Analytical Characterization of Aza-Indole Alkaloids in the Biosynthesis of Catharanthus Roseus

이향렬 한국응용과학기술학회 2012 한국응용과학기술학회지 Vol.29 No.2

Aza-indoles are important pharmacophores that have similar size and biological properties of indole. Here we have synthesized 4- and 7-azaindole tryptamines and showed that they are successfully incorporated in the biosynthesis of monoterepene indole alkaloids (MIAs) to form novel azaindole alkaloids by enzymatic reactions of strictosidine synthase(STR) and strictosidine glucosidase(SDG) monitored by UPLC/MS. By using HPLC equipped with a HPLC photo diode array(PDA) detector, each of the UV spectra of azaindole alkaloids was obtained and characterized. When hydrophilicity of azaindole alkaloids was compared, 4-azaindole alkaloids were more hydrophilic than 7-azaindole alkaloids.

Soluble arene-thiophene oligomers with aromatic central rings

이향렬 한국공업화학회 2015 한국공업화학회 연구논문 초록집 Vol.2015 No.0

Thiophene oligomers have received considerable attention due to their unique optical and electronic properties. Soluble dimethyl-n-octylsilyl end-capped arene-thiophene oligomers with central unit such as phenyl, biphenyl, fluorene and naphthalene were synthesized by Stille reaction. The optical, electrochemical and thermal properties of these oligomers were measured. The absorption maxima of arene-thiophene oligomers in dilute solutions are close to those obtained for DSi-4T(labs = 403 nm) and exhibit well-resolved fluorescence spectra in solution with emission maxima at 445 nm, 446 nm, 448 nm and 450 nm for DSi-TTPTT, DSi-TTPPTT, DSi-TTFTT, and DSi-TTNTT, respectively.

1P-557 Thermal properties of formaldehyde-free wood adhesives

이향렬 한국공업화학회 2017 한국공업화학회 연구논문 초록집 Vol.2017 No.0

베타-갈락토시데이즈를 이용하여 합성된 Benzyl Alcohol Galactoside의 NMR Spectroscopy 및 Mass spectrometry

이향렬,정경환 한국응용과학기술학회 2019 한국응용과학기술학회지 Vol.36 No.1

대장균 효소 β-gal를 이용하여 합성된 BzO-gal의 분자구조를 NMR ( 1 H-와 13 C-)과 고성능 mass spectrometry를 이용하여 분석하였다. BzO-gal은 1 H NMR에서 14개의 proton으로부터 12개의 피크를 나타내었다. 방향족 고리에서 오는 5개의 proton 피크와 벤질기의 CH 2 에서 오는 2개의 proton 피크는 벤질알코올이 존재함을 나타낸다. 지방족 사슬 영역인 d H 4.32 ~ 3.46 ppm에서 나타나는 7개의 proton 피크로부터 단당류가 도입되었음을 확인할 수 있었다. 13 C NMR 스팩트럼에서 나타난 11개의 carbon 피크도 또한 벤질알코올에 단당이 도입되었음을 나타낸다. BzO-gal의 분자량을 확인하기 위하여 mass spectrometry 로 분석한 결과 m/z가 293.0994인 BzO-gal의 sodium adduct ion ([M+Na] + )을 확인할 수 있었다. 이러한 결과를 바탕으로 세포독성이 감소된 첨가물 개발을 기대하고 있으며, 추가적인 후속연구를 진행할 예정이다. To characterize the molecular structure of BzO-gal synthesized using Escherichia coli β-gal, NMR ( 1 H- and 13 C-) spectroscopy and mass spectrometry of BzO-gal were conducted. 1 H NMR spectrum of BzO-gal showed multiple peaks corresponding to the galactosyl group, which is an evidence of galactosylation on BzOH. Five proton peaks around the aromatic region at d H 7.43 ~ 7.24 ppm and 2 peaks from d H 4.93 and 4.67 ppm were evidence of the presence of the benzyl group. Seven proton peaks at d H 4.32 ~ 3.46 ppm showed the presence of a monosaccharide and were indicative of galactosylation on BzOH. 13 C NMR spectrum also revealed the presence of 11 carbons suggestive of BzO-gal. The mass value (sodium adduct ion of BzO-gal, m/z = 293.0994) from mass spectrometry analysis of BzO-gal, and 1 H and 13 C NMR spectral data were in good agreement with the expecting structure of BzO-gal. We are expecting that through future study it will eventually be able to develop a new additive of low cytotoxicity.

