• Natural Product Sciences
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• 제5권2호
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• pp.80-84
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• 1999

Peroxynitrite is a cytotoxic intermediate produced by the reaction between the superoxide anion radical and nitric oxide. Flavonoids (afzelin, quercitrin and quercetin 3-O-sambubioside), and chlorogenic acid and its methyl ester obtained from leaves of loquat (Eriobotrya japonica) have recently been shown to scavenge 1,1-diphenyl-2-picrylhydrazyl radical and to inhibit lipid peroxidation in mouse liver homogenate. The aim of this study is to investigate the inhibitory effects of the above components on peroxynitrite produced stimulated by 3-morpholinosydnonimine (SIN-1) to produce superoxide anion radical and nitric oxide at the same time. In addition, the present study tests whether or not the components directly scavenge peroxynitrite itself. The results showed that the components with the aromatic ortho-dihydroxyl groups (catechol) were more potent inhibitors of peroxynitrite formation by SIN-1. In particular, the methyl ester form of chlorogenic acid showed the most potent inhibition. At $5\;{\mu}M$ concentration, the order of minimizing peroxynitrite formation were : methyl chlorogenic acid > quercitrin > quercetin 3-O-sambubioside > chlorogenic acid > afzelin. Authentic peroxynitrite was directly scavenged by the components in a manner similar to peroxynitrite formation by SIN-1. In particular, when compared with penicillamine as a positive control, methyl chlorogenate was as effective in inhibiting peroxynitrite formation and approximately 2 times more effective in scavenging an authentic peroxynitrite. These results demonstrate therefore, that components extracted from the leaves of Eriobotrya japonica effectively scavenged peroxynitrite.

• 한국작물학회지
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• 제59권4호
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• pp.435-444
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• 2014

본 연구는 옥수수수염에 함유된 flavonoid 계열의 물질인 maysin, luteolin 7-O-neohesperidoside, luteolin 3'-methyl ether 7-glucuronosyl-($1{\rightarrow}2$)-glucuronide 및 polyphenol성 물질인 chlorogenic acid을 추출 및 분리하는 방법에 관한 것으로, 얻어진 결과를 요약하면 다음과 같다. 1. 수정되지 않은 옥수수수염의 메이신 함량은 출사 후 3일에 함량이 최대치에 도달하고, 그 후 감소되는 것으로 나타났으며, 방임수분된 옥수수수염의 메이신 함량은 출사후 지속적으로 감소되는 것으로 나타나 화분의 수분 여부에 따라 메이신 함량에 많은 차이가 있음을 알 수 있었다. 2. 채취한 옥수수수염에 에탄올을 가하여 9일간 상온에서 추출 후 엽록소, 지질 및 당질 등을 제거시키고, $C_{18}$ column chromatography를 수행하여 분취물 I, II, III, IV를 얻었다. 3. 분취물의 흡광도를 분석한 결과 분취물 I은 327 nm 및 239 nm에서 최대 흡수 파장(${\lambda}_{max}$)을 나타내었고, 분취물 II는 339 nm 및 274 nm, 분취물 III는 345 nm 및 277 nm, 분취물 IV는 352 nm, 270 nm, 및 257 nm 에서 최대 흡수파장을 나타내었다. 4. 분취물 I은 m/z $355[M+H]^+$인 chlorogenic acid(3-(3,4-dihydroxycinnamoyl)quinic acid, $C_{16}H_{18}O_9$)이었으며, 분취물 II는 chlorogenic acid와 m/z $653[M+H]^+$인 luteolin 3'-methyl ether 7-glucuronosyl-($1{\rightarrow}2$)-glucuronide ($C_{28}H_{28}O_{18}$)를 함유한 혼합물, 분취물 III는 chlorogenic acid와 m/z $595[M+H]^+$인 luteolin 7-O-neohesperidoside ($C_{27}H_{30}O_{15}$) 및 luteolin 3'-methyl ether 7-glucuronosyl-($1{\rightarrow}2$)-glucuronide를 함유한 혼합물이었고, 분취물 IV는 m/z $577[M+H]^+$인 maysin ($C_{27}H_{28}O_{14}$, 2"-O-${\alpha}$-L-rhamnosyl-6-C-(6-deoxy-xylo-hexose-4-ulosyl)luteolin 임을 각각 확인 하였다. 5. 옥수수수염의 알코올 추출물로부터 분리된 분취물 I은 옥수수수염 생체 100 g 당 (수분함량 약 92%) 35 mg/100 g, 분취물 II는 48 mg/100 g, 분취물 III는 46 mg/100 g, 분취물 IV는 138 mg/100 g을 얻을 수 있었다.

