• Journal of Microbiology and Biotechnology
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• 제27권11호
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• pp.1916-1924
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• 2017

In this study, we synthesized a glycosylated derivative of caffeic acid phenethyl ester (CAPE) using the amylosucrase from Deinococcus geothermalis with sucrose as a substrate and examined its solubility, chemical stability, and anti-inflammatory activity. Nuclear magnetic resonance spectroscopy showed that the resulting glycosylated CAPE (G-CAPE) was the new compound caffeic acid phenethyl ester-4-O-${\alpha}-{\small{D}}$-glucopyranoside. G-CAPE was 770 times more soluble than CAPE and highly stable in Dulbecco's modified Eagle's medium and buffered solutions, as estimated by its half-life. The glycosylation of CAPE did not significantly affect its anti-inflammatory activity, which was assessed by examining lipopolysaccharide-induced nitric oxide production and using a nuclear factor erythroid 2-related factor 2 reporter assay. Furthermore, a cellular uptake experiment using high-performance liquid chromatography analysis of the cell-free extracts of RAW 264.7 cells demonstrated that G-CAPE was gradually converted to CAPE within the cells. These results demonstrate that the glycosylation of CAPE increases its bioavailability by helping to protect this vital molecule from chemical or enzymatic oxidation, indicating that G-CAPE is a promising candidate for prodrug therapy.

• 생약학회지
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• 제44권3호
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• pp.230-234
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• 2013

In the course of screening for antioxidant compounds by measuring the DPPH radical scavenging activity, a total extract of the aerial part of Trigonotis peduncularis (Boraginaceae) was found to show potent DPPH radical scavenging activity. Subsequent activity-guided fractionation of the methanolic extract of T. peduncularis led to the isolation of seven compounds, kaempferol (1), quercetin (2), trigonotin A (3), astragalin (4), trigonotin C (5), kaempferol-3-O-${\alpha}$-L-rhamnopyranosyl(1${\rightarrow}$6)-${\beta}$-D-glucopyranoside (6), and rutin (7) from the active ethyl acetate soluble fraction. Their structures were elucidated by spectroscopic studies. Among seven compounds, compounds 1, 2, 4, 6 and 7 were isolated for the first time from this plant, and compounds 2 and 7 showed the significant DPPH free radical scavenging activities.

• 생약학회지
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• 제45권4호
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• pp.338-345
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• 2014

HPL-4 is a new herbal formulation developed for the treatment of osteoarthritis. In this study, we took HPL-4 to develop a method for simultaneous determination of nine marker compounds (protocatechuic acid, chlorogenic acid, liriodendrin, nodakenin, ${\beta}$-$\small{D}$-(3-O-sinapoyl)frucofuranosyl-${\alpha}$-$\small{D}$-(6-O-sinapoyl)glucopyranoside, quercitrin, 6-gingerol, decursin and decursinol angelate) present in the formulation. The analytes were separated by UPLC system consisting of diode array detector at 205 nm and RP-amide column, and solvent system of $ACN/0.1%H_3PO_4$. Analytical method was validated to evaluate its linearity, limit of detection (LOD), limit of quantification (LOQ), precision, and accuracy. All standards showed good linearity ($R^2$ >0.99) in the rage of $0.25-400.0{\mu}g/mL$. The LOD and LOQ were within the range of 0.021-0.148 and $0.070-0.448{\mu}g/mL$, respectively. Intra- and inter-day precision was less than RSD 4.0% and the accuracy was range from 92.00-104.81% with RSD<4.2%. The results suggest that the developed UPLC method is precise, accurate and effective, and could be applied for quality control of HPL-4 formulation.

• Journal of Ginseng Research
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• 제42권1호
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• pp.42-49
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• 2018

Background: Ginsenoside F1 has been described to possess skin-whitening effects on humans. We aimed to synthesize a new ginsenoside derivative from F1 and investigate its cytotoxicity and melanogenesis inhibitory activity in B16BL6 cells using recombinant glycosyltransferase enzyme. Glycosylation has the advantage of synthesizing rare chemical compounds from common compounds with great ease. Methods: UDP-glycosyltransferase (BSGT1) gene from Bacillus subtilis was selected for cloning. The recombinant glycosyltransferase enzyme was purified, characterized, and utilized to enzymatically transform F1 into its derivative. The new product was characterized by NMR techniques and evaluated by MTT, melanin count, and tyrosinase inhibition assay. Results: The new derivative was identified as (20S)-$3{\beta},6{\alpha},12{\beta}$,20-tetrahydroxydammar-24-ene-20-O-${\beta}$-D-glucopyranosyl-3-O-${\beta}$-D-glucopyranoside(ginsenoside Ia), which possesses an additional glucose linked into the C-3 position of substrate F1. Ia had been previously reported; however, no in vitro biological activity was further examined. This study focused on the mass production of arduous ginsenoside Ia from accessible F1 and its inhibitory effect of melanogenesis in B16BL6 cells. Ia showed greater inhibition of melanin and tyrosinase at $100{\mu}mol/L$ than F1 and arbutin. These results suggested that Ia decreased cellular melanin synthesis in B16BL6 cells through downregulation of tyrosinase activity. Conclusion: To our knowledge, this is the first study to report on the mass production of rare ginsenoside Ia from F1 using recombinant UDP-glycosyltransferase isolated from B. subtillis and its superior melanogenesis inhibitory activity in B16BL6 cells as compared to its precursor. In brief, ginsenoside Ia can be applied for further study in cosmetics.

