Extraction and Study of the Essential Oil of Copal (Dacryodes peruviana), an Amazonian Fruit with the Highest Yield Worldwide
Abstract
:1. Introduction
2. Results
2.1. Essential Oil Extraction
2.2. Physical Properties of Essential Oil
2.3. Essential Oil Compounds Identification
2.4. Biological Activity
2.4.1. Antibacterial Activity
2.4.2. Antifungal Activity
2.4.3. Repellent Activity
2.4.4. Antioxidant Capacity
3. Discussion
4. Materials and Methods
4.1. Materials
4.2. Plant Material
4.3. Essential Oil Extraction
4.4. Determination of Physical Properties of Essential Oil
4.5. Essential Oil Compounds Identification
4.6. Biological Activity
4.6.1. Evaluation of Antibacterial Activity
4.6.2. Evaluation of Antifungal Activity
4.6.3. Evaluation of Repellent Activity
4.6.4. Evaluation of Antioxidant capacity
DPPH Radical Scavenging Activity
ABTS Radical Cation Scavenging Activity
4.7. Statistical Analysis
5. Conclusions
6. Patents
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
- Jørgesen, P.M.; León-Yáñez, S. Catalogue of the Vascular Plants of Ecuador. Available online: http://legacy.tropicos.org/ProjectAdvSearch.aspx?projectid=2 (accessed on 11 July 2020).
- The Plant List. Burseraceae. Available online: http://www.theplantlist.org (accessed on 3 July 2020).
- Pérez, A.J.; Hernández, C.; Romero-Saltos, H.; Valencia, R. Árboles emblemáticos de Yasuní, Ecuador. Available online: https://bioweb.bio/floraweb/arbolesyasuni/FichaEspecie/Dacryodes%20peruviana (accessed on 29 September 2020).
- Mestanza-Ramón, C.; Henkanaththegedara, S.M.; Vásconez Duchicela, P.; Vargas Tierras, Y.; Sánchez Capa, M.; Constante Mejía, D.; Jimenez Gutierrez, M.; Charco Guamán, M.; Mestanza Ramón, P. In-Situ and Ex-Situ Biodiversity Conservation in Ecuador: A Review of Policies, Actions and Challenges. Diversity 2020, 12, 315. [Google Scholar] [CrossRef]
- Jimborean, M.A.; Salanță, L.C.; Tofană, M.; Pop, C.R.; Rotar, A.M.; Fetti, V. Use of Essential Oils from Citrus sinensis in the Development of New Type of Yogurt. Food Sci. Technol. 2016, 73, 4. [Google Scholar] [CrossRef] [Green Version]
- Santos, D.L.; Ferreira, H.D.; Borges, L.L.; Paula, J.R.; Tresvenzol, L.M.F.; Santos, P.A.; Ferri, P.H.; Sá, S.D.; Fiuza, T.S. Chemical composition of essential oils of leaves, flowers and fruits of Hortia oreadica. Rev. Bras. De Farmacogn. 2016, 26, 23–28. [Google Scholar] [CrossRef] [Green Version]
- Lucia, A.; Licastro, S.; Zerba, E.; Masuh, H. Yield, chemical composition, and bioactivity of essential oils from 12 species of Eucalyptus on Aedes aegypti larvae. Entomol. Exp. Et Appl. 2008, 129, 107–114. [Google Scholar] [CrossRef]
- Morsy, N.F.S.; Hammad, K.S.M. Extraction of essential oil from methyl cinnamate basil (Ocimum canum Sims) with high yield in a short time using enzyme pretreatment. J. Food Sci. Technol. 2020. [Google Scholar] [CrossRef]
