Analysis of the volatile oils from three species of the gender Syzygium

Authors

DOI:

https://doi.org/10.33448/rsd-v10i7.16375

Keywords:

Syzygium malaccense; Syzygium jambos; Essential oil; Chemiodiversity; Jambo.

Abstract

The species Syzygium cumini, Syzygium malaccense and Syzygium jambos, belong to the family Myrtaceae and are popularly known, respectively, by jambolan, red jambo and yellow jambo. These species are used in traditional medicine to treat diabetes mellitus, asthma, bronchitis, diuresis, gastrointestinal and respiratory infections, properties antipyretic, anti-inflammatory, antirheumatic and several other uses. The objective of this work is to identify and quantify the volatile compounds in the leaves of S. cumini, S. malaccense and S. jambos. The volatile oils were obtained by hydrodistillation using Clevenger apparatus and analyzed by Gas Chromatography Coupled to Mass Spectrometry (GC-MS). It was possible to identify 44 compounds present in the volatile oils of the leaves, being 20 compounds of S. cumini, 9 compounds of S. malaccense and 15 compounds of S. jambos. The major compounds present in the species S. cumini were α-terpineol, β-caryophyllene and α-humulene; for the species S. malaccense were aristolochene, γ-himachalene and δ-amorphene; and for S. jambos species were β-cariophyllene, (E,E)-α-farnesene and cariophyllene alcohol. The species S. cumini, S. malaccense and S. jambos showed considerable differences in terms of volatile compounds, it is important to know their constituents in order to promote further studies focused on their medicinal potential.

Author Biographies

Amanda Silva Reis, Universidade Federal de Goiás

Graduanda em Farmácia na Universidade Federal de Goiás, Faculdade de Farmácia, Brazil

Liliane de Sousa Silva, Universidade Federal de Goiás

Possui graduação em Ciências Biológicas pela Universidade Estadual de Goiás (2012). Especialização em Neuropedagogia Aplicada à Educação (FABEC Brasil) 2013, Mestre em Ciências Farmacêuticas pela Universidade Federal de Goiás (UFG) 2013-2015. Doutoranda em Ciências Farmacêuticas (UFG) 2016 - 2019. Funcionário público (2010-2018) da Prefeitura Municipal de Itapuranga-GO, atuando na Secretaria de Saúde - Agência de Transfusão. Foi professora titular da Universidade Estadual de Goiás (UEG) (2014-2018) no curso de Licenciatura Plena em Ciências Biológicas nas disciplinas de: fisiologia vegetal, biologia molecular, bioestatística, biofísica, anatomia e fisiologia humana e comparativa e didática. Fui professor efetivo da Escola Estadual Paulo Freire em Primavera do Leste - MT (julho de 2018 a abril de 2019) nas aulas e 8º e 9º anos.

Christiane França Martins, Universidade Federal de Goiás

Farmacêutica, Mestre em Biotecnologia (UFPA), doutoranda em Ciências Farmacêuticas na Universidade Federal de Goiás, Faculdade de Farmácia, Brazil.

José Realino de Paula, Universidade Federal de Goiás

Professor titular da Universidade Federal de Goiás, Faculdade de Farmácia, Brazil.

References

Adams, R. P. (2017). Identification of essential oil components by gas chromatography/mass spectrometry (ed. 4.1). Carol Stream, IL: Allured publishing corporation.

Ahmed, R., Tariq, M., Ahmad, I. S., Fouly, H., Hasan, A., & Kushad, M. (2019). Poly (lactic-co-glycolic acid) nanoparticles loaded with Callistemon citrinus phenolics exhibited anticancer properties against three breast cancer cell lines. Journal of Food Quality.

Augusta, I. M., Resende, J. M., Borges, S. V., Maia, M. C. A., & Couto, M. A. P. G. (2010). Physical and chemical characterization of malay red-apple (Syzygium malaccensis,(L.) Merryl & Perry) Skin and pulp. Food Science and Technology, 30(4), 928-932.

Ayyanar, M., & Subash-Babu, P. (2012). Syzygium cumini (L.) Skeels: A review of its phytochemical constituents and traditional uses. Asian Pacific journal of tropical biomedicine, 2(3), 240-246.

Bairy, K. L., Sharma, A., & Shalini, A. (2005). Evaluation of the hypoglycemic, hypolipidemic and hepatic glycogen raising effects of Syzygium malaccense upon streptozotocin induced diabetic rats. Journal of Natural remedies, 5(1), 46-51.

