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Origanum majorana is a medicinal and aromatic plant that belongs to the Lamiaceae family. It is cultivated in several parts of the world and, due to its splendid aroma and taste, is widely used for culinary purposes and in perfumes. The essential oil of the plant, to which is attributed its aroma, contains many secondary metabolites with valuable biological activity. One of them is the pesticide activity, which has attracted much interest. Given the necessity of replacing synthetic pesticides, essential oils are studied in an attempt to find naturally derived products.
Plant Material | Extraction Method | Column Used for the GC Analysis | % Yield | Chemical Composition | Region | Reference |
---|---|---|---|---|---|---|
200 g of plant material (the part used is not identified) | Hydrodistillation (clevenger apparatus) | VB-5 30 × 0.25 mm, 0.25 μm |
0.8 mL/100 g dry material | 4-terpinene (28.96%), γ-terpinene (18.57%) and α-terpinene (12.72%), sabinene (8.02%) | Morocco | [26] |
1000 g of the aerial parts | Hydrodistillation (according to European Pharmacopeia 5th edition guidelines) | DB-5 30 m × 0.25 mm, 0.33 μm |
0.97 mL/100 g dry material | terpinen-4-ol (34.1%), α-terpinene (19.2%), terpineol (8.9%) | South West Morocco | [59] |
10 g of plant material | Steam distillation (Likens–Nickerson apparatus) |
CP-Sil 8 30 m, 0.32 mm |
- | thymol (14.0%), 3-carene (10.4%), 2-carene (7.8%), terpinen-4-ol (7.8%), sabinene hydrate (6.0%) | Greece | [56] |
100 g of aerial part (stems, leaves and flowers) | Hydrodistillation (clevenger apparatus) | HP-5MS 30 m × 0.25 mm, 0.25 μm |
1.85 mL/100 g dry material | terpinen-4-ol (23.2%), cis-sabinene hydrate (17.5%), γ-terpinene (10.5%), p-cymene (9%), α-terpineol (5.6%) | Tunisia | [57] |
100 g of leaves | Hydrodistillation (Quik-fit apparatus) | HP-5MS 30 m × 0.25 mm, 0.25 mm |
0.09 mL/100 g dry material | terpinen-4-ol (555.1 μg/g dw), γ-terpinene (192.8 mg/g dw), cis sabinene hydrate (168.8 mg/g dw) | Tunisia | [34] |
100 g of aerial parts) three developmental stages: vegetative, flowering and post-flowering) | Hydrodistillation (clevenger apparatus) | HP-5MS 30 m × 250 m, 0.25 μM |
- | terpinen-4-ol (76.94–37.15), cyclohexanol 3,3,5 trimethyl (15.99–5.41), α-terpineol (11.34–0.94); β-cymene (10.56–1.88) | Tunisia | [46] |
- | Steam distillation | Carbowax 20M 25 m × 0.3 mm |
0.20 mL/100 g dry material | terpinen-4-ol (37.10%), p-cymene (12.05%), α-terpineol (7.15%) | Greece | [68] |
Leaves | Hydrodistillation (clevenger apparatus) | DB-5MS 30 m × 0.25 mm × 0.25 μm |
1.2 mL/100 g dry material | terpinen-4-ol (29.97%), γ-terpinene (15.40%), trans-sabinene hydrate (10.93%), α-terpinene (6.86%) and α-terpineol (6.54%) | Egypt | [13] |
5 g | Hydrodistillation (clevenger apparatus) | Rtx-5MS 30 m × 0.25 mm × 0.25 μm |