- Elyemni, M.; Louaste, B.; Nechad, I.; Elkamli, T.; Bouia, A.; Taleb, M.; Chaouch, M.; Eloutassi, N. Extraction of Essential Oils of Rosmarinus officinalis L. by Two Different Methods: Hydrodistillation and Microwave Assisted Hydrodistillation. Sci. World J. 2019, 2019, 3659432. [Google Scholar] [CrossRef] [Green Version]
- Mollaei, S.; Sedighi, F.; Habibi, B.; Hazrati, S.; Asgharian, P. Extraction of essential oils of Ferulago angulata with microwave-assisted hydrodistillation. Ind. Crop. Prod. 2019, 137, 43–51. [Google Scholar] [CrossRef]
- Sodeifian, G.; Sajadian, S.A.; Saadati Ardestani, N. Optimization of essential oil extraction from Launaea acanthodes Boiss: Utilization of supercritical carbon dioxide and cosolvent. J. Supercrit. Fluids 2016, 116, 46–56. [Google Scholar] [CrossRef]
- Golmohammadi, M.; Borghei, A.; Zenouzi, A.; Ashrafi, N.; Taherzadeh, M.J. Optimization of essential oil extraction from orange peels using steam explosion. Heliyon 2018, 4, e00893. [Google Scholar] [CrossRef] [Green Version]
- Molares, S.; González, S.B.; Ladio, A.; Agueda Castro, M. Etnobotánica, anatomía y caracterización físico-química del aceite esencial de Baccharis obovata Hook. et Arn. (Asteraceae: Astereae). Acta Bot. Bras. 2009, 23, 578–589. [Google Scholar] [CrossRef]
- Young, D.G.; Chao, S.; Casablanca, H.; Bertrand, M.-C.; Minga, D. Essential Oil of Bursera graveolens (Kunth) Triana et Planch from Ecuador. J. Essent. Oil Res. 2007, 19, 525–526. [Google Scholar] [CrossRef]
- Rey-Valeirón, C.; Guzmán, L.; Saa, L.R.; López-Vargas, J.; Valarezo, E. Acaricidal activity of essential oils of Bursera graveolens (Kunth) Triana & Planch and Schinus molle L. on unengorged larvae of cattle tick Rhipicephalus (Boophilus) microplus (Acari:Ixodidae). J. Essent. Oil Res. 2017, 29, 344–350. [Google Scholar] [CrossRef]
- Ochoa Pumaylle, K.; Paredes Quiroz, L.R.; Bejarano Luján, D.L.; Silva Paz, R.J. Extraction, characterization and evaluation of antibacterial activity of essential oil of Senecio graveolens Wedd (Wiskataya). Sci. Agropecu. 2012, 3, 291–302. [Google Scholar] [CrossRef] [Green Version]
- Delgado Ospina, J.; Grande Tovar, C.D.; Menjívar Flores, J.C.; Sánchez Orozco, M.S. Relationship between refractive index and thymol concentration in essential oils of Lippia origanoides Kunth. Chil. J. Agric. Anim. Sci. 2016, 32, 127–133. [Google Scholar] [CrossRef] [Green Version]
- Badalamenti, N.; Bruno, M.; Gagliano Candela, R.; Maggi, F. Chemical composition of the essential oil of Elaeoselinum asclepium (L.) Bertol subsp. meoides (Desf.) Fiori (Umbelliferae) collected wild in Central Sicily and its antimicrobial activity. Nat. Prod. Res. 2020, 1–9. [Google Scholar] [CrossRef]
- Park, I.-K.; Lee, S.-G.; Choi, D.-H.; Park, J.-D.; Ahn, Y.-J. Insecticidal activities of constituents identified in the essential oil from leaves of Chamaecyparis obtusa against Callosobruchus chinensis (L.) and Sitophilus oryzae (L.). J. Stored Prod. Res. 2003, 39, 375–384. [Google Scholar] [CrossRef]
