Korean Journal of Food Science and Technology (한국식품과학회지)

Korean Society of Food Science and Technology (한국식품과학회)
권호 표지
DOI QR코드

DOI QR Code

Isolation and Identification of Low Molecular Volatile Compounds from Ethyl Acetate Layer of Korean Black Raspberry (Rubus coreanus Miq.) Wine

복분자(Rubus coreanus Miquel) 와인의 ethyl acetate 획분으로부터 저분자 휘발성 화합물들의 분리 및 구조해석

  • Cho, Jeong-Yong (Department of Food Science & Technology, and Functional Food Research Center, Chonnam National University) ;
  • Kim, Seong-Ja (Department of Food Science & Technology, and Functional Food Research Center, Chonnam National University) ;
  • Lee, Hyoung-Jae (Department of Food Science & Technology, and Functional Food Research Center, Chonnam National University) ;
  • Kim, Jin-Young (Department of Food Science & Technology, and Functional Food Research Center, Chonnam National University) ;
  • Lym, Ik-Jae (Yeonsudang Co., Ltd.) ;
  • Kang, Seong-Koo (Research Instrument Center, Sunchon National University) ;
  • Park, Keun-Hyung (Department of Food Science & Technology, and Functional Food Research Center, Chonnam National University) ;
  • Moon, Jae-Hak (Department of Food Science & Technology, and Functional Food Research Center, Chonnam National University)
  • 조정용 (전남대학교 식품공학과 및 기능성식품연구센터) ;
  • 김성자 (전남대학교 식품공학과 및 기능성식품연구센터) ;
  • 이형재 (전남대학교 식품공학과 및 기능성식품연구센터) ;
  • 김진영 (전남대학교 식품공학과 및 기능성식품연구센터) ;
  • 임익재 ((주)연수당) ;
  • 강성구 (순천대학교 공동실험실습관) ;
  • 박근형 (전남대학교 식품공학과 및 기능성식품연구센터) ;
  • 문제학 (전남대학교 식품공학과 및 기능성식품연구센터)
  • Received : 2011.05.10
  • Accepted : 2011.07.21
  • Published : 2011.10.31
Download PDF
⟨ Previous Next ⟩

Abstract

In the course of our investigation for chemical constituents in the ethyl acetate layer of Korean black raspberry wine, five compounds were isolated and purified by silica gel column chromatography and high-performance liquid chromatography. The isolated compounds were identified as ethyl succinate (1), vanillic acid (2), ethyl 3,4-dihydroxybenzoate (3), furan-2-ol (4), and 4-(4-hydroxyphenyl)butan-2(S)-ol (5) based on the spectroscopic data of electrospray ionization tandem mass spectrometry and nuclear magnetic resonance. The presence of 2 in Korean black raspberry has previously reported. However, 1 and 3-5 in Korean black raspberry and its wine were isolated for the first time.

복분자 와인은 복분자 열매를 발효 숙성시켜 제조한 것으로, 소비자에게 널리 음용되고 있으나 그 원재료인 복분자 열매에 대한 연구에 비해 복분자 와인에 존재하는 성분들에 대한 체계적인 연구는 거의 전무한 실정이다. 최근 우리는 복분자주에 함유되어 있는 화합물들의 분자 수준에서의 연구를 통하여 4-hydroxybenzoic acid, 3,4-dihydroxybenzoic acid, 4-(2-hydroxyethyl)-phenol, pyrocatechol, ethyl gallate 등의 5종의 저분자 페놀성 화합물을 단리 구조해석하여 보고한 바 있다. 그 연속된 연구로써 본 논문에서는 복분자주에 존재하는 성분들에 대한 추가적인 분리 및 구조해석을 행하였다. 제조된 복분자 와인(11 L, 복분자 열매 15.7 kg)을 용매분획하여 얻어진 EtOAc층(56.2 g)의 일부(20 g)를 silica gel column chromatography와 ODS-HPLC로 정제하여 5종의 화합물을 단리하였다. 이 화합물들을 대상으로 MS 및 NMR 등의 기기분석을 행한 결과, ethyl succinate(1, 13.1 mg), vanillic acid(2, 2.6 mg), ethyl 3,4-dihydroxybenzoate(3, 13. 1 mg), furan-2-ol(4, 1.3 mg), 그리고 4-(4-hydroxyphenyl) butan-2(S)-ol(5, 1.1 mg)로 동정하였다. 이 화합물들 대부분은 발효식품에서 향기성분으로 동정된 바 있으며, 화합물 2는 복분자 열매에 존재함이 이미 보고되어 있으나, 화합물 1과 3-5는 복분자 열매 및 복분자와인으로부터 처음으로 동정되었다.

