Universidade Federal de Santa Maria

Ci. e Nat., Santa Maria v.42, e6, 2020

DOI:10.5902/2179460X41392

ISSN 2179-460X

Received 01/12/19   Accepted: 30/03/20  Published:11/05/20

 

 

Chemistry

 

Extraction and identification of essential oil components from the leaves of Syzygium  malaccense (L.) MERR. & L.M. PERRY, MYRTACEAE

 

Fabiula Marta Feltrin I

Luciana Gibbert II

Nayana Cristina da Silva Santos III

Francisco de Assis Marques IV

Marilis Dallarmi Miguel V

Sandra Maria Warumby Zanin VI

Obdúlio Gomes Miguel VII

Cláudia Carneiro Hecke Krüger VIII

Josiane de Fátima Gaspari Dias IX

 

I     Universidade Federal do Paraná , Curitiba, Brasil. fabiulafeltrin@gmail.com

II    Universidade Federal do Paraná , Curitiba, Brasil. luci_gbt@yahoo.com.br

III  Universidade Federal do Paraná , Curitiba, Brasil. cristina_nayana@hotmail.com

IV  Universidade Federal do Paraná , Curitiba, Brasil. tic@ufpr.br

V   Universidade Federal do Paraná , Curitiba, Brasil. dallarmi@ufpr.br

VI  Universidade Federal do Paraná , Curitiba, Brasil. sandrazanin@ufpr.br

VII Universidade Federal do Paraná , Curitiba, Brasil. obdulio@ufpr.br

VIIIUniversidade Federal do Paraná , Curitiba, Brasil. cchecke@ufpr.br

VIXUniversidade Federal do Paraná , Curitiba, Brasil. jodias@ufpr.br

 

 

ABSTRACT

Popularly known as red jamb, the species Syzygium  malaccense (L.) Merr. & L.M. Perry is an Asian tree from India, Malaysia, Vietnam and Thailand that has adapted to the climate and soil of the North, Northeast and Southeast of Brazil. The antioxidant and anti-inflammatory activities of this species have already been cited in the literature. This study aimed to extract and identify the essential oil constituents of the leaves of this species. The leaves were dried and ground; and the essential oil was extracted by Clevenger apparatus. The essential oil presented yield of 0.03%, containing monoterpenes and sesquiterpenes and the major compounds were identified as spatulenol, sesquisabinene transhydrate and (E) -Caryophyllene.

Keywords: Spatulenol; Sesquisabinene transhydrate; (E) -Caryophyllene

 

RESUMO

Popularmente conhecido como jambo vermelho, a espécie Syzygium malaccense (L.) Merr. & L.M. Perry é uma árvore asiática da Índia, Malásia, Vietnã e Tailândia que se adaptou ao clima e ao solo do norte, nordeste e sudeste do Brasil. As atividades antioxidantes e anti-inflamatórias dessa espécie já foram citadas na literatura. Este estudo teve como objetivo extrair e identificar os constituintes do óleo essencial das folhas desta espécie. As folhas estavam secas e moídas; e o óleo essencial foi extraído pelo aparelho de Clevenger. O óleo essencial apresentou rendimento de 0,03%, contendo monoterpenos e sesquiterpenos e os principais compostos foram identificados como espatulenol, Trans-hidrato de tesquisabineno e (E) -cariofileno.

Palavras-chave: Espatulenol; Trans-hidrato de Sesquisabineno; (E) -cariofileno

[F1] 

 

1 INTRODUCTION

Myrtaceae is one of the most important Angiospermae families in Brazil (CRUZ; KAPLAN, 2004) and has wide economic use in food, ornamental, timber and as a source of energy (firewood) (LEUCENA et al., 2014). Many species of the Myrtaceae family are present in the daily life of Brazilians such as guava, pitanga, araçá and jabuticaba, that are consumed fresh or jam, are rich in vitamins and minerals, are aromatic and serve as inspiration for fragrances and cosmetics (EMBRAPA, 2012; CASTILHOS et al., 2017).