- Piccinelli, A.C.; Santos, J.A.; Konkiewitz, E.C.; Oesterreich, S.A.; Formagio, A.S.N.; Croda, J.; Ziff, E.B.; Kassuya, C.A.L. Antihyperalgesic and antidepressive actions of (R)-(+)-limonene, α-phellandrene, and essential oil from Schinus terebinthifolius fruits in a neuropathic pain model. Nutr. Neurosci. 2015, 18, 217–224. [Google Scholar] [CrossRef]
- Tisserand, R.; Young, R. Essential Oil Safety: A Guide for Health Care Professionals, 2nd ed.; Churchill Livingstone/Elsevier: London, UK, 2014. [Google Scholar]
- Obadiah, A.; Kannan, R.; Ramesh, P.; Ramasubbu, A.; Kumar, S.V. Isolation of carvone and phellandrene from Murraya koenigii and study of their antioxidant activity. Chem. Nat. Compd. 2012, 48, 149–150. [Google Scholar] [CrossRef]
- Lima, D.F.; Brandão, M.S.; Moura, J.B.; Leitão, J.M.R.S.; Carvalho, F.A.A.; Miúra, L.M.C.V.; Leite, J.R.S.A.; Sousa, D.P.; Almeida, F.R.C. Antinociceptive activity of the monoterpene α-phellandrene in rodents: Possible mechanisms of action. J. Pharm. Pharmacol. 2012, 64, 283–292. [Google Scholar] [CrossRef]
- Lin, J.-J.; Lin, J.-H.; Hsu, S.-C.; Weng, S.-W.; Huang, Y.-P.; Tang, N.-Y.; Lin, J.-G.; Chung, J.-G. Alpha-phellandrene promotes immune responses in normal mice through enhancing macrophage phagocytosis and natural killer cell activities. Vivo 2013, 27, 809–814. [Google Scholar]
- Lopez, S.; Lima, B.; Agüero, M.B.; Lopez, M.L.; Hadad, M.; Zygadlo, J.; Caballero, D.; Stariolo, R.; Suero, E.; Feresin, G.E.; et al. Chemical composition, antibacterial and repellent activities of Azorella trifurcata, Senecio pogonias, and Senecio oreophyton essential oils. Arab. J. Chem. 2018, 11, 181–187. [Google Scholar] [CrossRef] [Green Version]
- Souza, A.D.; Lopes, E.M.C.; Silva, M.C.D.; Cordeiro, I.; Young, M.C.M.; Sobral, M.E.G.; Moreno, P.R.H. Chemical composition and acetylcholinesterase inhibitory activity of essential oils of Myrceugenia myrcioides(Cambess.) O. Berg and Eugenia riedelianaO. Berg, Myrtaceae. Rev. Bras. De Farmacogn. 2010, 20, 175–179. [Google Scholar] [CrossRef]
- Van Vuuren, S.; Holl, D. Antimicrobial natural product research: A review from a South African perspective for the years 2009–2016. J. Ethnopharmacol. 2017, 208, 236–252. [Google Scholar] [CrossRef]
- Cos, P.; Vlietinck, A.J.; Berghe, D.V.; Maes, L. Anti-infective potential of natural products: How to develop a stronger in vitro ‘proof-of-concept’. J. Ethnopharmacol. 2006, 106, 290–302. [Google Scholar] [CrossRef]
- İşcan, G.; Kırımer, N.; Demirci, F.; Demirci, B.; Noma, Y.; Başer, K.H.C. Biotransformation of (−)-(R)-α-Phellandrene: Antimicrobial Activity of Its Major Metabolite. Chem. Biodivers. 2012, 9, 1525–1532. [Google Scholar] [CrossRef]