• Archives of Pharmacal Research
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• 제22권2호
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• pp.213-218
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• 1999

The antioxidant activity of Eriobotrya japonica was determined by measuring the radical scavenging effect on DPPH (1,1-diphenyl-2-picrylhydrazyl) radical and lipid peroxidation produced when mouse liver homogenate was exposed to the air at $37^{\circ}C$, using 2-thiobarbituric acid (TBA). The methanol extract and its factions of Eriobotrya japonica leaves showed strong antioxidant activity. The antioxidant activity of EtOAc and n-BuOH soluble fractions were stronger than the others, and were further purified by repeated silica gel, MCl gel CHP-20P, and Sephadex LH-20 column chromatography. Antioxidant chlorogenic acid, quercetin-3-sambubioside from n-BuOH fraction and methyl chlorogenate, kaempferol- and quercetin-3-rhamnosides, together with the inactive ursolic acid and$ 2{\alpha}$-hydroxyursolic acid from EtOAc fraction were isolated. Antioxidant flavonoids and chlorogenic acid also showed prominent inhibitory activity against free radical generation in dichlorofluorescein (DCF) method.

• Natural Product Sciences
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• 제16권1호
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• pp.20-25
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• 2010

Fourteen compounds were isolated from the n-BuOH fraction of the roots of Aralia cordata (syn. = A. continentalis). Through spectroscopic method, the chemical structures were elucidated as: caffeic acid (1), protocatechuic acid (2), thymidine (3), uridine (4), methyl-$\alpha$-D-fructofuranoside (5), a mixture (3 : 1) of $\beta$-D-fructopyranoside and $\beta$-D-fructofuranoside (6), 1-methyl 1,2,3,4-tetrahydro-$\beta$-carboline-3-carboxylic acid (7), methyl-$\beta$-D-fructofuranoside (8), sucrose (9), 5-caffeoylquinic acid (chlorogenic acid) (10), 3-caffeoylquinic acid (neochlorogenic acid) (11), 4-caffeoylquinic acid (cryptochlorogenic acid) (12), 3,5-di-O-caffeoylquinic acid (13), and 1-kestose [$\beta$-D-fructofuranosyl-($2{\rightarrow}1$)-$\beta$-D-fructofuranosyl-($2{\rightarrow}1$)-$\alpha$-D-glucopyranoside] (14). Among them, compounds 5, 7, 8, and 10 - 14 were isolated from this plant for the first time.

• 한국식품영양과학회지
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• 제45권8호
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• pp.1208-1213
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• 2016