대장균 베타-갈락토시데이즈를 이용하여 합성된 Phenylethanol Galactoside의 NMR Spectroscopy 및 Mass spectrometry

이향렬,정경환 한국응용과학기술학회 2020 한국응용과학기술학회지 Vol.37 No.5

To characterize the molecular structure of PhE-gal synthesized using Escherichia coli β-gal, NMR ( 1 H- and 13 C-) spectroscopy and mass spectrometry of PhE-gal were conducted. 1 H NMR spectrum of PhE-gal showed multiple peaks corresponding to the galactosyl group, which is an evidence of galactosylation on 2-phenylethanol (PhE). Downfield proton peaks at δ H 7.30~7.21 ppm showed the presence of aromatic protons of PhE as well as benzyl CH 2 protons at δ H 2.88 ppm. Up field proton peaks at δ H 4.31 ppm, 4.07 ppm and multiple peaks from δ H 3.86~3.38 ppm are indicative of galactocylation on PhE. 13 C NMR spectrum revealed the presence of 12 carbons suggestive of PhE-gal. Among 12 carbon peaks from PhE-gal, the four peaks at 138.7, 129.0, 128.6 and 126.5 were assigned aromatic carbons in the phenyl ring. Three peaks at 129.0, 128.6 and 126.5 showed high intensities, indicating CH aromatic carbons. 13 C NMR data of PhE-gal showed 6 monosaccharide peaks from galactose and 2 peaks from aliphatic chain of PhE, indicating that PhE-gal was galactosyl PhE. The mass value (sodium adduct ion of PhE-gal, m/z = 307.1181) from mass spectrometry analysis of PhE-gal, and 1 H and 13 C NMR spectral data were in good agreement with the expecting structure of PhE-gal. We are expecting that through future study it will eventually be able to develop a new additive with low cytotoxicity. 대장균 효소 β-gal를 이용하여 합성된 phenylethanol galactoside (PhE-gal)의 분자구조를 NMR ( 1 H-와 13 C-)과 고성능 mass spectrometry를 이용하여 분석하였다. 그 결과 PhE-gal은 1 H NMR에서 2-phenylethanol (PhE)에 갈락토실기가 도입되었음을 나타내는 피크가 나타났다. 방향족 고리에서 오는 δ H 7.30~7.21 ppm의 피크와 δ H 2.88 ppm에 나타난 벤질기 위치의 CH 2 에서 오는 피크는 PhE가 존재함을 나타낸다. 지방족 사슬 영역인 δ H 4.31 ppm, 4.07 ppm과 δ H 3.86~3.38 ppm에서 나타나는 7개의 proton 피크로부터 단당류가 도입되었음을 확인할 수 있었다. 13 C NMR 스펙트럼에서 나타난 12개의 탄소 피크 중 4개의 피크는 방향족 고리인 페닐기로부터, 또한 단당류에서 기인한 6 개의 탄소피크가 존재하므로 PhE에 단당이 도입되었음을 알 수 있다. PhE-gal의 분자량을 확인하기 위하여 질량분석기로 분석한 결과 m/z가 307.1181인 PhE-gal의 sodium adduct ion ([M+Na] + )이 나타나 생성물이 PhE-gal임을 알 수 있었다. 따라서 본 연구결과 E. coli b–galactosylase에 의한 촉매반응 으로 PhE에 갈락토즈가 첨가된 생성물인 PhE-gal이 성공적으로 생합성 되었음을 확인하였다.

Soluble arene-thiophene based co-oligomers

이향렬 한국공업화학회 2015 한국공업화학회 연구논문 초록집 Vol.2015 No.0

Soluble arene-thiophene based oligomers with aromatic central units were synthesized by Stille reaction and characterized their properties. Their HOMO energy levels were determined. The thermal stability of arene-thiophene oligomers are investigated by DSC and TGA. Their TGA results except for DSi-TTPTT show a 5% of weight loss at around 400oC, which indicate high thermal stability. Dimethyl-n-octylsilyl end substituents allow for solution-processability due to their high soluble nature. In the end, electrochemical analysis of arene-thiophene oligomers with a less electron-rich center indicate to have better oxidative stability than DSi.

