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Extraction and Study of the Essential Oil of Copal (Dacryodes Peruviana), an Amazonian Fruit with the Highest Yield Worldwide

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Extraction and Study of the Essential Oil of Copal (Dacryodes Peruviana), an Amazonian Fruit with the Highest Yield Worldwide plants Article Extraction and Study of the Essential Oil of Copal (Dacryodes peruviana), an Amazonian Fruit with the Highest Yield Worldwide Eduardo Valarezo * , Santiago Ojeda-Riascos , Luis Cartuche , Nathaly Andrade-González, Inés González-Sánchez and Miguel Angel Meneses Departamento de Química y Ciencias Exactas, Universidad Técnica Particular de Loja, Loja 110150, Ecuador; [email protected] (S.O.-R.); [email protected] (L.C.); [email protected] (N.A.-G.); [email protected] (I.G.-S.); [email protected] (M.A.M.) * Correspondence: [email protected]; Tel.: +593-7-3701444 Received: 30 October 2020; Accepted: 16 November 2020; Published: 26 November 2020 Abstract: Essential oils are highly demanded substances worldwide. They can be used without modification due to their different chemical and biological properties or as natural sources of chemical compounds. The limit in the use of these metabolites is their low yield. In the present investigation, the essential oil of fruits from Dacryodes peruviana collected in the Ecuadorian Amazon was extracted and studied. The essential oil was released from the plant matrix and isolated by hydrodistillation. The yields obtained were 4.8 0.2% and 11.3 0.2% for fresh and dried ± ± fruits, respectively, one of the highest yields on record to date. Twenty-five chemical compounds were identified by GC/MS and GC/FID techniques. The principal constituent was α-phellandrene, with 50.32 3.32%. The antimicrobial activity of the oil was assayed against five Gram negative ± bacteria, two Gram positive bacteria and two fungi. The essential oil exerted a moderate activity against Staphylococcus aureus. The repellent activity of the oil was assayed against mosquitoes (Diptera: Culicidae); the samples with 3%, 2% and 1% essential oil were class 4, and the sample with 0.5% showed to be class 3. The essential oil showed a weak antioxidant activity through the DPPH and ABTS methods. Keywords: Dacryodes peruviana; essential oil; α-phellandrene; antibacterial activity; antifungal activity; repellent activity; antioxidant activity 1. Introduction Burseraceae is a family of flowering plants belonging to order Sapindales, composed of about 18 genera, which includes over 649 currently accepted species of resinous trees and shrubs (The Plant List, 2013). Burseraceae are native primarily to tropical America with few species in Africa and Asia (Encyclopaedia Britannica, 2020). These species produce gum resins and essential oils, which are responsible of many medicinal properties (El-Shemy, 2018). From the literature, essential oils are recognized as a rich source of bioactive compounds, which present biological activities such as antifungal, antibacterial, anti-insecticidal, antiviral and antitumor; the identification of these activities has increased the interest in looking for biological properties of essential oils. In Ecuador, a megadiverse country with approximately 17,000 species of plants, the species of the Burseraceae family represent only 0.3% of the total species, with 40 individuals, most of which are native and one is endemic [1]. Within the Burseraceae family, the Dacryodes genus ranks fifth in number of species with 62 individuals, after the genera Commiphora (208 individuals), Bursera (120 individuals), Protium (104 individuals) and Canarium (88 individuals) [2]. Dacryodes peruviana (Loes.) H.J. Lam Plants 2020, 9, 1658; doi:10.3390/plants9121658 www.mdpi.com/journal/plants Plants 2020, 9, x 2 of 14 are native and one is endemic [1]. Within the Burseraceae family, the Dacryodes genus ranks fifth in numberPlants 2020 of, 9 ,species 1658 with 62 individuals, after the genera Commiphora (208 individuals), Bursera2 (120 of 13 individuals), Protium (104 individuals) and Canarium (88 individuals) [2]. Dacryodes peruviana (Loes.) H.J.(class: Lam Equisetopsida (class: Equisetopsida C. Agardh; C. subclass: Agardh; Magnoliidae subclass: Magnoliidae Novák ex Takht.; Novák superorder: ex Takht.; Rosanae superorder: Takht.; Rosanaeorder: Sapindales Takht.; order: Juss. Sapindales ex Bercht. Juss. & J. Presl;ex Bercht. family: & J. Burseraceae Presl; family: Kunth; Burseraceae genus: DacryodesKunth; genus:Vahl) Dacryodesis a native Vahl) species is a of native Ecuador, species widely of Ecuador, distributed wide inly the distributed Andean and in the Amazonian Andean regionsand Amazonian between regions0 and 2500 between m a.s.l., 0 and especially 2500 m ina.s.l., the especially Amazonian in the provinces Amazonian of Morona-Santiago, provinces of Morona-Santiago, Napo, Pastaza, Napo,Zamora-Chinchipe Pastaza, Zamora-Chinchipe [1]. The species [1]. isThe known species as is “ knowncopal”“ ascopal “copal comestible” “copal” comestible and “anime” and” (Spanish“anime” (Spanishlanguage), language), and “wigonkawe and “wigonkawe” (Wao tededo,” (Wao dialect tededo, of dialect the Amazon of the region)Amazon [3 region)]. The Dacryodes [3]. The Dacryodes peruviana peruvianaplant isa plant 20–25 is ma 20–25 tall tree m withtall tree alternate with alternate and odd-pinnate and odd-pinnate compound compound leaves, withleaves, 5–9 with leaflets 5–9 leaflets(12–30 (12–307–11 × cm). 