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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

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

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