• Journal of Ginseng Research
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• 제47권4호
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• pp.593-603
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• 2023

Background: Korean Red Ginseng is a major source of bioactive substances such as ginsenosides. Efficacy of red ginseng extract (RGE), which contains not only saponins but also various non-saponins, has long been studied. In the water-soluble component-rich fraction of RGE (WS), a byproduct generated in the process of extracting saponins from the RGE, we identified previously unidentified molecules and confirmed their efficacy. Methods: The RGE was prepared and used to produce WS, whose components were isolated sequentially according to their water affinity. The new compounds from WS were fractionized and structurally analyzed using nuclear magnetic resonance spectroscopy. Physiological applicability was evaluated by verifying the antioxidant and anti-inflammatory efficacies of these compounds in vitro. Results: High-performance liquid chromatography confirmed that the obtained WS comprised 11 phenolic acid and flavonoid substances. Among four major compounds from fractions 1-4 (F1-4) of WS, two compounds from F3 and F4 were newly identified in red ginseng. The analysis results show that these compound molecules are member of the maltol-structure-based glucopyranose series, and F1 and F4 are particularly effective for decreasing oxidative stress levels and inhibiting nitric oxide secretion, interleukin (IL)-1β and IL-6, and tumor necrosis factor-α. Conclusion: Our findings suggest that a few newly identified maltol derivatives, such as red ginseng-derived non-saponin in the WS, exhibit antioxidant and anti-inflammatory effects, making them viable candidates for application to pharmaceutical, cosmetic, and functional food materials.

• Journal of Microbiology and Biotechnology
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• 제34권3호
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• pp.725-734
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• 2024

CYP102A1 from Bacillus megaterium is an important enzyme in biotechnology, because engineered CYP102A1 enzymes can react with diverse substrates and produce human cytochrome P450-like metabolites. Therefore, CYP102A1 can be applied to drug metabolite production. Terpinen-4-ol is a cyclic monoterpene and the primary component of essential tea tree oil. Terpinen-4-ol was known for therapeutic effects, including antibacterial, antifungal, antiviral, and anti-inflammatory. Because terpenes are natural compounds, examining novel terpenes and investigating the therapeutic effects of terpenes represent responses to social demands for eco-friendly compounds. In this study, we investigated the catalytic activity of engineered CYP102A1 on terpinen-4-ol. Among CYP102A1 mutants tested here, the R47L/F81I/F87V/E143G/L188Q/N213S/E267V mutant showed the highest activity to terpinen-4-ol. Two major metabolites of terpinen-4-ol were generated by engineered CYP102A1. Characterization of major metabolites was confirmed by liquid chromatography-mass spectrometry (LC-MS), gas chromatography-MS, and nuclear magnetic resonance spectroscopy (NMR). Based on the LC-MS results, the difference in mass-to-charge ratio of an ion (m/z) between terpinen-4-ol and its major metabolites was 16. One major metabolite was defined as 1,4-dihydroxyp-menth-2-ene by NMR. Given these results, we speculate that another major metabolite is also a mono-hydroxylated product. Taken together, we suggest that CYP102A1 can be applied to make novel terpene derivatives.

• Journal of Ginseng Research
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• 제32권4호
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• pp.291-299
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• 2008

수삼으로부터 용매추출, 용매분획 및 silica gel column chromatography를 반복하여 ginsenoside $Rg_1$을 분리하였다. Ginsenoside $Rg_1$의 결정특성, 녹는점, 비선광도, IR 데이터, FAB/MS 데이터, TLC에서의 Rf 값, HPLC에서의 r.t. 및 NMR 데이터를 표준화한 조건으로 측정하여 문헌 값과 비교 고찰하였다. 특히 ginsenoside $Rg_1$의 $^{1}H-$ 및 $^{13}C$-NMR 데이터를 HSQC 및 HMBC와 같은 2D-NMR 실험을 통하여 정확하게 동정하였다.

