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Hindawi Publishing Corporation International Journal of Forestry Research Volume 2014, Article ID 982576, 6 pages http://dx.doi.org/10.1155/2014/982576 Research Article Essential Oil Constituents and Yields from Leaves of Blepharocalyx salicifolius (Kunt) O. Berg and Myracrodruon urundeuva (Allemão) Collected during Daytime 1 1 Olívia Bueno da Costa, Cláudio Henrique Soares Del Menezzi, Luiz Eduardo Celino 2 2 3 4 Benedito, Inês Sabioni Resck, Roberto Fontes Vieira, and Humberto Ribeiro Bizzo Department of Forest Engineering, University of Brasilia, 70904-970 Brasilia, DF, Brazil Institute of Chemistry, University of Brasilia, 70910-900 Brasilia, DF, Brazil Embrapa Genetic Resources and Biotechnology, 70770-917 Brasilia, DF, Brazil EmbrapaFood Technology,23020-470 RiodeJaneiro,RJ, Brazil Correspondence should be addressed to Ol´ıvia Bueno da Costa; firstname.lastname@example.org Received 18 October 2013; Revised 3 January 2014; Accepted 4 January 2014; Published 17 February 2014 Academic Editor: Piermaria Corona Copyright © 2014 Ol´ıvia Bueno da Costa et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The purpose of this study was to evaluate the essential oil composition and yield from leaves of two Brazilian species ( Myracrodruon urundeuva and Blepharocalyx salicifolius) harvested during daytime. Essential oils were obtained by steam distillation and had their yield determined. Blepharocalyx salicifolius presented yields of 0.049% (9 a.m.), 0.045% (1 p.m.), and 0.069% (5 p.m.). For Myracrodruon urundeuva, we found 0.13% (9 a.m.), 0.11% (1 p.m.), and 0.08% (5 p.m.). Finally, compound identification and quantification were carried out by GC-MS and GC-FID techniques, respectively. Thirteen major compounds were identified for Blepharocalyx salicifolius, representing 91.6% of the EOs, of which p-cymene (25.9%) was detected as amajor component. Nine major compounds were identified for Myracrodruon urundeuva, representing 90.3% of the EOs, whereas𝛽 -myrcene showed the greatest concentration (66.4%). 1. Introduction humidity, location, and genetics as well as the daytime upon which harvesting is made. Essentialoils(EOs) areproductsofthe secondarymetabo- The Brazilian savanna (Cerrado) consists of a rich flora lism of plants, defined as the volatile lipid soluble portion that comprises several species . Blepharocalyx is a common of plant u fl ids containing odiferous compounds of vegetable genus of the family Myrtaceae, widely spread in many coun- plant matter . Essential oils are obtained from plant mate- tries of Latin America, namely, Brazil, Argentina, Uruguay, rial: flowers, buds, twigs, bark, herbs, wood, fruits, and roots and Paraguay. It is commonly used for medicinal purposes in . They are widely used on pharmaceutics, cosmetics, food view of its antidiarrheal and digestive properties. Moreover, industry, and popular medicine, as well as aromatherapy and it is used to treat urethritis and cystitis , cough, bronchitis, pesticide industries. EOs are composed mainly of isoprene rheumatism, arthritis, and sinusitis. It is also used as hypoten- units in addition to alcohol, ester, aldehyde, ketone, car- sive, astringent, antibacterial, and antispasmodic . Recent boxylic acid, and alkane . reports investigating chemical composition of Blepharocalyx Qualitative and quantitative variation in essential oil salicifoliusEOsbyGC-MSanalysishavealreadyfoundseveral composition have been reported between different daytime constituents, such as 1,8-cineole, linalool, 𝛽 -caryophyllene and seasons of collection [3–5]. EOs may be affected by sev- , 𝛽 -pinene, limonene [10, 11], myrcene, 𝛼 -pinene , eral factors including nutrition, solar radiation, temperature, spathulenol, andpinene. 