- | terpinen-4-ol (19.7%), γ-terpinene (18.4), α-terpinene (11.4%), cis-sabinene hydrate (8.6%), sabinene (7.8%) | Commercial sample Germany |
[71] |
Leaves | Hydrodistillation (clevenger apparatus) | DB5 30 m × 0.25 mm × 0.25 µm |
- | carvacrol (57.86%), thymol (13.54%), trans-caryophyllene (11.52%), cymene (6.78%) | Iran | [48] |
Aerial parts | Hydrodistillation (clevenger apparatus) | DB-5 30 m × 0.25 mm, 0.25 μm | - | terpinen-4-ol (31.15%), cis-sabinene hydrate (15.76%), p-cymene (6.83%), sabinene (6.91%), trans-sabinene hydrate (3.86%), α-terpineol (3.71%) | India | [35] |
500 g of leaves | Hydrodistillation (clevenger apparatus) | HP-5MS 30 m × 0.25 mm, 0.25 μm |
0.6 mL/100 g dry material | cis-sabinene hydrate (30.2%), terpinen-4-ol (28.8%), γ-terpinene (7.2%), α-terpineol (6.9%), trans-sabinene hydrate (4.4%), linalyl acetate (3.8%), α-terpinene (3.6%) | Venezuela | [72] |
20 g of aerial part (two vegetative and two generative growth stages) | Hydrodistillation | HP-Innowax 30 m × 0.25 mm × 0.25 mm |
0.04 to 0.09 mL/100 g dry material | terpinen-4-ol (29.13–32.57%), cis-sabinene hydrate (19.9–29.27%), trans-sabinene hydrate (3.5–11.61%), γ-terpinene (2.11–8.20%), bornyl acetate (1.52–2.94%), linalool (1.05–1.39%) | Tunisia | [36] |
- | Hydrodistillation | Supelcowax 10, 60 m × 0.25 mm, 0.25 μm |
0.8 mL/100 g dry material | terpinen-4-ol (30.3%), γ-terpinene (14%), linalool (12%), p-cymol (9.8%), α-pinene (5.9%), camphene (5.8%) | Hungary | [37] |
Flowering plants | Hydrodistillation (clevenger apparatus) | Carbowax 20 M, 50 m × 0.32 mm i.d, 0.20 μm | 1 mL/100 g dry material | terpinen-4-ol (38.4%), cis-sabinene hydrate (15.0%), p-cymene (7.0%), γ-terpinene (6.9%). | Reunion Island | [38] |
- | Hydrodistillation (clevenger apparatus) | Equity-5 60 m × 0.32 mm, 0.25 μm |
0.45–0.50 mL/100 g dry material | cis-sabinene hydrate (20.23–46.27%), terpinen-4-ol (9.32–23.43%), γ-terpinene (5.67–13.76%), α-terpinene (2.98–8.38%), sabinene (4.90–8.17%), trans-sabinene hydrate (5.01–7.34%), α-terpineol (3.41–4.17%) | India | [49] |
Leaves | Hydrodistillation (clevenger apparatus) | DB-5 (5% phenylmethylpolysiloxane) capillary column, 60 m × 0.25 mm |
1.6 mL/100 g dry material | terpinen-4-ol (30.0%), γ-terpinene (11.3%), trans-sabinene hydrate (10.8%) |
Egypt | [25] |
131 g leaves | Hydrodistillation (clevenger apparatus) | OPTIMAL-5 0.25 μm, 30 M, 0.25 mm |
- | pulegone (57.05%), verbenone (16.92%), trans-menthone (8.57%) | Brasil | [59] |
0.5 kg of aerial part | Hydrodistillation (clevenger apparatus) | HP-5 30 m × 0.25 mm, 0.25 μm |
- | carvacrol (74.8%), thymol (2.7%) | Greece | [18] |
- | - | DB-1MS 30 m × 0.25 mm, 0.25 µm |
- | terpinen-4-ol (22.96%), linalool (15.32%), γ-terpinene (12.92%), p-cymene (6.37%) | Commercial sample, Korea | [23] |
- | - | VF-5MS 30 m × 0.25 mm, 0.25 µm |
- | terpinen-4-ol (33.8%), terpinolene (16.5%), linalool (14.7%), α-terpinene (6.8%) |
Commercial sample | [73] |