• 폴리머
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• 제39권1호
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• pp.56-63
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• 2015

본 연구의 목적은 다이이소시아네이트 화합물을 함유하는 마이크로캡슐을 제조하고 자기치유형 보호코팅재에 적용하여 공기 중 수분에 의한 자기치유 기능을 평가하는 것이다. 다이이소시아네이트 화합물의 공기 중 수분과의 반응 거동을 조사함으로써 치유 물질로서의 가능성을 확인하였다. 폴리우레탄을 캡슐막으로 하여 이소포론 다이이소시아네이트(isophorone diisocyanate, IPDI)의 마이크로캡슐화를 계면중합법에 의해 수행하였다. 마이크로캡슐의 생성여부는 FTIR 및 NMR으로 확인하였고, 마이크로캡슐의 직경 및 크기 분포, 표면 형상과 캡슐막의 두께는 광학현미경과 FE-SEM을 통하여 관찰하였다. 교반속도 및 다이올 구조 변화에 따른 마이크로캡슐의 특성 변화를 조사하였다. 자기치유형 보호코팅재를 제조하여 스크래치를 형성시킨 후 광학현미경으로 관찰한 결과, 스크래치 형성 직후 스크래치가 지나가는 자리에 위치하는 마이크로캡슐이 깨지면서 심물질이 흘러나와 스크래치를 메워주는 것을 확인하였다. 또한 CRC 보드에 마이크로캡슐을 함유한 자기치유 코팅재를 제조하여 스크래치 형성 후 상대습도 68~89%의 공기 중에 48시간 동안 방치한 후 SEM 분석 및 내투수 테스트를 진행한 결과, 스크래치가 자기치유된 것이 확인되었다.

• 한국생물공학회:학술대회논문집
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• 한국생물공학회 2003년도 생물공학의 동향(XII)
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• pp.40-44
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• 2003

Soil-borne infectious disease including Pythium aphanidermatum and Rhizoctonia solani causes severe damage to plants, such as cucumber. This soil-borne infectious disease was not controlled effectively by chemical pesticide. Since these diseases spread through the soil, chemical agents are usually ineffective. Instead, biological control, including antagonistic microbe can be used as a preferred control method. An efficient method was developed to select an antagonistic strain to be used as a biological control agent strain. In this new method, surface tension reduction potential of an isolate was included in the ‘decision factor’ in addition to the other factors, such as growth rate, and pathogen inhibition rate. Considering these 3 decision factors by a statistical method, an isolate from soil was selected and was identified as Bacillus sp. GB16. In the pot test, this strain showed the best performance among the isolated strains. The lowest disease incidence rate and fastest seed growth was observed when Bacillus sp. GB16 was used. Therefore this strain was considered as plant growth promoting rhizobacteria (PGPR). The action of surface tension reducing component was deduced as the enhancement of wetting, spreading, and residing of antagonistic strain in the rhizosphere. This result showed that new selection method was significantly effective in selecting the best antagonistic strain for biological control of soil-borne infectious plant pathogen. The antifungal substances against P. aphanidermatum and R. solani were partially purified from the culture filtrates of Bacillus sp. GB16. In this study, lipopeptide possessing antifungal activity was isolated from Bacillus sp. GB16 cultures by various purification procedures and was identified as a surfactin-like lipopeptide based on the Fourier transform infrared spectroscopy (FT-IR), nuclear magnetic resonance (NMR), high performance liquid chromatography mass spectroscopy (HPLC-MS), and quadrupole time-of-flight (Q-TOF) ESI-MS/MS data. The lipopeptide, named GB16-BS, completely inhibited the growth of Pythium aphanidermatum, Rhizoctonia solani, Penicillium sp., and Botrytis cineria at concentrations of 10 and 50 mg/L, respectively. A novel method to prevent the foaming and to provide oxygen was developed. During the production of surface active agent, such as lipopeptide (surfactin), large amount of foam was produced by aeration. This resulted in the carryover of cells to the outside of the fermentor, which leads to the significant loss of cells. Instead of using cell-toxic antifoaming agents, low amount of hydrogen peroxide was added. Catalase produced by cells converted hydrogen peroxide into oxygen and water. Also addition of corn oil as an oxygen vector as well as antifoaming agent was attempted. In addition, Ca-stearate, a metal soap, was added to enhance the antifoam activity of com oil. These methods could prevent the foaming significantly and maintained high dissolved oxygen in spite of lower aeration and agitation. Using these methods, high cell density, could be achieved with increased lipopeptide productivity. In conclusion to produce an effective biological control agent for soil-borne infectious disease, following strategies were attempted i) effective screening of antagonist by including surface tension as an important decision factor ii) identification of antifungal compound produced from the isolated strain iii) novel oxygenation by $H_2O_2-catalase$ with vegetable oil for antifungal lipopeptide production.

