Chemical composition of the essential oil and fixed oil Bauhinia pentandra (Bong.) D. Dietr
Macia C. S. de Almeida1, Luciana G. S. Souza1, Daniele A. Ferreira1, Francisco J. Q. Monte1, Raimundo Braz-Filho2, Telma L. G. de Lemos1
1 Departamento de Química Orgânica e Inorgânica, Universidade Federal do Ceará, Fortaleza-CE, Brazil
2 Setor de Química de Produtos Naturais, Universidade Estadual do Norte Fluminense, Campos dos Goytacazes-RJ, Brazil
|Date of Submission||01-Apr-2014|
|Date of Acceptance||02-May-2014|
|Date of Web Publication||24-Sep-2015|
Telma L. G. de Lemos
Departamento de Química Orgânica e Inorgânica, Universidade Federal do Ceará, Fortaleza-CE
Source of Support: Brazilian agencias of research: CAPES/CNPq, Conflict of Interest: None
| Abstract|| |
Background: Bauhinia pentandrais popularly known as "mororó" and inhabits the Caatinga and Savannah biomes. Objective: This paper reports the chemical composition of the essential and fatty oils of the leaves from B. pentandra. Materials and Methods: The essential oil was obtained by hydrodistillation and the fixed oil by extraction with hexane, followed by saponification with KOH/MeOH, and methylation using MeOH/HCl. The constituents were analyzed by gas chromatography-mass spectrometry. Results: The major constituent of the essential oil was the phytol (58.78% ±8.51%), and of the fatty oil were palmitic (29.03%), stearic (28.58%) and linolenic (10.53%) acids. Conclusion: Of the compounds identified in the essential oil, three are first reported in this species, and this is the first record of the chemical composition of the fixed oil.
Keywords: Bauhinia pentandra (Bong.) D. Dietr, essential oil, fixed oil, gas chromatography-mass spectrometry, Leguminosae
|How to cite this article:|
de Almeida MC, Souza LG, Ferreira DA, Monte FJ, Braz-Filho R, de Lemos TL. Chemical composition of the essential oil and fixed oil Bauhinia pentandra (Bong.) D. Dietr. Phcog Mag 2015;11, Suppl S2:362-4
|How to cite this URL:|
de Almeida MC, Souza LG, Ferreira DA, Monte FJ, Braz-Filho R, de Lemos TL. Chemical composition of the essential oil and fixed oil Bauhinia pentandra (Bong.) D. Dietr. Phcog Mag [serial online] 2015 [cited 2022 Jan 24];11, Suppl S2:362-4. Available from: http://www.phcog.com/text.asp?2015/11/44/362/166015
| Introduction|| |
The genus Bauhinia (Leguminosae) consists of about 300 species, distributed in most tropical countries, including Africa, Asia, and America. Species of the genus Bauhinia are present as trees, shrubs and vines, and in Brazil are used by the population as hypoglycemic agents. Multiple biological activities are allocated to Bauhinia species such as antidiabetic, diuretic, hypocholesterolemic, antimicrobial, analgesic, antioxidant, larvicidal, acetylcholinesterase, anti-inflammatory,,,,,, among others. Chemical compositions of essential oils of Bauhinias are cited in the literature, among them Bauhinia aculeata, B. brevipes, B. forficata, B. longifolia, B. pentandra, B. rufa, B. variegata, B. ungulata and B. acuruana.,,, The B. pentandra species inhabits the Caatinga and Savannah biomes and is known in the Northeast region of Brazil as "mororó". Literature reports the chemical composition of its essential oil from Rio de Janeiro-Brazil. Therefore, the aim of this work is to identify the chemical composition of the essential and fatty oils from the leaves of B. pentandra species collected in the Medicinal Garden of Plants-Federal University of Ceará (UFC)-Brazil, whose composition was different from already reported.
| Materials and Methods|| |
Bauhinia pentandra (Bong.) D. Dietr. leaves were collected at Medicinal Plants Garden, UFC. A voucher specimen (number 53444) is deposited in the Herbarium Prisco Bezerra of the Department of Biology, UFC.
Essential oil extraction
The fresh leaves (162 g) were subjected to hydrodistillation process in Clevenger-type apparatus for 5 h. The hydrodistilled volatiles were dried over anhydrous sodium sulfate and stored in a freezer at 4°C until the analysis procedure. The experiment was performed in triplicate.
