Volatile Components, Antioxidant and Phytotoxic Activity of the Essential Oil of Piper acutifolium Ruiz & Pav. from Peru
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemical Characterization of the Essential Oil of P. acutifolium
# | Compound | LRI Ref | LRI Exp | % | Molecular Formula/ Molecular Mass | Chemical Structure | Chemical Group |
---|---|---|---|---|---|---|---|
1 | α-Pinene | 950 | 948 | 2.82 | C10H16 (136.23) | Monoterpene hydrocarbon | |
2 | β-Myrcene | 960 | 958 | 29.48 | C10H16 (136.23) | Monoterpene hydrocarbon | |
3 | α-Phellandrene | 972 | 969 | 38.18 | C10H16 (136.23) | Monoterpene hydrocarbon | |
4 | o-Cymene | 1052 | 1042 | 1.55 | C10H14 (136.22) | Aromatic monoterpene hydrocarbon | |
5 | β-Phellandrene | 1082 | 1075 | 21.88 | C10H16 (136.23) | Monoterpene hydrocarbon | |
6 | α-Gurjunene | 1420 | 1419 | 0.38 | C15H24 (204.35) | Sesquiterpene hydrocarbon | |
7 | β-Caryophyllene | 1585 | 1579 | 1.20 | C15H24 (204.35) | Sesquiterpene Hydrocarbon | |
8 | Humulene | 1452 | 1579 | 0.26 | C15H24 (204.35) | Sesquiterpene hydrocarbon | |
9 | Germacrene D | 1480 | 1515 | 0.85 | C15H24 (204.35) | Sesquiterpene hydrocarbon | |
10 | Bicyclogermacrene | 1500 | 1492 | 0.63 | C15H24 (204.35) | Sesquiterpene hydrocarbon | |
11 | δ-Cadinene | 1513 | 1510 | 0.94 | C15H24 (204.35) | Sesquiterpene hydrocarbon | |
- | Unknown I | - | 1600 | 0.78 | C15H26O (222.37) | n.d. | Oxygenated Sesquiterpene |
- | Unknown II | - | 1623 | 0.27 | C15H26O (222.37) | n.d. | Oxygenated Sesquiterpene |
12 | Aromadendrene | 1656 | 1660 | 0.78 | C15H26O (222.37) | Oxygenated Sesquiterpene | |
Aromatic monoterpene hydrocarbons | 1.55% | ||||||
Monoterpene hydrocarbons | 92.36% | ||||||
Sesquiterpenes hydrocarbons | 4.26% | ||||||
Oxygenated sesquiterpenes | 1.83% | ||||||
Total identified | 100.00% |
2.2. Antioxidant Activity of the Essential Oil of P. acutifolium
2.3. Phytotoxic Activity of the Essential Oil of P. acutifolium on L. sativa Seeds and A. cepa Bulbs
2.4. Molecular Docking Studies
2.5. Molecular Dynamics Simulation
2.6. Molecular Mechanics Generalized Born Surface Area (MM-GBSA) Calculations
2.7. In-Silico Toxicological Study of P. acutifolium EO
3. Materials and Methods
3.1. Plant Material
3.2. Identification of the Volatile Compounds by Gas Chromatography–Mass Spectrometry (GC–MS)
3.3. Evaluation of the Antioxidant Activity of the EO of P. acutifolium against 2,2-Diphenyl-1-Picrylhydrazyl (DPPH) Radical
3.4. Evaluation of the Antioxidant Activity of the EO of P. acutifolium against 2,2′-Azinobis–(3-Ethylbenzothiazoline)-6- Sulfonic Acid (ABTS .+) Radical
3.5. Evaluation of the Antioxidant Activity of the EO of P. acutifolium against the Ferric Reducing/Antioxidant Power (FRAP)
3.6. Phytotoxicity Test on Lactuca sativa Seeds
3.7. Phytotoxicity Test on Allium cepa Bulbs
3.8. Molecular Docking
3.9. In-Silico Toxicity of the Volatile Components of P. acutifolium
3.10. Molecular Dynamics Simulation
3.11. Binding Free Energy Analysis
3.12. Statistical Analysis
4. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Antioxidant | Trolox Equivalent Antioxidant Capacity (µmol TE/g) | IC50 (µg/mL) |
---|---|---|
DPPH | 8.10 ± 0.05 | 160.12 ± 0.30 |
ABTS | 150.56 ± 8.27 | 138.10 ± 0.06 |
FRAP | 64.16 ± 1.40 | 450.10 ± 0.05 |
Groups | Seed Germination (%) | Root Length (cm) | Hypocotyl Length (cm) | Root Length/Stem Length |
---|---|---|---|---|
Negative control: DMSO 0.1% | 96.33 ± 5.51 * | 2.57 ± 0.06 * | 6.67 ± 0.58 * | 0.28 |
P. acutifolium 0.1% | 36.67 ± 5.77 * | 2.10 ± 0.17 * | 4.67 ± 0.58 * | 0.31 |