• 한국식품과학회지
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• 제25권2호
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• pp.148-153
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• 1993

최근 sucrose polyesters(SPE)와 더불어 유지대체 물질로서의 사용이 검토되고 있는 glucitol fatty acid polyesters(GPE)를 합성한 후, 화학적 구조 및 상대적 에스테르 분포에 따른 치환도를 조사하였다. 본 연구에서 합성한 GPE는 순상 HPLC에 의해 단일 에스테르 그룹으로 분리되었으며, 분리된 에스테르 그룹의 치환도는 6으로서 GPE 전체가 glucitol fatty acid hexaester임을 알 수 있었다. GPE의 IR 스펙트럼에서 $1747\;cm^{-1}$에 나타나는 흡수대는 GPE 분자내에 glucitol과 지방산을 연결하고 있는 에스테르 결합이 존재함을 보여주었다. GPE는 H-NMR 스펙트럼에서는 glucitol의 hydroxyl proton의 시그널이 존재하지 않음을 볼 때 glucitol의 모든 수산기가 지방산과의 에스테르 결합에 참여하고 있음을 알 수 있었다. 또한 GPE의 H-NHR 스펙트럼을 정량적으로 해석한 결과는 수산기가(hydroxyl value) 측정에 의해 결정된 GPE의 치환도와 일치하였다. 이상의 결과를 종합하여 볼 때 본 연구에서 합성한 GPE는 glucitol fatty acid hexaester임이 확인되었고 향후 유지대체물질로서 사용되어질 가능성을 지닌 것으로 생각되었다.

• Journal of Applied Biological Chemistry
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• 제54권1호
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• pp.1-6
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• 2011

Poly-${\gamma}$-glutamic acid (${\gamma}$-PGA)는 청국장이 발효할 때 생성되는 점질성 물질의 하나로, monomer glutamic acid의 ${\alpha}$-아미노기와 ${\gamma}$-카르복실기 사이의 amide linkage에 의해 결합된 D(-)와 L(-) glutamic acid repeat units로 이루어진 homopolymer이다. 주로 Bacillus sp.에 의해 생산된다. ${\gamma}$-PGA는 수용성, 음이온성, 무독성, 생분해성, 생체적 합성, 식용 등의 다양한 특성을 가지고 있기 때문에 여러 분야에서 응용되고 있다. 본 실험에서 ${\gamma}$-PGA를 생산하는 균주를 우리나라의 전통발효식품인 청국장으로부터 분리하였다. 분리균주의 형태 및 배양학적, 생리학적 특성, API kit 및 16S rRNA 서열을 사용하여 동정한 결과, 분리균주 GS-2는 B. subtilis와 가장 유사하여 B. subtilis GS-2로 명명하였다. 분리 정제된 ${\gamma}$-PGA의 동정은 TLC, HPLC, FTIR 그리고 $^1H$-NMR spectroscopy를 통하여 확인하였다.

