HPTLC, IR fingerprinting, and chemical composition analysis of commercial bitter orange (Citrus aurantium L.) hydrosols

Document Type : Original Article

Authors

1 Medicinal Plants Processing Research Center, Shiraz University of Medical Sciences, Shiraz, Iran.

2 Department of Phytopharmaceuticals (Traditional Pharmacy), School of Pharmacy, Shiraz University of Medical Sciences, Shiraz, Iran.

3 Chair of Proteomics and Bioanalytics, Technical University of Munich (TUM), 85354 Freising, Germany.

4 Department of Biostatistics, School of Medicine, Arak University of Medical Sciences, Arak, Iran.

Abstract

Citrus aurantium L. hydrosol extracted by steam distillation from its flowers is a highly consumed herbal product in the Iranian traditional market, widely used as a food flavor and therapeutic food and drinks. This study investigated ten commercial hydrosol samples of C. aurantium flowers produced by conventional extraction methods and industrial processes, as well as a laboratory-prepared control sample. A liquid-liquid extraction method and sonication were used to extract essential oils from commercial hydrosols. Samples were then subjected to GC/MS analysis. ATR-IR spectroscopy was another efficient tool used to analyze hydrosol samples. All HPTLC chromatograms exhibited a close resemblance between samples and controls. The cluster analysis was used to compare the results of GC/MS and IR screening. In the HCA dendrograms derived from the GC/MS data, most of the oil sample profiles were found to be very similar to those of the control. Linalool was the most abundant compound in eight samples and the control. α-Terpineol in all hydrosol samples and geraniol in five samples and control were other marker compounds. Ethyl disulfide, dillapiol, and hotrienol were detected in two samples that have not been reported in previous studies and might have resulted from the addition of other herbal hydrosols. Microbial content and pH values were within permissible limits in all samples, making them safe for oral consumption.

Highlights

Mohammad Ali Farboodniay Jahromi (Google Scholar)

Mohammad M. Zarshenas (Google Scholar)

