• Bulletin of the Korean Chemical Society
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• 제24권8호
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• pp.1053-1054
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• 2003

• Natural Product Sciences
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• 제29권1호
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• pp.10-16
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• 2023

We previously reported that dried Lysimachia christinae whole plant extract exerted significant neuroprotective activity. In this study, we tried to isolate neuroprotective compounds of L. christinae. We evaluated the neuroprotective activity of the four fractions (hexane, chloroform, ethyl acetate, and n-butanol fractions) of methanol extract. Among them, ethyl acetate and n-butanol fractions showed most potent neuroprotective activity against glutamate excitotoxicity. Nine compounds were isolated from ethyl acetate and n-butanol fractions of L. christinae extract and identified as cynaroside (1), (3,4,5,6-tetrahydroxytetrahydro-2H-pyran-2-yl)methyl-3-hydroxy-2-octyldopentaconta-23,33-dienoate (2), androst-16-ene-3,6-diol (3), 2-hydroxy-24-propoxytetracos-4-enoic acid (4), 2-hydroxy-24-methoxytetracos-4-enoic acid (5), 12-(stearoyloxy)octadec-9-enoic acid (6), β-sitosterol (7), (E)-4-(3,4-dimethoxyphenyl)but-3-en-1-yl palmitate (8) and (1S,2S,3R,4R)-4-(((2S,3R,4R,5R,6S)-2-(((2R,3R,4S,5R,6R)-2-(3,4-dimethoxyphenethoxy)-3,5-dihydroxy-6-(hydroxymethyl) tetrahydro-2H-pyran-4-yl)oxy)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-3-yl)oxy)cyclohexane-1,2,3-triol (9) by spectroscopic data such as UV, IR, NMR, Mass spectroscopy. Their neuroprotective activity was evaluated by MTT assay. Cynaroside (1) and androst-16-ene-3,6-diol (3) had significant neuroprotective activity against glutamate-injured HT22 cells. The neuroprotective efficacy of cynaroside (1) and androst-16-ene-3,6-diol (3) was related to their anti-oxidative activity.

• 공업화학
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• 제31권2호
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• pp.187-192
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• 2020

(2S,3R)-3-hydroxyhomoserine lactone (HSL)은 생리학적 활성을 가지는 다양한 종류의 화합물을 합성하기 위한 중간체로 활용되어 왔다. 본 논문에서는 OBO ester로 보호된 바이닐글라이신 유도체에 이중알콜화 반응을 수행하여 효율적인 HSL 합성 결과를 보고하고자 한다. 바이닐글라이신의 비고리 conformation은 크기가 큰 OBO ester에 의해 조절되었으며 N-inside conformation을 통해 이중알콜화 반응이 진행됨으로써 높은 anti 선택성(> 10 : 1)을 얻을 수 있었다. 이러한 결과를 바탕으로 N-Cbz-L-serine을 출발물질로 사용하여 총 7단계 34%의 수율로 HSL을 합성할 수 있었다. 본 연구의 결과는 amino diol 구조를 가지는 다양한 생리활성 천연물들의 입체선택적인 합성에 유용하게 활용될 수 있을 것으로 기대된다.

• Mass Spectrometry Letters
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• 제8권4호
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• pp.90-97
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• 2017

Androgenic anabolic steroids (AASs) are synthetic derivatives of testosterone with a common structure containing cyclopentanoperhydrophenanthrene nucleus. Their use enhances the muscle building capacity and is beneficial during performance. The AASs are one of the most abused group of substances in horse doping. Liquid chromatography tandem mass spectrometry ($LC/MS^n$) has been successfully applied to the detection of anabolic steroids in biological samples. However, the saturated hydroxysteroids viz: nandrolone, $5{\alpha}-estrane-3{\beta}$, $17{\alpha}-diol$ exhibit lower detection responses in electrospray ionisation (ESI) because of their poor ionisation efficiency. To overcome this limitation pre-column chemical derivatization has been introduced to enhance their detection responses in $LC-ESI-MS^n$ analysis. The aim of present study was to develop a sensitive method for identification and confirmation of nandrolone and its metabolite in horse urine incorporating pre-column derivatization using picolinic acid. The method consists of extraction of targeted steroid conjugates by solid phase extraction (SPE). The eluted steroid conjugates were hydrolysed by methanolysis and free steroids were recovered with liquid-liquid extraction. The resulting steroids were derivatized to form picolinoyl esters and identification was done using LC-ESI-MS/MS in positive ionization mode. The picolinated steroid adduct enhanced the detection levels in comparison to underivatized steroids.