2 International Journal of Forestry Research Geographic distribution of Blepharocalyx salicifolius Geographic distribution of Myracrodruon urundeuva Figure 1: Geographic distribution of Blepharocalyx salicifolius and Myracrodruon urundeuva. Myracrodruon is a genus in the family Anacardiaceae, Table 1: Weather conditions for collection months [ 23]. which presents tropical and subtropical distribution, com- Weather condition March April May prising about 70 genera and 700 species . The species Max. temperature ( C) 27.0 26.2 25.4 Myracrodruon urundeuva is popularly used for treating skin Min. temperature ( C) 18.0 14.9 14.3 disorders, ulcers, and respiratory and urinary tract problems Humidity (%) 90–50 47 62 [13–15]. Scientific studies showed anti-inflammatory, antiul- cer, analgesic , antibacterial, antifungal , antidiarrheal , and antiviral against rotavirus properties. It is a stored in sealed amber vials and kept under refrigeration potential larvicidal agent for Aedes aegypti control . The EOs obtained from leaves present nearly 16 constituents such (∼10 C/50% humidity). Ethyl acetate was used as solvent to separate both organic and aqueous phases. The former was as 𝛼 -Pinene, 𝛾 -Terpinene, 𝛽 -Caryophyllene , and 𝛿 -3- Carene . dried with sodium sulfate and submitted to rotary evapora- tion at 25 C to yield pure essential oil. Considering the scarcity of studies with regard to the eTh yield was calculated using the equation RO = chemistryofoilsfromBrazilian savannaspecies,thisstudy aims at analyzing the chemical compounds from leaves of the (𝑀/𝐵 )×100,where𝑀 is the mass of the extracted oil (g) and𝐵 is the initial plant biomass (g). Tukey’s test was used Brazilian savanna species known due to their EOs produc- with a 5% significance level. tion: Blepharocalyx salicifolius (Kunt) O. Berg and Myracro- druon urundeuva (Allemao). ˜ 2.2. GC-FID and GC-MS Analysis. Essential oil analy- sis was carried out in an Agilent 7890A gas chromato- 2. Experimental graph tfi ted with a HP-5 capillary column (5%-phenyl- Leaves were collected from an experimental station at Uni- 95%-methylpolysiloxane, 30 m× 0.32 mm× 0.25𝜇 m), using versity of Brasilia (Brasilia, Brazil). Blepharocalyx salicifolius hydrogen as carrier gas (1.5 mL/min). Oven temperature was ∘ ∘ is spread in south, center, and southeast Brazil . Myracro- programmed from 60 to 240 Cat3 C/min. A1%solutionof druon urundeuva is spread in center, southeast, and northeast the oil in dichloromethane was injected at 250 Cinsplitmode Brazil (Figure 1). (1 : 20). Results are expressed as normalized relative area, Blepharocalyx salicifolius species samples were collected calculated from a FID (280 C) signal. on March 24 and April 21, 2009, while Myracrodruon urun- In order to identify the oil components, an Agilent 6890 deuva samples were collected on May 23, 2009, at weather gaschromatograph coupledtoanAgilent 5973Nmassselec- conditions presented in Table 1. tive detector was used, tfi ted with a HP5MS capillary column (5%-phenyl-95%-methylpolysiloxane, 30 m × 0.25 mm × 2.1. Extraction and Yield Calculation. Leaves were collected 0.25𝜇 m). Helium was used as carrier gas (1.0 mL/min). Both during daytime (9 a.m., 1 p.m., and 5 p.m.), resulting in 18 the injection procedure and oven temperature program were samples (3 samples× 3periods× 2 species) of 250 g each. Dry equivalent to the latter. The mass selective detector was leaves samples were extracted by steam distillation using a operated in electron ionization mode (70 eV). Mass spectra Linux D1 distiller for 90 minutes. eTh resulting liquid was obtained were compared with data from a Wiley 6th edition International Journal of Forestry Research 3 0.16 library. Linear retention indices were calculated by injecting a series of n-alkanes in the same column and chromatographic 0.14 conditions as above . Retention indices were calculated using the equation of van den Dool and Kratz . Positive 0.12 identification was considered only when both mass spectrum and retention index were in good agreement with library data 0.1 . 