Syzygium  malaccense is an Asian tree, located especially in the region of India, Malaysia, Vietnam and Thailand and has adapted to the climate and soil of the North, Northeast and Southeast of Brazil (REATGUI, 2015; FERNANDES; RODRIGUES, 2018). Studies report the antioxidant potential of edible parts of fruits, anti-inflammatory and antioxidant activities in hydroalcoholic and aqueous extracts of their leaves. Secondary metabolites such as catecholamines, quercetin, carotenoids and flavonoids were found in leaves (aqueous and hydroalcoholic extracts) (BATISTA et al., 2017).

GC-MS analyzes of the essential oil of fresh leaves of Syzygium  malaccense showed that it was composed mainly of monoterpenes characterized mainly by α-pinene, β-pinene, p-cymene and α-terpineol. The sesquiterpenes constituting the oil have β-caryophyllene as the main component (KARIOTI et al., 2007).

This article aims to obtain the essential oil of Syzygium malaccense leaves, identify its components and compare it with compositions found in other parts of the world.

 

 

2. MATERIALS AND METHODS

The species Syzygium  malaccense was collected between July and August 2018, at the Paraná Agronomic Institute, Morretes unit, Paraná coast, (Latitude 25º30'6''S; Longitude 48º48'5.22''O). The identification of the vegetal species was made by comparison with the exsiccata registered at the MBM Herbarium of the Botanical Museum of the Curitiba City Hall, under the number MBM-379581.

After collection, the botanical material was separated into leaves and stem, the leaves were selected as object of study, cleaned with drinking water, dried in the shade and ground.

 

2.1 Obtaining the essential oil

The essential oil of Syzygium  malaccense (L.) Merr. & L.M. Perry leaves was obtained by means of the Clevenger apparatus modified by Wasicky (1963). Extraction was performed by water hydrodistillation, based on the technique described in the Brazilian Pharmacopoeia 5th edition (BRASIL, 2010). In a round bottom flask was added 600 g of plant material (dried leaves, crushed and kept in tightly sealed plastic bags at a temperature below 8 ° C), adding sufficient distilled water to cover the material and allow extraction (4500 mL). The balloon was coupled to Clevenger apparatus and kept under heating blanket with approximate temperature of 100ºC for 6 consecutive hours.

After cooling the extraction system at room temperature, the essential oil volume was read directly on the Clevenger apparatus separator tube scale, and then the milliliter (mL%) yield of essential oil per 100 g of the drug was calculated (Equation 1).

 

 

The obtained oil was conditioned and kept in a freezer, protected from light, to avoid its volatilization and degradation.

 

2.2 Identification of Essential Oil Constituents - Chemical analysis

The characterization of the essential oil components of Syzygium  malaccense leaves was performed by mass spectrum coupled gas chromatography (Laboratory of Chemical Ecology and Synthesis of Natural Products of the Department of Chemistry of UFPR).

Analysis was performed using a Shimadzu CGMS-QP2010 Plus system equipped with a quadrupole mass detector with a Rtx-5MS (Crossbond 5% diphenyl/95% dimethylpolysiloxane) low-bleeding column (30m × 0.25mm×0.25 μm), with helium as the carrier gas at a fow rate of 1.02mL/min. 1 µL of the sample was injected splitless at an initial oven temperature of 60 °C. Te injector and detector temperatures were adjusted to 250 °C. Te programmed oven temperature was 60–250 °C at 3 °C/min.; EIMS: electron energy, 70 eV; ion source temperature and connection parts at 180 °C (SILVA, et al., 2019).

 

2.2.1. Peak identifcation

Individual components were identifed by comparing retention indices (RIs) and mass spectra with those of authentic compounds given in Adams Libraries of mass spectral data and by a computer database using Wiley 275, NIST 21, NIST 10733 (ADAMS, 2005; NIST, 1998).