- Espina, L.; Gelaw, T.K.; de Lamo-Castellví, S.; Pagán, R.; García-Gonzalo, D. Mechanism of bacterial inactivation by (+)-limonene and its potential use in food preservation combined processes. PLoS ONE 2013, 8, e56769. [Google Scholar] [CrossRef] [Green Version]
- Viglianco, A.I.; Novo, R.J.; Cragnolini, C.I.; Nassetta, M.; Cavallo, E. Antifeedant and Repellent Effects of Extracts of Three Plants from Córdoba (Argentina) Against Sitophilus oryzae (L.) (Coleoptera: Curculionidae). BioAssay 2008, 3. [Google Scholar] [CrossRef] [Green Version]
- Gillij, Y.G.; Gleiser, R.M.; Zygadlo, J.A. Mosquito repellent activity of essential oils of aromatic plants growing in Argentina. Bioresour. Technol. 2008, 99, 2507–2515. [Google Scholar] [CrossRef]
- Jaenson, T.G.T.; Pålsson, K.; Borg-Karlson, A.-K. Evaluation of Extracts and Oils of Mosquito (Diptera: Culicidae) Repellent Plants from Sweden and Guinea-Bissau. J. Med Entomol. 2006, 43, 113–119. [Google Scholar] [CrossRef]
- Saeidi, M.; Moharramipour, S.; Sefidkon, F.; Aghajanzadeh, S. Insecticidal and repellent activities of Citrus reticulata, Citrus limon and Citrus aurantium essential oils on Callosobruchus maculatus. Integr. Prot. Stored Prod. 2011, 69, 289–293. [Google Scholar]
- Mata, A.T.; Proença, C.; Ferreira, A.R.; Serralheiro, M.L.M.; Nogueira, J.M.F.; Araújo, M.E.M. Antioxidant and antiacetylcholinesterase activities of five plants used as Portuguese food spices. Food Chem. 2007, 103, 778–786. [Google Scholar] [CrossRef]
- Singh, P.; Shukla, R.; Prakash, B.; Kumar, A.; Singh, S.; Mishra, P.K.; Dubey, N.K. Chemical profile, antifungal, antiaflatoxigenic and antioxidant activity of Citrus maxima Burm. and Citrus sinensis (L.) Osbeck essential oils and their cyclic monoterpene, dl-limonene. Food Chem. Toxicol. 2010, 48, 1734–1740. [Google Scholar] [CrossRef]
- Salanţă, L.-C.; Tofană, M.; Socaci, S.; Mudura, E.; Pop, C.; Pop, A.; Fărcaş, A. Determination of Volatiles in Hops from Romania by Solid Phase Fiber Microextraction and Gas Chromatography–Mass Spectrometry. Anal. Lett. 2016, 49, 477–487. [Google Scholar] [CrossRef]
- Valarezo, E.; Guamán, M.D.C.; Paguay, M.; Meneses, M.A. Chemical Composition and Biological Activity of the Essential Oil from Gnaphalium elegans Kunth from Loja, Ecuador. J. Essent. Oil Bear. Plants 2019, 22, 1372–1378. [Google Scholar] [CrossRef]
- Valarezo, E.; Tandazo, O.; Galán, K.; Rosales, J.; Benítez, Á. Volatile Metabolites in Liverworts of Ecuador. Metabolites 2020, 10, 92. [Google Scholar] [CrossRef] [Green Version]
- Adams, R.P. Identification of Essential Oil Components by Gas Chromatography/Mass Spectrometry, 4th ed.; Allured Publishing Corporation: Carol Stream, IL, USA, 2007. [Google Scholar]
- Mass Spectral Library (NIST/EPA/NIH); NIST 05; National Institute of Standards and Technology: Gaithersburg, MD, USA, 2005.
- NIST. Libro del Web de Química del NIST, SRD 69. in Base de Datos de Referencia Estándar del NIST Número 69. Available online: http://webbook.nist.gov (accessed on 19 May 2020).