Fixed oil extraction
The air-dried leaves (55 g) were extracted with hexane at room temperature for 5 days, followed by filtration and concentration under reduced pressure to yield a crude extract (0.924 g; 1.7%).
To the crude hexane extract (923 mg) was added MeOH (15 mL) and KOH (923 mg), which reacted for 1 h under reflux. After cooling, the mixture was diluted with H2O (40 mL) and extracted with hexane (2 mL × 50 mL). The aqueous phase was acidified to pH 3 with concentrated HCl and extracted with EtOAc (2 mL × 50 mL). The combined EtOAc fractions were dried (Na2 SO4) and concentrated under reduced pressure to give fatty acids (344 mg).
Fatty acids (344 mg) were refluxed for 1 h in MeOH (10 mL) in the presence concentrated HCl (1 mL). After cooling, the mixture was diluted with H2O (30 mL) and extracted with CH2 Cl2 (3 mL × 30 mL). The combined CH2 Cl2 fractions were dried (Na2 SO4) and concentrated under reduced pressure to give methyl esters (221 mg). The crude reaction was chromatographed on a column Si gel, eluted with hexane, followed by CH2 Cl2, and fractions were analyzed by thin-layer chromatography and gas chromatography-mass spectrometry (GC/MS).
Gas chromatography-mass spectrometry
Analysis of the oils was performed on a Shimadzu/QP2010 GC/MS instrument employing the following conditions: RTX-5 (5% phenyl e 95% dimethylpolysiloxane) capillary column (30 mm × 0.25 mm, 0.25 µm film thickness); carrier gas: Helium (1 mL/min); column temperature: 40°C–180°C at 4°C/min then of 180°C–280°C at 20°C/min and held at 280°C for 10 min, for essential oil and RTX-5 (5% phenyle 95% dimethylpolysiloxane) capillary column (30 mm × 0.25 mm, 0.25 µm film thickness); carrier gas: Helium (1.46 mL/min); column temperature: 80°C–280°C at 5°C/min then of 280°C–300°C at 20°C/min and held at 300°C for 5 min, for fatty oil. The retention indices Kovat's were calculated using a series of standard n-alkane (C7-C30). The identification of compounds was performed by comparing their mass spectra with those of NIST08 library, retention indices, and published data.
| Results and Discussion|| |
The essential oil yield from fresh leaves was 0.01%. The results of GC/MS analysis [Table 1] shows the presence of 6 components [Figure 1], which 5 were sesquiterpenes (1–5, 37.17%) and 1 diterpene (6, 58.78%), representing 95.95 ± 1.02% of the total composition. The main constituent was phytol (6, 58.78% ±8.51%), which was not reported in the previous study. Beyond of phytol, germacrene D (3, 8.40 ± 1.04%) and elixene (4, 11.73 ± 1.52%) arefirst recorded in B. pentandra. Germacrene is an important component identified in the essential oil with significant biological activities.
|Table 1: Chemical composition of the essential oil from the leaves of B. pentandra|
Click here to view
|Figure 1: Terpenoids identified in the essential oil extracted from B. pentandra (leaves fresh)|
Click here to view
From the fatty oil, 11 components were identified, representing 85.53% of the total composition. The results of GC/MS analysis [Table 2] from methylated derivatives showed that the major components were methyl hexadecanoate (29.03%), methyl (9Z,12Z,15Z)-9, 12, 15-octadecatrienoate (28.93%) and methyl octadecanoate (10.58%), or palmitic, linolenic and stearic acids, respectively. The major compounds identified in the fatty acids are considered healthy for the human consumption. This is the first report in the literature component of the fixed oil of this species.
|Table 2: Chemical composition of the fixed oil from the leaves of B. pentandra|
Click here to view
Analysis of chemical constituents of less polar fraction of this species revealed the presence of components without toxicity. This species is used in the form of infusion in folk medicine, therefore, is important to know the chemical constituents, especially of leaves.
| Conclusion|| |
Analysis of essential oil allowed the identification of six compounds, being the phytol (6, 58.78 ± 8.51%) the major constituent. Of the identified compounds, three are being reported for the first time in the species: germacrene D (3), elixene (4) and phytol (6).