Keywords

References

  1. Yuk CS. Coloured Medicinal Plants of Korea. Academy Publishing Co., Seoul, Korea. p. 275 (1990)
  2. Bea GH. The Medicinal Plants of Korea, Kyohaksa, Seoul, Korea. p. 231 (2001)
  3. Heo J. Donguibogam 1-5, Yeogang Publishing Co., Seoul, Korea. pp. 62, 296, 334, 617, 984, 1085, 2679 (1994)
  4. Lee MK, Lee HS, Choi GP, Oh DH, Kim JD, Yu CY, Lee HY. Screening of biological activities of the extracts from Rubus coreanum Miquel. Korea J. Med. Crop Sci. 1: 5-12 (2003)
  5. Cha HS, Park MS, Park KM. Physiological activities of Rubus coreanum Miquel. Korean J. Food Sci. Technol. 33: 409-415 (2001)
  6. Yoon I, Cho JY, Kook JH, Wee JH, Jang MY, Ahn TH, Park KH. Identification and activity of antioxidative compounds from Rubus coreanus fruit. Korean J. Food Sci. Technol. 34: 898-904 (2002)
  7. Yoon I, Wee JH, Ahn TH, Park KH. Isolation and identification of quercetin with antioxidative activity from the fruits of Rubus coreanus Miquel. Korean J. Food Sci. Technol. 35: 499-502 (2003)
  8. Chung TH, Kim JC, Lee CY, Moon MK, Chae SC, Lee IS, Kim SH, Hahn KS, Lee IP. Potential antiviral effects of Terminali schebula, Sanguisorba officinalis, Rubus coreanus and Rheum palmaum against duck hepatitis B virus (DHBV). Phytother. Res. 11: 179-182 (1997) https://doi.org/10.1002/(SICI)1099-1573(199705)11:3<179::AID-PTR50>3.0.CO;2-F
  9. Yang SW, Ho JN, LEE YH Shin DH, Hong BS, Cho HY. Isolation and characterization of Helicobacter pylori urease inhibitor from Rubus coreanus Miquel. Korean J. Food Sci. Nutr. 33: 769- 777 (2004) https://doi.org/10.3746/jkfn.2004.33.5.769
  10. Ohtani K, Miyajima C, Takahasi T, Kasai R, Tanaka O, Hahn DR, Naruhashi N. A dimeric triterpene glycoside from Rubus coreanus. Phytochemistry 29: 3275-3280 (1990) https://doi.org/10.1016/0031-9422(90)80199-Q
  11. Kim YH, Kang SS. Triterpenoids from Rubi fructus (Bogbunja). Arch. Pharm. Res. 16: 109-113 (1993) https://doi.org/10.1007/BF03036856
  12. Choi JW, Lee KT, Ha JH, Yun SY, Ko CD, Jung HJ, Park HJ. Antinociceptive and anti-inflammatory effects of niga-ichigoside $F_1$ and 23-hydroxytormentic acid obtained from Rubus coreanus. Biol. Pharm. Bull. 26: 1436-1441 (2003) https://doi.org/10.1248/bpb.26.1436
  13. Nam JH, Jung HJ, Choi JW, Lee KT, Park HJ. The anti-gastropathic and anti-rheumatic effect of niga-ichigoside $F_1$ and 23- hydroxytormentic acid isolated from the ripe fruits of Rubus coreanus in a rat model. Biol. Pharm. Bull. 29: 967-970 (2006) https://doi.org/10.1248/bpb.29.967
  14. Pang GC, Kim MS, Lee MW. Hydrolyzable tannnins from the fruits of Rubus coreanum. Korean J. Pharmacogn. 27: 366-370 (1996)
  15. Lee YA, Lee MW. Tannins from Rubus coreanus. Korean J. Pharmacogn. 26: 27-30 (1995)
  16. Lee MW. Phenolic compounds from the leaves of Rubus coreanus. Yakhak Hoeji 39: 200-204 (1995)
  17. Choi HS, Kim MR, Park HS, Kim YS. Alcoholic fermentation of Bokbunja wine. Korean J. Food Sci. Technol. 38: 543-547 (2006)
  18. Bokbunja wine. Korean J. Food Sci. Technol. 38: 543-547 (2006) 18. Park YS, Chang HG. Lactic acid fermentation and biological activities of Rubus coreanus. J. Korean Soc. Agric. Chem. Biotechol. 46: 367-375 (2003)
  19. Kwon KS, Kim YS, Song GS, Hong SP. Quality characteristic of bread with Rubi fructus (Rubus coreanus Miquel) Juice. Korean J. Food Nutr. 17: 272-277 (2004)
  20. Lee YN, Kim YS, Song GS. Quality of dry noodle prepared with wheat flour and immature Rubus coreanus (bokbunja) powder composites. J. Korean Soc. Agric. Chem. Biotechnol. 43: 271-276 (2000)
  21. Kim SJ, Lee HJ, Park KH, Rhee CO, Lim IK, Chung HJ, Moon JH. Isolation and identifiaction of low molecular phenolic antioxidants from ethylacetate layer of Korean black raspberry (Rubus coreanus) wine. Korean J. Food Sci. Technol. 40: 129-134 (2008)