• Journal of Applied Biological Chemistry
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• 제54권1호
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• pp.63-66
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• 2011

The bark of Machilus thunbergii was extracted with 80% aqueous methanol (MeOH), and the concentrated extract was partitioned using ethyl acetate (EtOAc), butanol (n-BuOH), and $H_2O$, successively. From the EtOAc fraction, five lignans were isolated through the repeated silica gel, octadecyl silica gel (ODS) and, Sephadex LH-20 column chromatography. Based on nuclear magnetic resonance (NMR), mass spectroscopy (MS), and infrared spectroscopy (IR) spectroscopic data, the chemical structures of the compounds were determined to be machilin A (1), machilin F (2), licarin A (3), nectandrin A (4), and nectandrin B, (5). This study presents comparative account of five lignans from M. thunbergii bark contributing inhibition of low density lipoprotein (LDL), ACAT-1, and ACAT-2. Compounds 2-5 showed varied degree of antioxidant activity on LDL with $IC_{50}$ values of 2.1, 11.8, 15.3, and $4.1{\mu}M$. Compounds 1, 2, and 3 showed inhibition activity on ACAT-1 with values $63.4{\pm}6.9%$ ($IC_{50}=66.8{\mu}M$), $53.7{\pm}0.9%$ ($IC_{50}=109.2{\mu}M$), and $78.7{\pm}0.2%$ ($IC_{50}=40.6{\mu}M$), respectively, at a concentration of 50 mg/mL, and on ACAT-2 with values $47.3{\pm}1.5%$ ($IC_{50}=149.7{\mu}M$), $39.2{\pm}0.2%$ ($IC_{50}=165.2{\mu}M$), and $52.1{\pm}1.0%$ ($IC_{50}=131.0{\mu}M$, respectively, at a concentration of 50 mg/mL.

• Korean Chemical Engineering Research
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• 제55권3호
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• pp.395-400
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• 2017

본 연구에서는 무회분 석탄을 바인더로 첨가한 코크스의 물리적 및 화학적 성질들을 실험적으로 분석하고 강도 향상 메커니즘에 대해 고찰하였다. 또한 제철소에서의 $CO_2$ 저감을 위해 반탄화 과정을 거친 바이오매스 연료를 이용하였다. 무회분 석탄과 함께 팽윤현상(Swelling)이 일어나지 않는 발전용 석탄을 함께 탄화시켜서 전자현미경(SEM)을 이용하여 인터페이스를 관찰하였다. 또한 코크스의 강도 분석을 위하여 I.T.T (Indirect Tensile Test)와 함께, 화학적 구조 고찰을 위하여 $^1H$ NMR 및 $^{13}C$ NMR 분석을 사용하였다. 무회분 석탄의 $^1H$ NMR 및 $^{13}C$ NMR 분석으로 도출된 분자 구조와 코크스 강도의 관계를 도출하였으며, 그 결과 코크스의 강도는 무회분 석탄을 바인더로 첨가함으로써 증가될 수 있음을 확인하였다.

• 공업화학
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• 제31권4호
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• pp.383-389
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• 2020

프로필 술폰산으로 개질된 메조기공 실리카 고체 산 촉매를 octamethylcyclotetrasiloxane (D₄)의 양이온 개환중합을 위해 합성하였다. 서로 다른 기공 크기를 갖는 두 세트의 MCM-41 (1.7 및 2.8 nm) 및 SBA-15 (8.1 및 15.9 nm)을 촉매의 지지체로 사용하였고, 이를 (3-mercaptopropyl)trimethoxysilane으로 표면개질하고 산화시켜 술폰산으로 개질된 고체 산촉매를 제조하였다. 제조된 촉매는 기공 크기와 비표면적, 기공 부피가 약간씩 감소하였음을 X선 회절, 질소흡탈착을 통하여 확인하였다. 또한 적외선분광법과 핵자기공명법의 분광학적 방법을 이용하여 술폰산이 개질되었음을 확인하였다. 입도의 촉매 활성에 대한 효과를 관찰하기 위하여 주사전자현미경으로 관찰하였다. D₄의 개환중합을 통한 PDMS 합성을 위하여 촉매를 사용하였으며, 중합 반응의 전환율과 중합 속도는 촉매의 기공 크기, 비표면적, 입자크기 및 입자의 응집도에 의존하였다. 중합 속도의 순서는 8.1 nm의 SBA-15으로 제조한 촉매가 가장 반응속도가 빨랐으며, 가장 좋은 촉매 활성을 보였다.