천연물로부터 당뇨합병증에 효과적인 소재를 개발하기 위하여 본 연구를 수행하였으며, 울릉도산 마가목 열매의 80% methyl alcohol 추출물의 ethyl acetate 가용부로부터 최종 당화산물 생성 억제능($IC_{50}$; $181.2{\pm}2.8{\mu}g/mL$)을 확인하였다. 효능성분의 동정을 위하여 $C_{18}$ 겔 등을 활용한 column chromatography를 수행하여 3종의 페놀성 화합물을 분리하였고, 각 화합물의 화학구조는 NMR 스펙트럼 데이터 해석 및 표품과의 HPLC 직접 비교를 통하여 neochlorogenic acid(1), cryptochlorogenic acid(2) 및 chlorogenic acid (3)로 동정하였다. 이들 화합물에 대해 최종당화산물 생성억제능을 평가한 결과 neochlorogenic acid(1)가 가장 강한 $167.5{\pm}3.5{\mu}M$의 $IC_{50}$ 값을 나타내었고, cryptochlorogenic acid(2)는 $185.9{\pm}3.7{\mu}M$의 $IC_{50}$ 값을 나타내었다. 또한, 이들 물질에 대해 $ONOO^-$ 소거 활성을 평가한 결과 cryptochlorogenic acid(2)가 가장 강한 라디칼 소거 활성인 $4.0{\pm}0.2{\mu}M$의 $IC_{50}$ 값을 나타내었고, 구조이성질체인 neochlorogenic acid(1)가 $4.5{\pm}0.3{\mu}M$의 $IC_{50}$ 값을 나타내었으며, 이들 활성은 caffeic acid가 결합 양상에 따른 화합물의 구조에 따라 다름이 시사되었다. 향후 이들 활성 물질의 활성 기작에 대한 연구가 필요하며 본 연구 결과는 더욱 우수한 최종당화산물 생성 억제능을 가지는 새로운 선도화합물 발굴을 위한 기초자료로 이용될 수 있을 뿐만 아니라 당뇨합병증 예방 및 치료에 효과적인 천연물질의 상업화를 위한 기초자료로 이용될 수 있을 것으로 생각한다.

• Natural Product Sciences
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• 제15권4호
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• pp.234-240
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• 2009

Phytochemical investigation of the MeOH extract of the aerial parts of Bistorta manshuriensis resulted in the isolation of two cerebrosides, two lactams, six phenolic compounds and seven flavonoids. Their chemical structures were characterized by spectroscopic methods to be pinelloside (1), soyacerebroside I (2), pterolactam (3), 5-hydroxypyrrolidine-2-one (4), vanillic acid (5), caffeic acid methyl ester (6), protocatechuic acid (7), caffeic acid (8), 3,5-di-O-caffeoyl quinic acid methyl ester (9), chlorogenic acid methyl ester (10), avicularin (11), afzelin (12), quercetin (13), isoorientin (14), quercetin 3-O-${\beta}$-D-glucoside (15), quercitrin (16), and luteolin (17). The isolated compounds (1 - 4, 7, 12, 14) were isolated for the first time from this plant source and the compounds 1 - 4, 9 and 10 were first reported from the genus Bistorta. Compound 17 exhibited moderate cytotoxicity and compound 6 exhibited weak cytotoxicity against four human cancer cell lines in vitro using an SRB bioassay.

• Natural Product Sciences
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• 제17권4호
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• pp.342-349
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• 2011

This study was performed to determine the composition of phenolic substances contained in the leaves of Cirsium setidens (Compositae), validate the high-performance liquid chromatography (HPLC) method, and determine the in vivo sedative effect of the main component pectolinarin. Six phenolic compounds isolated from C. setidens were spectroscopically identified as chlorogenic acid (1), hyperoside (2), 3,4-di-O-caffeoylquinic acid (3), caffeic acid methyl ester (4), linarin (5), and pectolinarin (6) and then used as standard compounds for HPLC analysis. HPLC proved to be precise, accurate, and sensitive for the simultaneous analysis of the phenolic substances. In particular, six compounds showed good regression ($R^2$ > 0.999) within test ranges and recovery was in the range of 95.4 - 104.8%. The content of pectolinarin was considerably higher (156.48 mg/g) than those of other phenolic substances including the other flavone glycoside, linarin (18.99 mg/g). The contents of other phenolic substances, in order, were chlorogenic acid (8.41 mg/g), 3,4-di-O-caffeoylquinic acid (5.74 mg/g), hyperoside (4.33 mg/g), and caffeic acid methyl ester (0.51 mg/g). Oral administration with compound 6 (10 and 20 mg/kg) enhanced the sleeping time induced by pentobarbital in mice, indicating that it has a sedative effect.