0.08 3. Results and Discussion 0.06 3.1. Extraction and Yield Calculation. B. salicifolius and M. urundeuva presentedyieldsare showninFigure 2. Yields 0.04 obtained by steam distillation technique were inferior to those found in the literature. Mattos (1983) cited by Marques 0.02  found 0.17% and Castelo et al. found 0.10%for Ble- pharocalyx salicifolius. Through statistical analysis results, one can conclude that 9 a.m. 1 p.m. 5 p.m. collection time has no role in EOs yield. However, a slight Sampling time (hr) trend towards a higher yield is observed for B. salicifolius Blepharocalyx salicifolius at 5 p.m. es Th e results can be explained by the fact that the Myracrodruon urundeuva temperature and humidity variation along the day are not Figure 2: Blepharocalyx salicifolius and Myracrodruon urundeuva significant as to aeff ct the production of EOs in these species, essentialoilsyieldsobtainedfromleavesharvested at daytime. which, as most Cerrado species, are known for their ability to withstand long periods of drought. Besides, Castello et al.  found that during the raining season the production of essen- tialoilcanbelowerthanduringthedroughtseason.eTh same species in view of differences in soil composition, climate, results were found for M. urundeuva,but atrend forhigher temperature, period of collection, and humidity. Geographic yields was observed for 9 a.m. samples. and genetic factors were indicated by Vitti and Brito . Differences between yields may be explained considering eTh chemical analyses also revealed that the major com- whether younger or older leaves were collected, although ponents are monoterpenes:𝛼 -pinene (9.0), p-cymene (25.9), extreme care was taken to guarantee uniform collection. and𝛾 -terpinene (12.5%), whereas for oxygenated monoter- Favorito  explained that young leaves have more tri- penes, 1.8-cineole (2.7%) was the principal constituent. chomes, the morphologic structures that produce EOs. At Caryophyllene oxide (9.6%), aromadendrene (4.6%), trans- the same time that leaf expands, the density of trichomes calamenene (3.5%), and 𝛽 -caryophyllene (3.2%) were the gets lower, resulting in a lower production of EOs . Also, main compounds of sesquiterpenes. Spathulenol (2.0%) was damage to the leaves, like the one caused by fungus, can the major constituent of oxygenated sesquiterpenes. damage glands that produce EOs. M. urundeuva EOs compounds, their respective retention indices, and relative peak area along with total area for each chemical class are shown in Table 3.Araujo ´ et al.  3.2. GC-FID and GC-MS Analysis. Results from GC-FID and studying the chemical composition of M. urundeuva in dif- GC-MS analysis (Table 2)present B. salicifolius identified ferent seasons extracted the essential oils by hydrodistillation compounds with respective retention indices and relative technique in a Clevenger apparatus and determined chemical peak area along with total area for each chemical class. Forty- composition by H-NMR. The results revealed a unique con- one components were identified in essential oil leaves of B. salicifolius, comprising 90.3% of the EOs. eTh results found stituent in major proportion (>90%) and vfi e principal com- could be compared to those reported by Limberger et al. pounds: limonene, 𝛽 -ocymene, 𝛿 -3-carene, 𝛼 -pinene, and (2001) , obtained through hydrodistillation method (oil myrcene. Souza and Lorenzi  found m-pentadecadienyl- extraction) and GC-MS technique (chemical compounds phenol in M. urundeuva studying the insecticidal activity identification), of B. salicifolius plants: 1,8-cineole (25.2%), against