Direct SPME/GC-MS analyzes of small citrus fruits cultivated in Turkey

Year 2020, Volume: 3 Issue: 3, 140 - 152, 31.12.2020

Hale Gamze Ağalar , Burak Temiz , Betül Demirci , Kemal Başer

Abstract

A headspace-solid phase microextraction (HS-SPME) procedure for isolation and investigation of volatile compounds in hybrid “limequat” and parents “Mexican lime and kumquat” fruits using Gas Chromatography-Mass Spectrometry (GC-MS) for the separation and identification of the volatiles was employed in the present study. Each of mature, fresh and whole fruits was freeze-dried, and each sample was powdered. In all samples, limonene (29.9-46.6%) was the most abundant monoterpene hydrocarbon among the identified monoterpenes. The common characteristic compounds are critically discussed.

Keywords

Kumquat, Limequat, Mexican lime, HS-SPME, GC-MS, Volatile compounds, Limonene

References

• Barboni T, Luro F, Chiaramonti N, Desjobert J-M, Muselli A, Costa J (2009). Volatile composition of hybrids Citrus juices by headspace solid phase micro extraction/gas chromatography/mass spectrometry. Food Chem 116: 382-390.
• Bassene J-B, Berti L, Constantino G, Carcouet E, Kamiri M, Tomi F, Dambier D, Ollitrault P, Froelicher Y (2009). Inheritance of characters involved in fruit quality in a Citrus interspecific allotetraploid somatic hybrid, J Agric. Food Chem 57: 5065-5070.
• Bona CM, Carvalho DC, Stelly DM, Miller JC, Louzada ES (2011). Symmetric and symmetric somatic hybridization in Citrus: review. Citrus Res Technol Cordeiropolis 32(3): 139-153.
• Baser KHC, Demirci (2011). Essential Oils, Kirk-Othmer Encyclopedia of Chemical Technology, 4th Ed, Wiley.
• Borges RS, Pio RM (2003). Comparative study of the mandarin hybrid fruit characteristics: Nova, Murcott and Ortanique in Capao Bonita – SP, Brazil. Rev Bras Frutic 25(3): 448-452.
• Butelli E, Licciardello C, Ramadugu C, Durand-Hulak M, Celant A, Recupero GR, Froelicher Y, Martin C (2019). Noemi controls production of flavonoid pigments and fruit acidity and illustrates the Domestication routes of modern citrus varieties. Curr Biol 29: 158-164.
• Bülow N, König WA (2000). The role of germacrene D as a precursor in sesquiterpene biosynthesis: investigations of acid catalyzed, photochemically and thermally induced rearrangements. Phytochem 55: 141-168.
• Centonze V, Lippolis V, Cervellieri S, Damascelli A, Casiello G, Pascale M, Logrieco AF, Longobardi F (2019). Discrimination of geographical origin of oranges (Citrus sinensis L. Osbeck) by mass spectrometry-based electronic nose and characterization of volatile compounds. Food Chem 277: 25-30.
• Costa R, Albergamo A, Arrigo S, Gentile F, Dugo G (2019). Solid-phase microextraction-gas chromatography and ultra-high performance liquid chromatography applied to the characterization of lemon wax, a waste product from citrus industry. J Chromatogr A 1603: 262-268.
• European Pharmacopoeia 9.0 (2016). Volume I, European Directorate for the Quality of Medicines & Health Care of the Council of Europe (EDQM), p. 814 Strasbourg Cedex, France.
• Gonzales-Mas MC, Rambla JL, Lopez-Gresa MP, Blazquez MA, Granell A (2019). Volatile compounds in Citrus essential oils: a compherensive review. Front Plant Sci 10.
• Goulet BE, Roda F, Hopkins R (2017). Hybridization in Plants: old ideas, new techniques. Plant Physiol 173: 65-78.