 

 

3 RESULTS AND DISCUSSION

3.1 Identification of essential oil constituents

Essential oils are widely used in the pharmaceutical and cosmetic industries because they have widely known medicinal properties (LAWAL et al., 2014). Differences in the composition of essential oil alter its pharmacological properties, and chemical analysis of the composition of essential oils is important (REZENDE et al., 2013).

The plant material was subjected to hydrodistillation in Clevenger apparatus. The extracted oil had a golden-yellow color with a mild odor and the yield was 0.03%. In previous studies the yield presented was 0.15% (KARIOTI et al., 2007) and 0.0297% (ISMAIL et al., 2010), both using fresh leaves of Syzygium  malaccense.

The resulting analysis chromatogram is shown in figure 1.

 

Figure 1 - Syzygium  malaccense essential oil gas chromatography

[F2] 

 

The chemical composition of the essential oil, its respective times and retention rates, classification and percentage are described in Table 1.

 

Table 1 - Syzygium  malaccense essential oil composition

Number[F3] 

Retention Time

AI*

AI Theoretical

Compound

[  ] %

Rating

1

7.915

1026

1024

Limonene

0.47

Monoterpene

2

10.370

1097

1095

Linalool

0.51

Oxygenated monoterpene

3

12.495

1151

1148

Menthone

0.64

Monoterpene

4

20.110

1335

1335

Elemene

0.61

Sesquiterpene

5

20.610

1347

1348

α –Cubebene

5.78

Sesquiterpene

6

21.515

1369

1373

α – Ylangene

0.60

Sesquiterpene

7

21.700

1373

1374

α – Copaene

1.27

Sesquiterpene

8

22.295

1388

1400

Sibirene

1.88

Sesquiterpene

9

22.375

1390

1389

β –Elemene

2.33

Sesquiterpene

10

23.475

1417

1417

E – Caryophyllene

6.56

Sesquiterpene

11

24.065

1431

1434

gamma – Elemene

0.54

Sesquiterpene

12

24.855

1451

1452

α – Humulene

2.04

Sesquiterpene

13

25.805

1474

1478

gamma – Muurolene

0.92

Sesquiterpene

14

25.960

1478

1430

β – Copaene

5.51

Sesquiterpene

15

26.170

1483

1458

allo - Aromadendrene

0.61

Sesquiterpene

16

26.390

1489

1513

gamma – Cadinene

0.45

Sesquiterpene

17

26.510

1492

1502

gamma – Patchoulene

0.71

Sesquiterpene

18

26.595

1494

1474

10 - epi - β - Acoradiene

1.05

Sesquiterpene

19

26.745

1498

1500

α – Muurolene

0.57

Sesquiterpene

20

27.280

1512

1513

gamma - Cadinene

1.73

Sesquiterpene

21

27.650

1521

1522

delta – Cadinene

5.27

Sesquiterpene

22

28.930

1555

1509

α – Bulnesene

5.98

Sesquiterpene

23

29.190

1562

1577

Trans-sesquisabinene hydrate

7.00

Sesquiterpene

24

29.720

1576

1577

Spathulenol

10.25

Oxigenated sesquiterpene

25

30.500

1596

1600

Guaiol

1.22

Oxigenated sesquiterpene

26

30.925

1607

1582

Caryophyllene oxide

2.14

Oxigenated sesquiterpene

27

32.155

1641

1638

epi - α – Cadinol

4.92

Oxigenated sesquiterpene

28

32.610

1653

1652

α –Cadinol

3.84

Oxigenated sesquiterpene

29

33.505

1678

1676

Mustakone

0.58

Sesquiterpene

30

45.370

2034

2042

Kaurene

0.83

Sesquiterpene

 

Total compounds identified

76.81%

* Concentrations above 0.4% have been identified.

