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Comparison of volatile flavor compounds of yuzu, kumquat, lemon and lime

유자, 금귤, 레몬 및 라임의 휘발성 향기성분의 비교

  • Hong, Young Shin (Department of Food and Nutrition, Chosun University) ;
  • Lee, Ym Shik (Risk Informaton Division, Ministry of Food and Drug Safety) ;
  • Kim, Kyong Su (Department of Food and Nutrition, Chosun University)
  • 홍영신 (조선대학교 식품영양학과) ;
  • 이임식 (식품의약품안전처 위해정보과) ;
  • 김경수 (조선대학교 식품영양학과)
  • Received : 2017.02.28
  • Accepted : 2017.06.07
  • Published : 2017.06.30

Abstract

This study was conducted to confirm the usefulness of essential oil components in yuzu and kumquat cultivated in Korea for comparison with those in lemon and lime. The volatile flavor compounds in citrus fruits (yuzu, kumquat, lemon and lime) were extracted for 3 h with 100 mL redistilled n-pentane/diethylether (1:1, v/v) mixture, using a simultaneous steam distillation and extraction apparatus (SDE). The volatile flavor compositions of the samples were analyzed by gas chromatography-mass spectrometry (GC-MS). The aroma compounds analyzed were 104 (3,713.02 mg/kg) in yuzu, 87 (621.71 mg/kg) in kumquat 103 (3,024.69 mg/kg) in lemon and 106 (2,209.16 mg/kg) in lime. Limonene was a major volatile flavor compound in four citrus fruits. The peak area of limonene was 35.03% in yuzu, 63.82% in kumquat, 40.35% in lemon, and 25.06% in lime. In addition to limonene, the major volatile flavor compounds were ${\gamma}$-terpinene, linalool, ${\beta}$-myrcene, (E)-${\beta}$-farnesene, ${\alpha}$-pinene and ${\beta}$-pinene in yuzu, and ${\beta}$-myrcene, ${\alpha}$-pinene, (Z)-limonene oxide, (E)-limonene oxide, geranyl acetate and limonen-10-yl acetate in kumquat. Furthermore, ${\gamma}$-terpinene, ${\beta}$-pinene, ${\beta}$-myrcene, geranyl acetate, neryl acetate and (Z)-${\beta}$-bisabolene in lemon and ${\gamma}$-terpinene, ${\beta}$-pinene, (Z)-${\beta}$-bisabolene, neral, geranial and neryl acetate in lime were also detected. As a result, it was confirmed that the composition of volatile flavor compounds in four citrus fruits was different. Also, yuzu and kumquat are judged to be worthy of use alternatives for lemon and lime widely used in the fragrance industry.

본 연구는 한국에서 재배된 유자와 금귤을 수입되는 레몬 및 라임과 비교하였을 때 정유성분의 유용적 가치를 확인하고자 하였다. 유자, 금귤, 레몬 및 라임의 휘발성 향기성분 분석을 위하여 재증류한 n-pentane/diethylether(1:1, v/v) 혼합용매 100 mL를 사용하여 SDE 방법으로 3시간동안 휘발성 화합물을 추출한 후 GC/MS로 확인하였다. 유자, 금귤, 레몬 및 라임에서는 각각 104종(3,713.02 mg/kg), 87종(621.71 mg/kg), 103종(3,024.69 mg/kg) 및 106종(2,209.16 mg/kg)의 향기성분이 동정되었다. 4종의 Citrus속 과일의 주요 휘발성 향기성분은 limonene으로 확인되었으며, peak area는 각각 유자 35.03%, 금귤 63.82%, 레몬 40.35% 및 라임 25.06%로 나타났다. Limonene 이외에 유자의 주요 휘발성 향기성분은 ${\gamma}$-terpinene, linalool, ${\beta}$-myrcene, (E)-${\beta}$-farnesene, ${\alpha}$-pinene 및 ${\beta}$-pinene 등이며, 금귤에서는 ${\beta}$-myrcene, ${\alpha}$-pinene, (Z)-limonene oxide, (E)-limonene oxide, geranyl acetate 및 limonen-10-yl acetate 등 순으로 동정되었다. 레몬의 주요 향기성분은 ${\gamma}$-terpinene, ${\beta}$-pinene, ${\beta}$-myrcene, geranyl acetate, neryl acetate 및 (Z)-${\beta}$-bisabolene 등 순이며, 라임은 ${\gamma}$-terpinene, ${\beta}$-pinene, (Z)-${\beta}$-bisabolene, neral, geranial 및 neryl acetate 등 순으로 나타났다. 본 연구 결과 4종류 과일의 특징적인 향기성분이 동정되었으며, 휘발성 향기성분 조성비의 차이를 확인할 수 있었다. 또한 국내산 유자 및 금귤은 향료산업에서 널리 사용되는 레몬과 라임의 대체제로 충분한 활용가치가 있다고 사료된다.