- Van Den Dool, H.; Dec Kratz, P. A generalization of the retention index system including linear temperature programmed gas—liquid partition chromatography. J. Chromatogr. A 1963, 11, 463–471. [Google Scholar] [CrossRef]
- Clinical and Laboratory Standards Institute. Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically, Approved Standard–Ninth Edition; CLSI Document M07-A9; Clinical and Laboratory Standards Institute: Wayne, PA, USA, 2012. [Google Scholar]
- Clinical and Laboratory Standards Institute. Reference method for Broth Dilution Antifungal Susceptibility Testing of Filamentous Fungi, Approved Standard–Second Edition; CLSI Document M38-A2; Clinical and Laboratory Standards Institute: Wayne, PA, USA, 2008. [Google Scholar]
- NCCLS. Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts, Approved Standard–Second Edition; NCCLS Document M27-A2; NCCLS: Wayne, PA, USA, 2002. [Google Scholar]
- Talukder, F.A.; Howse, P.E. Laboratory evaluation of toxic and repellent properties of the pithraj tree, Aphanamixis polystachya Wall & Parker, against Sitophilus oryzae (L.). Int. J. Pest Manag. 1994, 40, 274–279. [Google Scholar] [CrossRef]
- Valarezo, E.; Flores-Maza, P.; Cartuche, L.; Ojeda-Riascos, S.; Ramírez, J. Phytochemical profile, antimicrobial and antioxidant activities of essential oil extracted from Ecuadorian species Piper ecuadorense sodiro. Nat. Prod. Res. 2020, 1–6. [Google Scholar] [CrossRef]
- Arnao, M.B.; Cano, A.; Acosta, M. The hydrophilic and lipophilic contribution to total antioxidant activity. Food Chem. 2001, 73, 239–244. [Google Scholar] [CrossRef]
- Thaipong, K.; Boonprakob, U.; Crosby, K.; Cisneros-Zevallos, L.; Hawkins Byrne, D. Comparison of ABTS, DPPH, FRAP, and ORAC assays for estimating antioxidant activity from guava fruit extracts. J. Food Compos. Anal. 2006, 19, 669–675. [Google Scholar] [CrossRef]
Peak # | Compound a | RI | RIref | D. peruviana | Type | CF | MM | |
---|---|---|---|---|---|---|---|---|
%b | SD | (Da) | ||||||
1 | Tricyclene | 921 | 921 | 0.05 | 0.03 | ALM | C10H16 | 136.13 |
2 | α-Thujene | 926 | 924 | 1.90 | 0.14 | ALM | C10H16 | 136.13 |
3 | α-Pinene | 932 | 932 | 8.27 | 1.28 | ALM | C10H16 | 136.13 |
4 | Camphene | 947 | 946 | 0.13 | 0.04 | ALM | C10H16 | 136.13 |
5 | Sabinene | 969 | 969 | 1.44 | 0.40 | ALM | C10H16 | 136.13 |
6 | β-Pinene | 973 | 974 | 2.57 | 0.91 | ALM | C10H16 | 136.13 |
7 | Myrcene | 986 | 988 | 0.73 | 0.20 | ALM | C10H16 | 136.13 |
8 | α-Phellandrene | 1005 | 1002 | 50.32 | 3.32 | ALM | C10H16 | 136.13 |
9 | δ-3-Carene | 1010 | 1008 | 0.18 | 0.11 | ALM | C10H16 | 136.13 |
10 | α-Terpinene | 1013 | 1014 | 0.32 | 0.05 | ALM | C10H16 | 136.13 |
11 | ρ-Cymene | 1021 | 1020 | 3.06 | 0.80 | ARM | C10H14 | 134.10 |
12 | Limonene | 1025 | 1024 | 23.03 | 2.53 | ALM | C10H16 | 136.13 |
13 | γ-Terpinene | 1055 | 1054 | 0.23 | 0.24 | ALM | C10H16 | 136.13 |
14 | Terpinolene | 1082 | 1086 | 5.23 | 0.93 | ALM | C10H16 | 136.13 |
15 | Camphor | 1140 | 1141 | tr | - | OXM | C10H16O | 152.12 |
16 | Terpinen-4-ol | 1170 | 1174 | 0.07 | 0.05 | OXM | C10H18O | 154.14 |
17 | γ-Terpineol | 1202 | 1199 | 0.98 | 0.31 | OXM | C10H18O | 154.14 |