Keywords

References

1.    Brah AS, Armah FA, Obuah C, Akwetey SA, Adokoh CK. Toxicity and therapeutic applications of citrus essential oils (CEOs): A review. Int J Food Prop. 2023 Sep 22;26(1):301-326.
2.    Suryawanshi JA. An overview of Citrus aurantium used in treatment of various diseases. Afr J Plant Sci. 2011 Jul 31;5(7):390-395.
3.    Pultrini Ade M, Galindo LA, Costa M. Effects of the essential oil from Citrus aurantium L. in experimental anxiety models in mice. Life Sci. 2006 Mar 6;78(15):1720-5. doi: 10.1016/j.lfs.2005.08.004. Epub 2005 Oct 25. PMID: 16253279.
4.    Leite MP, Fassin Jr J, Baziloni EM, Almeida RN, Mattei R, Leite JR. Behavioral effects of essential oil of Citrus aurantium L. inhalation in rats. Rev bras farmacogn. 2008;18(suppl):661-666.
5.    Aghili Alavi khorasani Shirazi S: Makhzan-AL-Advieh. Tehran: Tehran University of Medical Science Press; 2011. 
6.    Bocco A, Cuvelier ME, Richard H, Berset C. Antioxidant activity and phenolic composition of Citrus peel and seed extracts. J Agric Food Chem. 1998 Jun 15;46(6): 2123-2129. 
7.    Miyazawa M, Okuno Y, Fukuyama M, Nakamura S, Kosaka H. Antimutagenic activity of polymethoxyflavonoids from Citrus aurantium. J Agric Food Chem. 1999 Dec;47(12):5239-44. doi: 10.1021/jf990176o. PMID: 10606602.
8.    Ellouze I, Abderrabba M, Sabaou N, Mathieu F, Lebrihi A, Bouajila J. Season's variation impact on Citrus aurantium leaves essential oil: chemical composition and biological activities. J Food Sci. 2012 Sep;77(9):T173-80. doi: 10.1111/j.1750-3841.2012.02846.x. Epub 2012 Aug 16. PMID: 22897411.
1750-3841.2012.02846.x.
9.    Mohamed A, Kouhila M, Jamali A, Lahsasni S, Mahrouz M. Moisture sorption isotherms and heat of sorption of bitter orange leaves (Citrus aurantium). J Food Eng. 2005 Apr 1;67(4):491-498. 
10.    Majnooni MB, Mansouri K, Gholivand MB, Mostafaie A, Mohammadi-Motlagh HR, Afnanzade NS, Abolghasemi MM, Piriyaei M. Chemical composition, cytotoxicity and antioxidant activities of the essential oil from the leaves of Citrus aurantium L. Afr J Biotechnol. 2014;11(2):498-503.
11.    Linck VM, da Silva AL, Figueiró M, Piato AL, Herrmann AP, Dupont Birck F, Caramão EB, Nunes DS, Moreno PR, Elisabetsky E. Inhaled linalool-induced sedation in mice. Phytomedicine. 2009 Apr;16(4):303-7. doi: 10.1016/j.phymed.2008.08.001. Epub 2008 Sep 27. PMID: 18824339.
12.    Monsef-Esfahani HR, Amanzade Y, Alhani Z, Hajimehdipour H, Faramarzi MA. 
GC/MS Analysis of Citrus aurantium L. Hydrolate and its comparison with the commercial samples. Iran J Pharm Res. 2004;3(3):177-179. 
13.    Labadie C, Ginies C, Guinebretiere MH, Renard CMGC, Cerutti C, Carlin F. Hydrosols of orange blossom (Citrus aurantium), and rose flower (Rosa damascena and Rosa centifolia) support the growth of a heterogeneous spoilage microbiota. Food Res Int. 2015 Oct;76(Pt 3):576-586. doi: 10.1016/j.foodres.2015.07.014. Epub 2015 Jul 12. PMID: 28455040.
14.    Jakubczyk K, Tuchowska A, Janda-Milczarek K. Plant hydrolates - Antioxidant properties, chemical composition and potential applications. Biomed Pharmacother. 2021 Oct;142:112033. doi: 10.1016/j.biopha.2021.112033. Epub 2021 Aug 17. PMID: 34416628.
15.    Shafie MH, Kamal ML, Razak NA, Hasan S, Uyup NH, Rashid NF, Zafarina Z. Antioxidant and antimicrobial activity of plant hydrosol and its potential application in cosmeceutical products. Jundishapur J Nat Pharm Prod. 2022 Nov 30;17(4):e124018. 
16.    Jahromi MA, Etemadfard H, Zebarjad Z. Chemical Characterization an Antimicrobial Activity of Essential oil from the Leaves of Bienertia cycloptera. Chem Nat Compd. 2016 Sep;52:936-938. 
17.    Adams RP, Identification of essential oil components by gas chromatography/mass spectrometry: 2007, Allured Publishing Corporation. 
18.    NIST Mass Spectral Library. 2001.NIST/ EPA/NIH: USA, http://www.nist.gov/srd/nlstla. htm.
19.    The Pherobase: the database of pheromones and semiochemicals, KovatsIndex:http://www.pherobase.com/database/kovats/kovats-index.php.
20.    Sakhteman A, Keshavarz R, Mohagheghzadeh A. ATR-IR fingerprinting as a powerful method for identification of traditional medicine samples: a report of 20 herbal patterns. Res J Pharmacogn. 2015 Jul 1; 2(3):1-8.
21.    Kılıç CS, Demirci B, Kırcı D, Duman H, Gürbüz İ. Essential Oils of Ferulago glareosa Kandemir&Hedge Roots and Aerial Parts: PCA and HCA Analyses. Chem Biodivers. 2023 May;20(5):e202300364. doi: 10.1002/cbdv.202300364. Epub 2023 Apr 18. PMID: 37070659.
22.    Yesilada E. Past and future contributions to traditional medicine in the health care system of the Middle-East. J Ethnopharmacol. 2005 Aug 22;100(1-2):135-7. doi: 10.1016/j.jep.2005.06.003. PMID: 15994043.