7–11 cm). It has It has inflorescence inflorescence in itsin its panicle panicle and and subminal, subminal, and andits its flowerflower is unisexual, unisexual, × with cupuliform calyx and three yellowish-green pe petals.tals. The The fruit fruit is is an an indehiscent indehiscent ovoid ovoid drupe, drupe, which is used as food for monkeys, birds and for human consumption. The The resin resin is is used used as as incense andand mosquito mosquito repellent. repellent. The The trunk trunk is is used used as as wood wood in in the the construction of of houses, cabinetry and and carpentrycarpentry [3]. [3]. Currently, Currently, there are no reportsreports of the toxicity of this species. Currently,Currently, EcuadorEcuador occupiesoccupies the the sixth sixth position position worldwide worldwide in in the the number number of plantof plant species species per unitper unitsurface surface area, area, which which makes makes this this country country a biodiversitya biodiversity hotspot hotspot [4 [4].]. However, However, therethere areare few studies ofof its its aromatic plant species, especially of of the ar aromaticomatic species of the Burs Burseraceaeeraceae family; for for this this reason,reason, the the aims aims of of this this research research are are (i) to contribute to to the knowledge of of the the aromatic aromatic species species of of the the BurseraceaeBurseraceae family, family, isolating and and studying the the essential oil oil of the species Dacryodes peruviana fromfrom Ecuador,Ecuador, (ii)(ii) toto promote promote the the use use of essentialof essential oils byoils providing by providing information information on their on availability, their availability, chemical chemicalcomposition composition and biological and biological properties, properties, and (iii) and to provide (iii) to provide an alternative an alternative for the for use the of use non-timber of non- timberresources, resources, by using by theusing fruits the as fruits a replacement as a replacem forent wood for andwood leaves. and leaves. In addition, In addition, as we as know, we know, this is thisthe firstis the report first ofreport the extraction of the extraction of essential of essent oil ofial this oil species of this and species the study and the of its study physical of its properties, physical properties,chemical composition chemical composit and biologicalion and activity. biological activity. 2.2. Results Results 2.1.2.1. Essential Essential Oil Oil Extraction Extraction FromFrom fresh fresh fruits, with 74 ± 3%3% of of moisture, moisture, a approximatelypproximately 480 480 mL mL of of essential essential oil oil (AE) (AE) from from ± 10,000 g g of of vegetal vegetal material material were were obtained, obtained, which which represented represented a a yield yield of of 4.8 4.8 ± 0.20.2% % ( (vv//ww)) or or 48 48 mL/Kg. mL/Kg. ± OnOn the the other other hand, hand, from from 10,000 10,000 g g of of dried dried fruit, fruit, with with 14 14 ± 11% % moisture, moisture, ~1130 mL mL of of essential essential oil oil were were ± obtained,obtained, which which represents represents a a yield yield of 11.3 ± 0.30.3 ( (v/wv/w)) or or 113 113 mL/Kg. mL/Kg. Figure Figure 1 showsshows thethe essentialessential oiloil ± extractionextraction raterate (accumulated(accumulated volume volume vs. vs. time); time); the amountthe amount of essential of essential oil extracted oil extracted per hour per decreases hour decreasesover time over from time 42 mL from/Kg 42 in mL/Kg the first in hour the tofirst 0.2 hour mL/ Kgto 0.2 in mL/Kg the last in hour. the last In both hour. cases In both (fresh cases and (fresh dried andfruits), dried 90% fruits), of essential 90% of oil essential is obtained oil is in obtained 0.75 h and in 0.75 95% h in and 1 h. 95% in 1 h. Figure 1. Essential oil extraction rate. Figure 1. Essential oil extraction rate. 2.2. Physical Properties of Essential Oil The essential oil of D. peruviana was a viscous liquid with a density of d20 = 0.8456 0.0023 g/cm3, ± 20 [α]20 refractive index of n = 1.4751 0.0002 and specific rotation of D = +12.2 0.7. ± ± Plants 2020, 9, 1658 3 of 13 2.3. Essential Oil Compounds Identification The identification of volatile compounds present in Dacryodes peruviana of Ecuador was carried out by GC/MS and GC/FID. The qualitative and quantitative data of the chemical composition of the oils of this species are shown in Table1. In essential oil, twenty-five chemical constituents were identified, representing 99.1% of the total composition. These constituents were mainly grouped into aliphatic monoterpene hydrocarbons (ALM, 94.40%); furthermore, a low amount of oxygenated monoterpenes (OXM, 1.17%) were identified and the presence of oxygenated sesquiterpene (OXS) was not determined. The principal constituents are found to be ALM (CF: C10H16, MM: 136.13 Da) α-phellandrene (50.32 3.32%), limonene (23.03 2.53%), α-pinene (8.27 1.28%) and terpinolene ± ± ± (5.23 0.93%).
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