Batista, Â. G., da Silva, J. K., Cazarin, C. B. B., Biasoto, A. C. T., Sawaya, A. C. H. F., Prado, M. A., & Júnior, M. R. M. (2017). Red-jambo (Syzygium malaccense): Bioactive compounds in fruits and leaves. LWT-Food science and technology, 76, 284-291.

Cock, I. E., & Cheesman, M. A. T. T. H. E. W. (2018). Plants of the genus Syzygium (Myrtaceae): A review on ethnobotany, medicinal properties and phytochemistry. Bioactive Compounds of Medicinal Plants: Properties and Potential for Human Health; Goyal, MR, Ayeleso, AO, Eds, 35-84.

Cruz, E. M. D. O., Pinto, J. A. O., Fontes, S. S., Arrigoni-Blank, M. D. F., Bacci, L., Jesus, H. C. R. D., ... & Blank, A. F. (2014). Water deficit and seasonality study on essential oil constituents of Lippia gracilis Schauer germplasm. The Scientific World Journal, 2014.

Dahham, S. S., Tabana, Y. M., Ahamed, M. B. K., & Majid, A. M. A. (2015). In vivo anti-inflammatory activity of β-caryophyllene, evaluated by molecular imaging. Molecules & Medicinal Chemistry, 1.

De Oliveira, C. C., de Oliveira, C. V., Grigoletto, J., Ribeiro, L. R., Funck, V. R., Grauncke, A. C. B., ... & Oliveira, M. S. (2016). Anticonvulsant activity of β-caryophyllene against pentylenetetrazol-induced seizures. Epilepsy & Behavior, 56, 26-31

Deepika, N., Eganathan, P., Sujanapal, P., & Parida, A. (2013). Chemical composition of Syzygium benthamianum (Wt. ex Duthie) Gamble essential oil-an endemic and vulnerable tree species. Journal of Essential Oil Bearing Plants, 16(2), 289-293.

Dias, C. N., Rodrigues, K. A., Carvalho, F. A., Carneiro, S. M., Maia, J. G., Andrade, E. H., & Moraes, D. F. (2013). Molluscicidal and leishmanicidal activity of the leaf essential oil of Syzygium cumini (L.) SKEELS from Brazil. Chemistry & biodiversity, 10(6), 1133-1141.

Domingos, A. L. R. . Da S.; Marco, C. A.; Machado, M. I. R.; Feitosa, A. J. S.; Palmeira, I. A.; Silva, J. H. da. (2020) Content and chemical identification of essential basil oil (ocimum basilicum, var. cinamon) l submitted to water stress in different environments. Research, Society and Development, [S. l.], v. 9, n. 8, p. e919985247.

Feltrin, F. M., Gibbert, L., da Silva Santos, N. C., de Assis Marques, F., Miguel, M. D., Zanin, S. M. W., ... & Dias, J. D. F. G. (2020). Extraction and identification of essential oil components from the leaves of Syzygium malaccense (L.) MERR. & LM PERRY, MYRTACEAE. Ciência e Natura, 42, 6.

Fernandes, E. S., Passos, G. F., Medeiros, R., da Cunha, F. M., Ferreira, J., Campos, M. M., ... & Calixto, J. B. (2007). Anti-inflammatory effects of compounds alpha-humulene and (−)-trans-caryophyllene isolated from the essential oil of Cordia verbenacea. European journal of pharmacology, 569(3), 228-236.

Ghareeb, M. A., Hamed, M. M., Abdel-Aleem, A. A. H., Saad, A. M., Abdel-Aziz, M. S., & Hadad, A. H. (2017). Extraction, isolation, and characterization of bioactive compounds and essential oil from Syzygium jambos. Extraction, 10(8).

Ghelardini, C., Galeotti, N., Mannelli, L. D. C., Mazzanti, G., & Bartolini, A. (2001). Local anaesthetic activity of β-caryophyllene. Il Farmaco, 56(5-7), 387-389.

Hajimehdipoor, H., Gohari, A. R., Ajani, Y., & Saeidnia, S. (2014). Comparative study of the total phenol content and antioxidant activity of some medicinal herbal extracts.

Hanif, M. U., Hussain, A. I., Aslam, N., Kamal, G. M., Chatha, S. A. S., Shahida, S., ... & Hussain, R. (2020). Chemical Composition and Bioactivities of Essential Oil from Leaves of Syzygium cumini (L.) Skeels Native to Punjab, Pakistan. Chemistry & biodiversity, 17(8), e1900733.