Keywords

Acknowledgement

Supported by : 한국연구재단

References

  1. Okwu DE, Emenike IN (2006) Evaluation of the phytonutrients and vitamins content of citrus fruits. Int J Mol Med Adv Sci, 2, 1-6
  2. Rapisarda P, Tomaino A, Lo Cascio RL, Bonina F, De Pasquale A, Saija A (1999) Antioxidant effectiveness as influenced by phenolic content of fresh orange juice. J Agric Food Chem, 47, 4718-4723 https://doi.org/10.1021/jf990111l
  3. Cristani M, D'Arrigo M, Mandalari G, Castelli F, Sarpietro MG, Micieli D, Venuti V, Bisignano G, Saija A, Trombetta D (2007) Interaction of four monoterpenes contained in essential oils with model membranes: implications for their antibacterial activity. J Agric Food Chem, 55, 6300-6308 https://doi.org/10.1021/jf070094x
  4. Viuda-Martos M, Ruiz-Navajas Y, Fernandez-Lopez J, Perez-Alvarez JA (2007) Antifungal activities of thyme, clove and oregano essential oils. J Food Saf, 27, 91-101
  5. KREI, Annual food supply (2014) http://www.krei.re.kr/web/www/23 (accessed on February 2017)
  6. Lan-Phi NT, Shimamura T, Ukeda H, Sawamura M (2009) Chemical and aroma profiles of yuzu (Citrus junos) peel oils of different cultivars. Food Chem, 115, 1042-1047 https://doi.org/10.1016/j.foodchem.2008.12.024
  7. Dowell P, Bailey A (1980) The book of ingredients. Penquin Books Ltd, london, UK, P 103
  8. Lee SJ, Shin JH, Kang MJ, Jeong CH, Ju JC, Sung NJ (2010) Physicochemical properties, free sugar and volatile compounds of Korean citrons cultivated in different areas. J Korean Soc Food Sci Nutr, 39, 92-98 https://doi.org/10.3746/jkfn.2010.39.1.092
  9. Kirbaslar SI, Boz I, Kirbaslar FG (2006) Composition of Turkish lemon and grapefruit peel oils. J Essent Oil Res, 18, 525-543 https://doi.org/10.1080/10412905.2006.9699161
  10. AL-Jabri NN, Hossain MA (2014) Comparative chemical composition and antimicrobial activity study of essential oils from two imported lemon fruits samples against pathogenic bacteria. Beni-Suef Univ J Basic Appl Sci, 3, 247-253 https://doi.org/10.1016/j.bjbas.2014.10.011
  11. Councid of Scientific and Industry Research (1995) The Wealth of India: A dictionary of indian raw materials and industrial products. CSIR, New Delhi, India, p 13, 351
  12. Woo DH (2000) Stabilization to sunlight of natural coloring matter by soluble methyl-hesperidin. Korean J Food Sci Technol, 32, 50-55
  13. Chae SC, Kho EG, Choi SH, Ryu GC (2008) Protective effect naringin on carbon tetrachloride induced hepatic injury in mice. J Environ Toxicol, 23, 325-335
  14. Correa M, Tapanes R, Pino J (1985) Analysis of cuban grapefruit peel oil. Acta Aliment, 14, 303-308
  15. Pino JA, Acevedo A, Rabelo J, Gonzalez C, Escandon J (1999) Chemical composition of distilled grapefruit oil. J Essent Oil Res, 11, 75-76 https://doi.org/10.1080/10412905.1999.9701076
  16. Seo HY, No KM, Shim SL, Ryu KY, Han KJ, Gyawali R, Kim KS (2006) Analysis of enantiomeric composition of chiral flavor components from dried ginger (Zingiber officinale roscoe). J Korean Soc Food Sci Nutr, 35, 874-880 https://doi.org/10.3746/jkfn.2006.35.7.874
  17. Schreier P (1986) Biogeneration of Plant Aromas. In: Developments in Food Flavours, Birch GG, Lindley MG (Editor), Elsevier Applied Science, New York, NY, USA p 89-106
  18. Furuta T, Yoshii H, Kobayashi T, Nishitarumi T, Yasunishi A (1994) Powdery encapsulation of d-limonene by kneading time with mixed powders of ${\beta}$-cyclodextrin and maltodextrin at low water content. Biosci Biotechnol Biochem, 58, 847-850 https://doi.org/10.1271/bbb.58.847
