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TEOP 21(2).Pmd Journal of Essential Oil Bearing Plants ISSN: 0972-060X (Print) 0976-5026 (Online) Journal homepage: http://www.tandfonline.com/loi/teop20 Volatile Secondary Metabolites in Cascarillo (Ocotea caparrapi (Sandino-Groot ex Nates) Dugand - Lauraceae) Geovanna Tafurt García & Amner Muñoz Acevedo To cite this article: Geovanna Tafurt García & Amner Muñoz Acevedo (2018) Volatile Secondary Metabolites in Cascarillo (Ocoteacaparrapi (Sandino-Groot ex Nates) Dugand - Lauraceae), Journal of Essential Oil Bearing Plants, 21:2, 374-387, DOI: 10.1080/0972060X.2018.1465856 To link to this article: https://doi.org/10.1080/0972060X.2018.1465856 Published online: 09 May 2018. Submit your article to this journal Article views: 24 View Crossmark data Full Terms & Conditions of access and use can be found at http://www.tandfonline.com/action/journalInformation?journalCode=teop20 TEOP 21 (2) 2018 pp 374 - 387 374 ISSN Print: 0972-060X ISSN Online: 0976-5026 Volatile Secondary Metabolites in Cascarillo (Ocotea caparrapi (Sandino-Groot ex Nates) Dugand - Lauraceae) Geovanna Tafurt García 1*, Amner Muñoz Acevedo 2 1* Universidad Nacional de Colombia, Sade Orinoquia, Research Group “Production, Structure and Aplication of Biomolecules” (PROBIOM), Medellín, Colombia 2 Universidad del Norte, División de Ciencias Básicas, Departamento de Química y Biología, Laboratorio de Investigaciones en Química, Barranquilla, Colombia Received 15 March 2017; accepted in revised form 21 December 2017 Abstract: In this work, the chemical analysis of the volatile fractions obtained by simultaneous distillation-extraction of aerial parts of a species of Ocotea aff. O. caparrapi known as “Cascarillo” was carried out by GC-MS. The main components identified were: α-pinene (23.9 %) and β-pinene (14.7 %), in the resin; α- terpineol (26.6 %) and methyleugenol (14.7 %), in the leaves; elemicin (31.3 %) and methyleugenol (31.1 %), in the branch bark; myristicin (35.4-46.1 %), terpinen-4-ol (14.9-26.3 %), and α-terpineol (17.5-21.3 %), in stem bark. A high content of monoterpene hydrocarbons (82.6 % and 51.8 %) were found in the resin and leaves; and propenylbenzenes (66.5 %), in the branch bark. Oxygenated monoterpenes (44.5-57.3 %) and propenylbenzenes (52.3-38.7 %) constituted the stem bark. The identification of methyleugenol, elemicin and myristicin, in the volatile fractions, allowed us to establish a relationship between the Ocotea sp. of our study with O. caparrapi and O. cymbarum. Key words: Ocotea; Cascarillo; volatile fractions; propenylbenzenes; SDE-GC-MS. Introduction and Canary Islands) 2-5. This genus includes tim- The Lauraceae family has ca. 55 genera and bers, which for its fragrant features are a great 3000 species, and is constituted by trees and source of essential oils (EO) constituted by ter- shrubs, which grow in wet and dry tropical for- penes, phenylpropanoids (e.g., safrole, asaricin, ests (0 m to 4000 m). It is widely distributed in myristicin, phenols, aldehydes) or related com- America, Asia and Australia, and with a little rep- pounds (e.g., caparratriene, caparrapi oxide) 4, 6- resentation in Africa 1-3. This family is important 8. Additionally, compounds belonging to classes: from the economic point of view by its woods, flavonoids, lignanes, neolignanes, and alkaloids resins, essential oils (Camphor - Cinnamomum (benzylisoquinolinics, aporfínics) are found in the camphora), spices (cinnamon - Cinnamomum Ocotea spp.3, 9-12. However, it has been carried zeylanicum; laurel - Laurus nobilis), and, fruits to endangered conditions due to the deforestation (avocado - Persea americana) 1. and unsustainable exploitation 4, 5, 13. Ocotea is the most diverse and abundant ge- Some Ocotea species (O. quixos, O. puchury- nus of the family, with about 350 species mainly major, O. longifolia, O. bullata, O. opifera, O. distributed in the neotropics, from Mexico to Ar- paulii) have pharmacological or therapeutic prop- gentina, and also is found in Africa (Madagascar erties as anti-rheumatic, analgesic, anesthetic, *Corresponding author (Geovanna Tafurt García) E-mail: < [email protected] > © 2018, Har Krishan Bhalla & Sons o Geovanna Tafurt García et al., / TEOP 21 (2) 2018 374 - 387 375 antidiarrheal, anti-inflammatory, antithrombotic, Simultaneous distillation - extraction solvent antiplaquet, antioxidant, antimicrobial, anti-ab- (SDE) scesses, gastroenteric, purgative, tonic, headache, The volatile fractions of the different parts of nervous disorders, sedative and appetizer. Other fresh plant were isolated using a Likens & species, O. pretiosa, O. sassafras, O. caudata, Nickerson microscale apparatus, modified by O. odorífera, O. caparrapi and O. cymbarum, Godefroot et al. 26, for high density solvents. 