20 g dried leaves | Hydrodistillation (clevenger apparatus) | - | 12.70 μL·g−1 | terpinen-4-ol (23.83%) cis-β-terpineol (21.63%), | - | [74] |
- | - | DB-5MS 30 m × 0.25 mm, 0.25 µm |
- | 1,8-cineole (50.96%), linalool (24.04%), limonene (6.38%) | India | [63] |
Two samples from different regions were analyzed | Hydrodistillation | - | 6.5–7.7 mL/100 g dry material | carvacrol (78.27–79.46%), p-cymene (4.31–4.68%), y-terpinene (3.72–4.84%) | Turkey | [55] |
100 g of fresh plant material | Steam distillation | SE-54 50 m × 0.32 mm | linalool (32.68%), terpinen-4-ol (22.30%), p-cymene (8.07%) | Morocco | [60] | |
80 g of aerial parts | Hydrodistillation (clevenger apparatus) | HP-5MS 30 m × 0.25 mm, 0.25 µm |
17.2 g/kg | terpinen-4-ol (20.9%), linalool (15.7%), linalyl acetate (13.9%), limonene (13.4%), α-terpineol (8.57%) | Pakistan | [39] |
1 kg of dried aerial parts | Hydrodistillation | DB-5 30 m × 0.25 mm, 0.33 µm |
0.4 mL/100 g dry material | terpinen-4-ol (29.6%), δ-2-carene (20.1%), camphene (13.4%), α-pinene (7.9%) | Italy | [11] |
100 g dried aerial parts | Hydrodistillation (clevenger apparatus) | Cp WAX 52 CB 50 m × 0.32 mm, 1.2 µm |
- | carvacrol (52.5%), linalool (45.4%), | Turkey | [50] |
100 g of dried aerial part |
|
TR-5 MS 30 m × 0.32 mm, 0.25 μm |
(HD) 0.73 mL/100 g dry material (MWE) 0.80 mL/100 g dry material (SD) 0.66 mL/100 g dry material |
terpinen-4-ol MWE: 22.28%, HD: 28.49%, SD: 26.72% trans-sabinene hydrate MWE: 13.05%, HD: 11.69%, SD: 3.04% γ-terpinene MWE: 13.20%, HD: 7.87%, SD: 13.72% α-terpinene MWE: 9.07%, HD 3.89%, SD: 9.46% |
Egypt | [47] |
300 g of plant material | Hydrodistillation (clevenger apparatus) | - | 1.7 mL/100 g dry material | terpin-4-ol (27.32%), γ-terpinene (15.67%), α-terpinene (11.08%) α-terpineol (6.90%), sabinene (5.53%) | Tunisia | [51] |
Aerial parts | Extraction with organic solvent | ZB-5MS (Phenomenex), 30 m × 0.25 mm, 0.25 µm |
trans-sabinene hydrate (16.0%), sabinene (14.1%), cis-sabinene hydrate (11.8%), γ-terpinene (10.2%), α-terpinyl acetate (10.0%), α-terpinene (8.9%) | Yemen | [62] | |
- | - | DB-5 30 × 0.25 × 2.5 mm |
- | terpinen-4-ol (20.55%), terpinene (13.13%), trans-terpineol (12.67%), 2-carene (7.67%), sabinene (6.96%) | - | [40] |
- | - | ZB-5 MS 30 m, 0.25 mm, 0.25 μm |
- | linalyl acetate (16.0%), linalool (14.7%), α-terpineol (13.8%), limonene (11.5%) | Commercial sample produced in Ukraine | [65] |
- | Hydrodistillation (clevenger apparatus) | HP-5MS 30 m× 0.25 mm, 0.25 mm |
- | terpinen-4-ol (32.69%), γ-terpinene (12.88%), trans-sabinene hydrate (8.47%), α-terpinene (7.98%), sabinene (6.21%) | - | [15] |
200 g of aerial part | Hydrodistillation (Dean–Stark apparatus) | VB5 30 m × 0.25 mm 0.25 μm |
1.06 mL/100 g dry material | Sabinene hydrate (14.08%), α-terpineol (13.95%), (-)-terpinen-4-ol (13.07%), (+)-sabinene (5.67%) | Morocco | [61] |
- | - | HP-5 30 m× 0.32 mm× 0.25 mm |