  19. Sadtler Research Laboratories (1986) The sadtler standard gas chromatography retention index library. Sadtler Research Laboratories, Philadelphia, PA, USA
  20. Kang SK, Jang MJ, Kim YD (2006) A study on the flavor constituents of the citron (Citrus junos), Korean J Food Preserv, 13, 204-210
  21. Elegbede JA, Elson CE, Tanner MA, Qureishi A, Gould MN (1986) Regression of rat primary mammary tumors following dietary d-Limonene. J Natl Cancer Inst, 76, 323-325
  22. Lee KH, Yoon WH (2007) Effects of protein-bound polysacharide isolated from Acanthopananx senticosus in reducing the toxic effects of cisplatin. Kor J Pharmacogn, 38, 152-156
  23. Park YJ, Chang HC (2000) Bioconversion of citron essential oil by co-culture of E. coli EC3, EC4, and EC6. Korean J Human Ecol, 4, 79-92
  24. Choi HS, Song HS, Ukeda H, Sawamura M (2000) Radical-scavenging activities of citrus essential oils and their components: Detection using 1,1-diphenyl-2-picryl hydrazyl. J Agric Food Chem, 48, 4156-4161 https://doi.org/10.1021/jf000227d
  25. Behr A, Johnen L (2009) Myrcene as a natural base chemical in sustainable chemistry: A critical review. ChemSusChem, 2, 1072-1095 https://doi.org/10.1002/cssc.200900186
  26. Furia TE, Bellanca N (1975) Fenaroli's Handbook of Flavor Ingredients. 2nd ed, CRC Press, Cleveland, OH, USA, p 283-285
  27. Kwag JJ, Kim DY, Lee KH (1992) Volatile components of kumquat (Fortunella margarita). Korean J Food Sci Technol, 24, 423-427
  28. Arctander S (1960) Perfume and flavor materials of natural origin. Elizabeth, NJ, USA, p 736
  29. Boelens MH, Jimenez R (1989) The chemical composition of some mediterranean citrus oils. J Essent Oil Res, 1, 151-159 https://doi.org/10.1080/10412905.1989.9697776
  30. Espina L, Somolinos M, Loran S, Conchello P, Garcia D, Pagan R (2011) Chemical comp osition of commercial citrus fruit essential oils and evaluation of their antimicrobial activity acting alone or in combined processes. Food Cont, 22, 896-902 https://doi.org/10.1016/j.foodcont.2010.11.021
  31. Lee, HY, Leem MH, Kim CS (2003) An analysis on essential oil of tea tree and lemon by GC. J Korea Soc Beauty Art, 4, 287-301
  32. Schieberle P, Grosch W (1988) Identification of potent flavor compounds formed in an aqueous lemon oil/citric acid emulsion. J Agric Food Chem, 36, 797-800 https://doi.org/10.1021/jf00082a031
  33. Nishida R, Acree TE (1984) Isolation and characterization of methyl epijasmonate from lemon (Citrus limon Burm). J Agric Food Chem, 32, 1001-1003 https://doi.org/10.1021/jf00125a012
  34. Lee SE (2011) Effect of volatile fragrance components of Citrus aurantiifolia and Eugenia caryophylla on electroencephalogram. Ph D Thesis, Kangwon National University, Korea, p 19-21
  35. Palaniappan K, Holley RA (2010) Use of natural antimicrobials to increase antibiotic susceptibility of drug resistant bacteria. Int J Food Microbiol, 140, 164-168 https://doi.org/10.1016/j.ijfoodmicro.2010.04.001
  36. Yasni S, Imaizumi K, Sin K, Sugano M, Nonaka G, Sidik (1994) Identification of an active principle in essential oils and hexane-soluble fractions of Curcuma xanthorrhiza Roxb. showing triglyceride-lowering action in rats. Food Chem Toxicol, 32, 273-278 https://doi.org/10.1016/0278-6915(94)90200-3

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