• Bulletin of the Korean Chemical Society
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• 제32권8호
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• pp.2689-2694
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• 2011

Novel 5'-norcarbocyclic adenine and guanine phosphonic acid analogues with 6'-electronegative moiety such as unsaturated C-C bond were designed and synthesized from commercially available 2-methylene-propane-1,3-diol (4). Regioselective Mitsunobu reaction successfully proceeded from an allylic functional group (${\pm}$)-12b at low reaction temperature in polar cosolvent (DMF/1,4-dioxane) to give purine phosphonate analogues (${\pm}$)-13 and (${\pm}$)-20. The purine nucleoside phosphonate and phosphonic acid analogues were subjected to antiviral screening against HIV-1. Guanine analogue (${\pm}$)-23 shows significant anti-HIV activity in PBM cell lines ($EC_{50}=8.1\;{\mu}M$).

• Bulletin of the Korean Chemical Society
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• 제18권8호
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• pp.856-860
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• 1997

The arene epoxides from naphthalene, 1β,2α-dihydroxy-3α,4α-epoxy- (1) and 1β,2α-dihydroxy-3β,4β-epoxy-1,2,3,4-tetrahydronaphthalene (2) (anti- and syn-diol epoxide), 1,2-epoxy-1,2,3,4-tetrahydronaphthalene (3), and 1,2-epoxy-l,2-dihydronaphthalene (4), are model compounds of the ultimate carcinogenic metabolites of polycyclic aromatic hydrocarbons, ubiquitous environmental pollutants which may be causal in several human cancers. The product distribution in the hydrolysis of 1-4 have been studied by HPLC analysis of reaction mixtures. The yields of the trans product from the hydronium-ion-catalyzed and pH-independent hydrolysis in 9 : 1 (v/v) 20 mM buffer-dioxane at 25 ℃, respectively, were; 1: 98, 100; 2: 74, 87, 3: 95, 97, 4:100, 100. The results were rationalized by conformational equilibria of the epoxides and the carbocationic and zwitterionic intermediates from the epoxides.

• Mycobiology
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• 제51권4호
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• pp.246-255
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• 2023

Genus Penicillium comprising the most important and extensively studied fungi has been well-known as a rich source of secondary metabolites. Our study aimed to analyze and investigate biological activities, including in vitro anti-cancer, anti-inflammatory and anti-diabetic properties, of metabolites from a marine-derived fungus belonging to P. levitum. The chemical compounds in the culture broth of P. levitum strain N33.2 were extracted with ethyl acetate. Followingly, chemical analysis of the extract leaded to the isolation of three ergostane-type steroid components, namely cerevisterol (1), ergosterol peroxide (2), and (3β,5α,22E)-ergosta-6,8(14),22-triene-3,5-diol (3). Among these, (3) was the most potent cytotoxic against human cancer cell lines Hep-G2, A549 and MCF-7 with IC₅₀ values of 2.89, 18.51, and 16.47 ㎍/mL, respectively, while the compound (1) showed no significant effect against tested cancer cells. Anti-inflammatory properties of purified compounds were evaluated based on NO-production in LPS-induced murine RAW264.7 macrophages. As a result, tested compounds performed diverse inhibitory effects on NO production by the macrophages, with the most significant inhibition rate of 81.37±1.35% at 25 ㎍/mL by the compound (2). Interestingly, compounds (2) and (3) exhibited inhibitory activities against pancreatic lipase and α-glucosidase enzymes in vitro assays. Our study brought out new data concerning the chemical properties and biological activities of isolated steroids from a P. levitum fungus.