• 임산에너지
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• 제19권2호
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• pp.93-101
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• 2000

아까시나무의 목질부와 현사시나무, 물푸레나무 및 느릅나무의 수피를 채취하여 아세톤-물 혼합용액(7:3, v/v) 으로 추출한 후 hexane, chloroform, ethylacetate 및 수용성으로 분획하고 동결건조하여 분말로 조제한 후 메탄올-물 등의 용리용매로 Sephadex LH-20 칼럼에서 크로마토그래피를 수행하였다. 물푸레나무에서는 aesculitin 및 그 파생물인 fraxetin 등 다량의 쿠마린 화합물과 에스테르화합물을 단리하였으며, 느릅나무로부터 C-7에 xylopyranose와 apiofuranose와 같은 5탄당이 결합된(+)-catechin 배당체 화합물과 procyanidn B-3를 단리하였다. 아까시나무에서는 leucorobinetinidin의 C-4에 ethoxyl 기가 결합된 flavan 유도체 화합물과 robinetin 등의 flavanonol 화합물을 단리하였다. 현사시나무에서는 taxifolin 등의 후라보노이드 화합물과 배당체인 sakuranetin-5-O-glucopyranoside를 단리하였으며 살리신 유도체인 salireposide 등을 단리하였다. 내후성 시험에서는 목재블록에 부후균을 접종하여 배양한 후 중량감소를 측정하는 방법과 목분-agar 배지에 부후균을 접종한 후 균사의 생장 직경을 측정하는 방법을 적용하였다. 아까시나무가 다른 시룓르보다 우수한 활성을 나타내었으며 특히 메탄올 추출머리를 하지 않은 시료가 처리한 시료보다 좋은 균사생장 저해효과를 나타냈다. 항산화 활성 시험에서는 물푸레나무의 에틸아세테이트 분획이 가장 높은 활성을 보였으며, 아까시나무의 에틸아세테이트 분획도 비교적 높은 효과를 나타내었고, 이 두 분획으로부터 단리된 주요 단리화합물에 대해서는 물푸레나무의 aesculetin이 가장 높았으며 아까시나무의 robinetinidin도 비교적 좋은 효과를 나타냈다.)나 틈새시장(niche market) 마케팅 등에 적용 가능하리라 여겨진다.된다.다.산물로 판단되었다.징하며 WLWQ에 적용되는 몇 가지 제약을 관찰하고 이를 일반적인 언어원리로 설명한다. 첫째, XP는 주어로만 해석되는데 그 이유는 XP가 목적어 혹은 부가어 등 다른 기능을 할 경우 생략 부위가 생략의 복원 가능선 원리 (the deletion-up-to recoverability principle)를 위배하기 때문이다. 둘째, WLWQ가 내용 의문문으로만 해석되는데 그 이유는 양의 공리(the maxim of quantity: Grice 1975) 때문이다. 평서문으로 해석될 경우 WP에 들어갈 부분이 XP의 자질의 부분집합에 불과하므로 명제가 아무런 정보제공을 하지 못한다. 반면 의문문 자체는 정보제공을 추구하지 않으므로 앞에서 언급한 양의 공리로부터 자유롭다. 셋째, WLWQ의 XP는 주제어 표지 ‘는/-은’을 취하나 주어표지 ‘가/-이’는 취하지 못한다(XP-는/-은 vs. XP-가/-이). 이는 IP내부 에 비공범주의 존재 여부에 따라 C의 음운형태(PF)가 시성이 정해진다는 가설로 설명하고자 했다. WLWQ에 대한 우리의 논의가 옳다면, 본 논문은 다음과 같은 이론적 함의를 기닌다. 첫째, WLWQ의 존재는 생략에 대한 두 이론 즉 LF 복사 이론과 PF 삭제 이론 중 전자의 입장을 지지한다. 둘째, WP를 XP로부터 복원할 때 부분 자질만 복사된다. 이는 어휘가 통사층위로 들어온 이후에도 어휘 자질들이 완전히 동결되는 것이 아니라 계속 지시될 수 있다는 가설을 지지한다.ance and stress, and high threshold voltage. Besides, sheet resistance and stress value, rms(root mean square) by AFM were observed. On the electrical

• Molecules and Cells
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• 제19권1호
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• pp.137-142
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• 2005

We showed recently that ginsenosides inhibit the activity of various types of ion channel. Here we have investigated the role of the carbohydrate component of ginsenoside $Rg_3$ in the inhibition of $Na^+$ channels. The channels were expressed in Xenopus oocytes by injecting cRNAs encoding rat brain Nav1.2 ${\alpha}$ and ${\beta}1$ subunits, and analyzed by the two-electrode voltage clamp technique. Treatment with $Rg_3$ reversibly inhibited the inward $Na^+$ peak current ($I_{Na}$) with an $IC_{50}$ of $32.2{\pm}4.5{\mu}M$, and the inhibition was voltage-dependent. To examine the role of the sugar moiety, we prepared a straight chain form of the second glucose and a conjugate of this glucose with 3-(4-hydroxyphenyl) propionic acid hydrazide (HPPH). Neither derivative inhibited $I_{Na}$. Treatment with the carbohydrate portion of ginsenoside $Rg_3$, sophorose [${\beta}-D-glucopyranosyl$ ($1{\rightarrow}2$)-${\beta}-glucopyranoside$], or the aglycone (protopanaxadiol), on their own or in combination had no effect on $I_{Na}$. These observations indicate that the carbohydrate portion of ginsenoside $Rg_3$ plays an important role in its effect on the $Na^+$ channel.