (essential oil + aromatic water) |
Terpenes and polyphenols |
Lipase inhibition Standard: (not used) |
Inhibition activity: - essential oil = 70.14 mg OE/g oil - aromatic water = nd |
[94] |
IPC50: concentration providing 50% inhibition of lipid peroxidation/CC50: concentration providing 50% metal chelating activity. IC50: concentration of the sample that inhibits 50% expressed in mg/mL/ID: inhibition diameter (mm). EDTA: ethylenediaminetetraacetic acid./GAE: gallic acid equivalent./RE: rutin equivalent./CE: caffeic acid equivalent./TE: trolox equivalent. EDTAE: ethylenediaminetetraacetic acid equivalent./MIC: minimum inhibitory concentration./MBC: minimum bactericidal concentration. MCF-7: estrogen-dependent breast cancer cells./MDA-MB-468: triple-negative breast cancer cells./CACO-2: colorectal adenocarcinoma cells./MZ-CHA-1: cholangiocarcinoma cells.