 

The GC/MS analysis of the essential oil of Syzygium  malaccense leaves identified 37 components, 30 terpenes (monoterpenes and sesquiterpenes) corresponding to 76.81% of the components present in the analyzed essential oil. Of the identified terpenes, two were monoterpenes (1.44%), one oxygenated monoterpene (0.66%), 21 sesquiterpenes (68.76%) and 5 oxygenated sesquiterpenes (29.12%).

The major compounds found were oxygenated sesquiterpene spatulenol (13.34%), sesquiterpenes sesquisabinene transhydrate (9.11%), (E) –caryophyllene (8.54%). The molecular formula of these compounds is shown in FIGURE 2.

 

Figure 2 - Chemical structures of major constituents of essential oil of leaves of Syzygium  malaccense.

 

In the study by Santos (2016) with fresh leaves of Syzygium  malaccense 25 substances were identified, the sesquiterpenes were 16.95% of the extracted compounds and the major compounds were β-selinene (3.85%) and α-humulene (3.63%). The chemical pattern was similar to the study presented by Ismail et al. (2010), but differing in the identity of the major compounds.

Unlike the results found in the present study, Karioti et al. (2007), described that the essential oil extracted from the fresh leaves of a species cultivated in Ile-Ife (Nigeria) presented 38 substances, being the monoterpenes the majority compounds (61.1%), represented mainly by para-cymene (13.5 %), β-pinene (8.0%), α-terpineol (7.5%) and α-pinene (7.3%). Sesquiterpenes made up 30.8% of this essential oil, whose main component was β-caryophyllene (9.0%). A chemical pattern very similar to the previous one was reported by Lawal et al. (2014) who also analyzed fresh leaves grown in Nigeria (Ikotun region), the essential oil obtained was rich in monoterpenes (79.9%), but differed from Karioti et al. (2007) in the identity of the majority, represented by limonene (48.8%) and α-terpinene (26.2%).

In the study by Ismail et al. (2010) the analyzed species was cultivated in Malaysia, 180 substances were identified in the oil obtained, the major compounds were identified as hexanoic acid (12.16%), methyl salicylate (8.27%), 3-hexen-1-ol (7.81%), 1-octen-3-ol (5.89%), n-hexadecanoic acid (5.07%), 2-hexenal (4.89%) and 3-buten-2-one (3, 68%).

Morais et al. (1996) also explains that the composition of the essential oil may be different due to chemotypes, where the chemical constitution developed by a given plant occurs due to its necessity to adapt to the environmental factors of the ecosystem where it is found, such as climate, soil composition, altitude, water scarcity, light, as well as variations that occur due to the time of harvest and the method of extraction of the essential oil. These variables influence the relative concentration of each component in the oil (MAGINA et al., 2009).

Lopes (2008) demonstrated in his work that secondary metabolites vary during the seasons, as well as genetic differences (CERQUEIRA et al., 2009) and climatic factors such as temperature, water availability, soil nutrients, altitude, radiation, among others, which could explain the variations found in the essential oils obtained from the leaves.

 

3.2 Major constituents of Syzigium malaccense essential oil

Caryophyllene is a natural bicyclic sesquiterpene that is a constituent of many essential oils, including Syzygium  aromaticum (clove). It is a sweet-tasting compound that can be found in foods such as allspice, fig and marjoram, which makes β-caryophyllene a potential biomarker for these products (NATIONAL CENTER FOR BIOTECHNOLOGY INFORMATION, 2019).

Positive results have already been found in the literature to evaluate the anti-mutagenicity of natural sesquiterpene β-caryophyllene and its metabolite β-caryophyllene oxide (NGUYEN et al., 2017; ZHANG et al., 2017; GIACOMO et al., 2018).

In other studies treatment with β-caryophyllene caused hypolipemic effect, improved hepatic oxidative damage, reduced cardiac lipid content, was able to improve antioxidant / oxidant status in cardiac tissue of hypercholesterolemic animals; showing antioxidant properties, preventing lipid oxidative damage and improving the activity of GPx, an important enzyme linked to the prevention of atherosclerosis (BALDISSERA et al., 2017). 

