Chemical composition and anti-inflammatory activity of Boswellia ovalifoliolata essential oils from leaf and bark

Abstract

We isolated the essential oils from Boswellia ovalifoliolata N.P.Balakr and A.N.Henry using hydrodistillation, identified the obtained compounds using gas chromatography–mass spectrometry (GC–MS) and Fourier transform-infrared spectroscopy (FT-IR), and studied the photophysical and electrochemical properties using UV–visible and fluorescence spectroscopy and cyclic voltammetry. On the basis of GC–MS spectra, 38 compounds were identified in the essential oil from leaves and 26 in the oil from bark. The bark oil contained 13.44% β-Farnesene (sesquiterpene), 10.45% caryophyllene oxide (sesquiterpene) and 6.6% spathulenol, (2Z,6E)-(sesquiterpene alcohol); the leaf oil contained 11.1% spathulenol (sesquiterpene alcohol), 9.0% caryophyllene oxide (sesquiterpenoids) and 6.3% decyl acetate (ester). FT-IR spectra confirmed the presence of aliphatic aldehydes and ketones, carboxylic acid, alcohols, esters and ethers in both oil types. UV–visible absorption spectra showed maximum absorbance at 245, 290 and 402 nm for bark oil, and 250, 285 and 325 nm for leaf. Bark oil showed strong emission with maximum emission wavelength at 456 nm was higher than that of leaf oil at 414 nm. The essential oil had significant anti-inflammatory activity, and the reduction potential of the leaf oil was −0.44 and −0.56 eV for bark.

Keywords

Essential oil / Boswellia ovalifoliolata / Gas chromatography–mass spectrometry / Fourier transform-infrared spectroscopy / Cyclic voltammetry fluorescence spectroscopy

References

[1] Al-Harrasi A, Al-Saidi S. Phytochemical analysis of the essential oil from botanically certified oleo gum resin of Boswellia sacra (Omani Luban). Molecules, 2008, 13(9): 2181-2189.

[2] Anderson J, Davis M. Boswellic acids: potent active ingredients from a traditional remedy. Cosmet Sci Technol, 2007, 4(2): 5-9.

[3] Anitha G, Sudarsanam G. Studies on antimicrobial activity of Boswellia ovalifoliolata against Xanthomonas citri and salmonella Typhynurium. Int J Appl Biol Pharm, 2013, 4(1): 243-247.

[4] Babushok VI, Zenkevich IG. Retention indices for most frequently reported essential oil compounds in GC. Chromatographia, 2009, 69(3–4): 257-269.

[5] Babushok VI, Linstrom PJ, Zenkevich IG. Retention indices for frequently reported compounds of plant essential oils. J Phys Chem Ref Data, 2011 40 4 043101

[6] Basappa G, Kumar V, Sarojini BK, Poornima DV, Gajula H, Sannabommaji TK, Rajashekar J. Chemical composition, biological properties of Anisomeles indica Kuntze essential oil. Ind Crops Prod, 2015, 77: 89-96.

[7] Boschi F, Fontanella M, Calderan L, Sbarbati A. Luminescence and fluorescence of essential oils. Fluorescence imaging in vivo of wild chamomile oil. Eur J Histochem, 2011, 55(2): 97-100.

[8] Carriedo Gabino. The use of cyclic voltammetry in the study of the chemistry of metal carbonyls. J chem edu, 1988, 65: 1020.

[9] Chandra S, Chatterjee P, Dey P, Bhattacharya S. Evaluation of in vitro anti-inflammatory activity of coffee against the denaturation of protein. Asian Pac J Trop Biomed, 2012 2 1 178

[10] Charles DJ, Simon JE. Comparison of extraction methods for the rapid determination of essential oil content and composition of basil. J Am Soc Hortic Sci, 1990, 115(3): 458-462.

[11] Chib R, Kumar M, Rizvi M, Sharma S, Pandey A, Bani S, Shah BA. Anti-inflammatory terpenoids from Boswellia ovalifoliolata. RSC Adv, 2014 4 17 8632

[12] El Asbahani A, Miladi K, Badri W, Sala M, Addi EA, Casabianca H, El Mousadik A, Hartmann D, Jilale A, Renaud FN, Elaissari A. Essential oils: from extraction to encapsulation. Int J Pharm, 2015, 483(1–2): 220-243.

[13] Goncalves RS, Battistin A, Pauletti G, Rota L, Serafini LA. Antioxidant properties of essential oils from Mentha species evidenced by electrochemical methods. Rev Bras Plantas Med, 2009, 11(4): 372-382.