18 | Ascaridole | 1236 | 1234 | 0.12 | 0.02 | OXM | C10H16O2 | 168.12 |
19 | δ-Elemene | 1338 | 1335 | 0.06 | 0.07 | ALS | C15H24 | 204.19 |
20 | α-Copaene | 1366 | 1374 | 0.05 | 0.03 | ALS | C15H24 | 204.19 |
21 | trans-Caryophyllene | 1415 | 1417 | 0.13 | 0.09 | ALS | C15H24 | 204.19 |
22 | α-Humulene | 1451 | 1452 | tr | - | ALS | C15H24 | 204.19 |
23 | Germacrene D | 1476 | 1480 | 0.15 | 0.01 | ALS | C15H24 | 204.19 |
24 | δ-Amorphene | 1509 | 1511 | tr | - | ALS | C15H24 | 204.19 |
25 | β-Curcumene | 1514 | 1514 | 0.07 | 0.09 | ALS | C15H24 | 204.19 |
Aliphatic monoterpene hydrocarbons (ALM) | 94.40 | |||||||
Aromatic monoterpene hydrocarbons (ARM) | 3.06 | |||||||
Oxygenated monoterpenes (OXM) | 1.17 | |||||||
Aliphatic sesquiterpene hydrocarbons (ALS) | 0.47 | |||||||
Total identified | 99.10 |
Microorganism | D. Peruviana | Positive Control b |
---|---|---|
MIC (μg/mL) a | ||
Gram-Negative Bacteria | ||
Pseudomonas aeruginosa (ATCC 27853) | 5000 | 3.91 |
Klebsiella pneumoniae (ATCC 9997) | 2500 | 1.95 |
Proteus vulgaris (ATCC 8427) | 2500 | 3.91 |
Escherichia coli (ATCC 25922) | 2500 | 1.95 |
Salmonella typhimurium (LT2) | >5000 | 1.95 |
Gram-positive Bacteria | ||
Enterococcus faecalis (ATCC 29212) | 2500 | 15.62 |
Staphylococcus aureus (ATCC 25923) | 625 | 15.62 |
Dermatophytes Fungi | ||
Trichophyton rubrum (ATCC 28188) | 2500 | 20 |
Trichophyton mentagrophytes (ATCC 28185) | 2500 | 20 |
Essential Oil Concentration | Repellency (%) a | Mean Repellency | Class Repellency | ||||
---|---|---|---|---|---|---|---|
1 h | 2 h | 3 h | 4 h | 5 h b | |||
3% | 100 | 60 | 60 | 60 | 60 | 70% | 4 |
2% | 80 | 60 | 60 | 60 | 60 | 65% | 4 |
1% | 80 | 60 | 60 | 60 | 60 | 65% | 4 |
0.5% | 60 | 40 | 40 | 40 | 40 | 45% | 3 |
Control (+) c | 100 | 100 | 100 | 100 | 100 | 100% | 5 |
Sample | DPPH | ABTS |
---|---|---|
IC50 a (μg/mL) | ||
D. peruviana EO | >1000 | > 1000 |
BHT | 430 ± 30 | 290 ± 20 |
Trolox | 460 ± 50 | 260 ± 30 |
Class | Repellency Rate (%) |
---|---|
0 | >0.01 to <0.1 |
1 | 0.1 to 20 |
2 | 20.1 to 40 |
3 | 40.1 to 60 |
4 | 60.1 to 80 |
5 | 80.1 to 100 |
Publisher’s Note: MDPI stays neutral with regard to jurisdictional claims in published maps and institutional affiliations. |
© 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
Share and Cite
Valarezo, E.; Ojeda-Riascos, S.; Cartuche, L.; Andrade-González, N.; González-Sánchez, I.; Meneses, M.A. Extraction and Study of the Essential Oil of Copal (Dacryodes peruviana), an Amazonian Fruit with the Highest Yield Worldwide. Plants 2020, 9, 1658. https://doi.org/10.3390/plants9121658
Valarezo E, Ojeda-Riascos S, Cartuche L, Andrade-González N, González-Sánchez I, Meneses MA. Extraction and Study of the Essential Oil of Copal (Dacryodes peruviana), an Amazonian Fruit with the Highest Yield Worldwide. Plants. 2020; 9(12):1658. https://doi.org/10.3390/plants9121658
Chicago/Turabian StyleValarezo, Eduardo, Santiago Ojeda-Riascos, Luis Cartuche, Nathaly Andrade-González, Inés González-Sánchez, and Miguel Angel Meneses. 2020. "Extraction and Study of the Essential Oil of Copal (Dacryodes peruviana), an Amazonian Fruit with the Highest Yield Worldwide" Plants 9, no. 12: 1658. https://doi.org/10.3390/plants9121658