P. acutifolium 0.5% | 25.33 ± 5.03 * | 1.57 ± 0.06 * | 3.33 ± 0.58 * | 0.32 |
P. acutifolium 1% | 12.33 ± 2.52 * | 1.10 ± 0.10 * | 1.83 ± 0.29 * | 0.38 |
P. acutifolium 5% | 4.00 ± 1.73 | 0.93 ± 0.06 | 1.07 ± 0.12 | 0.47 |
P. acutifolium 10% | 0.0 ± 0.00 * | 0.60 ± 0.17 * | 0.63 ± 0.15 * | 0.49 |
Positive control: glyphosate 2% | 6.67 ± 2.89 | 1.03 ± 0.25 | 1.03 ± 0.25 | 0.08 |
Ligand | Binding Energy (kcal/mol) | Interactions |
---|---|---|
α-Phellandrene | −5.8 | Alkyl bond: Ala174, Arg200, Ile325 |
β-Myrcene | −4.7 | Alkyl bond: Lys28, Ala174, Arg200 |
β-Phellandrene | −5.2 | Alkyl bond: Ala174, Arg200, Ile325 |
Glyphosate (Control) | −6.3 | Hydrogen Bond: Lys28, Thr101, Ala100, Arrg405, Arg357 |
Energies (kcal/mol) | 3FJZ-Beta-Phellandrene | 3FJZ-Beta-Myrcene | 3FJZ-Glyphosate | 3FJZ-Alpha-Phellandrene |
---|---|---|---|---|
ΔGbind | −36.59 ± 2.63 | −35.75 ± 2.99 | −48.53 ± 4.1 | −46.15 ± 1.13 |
ΔGbindLipo | −13.96 ± 1.03 | −11.50 ± 3.1 | −19.83 ± 2.3 | −13.43 ± 1.6 |
ΔGbindvdW | −11.10 ± 2.0 | −10.63 ± 2.63 | −12.68 ± 2.17 | −14.160 ± 3.0 |
ΔGbindCoulomb | −8.12 ± 1.99 | −13.66 ± 2.88 | −2.14 ± 1.01 | −6.22 ± 0.99 |
ΔGbindHbond | −0.41 ± 0.22 | −1.87 ± 0.5 | −0.06 ± 0.01 | −0.62 ± 0.16 |
ΔGbindSolvGB | 16.5 ± 1.09 | 60.54 ± 2.8 | 13.65 ± 2.27 | 21.2 ± 1.7 |
GbindCovalent | 1.56 ± 1.2 | 4.22 ± 1.07 | 0.85 ± 0.5 | 2.66 ± 1.12 |
Toxicity | Environmental Toxicity | ||||||
---|---|---|---|---|---|---|---|
# | HH | AMES Toxicity | Carcinogenicity | Bioconcentration Factors | IGC50 | LC50FM | LC50DM |
1 | 0.196 | 0.002 | 0.056 | 2.986 | 4.327 | 5.287 | 5.948 |
2 | 0.61 | 0.025 | 0.802 | 2.021 | 4.471 | 5.331 | 5.45 |
3 | 0.76 | 0.011 | 0.344 | 2.36 | 3.08 | 3.674 | 4.176 |
4 | 0.03 | 0.032 | 0.456 | 2.231 | 3.598 | 4.033 | 4.107 |
5 | 0.269 | 0.024 | 0.874 | 2.154 | 4.09 | 4.242 | 4.328 |
6 | 0.174 | 0.007 | 0.048 | 3.263 | 4.796 | 5.861 | 6.647 |
7 | 0.26 | 0.012 | 0.357 | 3.129 | 4.024 | 4.957 | 6.196 |
8 | 0.182 | 0.002 | 0.938 | 3.083 | 3.323 | 4.45 | 5.997 |
9 | 0.411 | 0.012 | 0.9 | 2.864 | 4.253 | 4.966 | 5.405 |
10 | 0.582 | 0.005 | 0.062 | 3.262 | 4.214 | 6.018 | 6.783 |
11 | 0.172 | 0.018 | 0.229 | 3.174 | 3.562 | 5.018 | 5.582 |
12 | 0.256 | 0.011 | 0.043 | 3.295 | 4.705 | 5.41 | 6.639 |
Glyphosate | 0.184 | 0.02 | 0.041 | 0.151 | 2.351 | 3.794 | 3.503 |
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Cuadros-Siguas, C.F.; Herrera-Calderon, O.; Batiha, G.E.-S.; Almohmadi, N.H.; Aljarba, N.H.; Apesteguia-Infantes, J.A.; Loyola-Gonzales, E.; Tataje-Napuri, F.E.; Kong-Chirinos, J.F.; Almeida-Galindo, J.S.; et al. Volatile Components, Antioxidant and Phytotoxic Activity of the Essential Oil of Piper acutifolium Ruiz & Pav. from Peru. Molecules 2023, 28, 3348. https://doi.org/10.3390/molecules28083348
Cuadros-Siguas CF, Herrera-Calderon O, Batiha GE-S, Almohmadi NH, Aljarba NH, Apesteguia-Infantes JA, Loyola-Gonzales E, Tataje-Napuri FE, Kong-Chirinos JF, Almeida-Galindo JS, et al. Volatile Components, Antioxidant and Phytotoxic Activity of the Essential Oil of Piper acutifolium Ruiz & Pav. from Peru. Molecules. 2023; 28(8):3348. https://doi.org/10.3390/molecules28083348
Chicago/Turabian StyleCuadros-Siguas, Carmela Fiorella, Oscar Herrera-Calderon, Gaber El-Saber Batiha, Najlaa Hamed Almohmadi, Nada H. Aljarba, José Alfonso Apesteguia-Infantes, Eddie Loyola-Gonzales, Freddy Emilio Tataje-Napuri, José Francisco Kong-Chirinos, José Santiago Almeida-Galindo, and et al. 2023. "Volatile Components, Antioxidant and Phytotoxic Activity of the Essential Oil of Piper acutifolium Ruiz & Pav. from Peru" Molecules 28, no. 8: 3348. https://doi.org/10.3390/molecules28083348