Hassan, S. B., Gali-Muhtasib, H., Göransson, H., & Larsson, R. (2010). Alpha terpineol: a potential anticancer agent which acts through suppressing NF-κB signalling. Anticancer Research, 30(6), 1911-1919.

Ismail, I. S., Ismail, N., & Lajis, N. (2010). Ichthyotoxic properties and essential oils of Syzygium malaccense (Myrtaceae). Pertanika Journal of Science & Technology, 18(1), 1-6.

Jang, H. I., Rhee, K. J., & Eom, Y. B. (2020). Antibacterial and antibiofilm effects of α-humulene against Bacteroides fragilis. Canadian journal of microbiology, 66(6), 389-399.

Karioti, A., Skaltsa, H., & Gbolade, A. A. (2007). Analysis of the leaf oil of Syzygium malaccense Merr. et Perry from Nigeria. Journal of Essential Oil Research, 19(4), 313-315.

Kuiate, J. R., Mouokeu, S., Wabo, H. K., & Tane, P. (2007). Antidermatophytic triterpenoids from Syzygium jambos (L.) Alston (Myrtaceae). Phytotherapy Research: An International Journal Devoted to Pharmacological and Toxicological Evaluation of Natural Product Derivatives, 21(2), 149-152.

Legault, J., Dahl, W., Debiton, E., Pichette, A., & Madelmont, J. C. (2003). Antitumor activity of balsam fir oil: Production of reactive oxygen species induced by α-humulene as possible mechanism of action. Planta medica, 69(05), 402-407.

Migliato, K. F., Moreira, R. R., Mello, J. C., Sacramento, L. V., Corrêa, M. A., & Salgado, H. (2007). Quality control of Syzygium cumini (L.) Skeels fruits. Revista Brasileira de Farmacognosia, 17(1), 94-101.

Mohamed, A. A., Ali, S. I., & El-Baz, F. K. (2013). Antioxidant and antibacterial activities of crude extracts and essential oils of Syzygium cumini leaves. Plos one, 8(4), e60269.

Moo, C. L., Yang, S. K., Osman, M. A., Yuswan, M. H., Loh, J. Y., Lim, W. M., ... & Lai, K. S. (2020). Antibacterial Activity and Mode of Action of β-caryophyllene on Bacillus cereus. Polish journal of microbiology, 69(1), 49.

Nawwar, M. A., Hashem, A. N., Hussein, S. A., Swilam, N. F., Becker, A., Haertel, B., ... & Linscheid, M. W. (2016). Phenolic profiling of an extract from Eugenia jambos L. (Alston)-the structure of three flavonoid glycosides–antioxidant and cytotoxic activities. Die Pharmazie-An International Journal of Pharmaceutical Sciences, 71(3), 162-168.

Negreiros, P. S, da Costa, D. S., da Silva, V. G., de Carvalho Lima, I. B., Nunes, D. B., de Melo Sousa, F. B., ... & Oliveira, R. D. C. M. (2019). Antidiarrheal activity of α-terpineol in mice. Biomedicine & Pharmacotherapy, 110, 631-640.

Nist (National Institute of Standards and Technology), 1999. PC version 1.7 of the NIST/EPA/NIH Mass Spectral Library Norwalk. Perkin–Elmer Corp., CT, USA

Noudogbessi, J. P., Yédomonhan, P., Sohounhloué, D. C., Chalchat, J. C., & Figuérédo, G. (2008). Chemical composition of essential oil of Syzygium guineense (Willd.) DC. var. guineense (Myrtaceae) from Benin. Records of natural products, 2(2).

Park, S. N., Lim, Y. K., Freire, M. O., Cho, E., Jin, D., & Kook, J. K. (2012). Antimicrobial effect of linalool and α-terpineol against periodontopathic and cariogenic bacteria. Anaerobe, 18(3), 369-372.

Raina, V. K., Srivastava, S. K., Aggarwal, K. K., Syamasundar, K. V., & Kumar, S. (2001). Essential oil composition of Syzygium aromaticum leaf from Little Andaman, India. Flavour and fragrance journal, 16(5), 334-336.

Rezende, W. P., Borges, L. L., Alves, N. M., Ferri, P. H., & Paula, J. R. (2013). Chemical variability in the essential oils from leaves of Syzygium jambos. Revista Brasileira de Farmacognosia, 23(3), 433-440.