Aedes aegypti. linalool (20.4%), and𝛽 -caryophyllene (22.9%), as well as𝛼 - The monoterpene 𝛽 -myrcene comprised 66.4% of the pinene (1.1%),𝛽 -pinene (0.2%), limonene (3.0%), terpinen-4- identified components, appearing as the main compound. ol (1.2%),𝛼 -terpineol (2.0%), and caryophyllene oxide (1.3%). Linalool (3.6%) was the main oxygenated monoterpene. Castello et al. , using the same technique, found differ- trans-Caryophyllene (3.7%) was the main compound of ences in chemical composition throughout the seasons and sesquiterpenes, followed by 𝛿 -cadinene (3.6%), 𝛿 -selinene that p-cymene,𝛼 -pinene,𝛼 -terpineol, aromadendrene, glob- (2.9%), and 14-hydroxy-9-epi-caryophyllene (2.8%). Spathu- ulol, and caryophyllene oxide are major compounds of B. lenol (0.3%), caryophyllene oxide (1.0%), and epi-𝛼 -cadinol salicifolius EOs. Tucker et al.  found limonene (5.26%),𝛼 - (1.0%) were the only representatives of oxygenated sesquiter- pinene (9.18%), spathulenol (5.30%), 1,8-cineole (1.32%), and penes (2.3%), with minor proportion in the total identified linalool (0.14%). The compositions varied within the same components compared with major subclasses. Yield (%) 4 International Journal of Forestry Research Table 2: Blepharocalyx salicifolius EOs chemical compounds, retention indices, and relative peak area. Peak Identification Retention index Peak area (%) 1 𝛼 -Thujene 925 1.9 2 𝛼 -Pinene 932 9.0 3 𝛽 -Pinene 976 0.1 4 1-Felandrene 1005 0.1 5 𝛿 -3-Carene 1010 0.9 6 𝛼 -Terpinene 1016 0.9 7 p-Cymene 1023 25.9 8Limonene 1027 1.5 9 1,8-Cineole 1030 2.7 10 cis-Ocimene 1035 0.1 11 trans-Ocimene 1045 0.1 12 𝛾 -Terpinene 1057 12.5 13 𝛾 -Terpinolene 1087 3.3 14 Linalool 1099 0.3 20 4-Terpineol 1176 0.2 21 p-Cymen-8-ol 1184 0.2 22 𝛼 -Terpineol 1189 0.1 24 p-Menth-2-en-1,4-diol 1267 0.2 33 𝛼 -Cubebene 1348 0.1 36 𝛼 -Copaene 1376 0.3 37 𝛼 -Gurjunene 1408 0.5 38 𝛽 -Caryophyllene 1418 3.2 39 Aromadendrene 1437 4.6 41 𝛼 -Humulene 1452 0.6 45 allo-Aromadendrene 1459 0.6 48 𝛽 -Selinene 1484 0.3 50 𝛿 -Selinene 1493 1.1 53 𝛾 -Cadinene 1513 0.2 54 trans-Calamenene 1522 3.5 55 Cadina-1,4-diene 1531 0.6 59 Nerolidol 1563 0.4 63 Spathulenol 1576 2.0 64 Caryophyllene oxide + globulol 1582 9.6 65 Viridiflorol 1590 0.7 66 Cubeban-11-ol 1592 0.4 67 Rosifoliol + ledol 1601 0.8 68 Humulene epoxide II 1607 0.6 74 1-epi-Cubenol 1627 0.7 79 𝛿 -Cadinol 1645 0.2 80 𝛽 -Eudesmol 1649 0.2 81 𝛼 -Cadinol 1653 0.4 Total 91.6 Group Total peak area (%) Monoterpenes 56.1 Oxygenated monoterpenes 3.5 Sesquiterpenes 25.9 Oxygenated sesquiterpenes 5.8 International Journal of Forestry Research 5 Table 3: Myracrodruon urundeuva EOs chemical compounds, species in Bioma Cerrado are needed for a full understanding retention indices, and relative peak area. of the complex equilibriums involved in the production of EOs. Retention Peak area Peak Identification index (%) Conflict of Interests 1 𝛽 -Myrcene 990 66.4 2 Limonene 1027 0.7 eTh authors declare that there is no conflict of interests 3 1,8-Cineol 1030 0.3 regarding the publication of this paper. 5 𝛾 -Terpinene 1057 0.5 6Linalool 1100 3.6 References 7 𝛼 -Copaene 1374 0.3  D. Stewart, eTh Chemistry of Essential Oils Made Simple ,Care, 8 trans-Caryophyllene 1418 3.7 Marble Hill, Mo, USA, 2006. 9 Aromadendrene 1437 0.4  S. Burt, “Essential oils: their antibacterial properties and poten- 10 𝛼 -Humulene 1452 0.3 tial applications in foods—a review,” International Journal of Food Microbiology,vol.94, no.3,pp. 223–253, 2004. 13 𝛽 -Selinene 1485 1.3  N.S.Sangwan,A.H.A.Farooqi, F. Shabih,and R. S. Sangwan, 15 𝛿 -Selinene 1493 2.9 “Regulationofessential oilproductioninplants,” Plant Growth 16 𝛼 -Muurolene 1499 0.4 Regulation,vol.34, no.1,pp. 3–21,2001. 18 𝛾 -Cadinene 1513 0.8  A. H. A. Farooqi, N. S. Sangwan, and R. S. 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