• 공업화학
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• 제29권4호
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• pp.405-412
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• 2018

알칸디올로부터 유래된 주사슬의 탄소수가 6, 9, 11인 bis[3-(dialkyloxylphosphorothionyl)thio-2-methylpropanyloxy]alkane (BAPA)를 합성하였으며, 이를 zinc dialkyl dithiophosphates (ZDDP)와 비교하여 마모억제성능을 살펴보았다. 탄소 주사슬의 길이에 따른 BAPA의 내마모성능을 확인하기 위하여 4-ball 시험을 하였다. 기유무게의 1% 농도로 첨가제를 넣고 WSD (wear scar diameter)를 측정하였고, 각 0.472, 0.459, 0.480 mm로 나타났다. 또한 BAPA 화합물 중 bis[methacryloyloxy]nonane (BMOO9)의 곁사슬인 dialkyl dithiophosphoric acid (DDP)의 탄소수를 4, 8, 12로 변화시켜 합성하여, 4-ball 시험을 하였다. 그 결과로 WSD의 값은 각각 0.537, 0.459, 0.531 mm로 측정되었다. 곁사슬이 짧으면 필름이 얇게 형성되고, 길면 필름형성을 방해하여 탄소수가 8개일 때의 값이 제일 좋게 나타났다. ZDDP의 경우 동일한 조건에서 WSD의 값이 0.563 mm로 측정되었고, 합성한 BAPA의 화합물이 마모억제용 첨가제로 더 우수한 성능을 갖는다는 것을 확인하였다.

• Journal of the Korean Wood Science and Technology
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• 제48권6호
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• pp.888-895
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• 2020

Ulmus genus has excellent various physiological activities, including anti-ulcer, antioxidant, antibacterial, anti-cancer, immunity, and homeostasis maintenance effects, and it is known to have many additional drug effects And one of reasons for these excellentbiological activities is a flavan-3-ol chemical group in Ulmus genus. In this study a new flavan-3-ol compound was identified in Ulmus davidiana var. japonica. A flavan-3-ol,(2R,3S)-7-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5-diol, named as catechin 7-O-beta-D apiofuranoside, was isolated from the stems and barks of Ulmus davidiana var. japonica for. suberosa, which is a species belonging to the genus Ulmus, growing throughout the Korea peninsula. The structure was elucidated by various spectroscopic methods including high-resolution TOF mass spectrometry, ¹H-NMR and ¹³C-NMR spectrometry and comparison with chemical structures of defined compounds.

• Korean Chemical Engineering Research
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• 제52권4호
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• pp.451-458
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• 2014

Isophrone diisocyanate (IPDI), polycarbonate diol (PCD)과 dimethylol propionic acid (DMPA)를 출발물질로 하여 수분산 폴리우레탄(waterborne polyurethane dispersion, WPUD)을 합성하였다. 이 WPUD에 아크릴 단량체인 methyl methacrylate (MMA), 2-hydroxyethyl methacrylate (HEMA)와 butyl acrylate (BA)를 각각 첨가하여 다양한 종류의 수분산 아크릴 폴리우레탄(waterborne acrylic polyurethane dispersion, AUD)을 합성하였다. 이 AUD와 물에 분산된 다중벽 탄소나노튜브(multi-walled carbon nanotube, MWCNT)를 혼합하여 전도성 코팅 용액을 제조한 후 polycarbonate 시트 위에 도포하여 코팅 도막을 형성하고 물성을 살펴보았다. AUD로부터 제조된 코팅 도막의 연필경도, 내마모성 및 내약품성은 WPUD 보다 향상되었으나, 전기 전도도는 감소하였다. 또한 아크릴 단량체의 종류 변화 실험에서는 코팅 도막의 연필경도는 HEMA를 사용한 경우가 가장 우수하였으나, 내마모성, 내약품성 및 전기 전도도는 MMA를 사용한 경우가 가장 우수하였다.