The effect of β-caryophyllene on hyperglycemia-mediated oxidative and inflammatory stress was observed in streptozotocin-induced diabetic rats. Oral administration of β-caryophyllene rescued pancreatic β cells, mitigating hyperglycemia by increasing insulin release and also prevented oxidative / inflammatory stress in pancreatic tissue of diabetic rats, compared with a standard antidiabetic such as glibenclamide (BASHA; SANKARANARAYANAN, 2016).

Transsesquisabinene hydrate is involved in studies of antibacterial activity of essential oils, and its relevance to antimicrobial action against Gram-positive strains such as Staphylococcus aureus, Bacillus cereus, Bacillus subtilis and Enterococcus faecalis, Candida albicans is not yet clear (BENOMARI et al., 2016).

Spatulenol has antibacterial and anti-inflammatory properties when in complex essential oil compositions (MALTI et al., 2019). The antioxidant, anti-inflammatory, antiproliferative and antimicobacterial properties of spatulenol have already been described in the literature (NASCIMENTO et al., 2018).

 

 

4. FINAL CONSIDERATIONS

 

From the literature review on the species Syzygium  malaccense it was known that it has wide popular use, mainly in Indian countries (native region of the plant). According to the literature, catechin, mearnsitrin, myricitrin and quercitrin are the main contributors to the antioxidant, anti-inflammatory and antiglycemic properties of Syzygium  malaccense leaf extracts. The essential oil, obtained from the leaves of Syzygium  malaccense, was extracted by water vapor drag hydrodistillation and yielded 0.03%.

 

 

ACKNOWLEDGMENT

The authors are thankful to the Commission for the Improvement of Higher Education Personnel (CAPES) from Brazil for the financial support (Financing Code 001).

 

 

REFERENCES

 

ADAMS, R. P. Identification of Essential Oil Components by Gas Chromatography / Mass Spectrometry. 4th editio ed. Allured Pub Corp, 2007.

 

BALDISSERA, M. D.; SOUZA, C. F.; GRANDO, T. H.; STEFANI, L. M.; MONTEIRO, S. G. β-caryophyllene reduces atherogenic index and coronary risk index in hypercholesterolemic rats: The involvement of cardiac oxidative damage. Chemico-Biological Interactions, v. 270, p. 9–14, 2017. Disponível em: https://linkinghub.elsevier.com/retrieve/pii/S0009279717302661.

 

BASHA, R. H.; SANKARANARAYANAN, C. β-Caryophyllene, a natural sesquiterpene lactone attenuates hyperglycemia mediated oxidative and inflammatory stress in experimental diabetic rats. Chemico-Biological Interactions, v. 245, p. 50–58, 2016. Disponível em: https://linkinghub.elsevier.com/retrieve/pii/S000927971530154X.

 

BATISTA, Â. G.; DA SILVA, J. K.; BETIM CAZARIN, C. B.; et al. Red-jambo (Syzygium malaccense): Bioactive compounds in fruits and leaves. LWT - Food Science and Technology, v. 76, p. 284–291, 2017. Academic Press. Disponível em: https://www-sciencedirect-com.ez22.periodicos.capes.gov.br/science/article/pii/S0023643816302699?via%3Dihub. Acesso em: 25/4/2018.

 

BENOMARI, F. Z.; DJABOU, N.; MEDBOUHI, A.; et al. Chemical Variability and Biological Activities of Essential Oils of Micromeria inodora ( Desf .) Benth . from Algeria. Chemistry & Biodiversity, v. 13, n. 11, p. 1559–1572, 2016. Disponível em: http://doi.wiley.com/10.1002/cbdv.201600098.