  22. Rojatkar SR, Sawaikar DD, Sinha B, Ravindranathan T, Nagasampagi BA. 4-(p-hydroxyphenyl)-(2S)-butanol from the needles of Taxus baccata. Phytochemistry 39: 259-260 (1995) https://doi.org/10.1016/0031-9422(94)00891-V
  23. Patel S, Shibamoto T. Flavor compounds in wines produced from chardonnay grapes fermented with fruit juices. Food Sci. Technol. Res. 9: 84-86 (2003) https://doi.org/10.3136/fstr.9.84
  24. Garcia A, Carcel C, Dulau L, Samson A, Aguera E, Agosin E, Gunata Z. Influence of a mixed culture with Debaryomyces vanriji and Saccharomyces cerevisiae on the volatiles of a Muscat wine. J. Food Sci. 67: 1138-1444 (2002) https://doi.org/10.1111/j.1365-2621.2002.tb09466.x
  25. Matejicek D, Mikes O, Klejdus B, Sterbova D, Kuban V. Changes in contents of phenolic compounds during maturing of barrique red wines. Food Chem. 90: 791-800 (2005) https://doi.org/10.1016/j.foodchem.2004.05.057
  26. Hard PJ, Michael BJ. Volatile components of Feijoa fruits. Phytochemistry 9: 1355-1357 (1970) https://doi.org/10.1016/S0031-9422(00)85331-5
  27. Balcerek M, Szopa SJ. Optimization of the technology of aroniaspirit production - Part 2: Influence of the fermentation conditions on the aroma compounds. Deut. Lebensm.-Rundsch. 101: 16-19 (2005).
  28. Schinz H, Seidel CF. Ueber das himbeer aroma (on the raspberry aroma). Helv. Chim. Acta 40: 1839-1950 (1957) https://doi.org/10.1002/hlca.19570400635
  29. Fronza G, Fuganti C, Pedrocchi-Fantoni G, Serra S, Zucchi G. Stable isotope characterization of raspberry ketone extracted from Taxus baccata and obtained by oxidation of the accompanying alcohol (betuligenol). J. Agr. Food Chem. 47: 1150-1155 (1999) https://doi.org/10.1021/jf980717u
  30. Reddy PS, Jamil K, Madhusudhan P, Anjani G, Das B. Antibacterial activity of isolates from Piper longum and Taxus baccata. Pharm. Biol. 39: 236-238 (2001) https://doi.org/10.1076/phbi.39.3.236.5926
  31. Morimoto C, Satoh Y, Hara M, Inoue S, Tsujita T, Okuda H. Anti-obese action of raspberry ketone. Life Sci. 77: 194-204 (2005) https://doi.org/10.1016/j.lfs.2004.12.029
  32. Shimoda K, Harada T, Hamada H, Nakajima N, Hamada H. Biotransformation of raspberry ketone and zingerone by cultured cells of Phytolacca americana. Phytochemistry 68: 487-492 (2007) https://doi.org/10.1016/j.phytochem.2006.11.030
  33. Jang MY, Cho JY, Cho JI, Moon JH, Park KH. Isolation and characterization of antioxidative active compounds from quickfermented soybean food. Food Sci. Biotechnol. 15: 214-219 (2006)
  34. Ko SR, Suzuki Y, Suzuki K, Choi KJ, Cho BG. Marked production of ginsenoside Rd,$F_2,\;Rg_3$, and compound K by enzymatic method. Chem. Pharm. Bull. 55: 1522-1527 (2007) https://doi.org/10.1248/cpb.55.1522
  35. Fronza G, Fuganti C, Pedrocchi-Fantoni G, Perozzo V, Servi S, Zucchi G. Stereochemistry of the Baeyer-Villiger-type conversion of 4-(4-hydroxyphenyl) buta-2-one (raspberry ketone) into tyrosol mediated by Beauveri abassiana. J. Org. Chem. 61: 9362-9367 (1996) https://doi.org/10.1021/jo9614553

Cited by

  1. Physiological Activities of Rubus coreanus Miq. Extracts Using Different Extraction Methods vol.28, pp.1, 2012, https://doi.org/10.9724/kfcs.2012.28.1.025
  2. Screening of Biogenic Amine Non-Producing Yeast and Optimization of Culture Conditions Using Statistical Method for Manufacturing Black Raspberry Wine vol.44, pp.4, 2015, https://doi.org/10.3746/jkfn.2015.44.4.592
  3. Change in the content of phenolic compounds and antioxidant activity during manufacturing of black raspberry (Rubus coreanus Miq.) wine vol.22, pp.5, 2013, https://doi.org/10.1007/s10068-013-0207-5
  4. Two novel glycosyl cinnamic and benzoic acids from korean black raspberry (Rubus coreanus) wine vol.23, pp.4, 2014, https://doi.org/10.1007/s10068-014-0148-7