The study of fatty acid profile in the hexane extract from leaves presented as major components the palmitic (29.03%), linolenic (28.93%) and stearic (10.58%) acids. To the best of our knowledge, this is the first report on the chemical composition of the fixed oil this species.
| Acknowledgments|| |
The authors thank the institutions that foster research, CAPES and CNPq for financial support.
| References|| |
Cechinel Filho V. Chemical composition and biological potential of plants from the genus Bauhinia
. Phytother Res 2009;23:1347-54.
Kerntopf MR, Nascimento NR, Fonteles MC. Bauhinia ungulata
Linn. (pata-de-vaca). In: Viana GS, Leal LK, Vasconcelos SM, Medicinal plants of Caatinga: Biological and Therapeutic Potential activities. Fortaleza: Graphic Expression and Publisher; 2013. p. 93-123.
Menezes FS, Minto AB, Ruela HS, Kuster RM, Sheridan H, Frankish N. Hypoglycemic activity of two Brazilian Bauhinia
species: Bauhinia forficata
L. and Bauhinia monandra
Kurz. Rev Bras Farmacognosia 2007;17:8-13.
Silva KL, Filho VC. Plants of the genus Bauhinia: chemical composition and pharmacological potential. Quim Nova 2002;25:449-54.
Argolo AC, Sant'Ana AE, Pletsch M, Coelho LC. Antioxidant activity of leaf extracts from Bauhinia monandra
. Bioresour Technol 2004;95:229-33.
Gois. Phytochemical and biological studies Bauhinia acuruana Moric. Dissertation in Chemistry. Ceará, Brazil: Federal University of Ceará; 2010.
Santos KM, Gonçalves PS, Paiva MJ, Lacerda GA. Acetylcholinesterase inhibition starting from extracts of Bauhinia variegata
(Aiton) Buch.-Ham. and Bauhinia ungulata
L. Rev Soc Bras Med Trop 2011;44:781-3.
Duarte-Almeida JM, Negri G, Salatino A. Volatile oils in leaves of Bauhinia
(Fabaceae Caesalpinioideae). Biochem Syst Ecol 2004;32:747-53.
Sartorelli P, Correa DS. Constituents of essential oil from Bauhinia forficata
link. J Essent Oil Res 2007;19:468-9.
Gramosa NV, Freitas JV, Neto MN, Silveira ER, Nunes, EP. Volatile components of the essential oil from Bauhinia ungulata
L. J Essent Oil Res 2009;21:495-6.
Gois RW, Sousa LM, Lemos TL, Arriaga AM, Andrade-Neto M, Santiago GM, et al
. Chemical composition and larvicidal effects of essential oil from Bauhinia acuruana
(Moric) against Aedes aegypti
. J Essent Oil Res 2011;23:59-62.
Adams RP. Identification of Essential Oil Components by Gas Chromatography/Mass Spectrometry. Carol Stream: Allured Pub. Corp.; 2007.
Almeida MC, Alves LA, Souza LG, Machado LL, Matos MC, Oliveira MC, et al
. Flavonoids and other substances from lippia sidoides
and their antioxidant activities. Quim Nova 2010;33:1877-81.
Vianni R, Braz-Filho R. Fatty Acids Natural: Importance and occurrence in foods. Quim Nova 1996;19:400-7.
[Table 1], [Table 2]
|This article has been cited by|
||Chemical constituents and acetylcholinesterase inhibitory activity from the stems of Bauhinia pentandra
| ||Horlando C. da Silva, Francisco das Chagas L. Pinto, Anderson F. de Sousa, Otília Deusdenia L. Pessoa, Maria Teresa Salles Trevisan, Gilvandete M. P. Santiago |
| ||Natural Product Research. 2020; : 1 |
|[Pubmed] | [DOI]|
||7-epi-griffonilide, a new lactone from Bauhinia pentandra: complete 1H and 13C chemical shift assignments
| ||MACIA C.S. DE ALMEIDA,LUCIANA G.S. SOUZA,DANIELE A. FERREIRA,FRANCISCO C.L. PINTO,DÉBORA R. DE OLIVEIRA,GILVANDETE M.P. SANTIAGO,FRANCISCO J.Q. MONTE,RAIMUNDO BRAZ-FILHO,TELMA L.G. DE LEMOS |
| ||Anais da Academia Brasileira de Ciências. 2017; 89(1): 65 |
|[Pubmed] | [DOI]|