 

BRAGA, E. C. O.; MARTINS, V. C.; SANTIAGO, M. C. P. A.; et al. CARACTERIZAÇÃO DE SUBSTÂNCIAS FENÓLICAS DO PÓ DA CASCA DE JAMBO (Syzygium malaccense L. Merry & Perry) OBTIDO POR SECAGEM CONVECTIVA. , 2017. Gramado , RS: Congresso Brasileiro de Quimica. Disponível em: http://www.abq.org.br/cbq/2017/trabalhos/10/12554-15806.html. Acesso em: 7/7/2018.

 

BRASIL. Farmacopeia Brasileira. BRASIL, 2010.

 

CASTILHOS, T. F.; NORONHA, A. H.; MOLINA, A. R.; GOMES, G. C. E. V. S.; GUARINO, E. DE S. G. Fabaceae e Myrtaceae arbustivas e arbóreas do bioma Pampa: restauração ecológica e usos econômicos. Cadernos de Agroecologia – Anais do VI CLAA, X CBA e V SEMDF– Anais do VI CLAA, X CBA e V SEMDF, v. 13, n. 1, p. 6–12, 2017.

 

CERQUEIRA, M. D. MARQUES, E. J.; MARTINS, D.; CRUZ, N. F. R. F. G. VARIAÇÃO SAZONAL DA COMPOSIÇÃO DO ÓLEO ESSENCIAL DE Myrcia salzmannii Berg. (Myrtaceae). Química Nova, v. 32, p. 1544–1548, 2009.

 

CRUZ, A. V. DE M.; KAPLAN, M. A. C. USO MEDICINAL DE ESPÉCIES DAS FAMÍLIAS MYRTACEAE E MELASTOMATACEAE NO BRASIL. FLORESTA E AMBIENTE, v. 11, n. 1, p. 47–52, 2004.

 

EMBRAPA. International Symposium on Guava and OtherInternational Symposium on Guava and Other Myrtaceae. Abstracts of the 3rd International Symposium on Guava and Other Myrtaceae. , 2012. Petrolina.

 

FERNANDES, F. A. N.; RODRIGUES, S. Jambo— Syzygium malaccense. Exotic Fruits. p.245–249, 2018. Elsevier. Disponível em: http://linkinghub.elsevier.com/retrieve/pii/B9780128031384000319. Acesso em: 16/4/2018.

 

GIACOMO, S.; ABETE, L.; COCCHIOLA, R.; et al. Caryophyllane sesquiterpenes inhibit DNA-damage by tobacco smoke in bacterial and mammalian cells. Food and Chemical Toxicology, v. 111, p. 393–404, 2018. Disponível em: https://linkinghub.elsevier.com/retrieve/pii/S0278691517306853.

 

ISMAIL, I. S.; ISMAIL, N.; LAJIS, N. Ichthyotoxic properties and essential oils of syzygium malaccense (Myrtaceae). Pertanika Journal of Science and Technology, v. 18, n. 1, p. 1–6, 2010.

 

KARIOTI, A.; SKALTSA, H.; GBOLADE, A. A. Analysis of the leaf Oil of Syzygium malaccense Merr. et Perry from Nigeria. Journal of Essential Oil Research, v. 19, n. 4, p. 313–315, 2007. Disponível em: http://www.tandfonline.com/doi/abs/10.1080/10412905.2007.9699290. Acesso em: 12/6/2018.

 

LAWAL, O. A.; OGUNWANDE, I. A.; BULLEM, C. A.; TAIWO, O. T.; OPOKU, A. R. Essential oil compositions and in vitro biological activities of three szyzgium species from Nigeria. . p.93–111, 2014. Nova Science Publishers, Inc.

 

LEUCENA, E. M. P. DE; ALVES, R. E.; CISNEROS-ZEVALLOS, L.; LUZ, E. W. M. E; BRITO, E. S. DE. Biodiversidade das Myrtaceae Brasileiras Adaptadas à Flórida, EUA. Revista Brasileira de Geografia Física, v. 07, n. 02, p. 327–340, 2014.

