Journal of the Korean Applied Science and Technology (한국응용과학기술학회지)

The Korean Society of Applied Science and Technology (한국응용과학기술학회)
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Synthesis and Structural Characterization of β-Carboline Compounds

β-카볼린 화합물의 합성 및 구조분석

  • Byeon, Hong-Ju (Department of Biotechnology, Korea National University of Transportation) ;
  • Han, Min-Hui (Department of Biotechnology, Korea National University of Transportation) ;
  • Moon, Gi-Seong (Department of Biotechnology, Korea National University of Transportation) ;
  • Jung, Kyung-Hwan (Department of Biotechnology, Korea National University of Transportation) ;
  • Lee, Hyang-Yeol (Department of Biotechnology, Korea National University of Transportation)
  • 변홍주 (한국교통대학교 생명공학과) ;
  • 한민희 (한국교통대학교 생명공학과) ;
  • 문기성 (한국교통대학교 생명공학과) ;
  • 정경환 (한국교통대학교 생명공학과) ;
  • 이향렬 (한국교통대학교 생명공학과)
  • Received : 2019.06.06
  • Accepted : 2019.06.28
  • Published : 2019.06.30
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Abstract

The Pictet-Spengler reactions have widely known for the organic synthesis or biosynthesis of biologically active compounds, tetrahydro-${\beta}$-carbolines. We have developed the simple and efficient synthetic method for the synthesis of ${\beta}$-carbolines in water. Their chemical structures were characterized by nmr and UPLC/MS/QTOF. Calculated masses of compound 1 ($C_{17}H_{17}N_2$ 249.1392), 2 ($C_{17}H_{23}N_2$ 255.1861), 3 ($C_{19}H_{21}N_2O_3$ 325.1552) and 4 ($C_{19}H_{19}N_2O$ 279.1497) were almost identical with the detected masses of compound 1 (249.1315), 2 (255.1789), 3 (325.1460) and 4 (279.1364) respectively. Those synthesized four compounds showed strong antibiotic activity against the common E. coli.

자연에서도 생합성이 되는 테트라하이드로-${\beta}$-카볼린 화합물은 Pictet-Spengler반응을 통해서 화학적으로도 합성된다. 본 연구에서는 ${\beta}$-카볼린 화합물을 쉽고 효과적으로 합성할 수 있는 친환경 합성법을 개발하여 유기용매가 아닌 물을 사용하여 합성하였다. 이 화합물은 투명한 결정형의 생성물로 얻어지므로 복잡한 분리과정이 필요하지 않다. 합성된 화합물은 NMR 및 UPLC/MS를 이용하여 구조를 확인하였다. 화합물 1의 이론적 분자량($C_{17}H_{17}N_2$ 249.1392), 화합물 2 ($C_{17}H_{23}N_2$ 255.1861), 화합물 3($C_{19}H_{21}N_2O_3$ 325.1552), 화합물 4($C_{19}H_{19}N_2O$ 279.1497)과 측정된 화합물들의 질량과 비교하였다. 그 결과 측정된 화합물 1의 분자량 ($[M+H]^+m/z$ detected 249.1315), 2 (detected 255.1789), 3 (detected 325.1460) 그리고 4 (detected 279.1364)와 거의 일치함으로써 생성된 화합물이 1~4의 구조를 가지고 있음을 확인하였다. 합성된 화합물들을 그람 음성균인 E. coli $DH5{\alpha}$를 대상으로 항균효과를 조사한 결과 강한 저해효과를 확인할 수 있었다.

Keywords

HGOHBI_2019_v36n2_676_f0001.png 이미지

Fig. 1. β-Carboline compounds 1~4.

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Fig. 2. NMR spectra of compound 1. A: 1H-NMR, B: 13C-NMR. *NMR solvent: MeOD

HGOHBI_2019_v36n2_676_f0003.png 이미지

Fig. 3. NMR spectra of compound 2. A: 1H-NMR, B: 13C-NMR. *NMR solvent: MeOD

HGOHBI_2019_v36n2_676_f0004.png 이미지

Fig. 4. NMR spectra of compound 3. A: 1H-NMR, B: 13C-NMR. *NMR solvent: MeOD

HGOHBI_2019_v36n2_676_f0005.png 이미지

Fig. 5. NMR spectra of compound 4. A: 1H-NMR, B: 13C-NMR. *NMR solvent: MeOD

HGOHBI_2019_v36n2_676_f0006.png 이미지

Fig. 6. Anti-microbial effect of compounds 1~4 in E. coli DH5α. A: 3, B: 4, C: 1, D: 2.

HGOHBI_2019_v36n2_676_f0007.png 이미지

Fig. 7. UPLC/MS/QTOF spectra of β-carboline compounds. A: 1, B: 2, C: 3, D: 4.

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