The preparation of functional hydrogel mask pack using the Natural substances

이향렬 한국공업화학회 2015 한국공업화학회 연구논문 초록집 Vol.2015 No.1

Hydrogel mask packs are attracting cosmetic materials due to it’s high elasticity and penetration properties of oxygen and nourishment that essentially need for skin. In this study, the physical properties of mask packs using natural materials such as ceratonia siliqua gum, agarose, gelatin, carrageenan, xanthan gum and cotton have been investigated. When carrageenan was added, tensile strength of the sample was increased significantly. In comparsion, agarose, gelatin, xanthan gum have no effect or slightly decreased their tensile strength. Cotton was also an effective natural material increasing tensile strength 20% more than mask pack sample without cotton.

생분해성 amidoximated cellulose계 chelate 수지의 합성 및 Cu??흡착에 관한 영구

이향렬,이수 國立昌原大學校 基礎科學硏究所 1994 基礎科學硏究所論文集 Vol.6 No.-

2h of premixing, rapid agitation was found to enduce cyanoethylation of cellulose at room temperature, and 80℃, 3h of reaction condition in cosolvent (DMSO:H₂O=50:50) was suitable for over 90% amidoximation of the corresponding cyanoethylcellulose. Amidoximated cellulose did not adsorb copper ion at all at pH below 3 and adsorbed more copper ion in higher pH with the range of 3 to 7. These copper ion adsorbability was determined by atomic absorption spectroscopy. AMC adsorbed more metal ions in the order of Cu²?> Cr³?> Ni²?. In addition, the fourth regenerated AMC by treatment in IN H₂SO₄ for 1h showed a same copper ion adsorbability as original AMC did.

Mass spectrometry와 NMR Spectroscopy를 이용한 1, 2-Octanediol Galactoside의 효소합성 확인

이향렬(Hyang-Yeol Lee),진홍종(Hong-Jong Jin),안승혜(Seung Hye An),이혜원(Hye Won Lee),정경환(Kyung-Hwan Jung) 한국응용과학기술학회 (구.한국유화학회) 2021 한국응용과학기술학회지 Vol.38 No.3

안전한 화장품용 방부제에 대한 연구를 위하여 1, 2-octanediol (OD)에 galactose 한 분자가 결합된 1, 2-octanediol galactoside (OD-gal)의 합성을 시도하였다. 이를 위하여, 재조합 대장균의 β-galactosidase (β-gal)를 이용하여 transgalactosylation 반응을 수행하였으며, OD-gal 합성을 확인 하기 위하여 mass spectrometry 분석과 NMR ( 1 H- and 13 C-) spectroscopy 분석을 실시하였다. 합성 반응물에서 m/z=331.1732의 sodium adduct ion 형태로 OD-gal 분자의 합성을 확인하였고, 정제된 OD-gal의 NMR 분석을 통하여 OD-gal의 1 H NMR 스펙트럼에서 OD에 갈락토실화가 되었음을 보여주는 다양한 피크를 확인하였다. 1 H NMR 스펙트럼의 다운필드인 δ H 4.39 ppm과 δ H 3.98~3.55 ppm에서 나타나는 다양한 피크들은 이들이 OD에 갈락토실화가 되었다는 것을 잘 암시하고 있으며, 또한 1 H NMR 스펙트럼의 업필드에서 나타나는 δ H 1.52~1.26 ppm과 0.89 ppm의 피크는 OD의 CH 2 와 CH 3 작용기로 부터 나타나는 피크로써 OD가 본 물질에 존재함을 알 수 있었다. 13 C NMR 스펙트 럼에서는 OD-gal의 알파-아노머와 베타-아노머의 구조에서 기인하는 총 24개의 탄소피크가 나타났고, 각 아노머 마다 14개의 탄소가 존재하는데 이중 δc 31.4, 29.0, 22.3 그리고 13.7 ppm에 보이는 OD 4개의 탄소는 지방족 사슬의 끝부분에 해당하며 화학적 구조의 유사성으로 인하여 탄소 피크가 겹쳐서 나타난 것으로 보인다. 따라서 총 28개의 탄소 피크 중 24개가 나타났다. 마지막으로, 합성된 OD-gal 의 β-gal을 이용한 가수분해 반응을 통하여 OD-gal에 gal이 결합되어 있다는 것을 확인하였다. 이러 한 결과를 바탕으로 세포독성이 감소된 첨가물 개발을 기대하고 있으며, 추가적인 후속연구를 진행할 예정이다. 1, 2-Octanediol galactoside (OD-gal) has been synthesized from 1, 2-octanediol (OD), as a safer cosmetic preservative, using recombinant Escherichia coli β-galactosidase (β-gal). To confirm the molecular structure of synthesized OD-gal, mass spectrometry and NMR ( 1 H- and 13 C-) spectroscopy of OD-gal were carried out. In the reaction mixture, a sodium adduct ion of OD-gal (m/z=331.1732) was identified using mass spectrometry analysis. In addition, 1 H NMR spectrum of OD-gal showed multiple peaks corresponding to the galactosyl group, which is evidence of galactosylation on OD. Downfield proton peaks at δ H 4.39 ppm and multiple peaks from δ H 3.98~3.55 ppm were indicative of galactosylation on OD. Up field proton peaks at δ H 1.52~1.26 ppm and 0.89 ppm showed the presence of CH 2 and CH 3 protons of OD. 13 C NMR spectrum revealed the presence of 24 carbons suggestive of α- and β-anomers of OD-gal. Among 14 carbon peaks from each anomer, the 4 peaks at δ C 31.4, 29.0, 22.3, and 13.7 ppm were assigned to be overlapped showing only 24 peaks out of a total of 28 peaks. The mass value from mass spectrometry analysis of OD-gal, and 1 H and 13 C NMR spectral data were in good agreement with the expecting structure of OD-gal. Finally, we identified a galactose molecule from the hydrolysate of OD-gal using β-gal. We are expecting that through future study it will eventually be able to develop a safe cosmetic preservative.