Ruan, Z. P., Zhang, L. L., & Lin, Y. M. (2008). Evaluation of the antioxidant activity of Syzygium cumini leaves. Molecules, 13(10), 2545-2556.

Sangwan, N. S., Farooqi, A. H. A., Shabih, F., & Sangwan, R. S. (2001). Regulation of essential oil production in plants. Plant growth regulation, 34(1), 3-21.

Santos, C. V. Dos .; Mallmann, A. P.; Toledo, A. G.; Bandeira, D. M.; Costa, W. F. Da .; Marins, D. M. Ávila .; Corrêa, J. M.; Pinto, F. G. Da S. (2021). Chemical composition, antimicrobial and antioxidant activity of leaves essential oil the Myrcia palustris DC. (Myrtaceae). Research, Society and Development, [S. l.], v. 10, n. 3, p. e20510313303.

Saranya, J., Eganathan, P., Sujanapal, P., & Parida, A. (2012). Chemical composition of leaf essential oil of Syzygium densiflorum wall. ex wt. & arn.-a vulnerable tree species. Journal of Essential Oil Bearing Plants, 15(2), 283-287.

Siani, A. C., Souza, M. C., Henriques, M. G., & Ramos, M. F. (2013). Anti-inflammatory activity of essential oils from Syzygium cumini and Psidium guajava. Pharmaceutical biology, 51(7), 881-887.

Simões, C. M. O., Schenkel, E. P., Gosmann, G., Mello, J. C. P., Mentz, L. A., & Petrovick, P. R. (2007). Farmacognosia: da planta ao medicamento. 1002 pg. Porto Alegre/Florianópolis: Editora da UFSC/Editora da UFRGS.

Souza, R. H. L., Cardoso, M. S. P., Menezes, C. T., Silva, J. P., De Sousa, D. P., & Batista, J. S. (2011). Gastroprotective activity of α-terpineol in two experimental models of gastric ulcer in rats. Daru: journal of Faculty of Pharmacy, Tehran University of Medical Sciences, 19(4), 277.

Teng, Z. Q., & Shen, Y. (2015). Research progress of genetic engineering on medicinal plants. China journal of Chinese materia medica, 40(4), 594-601

The plant list. (sf). Syzygium. Recuperado de http://www.theplantlist.org/tpl1.1/search?q=Syzygium

Trancoso, M. D. (2013). Projeto Óleos voláteis: extração, importância e aplicações no cotidiano. Revista Práxis, 5(9).

Trevizan, L. N. F., do Nascimento, K. F., Santos, J. A., Kassuya, C. A. L., Cardoso, C. A. L., do Carmo Vieira, M., ... & Formagio, A. S. N. (2016). Anti-inflammatory, antioxidant and anti-Mycobacterium tuberculosis activity of viridiflorol: The major constituent of Allophylus edulis (A. St.-Hil., A. Juss. & Cambess.) Radlk. Journal of ethnopharmacology, 192, 510-515.

Verma, R. S., Padalia, R. C., & Chauhan, A. (2014). Essential oil composition of Aegle marmelos (L.) Correa: chemotypic and seasonal variations. Journal of the Science of Food and Agriculture, 94(9), 1904-1913.

Vernin, G., Vernin, G., Metzger, J., Roque, C., & Pieribattesti, J. C. (1991). Volatile constituents of the Jamrosa aroma Syzygium jambos L. Aston from Reunion Island. Journal of Essential Oil Research, 3(2), 83-97.

Vignesh, R., Puhazhselvan, P., Sangeethkumar, M., Saranya, J., Eganathan, P., & Sujanapal, P. (2013). GC-MS analysis, antimicrobial, scavenging ability and cytotoxic activity of leaves of Syzygium calophyllifolium Walp. Journal of Biologically Active Products from Nature, 3(2), 121-129.

World Health Organization. (2013). Sustaining the drive to overcome the global impact of neglected tropical diseases: second WHO report on neglected diseases (No. WHO/HTM/NTD/2013.1). World Health Organization

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Published

16/06/2021

How to Cite

REIS, A. S. .; SILVA, L. de S.; MARTINS, C. F. .; PAULA, J. R. de . Analysis of the volatile oils from three species of the gender Syzygium . Research, Society and Development, [S. l.], v. 10, n. 7, p. e13510716375, 2021. DOI: 10.33448/rsd-v10i7.16375. Disponível em: https://www.rsdjournal.org/index.php/rsd/article/view/16375. Acesso em: 26 apr. 2024.

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Agrarian and Biological Sciences