Catharanthus roseus의 식물세포 배양액을 이용한 vindoline 생합성 경로 연구

Hyang-Yeol Lee 한국식품영양과학회 2012 한국식품영양과학회 학술대회발표집 Vol.2012 No.10

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

( Hyang Yeol Lee ) 한국유화학회 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.

Construing temporal metabolomes for acetous fermentative production of <i>Rubus coreanus</i> vinegar and its <i>in vivo</i> nutraceutical effects

Lee, Mee Youn,Kim, Hyang Yeon,Lee, Da Eun,Singh, Digar,Yeo, Soo Hwan,Baek, Seong Yeol,Park, Yoo Kyoung,Lee, Choong Hwan Elsevier 2017 Journal of Functional Foods Vol.34 No.-

<P><B>Abstract</B></P> <P>The temporal metabolomes associated with <I>Rubus coreanus</I> (RC) vinegar production were delineated using mass spectrometry-based metabolomic analyses with multivariate studies. We observed a clustered pattern of 27 discriminant metabolites: 4 organic acids, 9 sugars and sugar derivatives, 2 alcohol and carboxylic acid, 6 esters, and 6 terpenes. The levels of organic acids and alcohols were steadily decreased throughout fermentation, whereas those of sugars and sugar derivatives, carboxylic acids, esters, and terpenes peaked at 6days. Further, the <I>in vivo</I> nutraceutical potentials of RC vinegar were examined with its metabolomic implications for bone health in growing rat model. Intriguingly, the plasmatic metabolomes among treated rat groups were observed with lower levels of non-essential amino acids and lysophosphatidylcholines (LysoPCs) coupled with higher levels of fatty acids and bile acids. The plasmatic metabolomes complemented with bone morphometric and clinical parameters suggest the bone health ameliorating effects of RC vinegar.</P> <P><B>Highlights</B></P> <P> <UL> <LI> We construed temporal metabolomes for <I>Rubus coreanus</I> (RC) vinegar fermentation. </LI> <LI> Overall 27 discriminant metabolites were identified towards fermentative stages. </LI> <LI> Dietary RC vinegar supplementation promotes bone health in growing rats. </LI> <LI> Serum metabolomes and clinical parameters of bone health were positively affected. </LI> </UL> </P>

Cherry fruit anthocyanins cyanidin-3-O-glucoside and cyanidin-3-O-rutinoside protect against blue light-induced cytotoxicity in HaCaT cells

Lee Hyang-Yeol,Kim Jun-Sub 한국응용생명화학회 2023 Applied Biological Chemistry (Appl Biol Chem) Vol.66 No.-

Blue light derived from multiple sources, including sunlight, generates reactive oxygen species (ROS) and negatively affects the skin in a manner similar to that of ultraviolet light. Cyanidin-3-O-glucoside (C3OG) and cyanidin-3-O-rutinoside (C3OR) are anthocyanin antioxidants that have protective effects on various tissues and cell types. However, the effects of anthocyanins on blue light-mediated changes remain unconfirmed. In this study, we determined the protective effects of C3OG and C3OR isolated and purified from waste cherry fruits (Prunus serrulata L. var. tomentella Nakai) against the blue light-induced ROS formation and inflammatory responses in HaCaT cells. It is showed that the treatment of C3OG and C3OR significantly reduced the blue light-induced cytotoxicity and ROS production in a dose dependent manner. Furthermore, we found that focal adhesion kinase (FAK) is a major upstream of blue light-induced expression of inflammatory cytokines (TNF-α, IL-6 and IL-8), and these effects were attenuated by C3OG or C3OR treatment. In the initial reaction, blue lights increased the phosphorylation of inhibitory-κB Kinase α (IKKα), c-jun N-terminal kinase (JNK), and p38. The phosphorylation of these intracellular proteins was reduced via FAK inhibitor, NAC (ROS scavenger), and anthocyanin treatments. After 24 h of blue light irradiation, C3OG or C3OR treatment markedly inhibited caspase-3-mediated apoptosis and cleaved-FAK-mediated anoikis, which is cell detachment-induced apoptosis. Therefore, our results indicate that C3OG and C3OR effectively protected human keratinocytes from harmful blue light-induced cytotoxicity and inflammation.

2-Ethylnylnaphthalene that have indole based moiety shows inhibition of human CYP 2A6

Hyang-Yeol Lee 한국식품영양과학회 2013 한국식품영양과학회 학술대회발표집 Vol.2013 No.11

Analysis of aza-indole alkaloids in the biosynthesis of Vinca rosea

Hyang-Yeol Lee 한국식품영양과학회 2013 한국식품영양과학회 학술대회발표집 Vol.2013 No.11

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

Lee, Hyang-Yeol The Korean Society of Applied Science and Technolo 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.

Enzymatic Synthesis of 2-Phenoxyethanol Galactoside by Whole Cells of β-Galactosidase-Containing Escherichia coli

( Hyang Yeol Lee ),( Kyung Hwan Jung ) 한국미생물 · 생명공학회 2014 Journal of microbiology and biotechnology Vol.24 No.9

We investigated whether β-galactosidase (β-gal)-containing Escherichia coli cells could transfer a galactose to 2-phenoxyethanol, resulting in 2-phenoxyethanol galactoside (PE-Gal). PE-Gal was confirmed by liquid chromatography-mass spectrometry. In addition, we also confirmed that a galactose molecule was covalently bonded with PE during thin-layer chromatography analysis of the β-gal hydrolysate of PE-Gal. The yield for PE-Gal synthesis was about 37.5% (weight basis), which was about 7-8 times greater than that of a previous report. In addition, the concentration of β-gal (0.96 U/ml) used in this PE-Gal synthesis was about 20 times less than that in a previous report.

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.

Preparation of Wood Adhesives from the Rice Powder and pMDIs; Characterizations of Their Properties

Sang-Min Lee,Ji-Hye Joo,Hyang-Yeol Lee 한국유화학회 2015 한국응용과학기술학회지 Vol.32 No.4

To investigate the adhesion effect of various kinds and contents of polymeric methylene diphenyl diisocyanates (pMDIs) on adhesion performance, wood adhesives (A-1~5) were synthesized and characterized. As results, when the amount of pMDI increased in adhesives, the dry tensile strength was found to be proportionally increased sustaining at around 16.0~21.6 kgf/cm2. The polyurethane (PU) resin, which used M11S as a source of pMDI showed the best wet tensile strength at 11.9 kgf/cm2 and cyclic boil tensile strength at 8.1 kgf/cm2, which satisfied the requirement of over 7 kgf/cm2. Thermal properties of the rice powder (RP) based polyurethane resins were characterized by differential scanning calorimetry (DSC) and Thermal gravimetric analysis (TGA). Thermal stability of polyurethane resins increased to 250℃ with adding pMDIs. The more pMDI (M5S) was added to adhesive, the higher thermal stability of the resin was observed by TGA.