• Guney M, Oz AT, Kafkas E (2015). Comparison of lipids, fatty acids and volatile compounds of various kumquat species using HS/GC/MS/FID techniques. J Sci Food Agric 95: 1268-1273.
• Jerkovic I, Prdun S, Marijanovic Z, Zekic M, Bubalo D, Svecnjak L, Tuberoso CIG (2016). Traceability of satsuma mandarin (Citrus unshiu Marc.) honey through nectar/honey-sac7honey pathways of the headspace, volatiles, and semi-volatiles: chemical markers. Molecules 21(10): 1302.
• Kamiya S, Esaki S, Konishi F (1979). Flavonoids in Citrus hybrids, Agric Biol Chem 43(7): 1529-1536.
• Kringel DH, Antunes MD, Klein B, Crizel RL, Wagner R, Oliveira RP, Dias ARG, Zavareze ER (2017). Production, chracterization, and stability of orange or eucalyptus essential oil/-cyclodextrin inclusion complex. J Food Sci 82(11): 2598-2605.
• Kusch P (2017). The application of headspace-solid-phase microextraction (HS-SPME) coupled with Gas chromatography/Mass spectrometry (GC/MS) for the characterization of polymers. In: Gas Chromatography: Analysis, Methods and Practices (Ed: V. Warren), Chp 3, pp. 69-103 Nova Science Publishers, NY, USA.
• Ledesma-Escobar CA, Priego-Capote F, Robles-Olvera VJ, Garcia-TorresR, Corcuera JIR, Castro MDL (2019). GC-MS study of changes in polar/mid polar and volatile compounds in persian lime (Citrus latifolia) during fruit growth. Sci Food Agric 99(3): 1020-1028.
• Lim TK (2012). Citrus x floridana. In: Edible Medicinal and Non-Medicinal Plants: Volume 4, Fruits. pp 843-845 Springer, Dordrecht.
• Liu C, Jiang D, Cheng Y, Deng X, Chen F, Fang L, Ma Z, Xu J (2013). Chemotaxonomic study of Citrus, Poncirus and Fortunella Genotypes based on peel oil volatile compounds- deciphering the genetic origin of Mangshanyegan (Citrus nobilis Lauriro). Plos One 8(3): e58411.
• Lota M-L, Serra DR, Tomi F, Jacquemond C, Casanova J (2002). Volatile components of peel and leaf oils of lemon and lime species. J Agric Food Chem 50: 796-805.
• Luro F, Venturini N, Costantino G, Paolini J, Ollitrault P, Costa J (2012). Genetic and chemical diversity of citron (Citrus medica L.) based on nuclear and cytoplasmic markers and leaf essential oil composition. Phytochem 77: 186-196.
• Mahato N, Sharma K, Koteswararao R, Sinha M, Baral E, Cho MH (2019). Citrus essential oils: extraction, authentication and application in food preservation. Crit Rev Food Sci Nutr 59(4): 611-625.
• Nouri A, Shafaghatlonbar A (2016). Chemical constituents and antioxidant activity of essential oil and organic extract from the peel and kernel parts of Citrus japonica Thunb. (kumquat) from Iran. Nat Prod Res 30(9): 1093-1097.
• Palazzolo E, Laudicina VA, Germana MA (2013). Current and potential use of Citrus essential oils. Curr Org Chem 17: 3042-3049.
• Perestrelo R, Nogueira JMF, Camara JS (2009). Potentialities of two solventless extraction approaches-Stir bar sorptive extraction and headspace solid-phase microextraction for determination of higher alcohol acetates, isoamyl esters and ethyl esters in wines. Talanta 80: 622-630.
• Pini GF, deBrito ES, Garcia NHP, Valente ALP, Augusto F (2004). A headspace solid phase microextraction (HS-SPME) method for the chromatographic determination of alkylpyrazines in cocoa samples. J Braz Chem Soc 15(2): 267-271.