 

LOPES, M. M. Composição química, atividade antibacteriana e alelopática dos óleos essenciais de Eugenia uniflora L. e Myrciaria glazioviana (Kiaersk) G. M. Barroso e Sobral (myrtaceae)., 2008. Universidade Federal de Viçosa Minas Gerais, Viçosa, MG.

 

MAGINA, M. D. A.; DALMARCO, E. M.; WISNIEWSKI JR., A.; et al. Chemical composition and antibacterial activity of essential oil of Eugenia species. Journal of Natural Medicines, v. 63, p. 345–350, 2009.

 

MALTI, C.; BACCATI, C.; MARIANI, M.; et al. Biological Activities and Chemical Composition of Santolina africana Jord. et Fourr. Aerial Part Essential Oil from Algeria: Occurrence of Polyacetylene Derivatives. Molecules, v. 24, n. 1, p. 204, 2019. Disponível em: http://www.mdpi.com/1420-3049/24/1/204.

 

MORAIS, S. M.; CRAVEIRO, A. A.; MACHADO, M. I. L.; ALENCAR, J. W.; MATOS, J. A. Volatiles constituents of Eugenia uniflora leaf oil from northeastern Brazil. Journal Essential Oil Resesearch, v. 8, p. 449–451, 1996.

 

NATIONAL CENTER FOR BIOTECHNOLOGY INFORMATION, U. S. Caryophyllene. Disponível em: https://pubchem.ncbi.nlm.nih.gov/compound/beta-caryophyllene#section=Biological-Test-Results. Acesso em: 26/1/2019.

 

NGUYEN, L. T.; MYSLIVEČKOVÁ, Z.; SZOTÁKOVÁ, B.; et al. The inhibitory effects of β-caryophyllene, β-caryophyllene oxide and α-humulene on the activities of the main drug-metabolizing enzymes in rat and human liver in vitro. Chemico-Biological Interactions, v. 278, p. 123–128, 2017. Disponível em: https://linkinghub.elsevier.com/retrieve/pii/S000927971730491X.

 

REATGUI, W. DA S.; BARATTO, L. C. ESTUDO MORFOANATÔMICO DAS FOLHAS DO JAMBEIRO-VERMELHO (Syzygium malaccense, MYRTACEAE). Santarém, 2015.

 

SILVA, S.E.B., AUAD, A.M., MORAES, J.C. et al. Olfactory response of Mahanarva spectabilis (Hemiptera: Cercopidae) to volatile organic compounds from forage grasses. Scientific Report 9, 10284, 2019.

 

REZENDE, W. P.; BORGES, L. L.; ALVES, N. M.; FERRI, P. H.; PAULA, J. R. Chemical variability in the essential oils from leaves of Syzygium jambos. Revista Brasileira de Farmacognosia, v. 23, n. 3, p. 433–440, 2013.

 

WASICKY, R. Uma modificação do aparelho de clevenger para extração de óleos essenciais. Revista da Faculdade de Farmácia e Bioquímica da Universidade de São Paulo, v. 1, n. 1, p. 1–112, 1963.

 

ZHANG, Z.; YANG, C.; DAI, X.; AO, Y.; LI, Y. Inhibitory effect of trans -caryophyllene (TC) on leukocyte-endothelial attachment. Toxicology and Applied Pharmacology, v. 329, p. 326–333, 2017. Disponível em: https://linkinghub.elsevier.com/retrieve/pii/S0041008X17302727.

 


 [F1]TEXTO ADICIONADO A PEDIDO DO EDITOR

 [F2]FIGURA REVISADA A PEDIDO DO EDITOR, COM NUMERAÇÃO E MAIOR RESOLUÇÃO

 [F3]ESSA COLUNA FOI INSERIDA PARA ESCLARECER  A FIGURA 1

Refbacks

  • There are currently no refbacks.


Copyright (c) 2020 Ciência e Natura

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License.

Creative Commons License

This work is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License.