[14] Govindappa M, Poojashri MN. Antimicrobial, antioxidant and in vitro anti-inflammatory activity of ethanol extract and active phytochemical screening of Wedelia trilobata (L.) Hitchc. J Pharmacogn Phytochem, 2011, 3(3): 43-51.

[15] Ichi KEN. Monoterpene composition of the essential oil of the aquatic liverwort Jungermannia vulcanicola Steph. The Bryologist, 2016, 87(4): 323-326.

[16] Kirti RJ, Jha SK, Pal RK, Jha GK, Samuel DVK. Effect of species and particle size on essential oil yield of citrus peel (Citrus spp). Indian J Agric Sci, 2013, 83(12): 9-12.

[17] Leelaprakash G, Dass SM, Road B. Invitro anti-inflammatory activity of methanol extract of Enicostemma axillare. Int J Drug Dev Res, 2011, 3(3): 189-196.

[18] Li YQ, Kong DX, Wu H. Analysis and evaluation of essential oil components of cinnamon barks using GC–MS and FTIR spectroscopy. Ind Crops Prod, 2013, 41: 269-278.

[19] Mahesh BU, Shrivastava S, Pragada RR, Naidu VGM, Sistla R. Antioxidant and hepatoprotective effects of Boswellia ovalifoliolata bark extracts. Chinese J Nat Med, 2014, 12(9): 663-671.

[20] Maksimovic S, Ivanovic J, Skala D. Supercritical extraction of essential oil from Mentha and mathematical modelling–the influence of plant particle size. Proced eng, 2012, 42: 1767-1777.

[21] Marella S, Konda PY, Mohammad SA, Nabi SA, Kumar J, Venkateshwarulu M, Chippada AR. Antihyperlipidemic activity of the stem bark of Boswellia ovalifoliolata in high fat diet fed rats. Photon J, 2014, 107: 572-576.

[22] Masek A, Chrzescijanska E, Zaborski M. Characteristics of curcumin using cyclic voltammetry, UV–vis, fluorescence and thermogravimetric analysis. Electrochimica Acta, 2013, 107: 441-447.

[23] Masek A, Chrzescijanska E, Kosmalska A, Zaborski M. Characteristics of compounds in hops using cyclic voltammetry, UV–VIS, FTIR and GC–MS analysis. Food Chem, 2014, 156: 353-361.

[24] Mothana RAA, Hasson SS, Schultze W, Mowitz A, Lindequist U. Phytochemical composition and in vitro antimicrobial and antioxidant activities of essential oils of three endemic Soqotraen Boswellia species. Food Chem, 2011, 126(3): 1149-1154.

[25] Murthy KSR, Reddy MC, Rani SS, Pullaiah T. Bioactive principles and biological properties of essential oils of Burseraceae: a review. J Pharmacogn Phytochem, 2016, 5(2): 247-258.

[26] Nicolson RS. Theory and application of cyclic voltammetry for measurement of electrode reaction kinetics. Anal Chem, 1965, 37(11): 1351-1355.

[27] Perez GS, Zavala SM, Arias GL, Ramos LM. Anti-inflammatory activity of some essential oils. J Essent Oil Res, 2011, 23(5): 38-44.

[28] Prabhakar Y, Ali MS, kumar MJ, Tilak TK, Rao CA. Evaluation of antioxidant activities of aqueous extract of stem bark of Boswellia ovalifoliolata in streptozotocin induced diabetic rats. J Pharm Chem, 2013, 7(4): 19-24.

[29] Prasanna Anjaneya Reddy L, Venkata Ratnam L. Chemical profile, antioxidant and antimicrobial activity of essential oils from Boswellia ovalifoliolata Bal. et. Henry. Int J Pharm Clin Res, 2015, 7(1): 96-101.

[30] Raut JS, Karuppayil SM. A status review on the medicinal properties of essential oils. Ind Crops Prod, 2014, 62: 250-264.

[31] Sodeifian G, Ardestani NS, Sajadian SA. Application of supercritical carbon dioxide to extract essential oil from Cleome coluteoides Boiss: experimental, response surface and grey wolf optimization methodology. J Supercrit Fluids, 2016, 114: 55-63.

[32] Sodeifian G, Sajadian SA, Ardestani NS. Optimization of essential oil extraction from Launaea acanthodes Boiss: utilization of supercritical carbon dioxide and cosolvent. J Supercrit Fluids, 2016, 116: 46-56.

[33] Woolley CL, Suhail MM, Smith BL, Boren KE, Taylor LC, Schreuder MF, Young DG. Chemical differentiation of Boswellia sacra and Boswellia carterii essential oils by gas chromatography and chiral gas chromatography–mass spectrometry. J Chromatogr A, 2012, 1261: 158-163.