• 한국자원식물학회지
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• 제20권3호
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• pp.221-225
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• 2007

The plant Ligularia fischeri var. spiciformis (Compositae) is a candidate for available functional foods. It has been used to treat diabetes mellitus and rheumatoid arthritis. We have reported the isolation of a new eremophilanolide named 6-oxoeremophilenolide and cytotoxic intermedeol together with the isolation of hydrophilic constituents, chlorogenic acid, 3,4-di-O-caffeoylquinic acie (3), and 5-O-[1-butyl]-3,4-di-O-caffeoylquinic acid. Compound 3 was again isolated by combination of silica gel- and ODS column chromatography for the anti-nociceptive action. Compound 3 and 4 were assayed in hot plate- and writhing tests in the rat. Although the three derivatives of caffeic acid exhibited significant anti-nociceptive effects at 10 mg/kg dose (i.p.),(activity potency: 4>3). These results suggest that compound 3 is responsible for at least rheumatoid arthritis, and caffeic acid moiety is the active moiety of dicaffeoylquinic acid.

• 통합자연과학논문집
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• 제10권1호
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• pp.1-6
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• 2017

Demand for a new anti-malarial drug has been dramatically increasing in the recent years. Plasmodium falciparum enoyl-acyl carrier protein reductase (PfENR) plays a vital role in fatty acid elongation process, which now emerged as a new important target for the development of anti-microbial and anti-parasitic molecules. In the present study, 19 compounds namely alginic acid, atropine, chlorogenic acid, chrotacumine A & B, coenzyme $Q_1$, 4-coumaric acid, curcumin, ellagic acid, embelin, 5-O-methyl embelin, eugenyl glucoside, glabridin, hyoscyamine, nordihydroguaiaretic acid, rohitukine, scopolamine, tlatlancuayin and ursolic acid were evaluated on their docking behaviour on P. falciparum enoyl-acyl carrier protein reductase (PfENR) using Auto dock 4.2. The docking studies and binding free energy calculations exhibited that glabridin gave the highest binding energy (-8.07 kcal/mol) and 4-coumaric acid in contrast showed the least binding energy (-4.83 kcal/mol). All ligands except alginic acid, ellagic acid, hyoscyamine and glabridin interacted with Gln409 amino acid residue. Interestingly four ligands namely coenzyme $Q_1$, 4-coumaric acid, embelin and 5-O-methyl embelin interacted with Gln409 amino acid residue present in both chains (A & B) of PfENR protein. Thus, the results of this present study exhibited the potential of these 19 ligands as P. falciparum enoyl-acyl carrier protein reductase (PfENR) inhibitory agents and also as anti-malarial agents.

• 생약학회지
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• 제47권1호
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• pp.92-101
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• 2016

In this study, an ultra-performance liquid chromatography-electrospray ionization-mass spectrometry (UPLC-ESI-MS/MS) method was established for simultaneous determination of the 25 marker components, including chlorogenic acid, gallic acid, oxypaeoniflorin, homogentisic acid, methyl gallate, caffeic acid, 3,4-dihydroxybenzaldehyde, paeoniflorin, albiflorin, liquiritin, nodakenin, ferulic acid, ginsenoside Rg1, liquiritigenin, coumarin, cinnamic acid, benzoylpaeoniflorin, ginsenoside Rb1, cinnamaldehyde, paeonol, glycyrrhizin, 6-gingerol, evodiamine, rutecarpine, and spicatoside A in traditional Korean formula, Onkyung-tang. All analytes were separated on a Waters Acquity UPLC BEH $C_{18}$ analytical column ($2.1{\times}100mm$, $1.7{\mu}m$) at $45^{\circ}C$ using a mobile phase of 0.1% (v/v) formic acid in water and acetonitrile with gradient elution. The MS analysis was carried out using a Waters ACQUITY TQD LC-MS/MS coupled with an electrospray ionization (ESI) source in the positive and negative modes. The flow rate and injection volume were 0.3 mL/min and $2.0{\mu}L$, respectively. The correlation coefficient of all analytes in the test ranges was greater than 0.98. The limits of detection and quantification values of the 25 marker compounds were in the ranges 0.03-19.43 and 0.09-58.29 ng/mL, respectively. As a result, methyl gallate, 3,4-dihydroxybenzaldehyde, evodiamine, and rutecarpine were not detected in this sample and the concentrations of the 21 compounds except for the above 4 compounds were $33.09-3,496.32{\mu}g/g$ in Onkyung-tang decoction. Among these compounds, paeonol was detected at the highest amount as a $3,496.32{\mu}g/g$.