• Raza A, Begum N, Song H, Li K, Li P (2019). Optimization of headspace solid-phase microextraction (HS-SPME) parameters for the analysis of pyrazines in yeast extract via gas chromatography mass spectrometry (GC-MS). J Food Sci 84(8): 2031-2041.
• Schirra M, Palma A, D’Aquino S, Angioni A, Minello EV, Melis M, Cabras P (2008). Influence of postharvest hot water treatment on nutritional and functional properties of kumquat (Fortunella japonica Lour. Swingle Cv. Ovale) fruit. J Agric Food Chem 56: 455-460.
• Schmidt CO, Bouwmeester HJ, Franke S, König WA (1999). Mechanisms of the biosynthesis of sesquiterpene enantiomers (+)- and (-)-Germacrene D in Solidago canadensis. Chirality 11: 353-362.
• Shaw PE, Goodner KL, Moshonas MG, Hearn CJ (2001). Comparison of grapefruit hybrid with parent fruit based on composition of volatile components. Sci Hortic 91: 71-80.
• Silva CM, Bolzan AA, Mallmann CA, Pozzatti P, Alves HS, Heinzmann BM (2010). Sesquiterpenoids of Senecio bonariensis Hook. & Arn., Asteraceae. Rev Bras Farmacogn 20(1): 87-92.
• Simeone GR, Matteo A, Rao MA, Vaio C (2020). Variations of peel essential oils during fruit ripening in four lemon (Citrus lemon (L.) Burm. F.) cultivars. J Sci Food Agric 100(1): 193-200.
• Song N-E, Lee J-Y, Lee Y-Y, Park J-D, Jang HW (2019). Comparison of headspace-SPME and SPME-arrow-GC-MS methods for the determination of volatile compounds in Korean salt-fermented fish sauce. Appl Biol Chem 62.
• Spadaro F, Costa R, Circosta C, Occhiuto F (2012). Volatile composition and biological activity of key lime Citrus aurantifolia essential oil. Nat Prod Commun 7(11): 1523-1526.
• Spietelun A, Kloskowski A, Chrzanowski W, Namiesnik J (2013). Understanding Solid-Phase Microextraction: Key factors influencing the extraction process and trends in improving the technique. Chem Rev 113: 1667-1685.
• Stashenko EE, Mora AL, Cervantes ME, Martinez JR (2006). HS-SPME determination of volatile carbonyl and carboxylic compounds in different matrices. J Chromatogr Sci 44(6): 347-353.
• Sutour S, Luro F, Bradesi P, Casanova J, Tomi F (2016). Chemical composition of the fruit oils of five Fortunella species grown in the same pedoclimatic conditions in Corsica (France). Nat Prod Commun 11(2): 259-262.
• Vieira AJ, Beserra FP, Souza MC, Totti BM, Rozza AL (2018). Limonene: aroma of innovation in health and disease. Chem Biol Interact 283: 97-106.
• Xu Y, Zhou X, Zhang D, Lan Z, Zhang Y, Wan J (2016). Headspace solid-phase microextraction (HS-SPME) coupled with gas chromatography-mass spectrometric (GC-MS) analysis of volatile profiles during the stir-frying process of malt. Anal Methods 8: 1699-1704.
• Yang E-J, Kim S, Moon J-Y, Oh T-H, Baik J, Lee N, Hyun C-G (2010). Inhibitory effects of Fortunella japonica var. margarita and Citrus sunki essential oils on nitric oxide production and skin pathogens. Acta Microbiol Immunol Hung 57(1): 15-27.
• Yeo SK, Ali AY, Hayward OA, Turnham D, Jackson T, Bowen ID, Clarkson R (2015). -Bisabolene, a sesquiterpene from the essential oil extract of Opoponax (Commiphora guidottii), exhibits cytotoxic in breast cancer cell lines. Phytother Res 30: 418-425.
• Zhang M, Li L, Wu Z, Wang Y, Zang Y, Liu G (2017). Volatile composition in two pummelo cultivars (Citrus grandis L. Osbeck) from different cultivation regions in China. Molecules 22: 716.