10 g have a recognized position in the market, specifi- of vegetal material were used, the extraction sol- cally in perfumery. And, the others, O. bofo, O. vent was dichloromethane (2 mL), and the pro- austinii and O. corymbosa, have been used as cess was carried out during 2 h. The extracts were flavoring, furniture and construction 4, 5, 7, 9-19. dehydrated with anhydrous sodium sulfate. For In this work, we carried out the chemical analy- the case of resin, 50 μL of pure resin were dis- sis of an Ocotea aff. O. caparrapi, called solved in 500 μL of acetone. Finally, 1 mL of the “Cascarillo”. Gas Chromatography coupled to extracts was analyzed by GC-MS. Mass Spectrometry (GC-MS) was used for the analysis the volatile fractions of this species. Si- Gas chromatography-Mass spectrometry multaneous Distillation-Extraction technique (GC-MS) (SDE) was used for obtaining volatile fractions The separation and analysis of the components of different parts of the plant material (resin, present in the SDE extracts were carried out in a leaves, and branch and stem barks). The impor- Trace 1310 gas chromatograph coupled to a mass tance of this work lies in the commercial potential selective detector ISQ (Thermo Fisher Scientific, of this species for the production of essential oils, Inc.), with split/splitless inlet (ratio split 20:1), au- resins and wood; in addition, because for this en- tomatic injection system (AI/AS 1310 Thermo Sci- dangered species there are few documented stud- entific). Rxi®-1ms column (30 m x 0.25 mm I.D. 6, 20-25 μ ies for Colombia . x 0.5 m df), with stationary phase of 100 % dim- ethyl-polysiloxane, was used for the separation. Methods Helium (99.999 %) was the carrier gas (constant Reagent flow, 1.0 mL/min). Oven temperature program- The solvents employed were dichloromethane ming was from 50oC (5 min) to 150oC (10 min) at (ACS grade, Riedel-de Haën) and distilled water. a rate of 2oC/min, a second rate of 3oC/min to Anhydrous sodium sulfate (Analytical grade, 250oC (5 min). Ion source and transfer line tem- Biopack) was used as a dehydrating agent. peratures were maintained at 230oC and 250oC, respectively. Mass spectra were obtained by elec- Plant material tron impact (EI, 70 eV) using quadrupole mass “Cascarillo” (Ocotea aff. O. caparrapi, Nº analyzer. Total ion currents (TIC) were acquired 0.38 of Orinoquía´s Science Research Group) by full scan mode, with a mass range of m/z 40- was collected in “El Porvenir” village, municipal- 350. Chromatographic and spectroscopic data ity of Toledo, Departamento de Norte de were processed using by Thermo XcaliburTM (Ver- Santander (Colombia). Between 100 g and 1000 sion 2.2 SP1.48, Thermo Fisher Scientific, Inc.) g of each part of the plant material was collected. and AMDIS (Automated Mass Spectral The resin was obtained by drilling the stem of the Deconvolution and Identification System, 13 May tree to the marrow. The preliminary taxonomic 2011, Build 130.53, Version 2.70) softwares. identification of botanical sample was performed Linear temperature-programmed retention in- by Gerardo Aymard Antonio Corredor dices were calculated from the data of a homolo- (UNELLEZ - Guanare - Venezuela), expert in gous series of saturated aliphatic hydrocarbons Venezuelan forest. The plant collection was made (C7-C35) and analyzed under the same conditions under Resolution No. 739 of July 8, 2014, con- that the extracts. The secondary metabolites were ferred by the Agencia Nacional de Licencias identified by comparing their mass spectra with Ambientales (ANLA). those of the databases (NIST11, NIST Retention Geovanna Tafurt García et al., / TEOP 21 (2) 2018 374 - 387 376 Index and Wiley9), and with linear retention indi- According to the Table, α-pinene (23.9 %), β- ces reported in the existing literature 27-29. pinene (14.7 %), p-cymene (7.8 %), and α-terpi- neol (7.3 %) were the main constituents of the Results and discussion resin sample; linalool (8.6 %), terpinen-4-ol (8.7 Table 1 contains the identified compounds from %), α-terpineol (26.6 %), methyleugenol (14.7 %), the volatile fractions (VF) isolated of the resin, and bicyclogermacrene (6.7 %), were identified leaves, and branch and stem barks of Ocotea aff. in the leaves sample; also, in the branch bark O. caparrapi, along with their relative amounts sample were found α-terpineol (12.6 %), and retention indices (calculated and literature). methyleugenol (31.1 %), elemicin (31.3 %) and Figure 1 shows the total ion currents (TIC) ob- myristicin (2.9 %), as the most abundant com- tained by GC-MS of each VF analyzed. pounds; on the other hands, the stem barks of the Table 1. Chemical composition by GC-MS, for resin and VF of leaves, and branch and stem barks of Ocotea aff. O. caparrapi Relative amount, % IR No. Compound Resin Leaves Branch Stem Stem
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