23.    Golmakani MT, Rezaei K. Comparison of microwave-assisted hydrodistillation withthe traditional hydrodistillation method in the extractionof essential oils from Thymus vulgaris L. Food Chem. 2008 Aug 15;109(4):925-30. doi: 10.1016/j.foodchem.2007.12.084. Epub 2008 Jan 26. PMID: 26050009.
24.    Yingngam B, Brantner A, Treichler M, Brugger N, Navabhatra A, Nakonrat P. Yingngam B, Brantner A, Treichler M, Brugger N, Navabhatra A, Nakonrat P. Optimization of the eco-friendly solvent-free microwave extraction of Limnophila aromatica essential oil. Ind Crops Prod. 2021 Jul 1;165:113443. 
25.    Bayramoglu B, Sahin S, Sumnu G. Solvent-free microwave extraction of essential oil from oregano. J Food Eng. 2008 Oct 1;88(4):535-540. 
26.    Sarrou E, Chatzopoulou P, Dimassi-Theriou K, Therios I. Volatile constituents and antioxidant activity of peel, flowers and leaf oils of Citrus aurantium L. growing in Greece. Molecules. 2013 Sep 2;18(9):10639-47. doi: 10.3390/molecules180910639. PMID: 24002139; PMCID: PMC6270488.  
27.    Elisabetsky E, Marschner J, Souza DO. Effects of Linalool on glutamatergic system in the rat cerebral cortex. Neurochem Res. 1995 Apr;20(4):461-5. doi: 10.1007/BF00973103. PMID: 7651584.
28.    Leal-Cardoso JH, da Silva-Alves KS, Ferreira-da-Silva FW, dos Santos-Nascimento T, Joca HC, de Macedo FH, et al. Linalool blocks excitability in peripheral nerves and voltage-dependent Na+ current in dissociated dorsal root ganglia neurons. Eur J Pharmacol. 2010 Oct 25;645(1-3):86-93. doi: 10.1016/j.ejphar.2010.07.014. Epub 2010 Jul 22. PMID: 20655301. 
29.    Linck VM, da Silva AL, Figueiró M, Caramão EB, Moreno PR, Elisabetsky E. Effects of inhaled Linalool in anxiety, social interaction and aggressive behavior in mice. Phytomedicine. 2010 Jul;17(8-9):679-83. doi: 10.1016/j.phymed.2009.10.002. Epub 2009 Dec 3. PMID: 19962290.
30.    Xu L, Li X, Zhang Y, Ding M, Sun B, Su G, Zhao Y. The effects of linalool acupoint application therapy on sleep regulation. RSC Adv. 2021 Feb 3;11(11):5896-5902. doi: 10.1039/d0ra09751a. PMID: 35423146; PMCID: PMC8694721.
31.    Belletti N, Kamdem SS, Tabanelli G, Lanciotti R, Gardini F. Modeling of combined effects of citral, linalool and beta-pinene used against Saccharomyces cerevisiae in citrus-based beverages subjected to a mild heat treatment. Int J Food Microbiol. 2010 Jan 1;136(3):283-9. doi: 10.1016/j.ijfoodmicro.2009.10.030. Epub 2009 Nov 6. PMID: 19939485. 
32.    do Socorro S Rosa Mdo S, Mendonça-Filho RR, Bizzo HR, de Almeida Rodrigues I, Soares RM, Souto-Padrón T, et al. Antileishmanial activity of a linalool-rich essential oil from Croton cajucara. Antimicrob Agents Chemother. 2003 Jun;47(6):1895-901. doi: 10.1128/AAC.47.6.1895-1901.2003. PMID: 12760864; PMCID: PMC155815.
33.    Huo M, Cui X, Xue J, Chi G, Gao R, Deng X, et al. Anti-inflammatory effects of linalool in RAW 264.7 macrophages and lipopolysaccharide-induced lung injury model. J Surg Res. 2013 Mar;180(1):e47-54. doi: 10.1016/j.jss.2012.10.050. Epub 2012 Dec 4. PMID: 23228323.
34.    Yamada K, Mimaki Y, Sashida Y. Effects of inhaling the vapor of Lavandula burnatii super-derived essential oil and linalool on plasma adrenocorticotropic hormone (ACTH), catecholamine and gonadotropin levels in experimental menopausal female rats. Biol Pharm Bull. 2005 Feb;28(2):378-9. doi: 10.1248/bpb.28.378. PMID: 15684505.
35.    Chang MY, Shen YL. Linalool exhibits cytotoxic effects by activating antitumor immunity. Molecules. 2014 May 22;19(5):6694-706. doi: 10.3390/molecules19056694. PMID: 24858101; PMCID: PMC6271996.
36.    Högnadóttir A, Rouseff RL. Identification of aroma active compounds in orange essence oil using gas chromatography-olfactometry and gas chromatography-mass spectrometry. J Chromatogr A. 2003 May 23;998(1-2):201-11. doi: 10.1016/s0021-9673(03)00524-7. PMID: 12862384.
37.    Minh Tu NT, Thanh LX, Une A, Ukeda H, Sawamura MH. Volatile constituents of Vietnamese pummelo, orange, tangerine, and lime peel oils. Flavor Fragr J. 2002 May;17(3):169-174.
38.    Solhi H, Delavar M, Cheshm Jahanbin A, Abdolahi M. Comparison of methanol concentration in handmade herbal essences produced in Arak city with industrial produced herbal essences with different commercial brands. J Arak Uni Med Sci. 2009; 12 (3) :85-91.
39.    Delirrad M, Ghasempour Z, Hassanzadazar H, Roshani Y, Danesh Mohammadi D, Forouzan S, et al. Determination of methanol content in herbal distillates produced in Urmia using spectrophotometry. Iran J Toxicol. 2012 Apr 10;6(16):594-599.  
40.    Jacobsen D, McMartin KE. Methanol and ethylene glycol poisonings. Mechanism of toxicity, clinical course, diagnosis and treatment. Med Toxicol. 1986 Sep-Oct;1(5):309-34. doi: 10.1007/BF03259846. PMID: 3537623.
41.    Hartigan JA. Statistical theory in clustering. J classif. 1985 Dec;2(1):63-76.
Trends in Pharmaceutical Sciences
Volume 10, Issue 2
June 2024
Pages 141-152

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