- | 1,8-cineole (20.9%), terpinen-4-ol (20.4%), p-cymene (7.0%), sabinene (6.7%) | Commercial sample Egypt | [64] |
Dried leaves | Hydrodistillation (clevenger apparatus) | DB-5 30 m × 0.25 mm 0.25 mm |
1.20 mL/100 g dry material | terpinen-4-ol (30.41%), γ-terpinene (13.94%), cis-sabinene hydrate (9.64%), α-terpinene (7.70%) | Egypt | [52] |
- | - | Restek 30 m × 0.32 mm, 0.50 μm |
- | terpinen-4-ol (21.3%), trans-sabinene hydrate (15.5%), γ-terpinene (14.0%) and α-terpinene (8.9%) |
Commercial product Albania | [53] |
Aerial parts of plant material collected in different regions | Hydrodistillation (clevenger apparatus) | FSC 60 m × 0.25 mm, 0.25 µm |
- | terpinen-4-ol (8–14%), linalyl acetate (7–10%), trans-sabinene hydrate (6–7%) | Turkey | [41] |
100 g of air-dried aerial parts |
Hydrodistillation (Dean–Stark apparatus) |
HP-101 25 m × 0.32 mm |
1.40 mL/100 g dry material | terpinen-4-ol (32.8%), y-terpinene (9.9%), cis-sabinene hydrate (8.6%) | Tunisia | [54] |
Dried leaves | Hydrodistillation (clevenger apparatus) | TR-5MS 30 m × 0.25 mm, 0.25 μm |
2.5 mL/100 g dry material | terpinen-4-ol (33.0%), caryophyllene oxide (11.9%), p-cymene (6.8%), α-terpineol (6.7%) spathulenol (6.0%) | Commercial sample China |
[42] |
200 g dried flowers 200 g dried leaves |
Hydrodistillation (clevenger apparatus) | Supelcowax 10 30 m × 0.32 mm, 0.5 pm |
12.8 mL/100 g dry material (flowers) 8% ml/100 g dry material (leaves) |
Leaves: cis-sabinene hydrate (33.3%), terpinen-4-ol (21.6%), y-terpinene (8.3%), α-terpineol (7.3%), trans-sabinene hydrate (4.7% ) Flowers: cis-sabinene hydrate (24%), terpinen-4-ol (16.6%), α-terpineol (12.4%), y-terpinene (10.6%) Stems: terpinen-4-ol (19%), α-terpineol (14.25%), y-terpinene (11.1%), cis-sabinene hydrate (7.4%) |
Cyprus | [69] |
Flowers | Steam distillation | DB-1 60 m × 0.25 mm, 0.25 pm |
0.3 mL/100 g dry material | linalyl acetate (26.1%), sabinene (12%), y-terpinene (8.8%), cis-sabinene hydrate (8.7%) | Iran | [66] |
- | - | - | - | - | Egypt | [43] |
- | - | DB-1 30 m × 0.25 mm, 0.25 μm |
- | terpinen-4-ol (20.8%), γ-Terpinene (14.1%), cis-sabinene hydrate (10.8%) sabinene (9.3%), α-terpinene (9.2%) | Commercial sample UK |
[44] |
300 g of aerial parts | Hydrodistillation (clevenger apparatus) | - | 1.72 mL/100 g dry material | terpinen-4-ol (26.7%), γ-terpinene (16.96%), p-menthenol (11.85%), α-terpinen (9.22%), α-terpineol (5.76%), p-cymene (5.27%) |
Tunisia | [45] |
Dried leaves | Hydrodistillation (clevenger apparatus) | Durabond-DB5 30 m × 0.25 mm × 0.25 μm |
- | γ-terpinene (25.73%), α-terpinene (17.35%), terpinen-4-ol (17.24%), sabinene (10.8%), β-phellandrene | Egypt | [67] |
200 g aerial part |
|
HP-5 ms capillary 30 m × 0.25 mm, 0.25 μm |
5 mL/100 g of dry material |
|
Greece | [70] |
- | Hydrodistillation (clevenger apparatus) | - | 0.2 mL/100 g of dry material | carvacrol (43.7%), thymol (18.3%), γ-terpinene (14.1%), o-cymene (8.1%), α-terpinene (2.0%) | Greece | [75] |