빈카 마이너 추출물의 항균 및 면역활성 연구

김준섭,강조은,유일환,정경환,문기성,이향렬 한국유화학회 2015 한국응용과학기술학회지 Vol.32 No.1

EtOH 추출법과 열수 추출법을 사용하여 빈카민 등의 빈카 알칼로이드 화합물을 함유한 빈카 마이너 추출물을 얻었다. 이들 추출물을 사용하여 비듬균, 효모, 그람양성 및 음성세균에 대한 항균활성을 측정 하였다. 비듬균(Malassezia furfur)에 대하여 표준물질인 빈카민과 EtOH 추출물은 항균활성을 보이 지 않은 반면 열수 추출물은 항균활성을 나타내었다. 또한 열수 추출물은 그람양성 및 음성세균에 속하는 바실러스(Bacillus sp.)와 대장균(Escherichia coli)에 대해서도 항균활성을 나타내었다. 추출물의 세포독성 은 HaCaT 세포(인간 케라티노사이트 세포), HT-29 세포(인간 결직장 선종암 세포), Raw 세포(인간 대 식세포)를 대상으로 측정하였으며, 해당 세포들에 대해 특별한 세포독성은 발견 되지 않았다. 또한 형광 기반의 탐색물질인 디클로로플루오신 디아세테이트(DCFDA)를 이용한 활성산소종을 측정하였다. 그 결과 HaCaT 세포와 HT-29 세포군에서 활성산소종의 형성이 약 20% 정도 증가하는 것을 알 수 있었다. Vinca alkaloid compounds including vincamine from Vinca minor L. have been extracted by ethanol and hot water extraction methods. Antimicrobial properties of those extracts have been investigated against dandruff causing microorganism Malassezia furfur, yeast, Gram positive and negative bacteria. Vincamine standard and ethanol extract showed no sign of antimicrobial activity, whereas hot-water extract had the activity against M. furfur. Furthermore hot water extract had antimicrobial activity against Gram positive Bacillus sp. and Gram negative Escherichia coli. Cytotoxic properties of those extracts have also been investigated with HaCaT cell (human keratinocyte), HT-29 cell (human colorectal adenocarcinoma cell) and Raw cell, showing no significant cytotoxic effects. We also measured the ROS using dichlorofluorescein diacetate (DCFDA), a popular fluorescence-based probe for reactive oxygen species detection. The result showed the increasement of reactive oxygen species formation (20%) in HaCaT and HT-29 cell lines.