• 제목/요약/키워드: caffeoylquinic acid

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엄나무 유래 신규 항산화 활성물질 (Antioxidants Isolated from Kalopanax pictus)

  • 김영희
    • 한국자원식물학회지
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    • 제11권
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    • pp.89-109
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    • 1998
  • Screening of new antioxidants form oriental medicines resulted in the isolation of a new antioxidative compound and eight known compounds from the stem bark of Kalopanax pictus. On the basis of various spectrosopic studies, the structure of the new compound was determined to be 4-rhamnose-3,5-dimethoxybenzoic acid methly ester. Other known compounds were identified as ferulic acid, 4,5,6,-trihydroxyflavanone, 2', 4',4' -trihydroxychalcone, caffeic acid, coniferyl alcohol, syringin, 1,3-di-O-caffeoylquinic acid. These compounds showed lipid peroxidation inhibitory acitivity in rat liver microsomes and free radical scavenging acitivity.

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Antioxidant and Neuronal Cell Protective Effects of Columbia Arabica Coffee with Different Roasting Conditions

  • Jeong, Ji Hee;Jeong, Hee Rok;Jo, Yu Na;Kim, Hyun Ju;Lee, Uk;Heo, Ho Jin
    • Preventive Nutrition and Food Science
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    • 제18권1호
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    • pp.30-37
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    • 2013
  • In vitro antioxidant activities and neuronal cell protective effects of ethanol extract from roasted coffee beans were investigated. Colombia arabica coffee (Coffea arabica) green beans were roasted to give medium ($230^{\circ}C$, 10 min), city ($230^{\circ}C$, 12 min) and french ($230^{\circ}C$, 15 min) coffee beans. Total phenolics in raw green beans, medium, city and french-roasted beans were $8.81{\pm}0.05$, $9.77{\pm}0.03$, $9.92{\pm}0.04$ and $7.76{\pm}0.01$ mg of GAE/g, respectively. The content of 5-O-caffeoylquinic acid, the predominant phenolic, was detected higher in medium-roasted beans than others. In addition, we found that extracts from medium-roasted beans particularly showed the highest in vitro antioxidant activity on ABTS radical scavenging activity and FRAP assays. To determine cell viability using the MTT assay, extracts from medium- roasted beans showed higher protection against $H_2O_2$-induced neurotoxicity than others. Lactate dehydrogenase (LDH) leakage was also inhibited by the extracts due to prevention of lipid peroxidation using the malondialdehyde (MDA) assay from mouse whole brain homogenates. These data suggest that the medium-roasting condition to making tasty coffee from Columbia arabica green beans may be more helpful to human health by providing the most physiological phenolics, including 5-O-caffeoylquinic acids.

Validation of High-Performance Liquid Chromatography Analysis on Phenolic Substances of Cirsium setidens and Sedative Effect of Pectolinarin as the Active Principle

  • Nugroho, Agung;Kim, Myung-Hoe;Lim, Sang-Cheol;Choi, Jong-Won;Choi, Jae-Sue;Park, Hee-Juhn
    • 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.

섬쑥부쟁이로부터 건강기능식품 제조를 위한 추출법 개발 (Development of the Extraction Method for a Functional Food from Aster glehni)

  • 박희준
    • 한국자원식물학회:학술대회논문집
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    • 한국자원식물학회 2011년도 임시총회 및 추계학술발표회
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    • pp.19-19
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    • 2011
  • 예비실험 중 한국의 울릉도에 자생하고 취나물로 이용되고 있는 섬쑥부쟁이(Aster glehni Franchet et Sckmidt, Compositae)가 페놀성 화합물 함량이 높고 peroxynitrite 소거효과가 높았기 때문에 이를 이용한 추출물의 제조를 통한 건강기능식품을 창출하고자 하였다. 건강식품을 위한 추출물 제조를 위하여 물과 에탄올만을 이용하여 페놀성 화합물 고함유 추출물의 제조가 가능하고 높은 peroxynitrite 소거효과를 나타내는 추출물을 결정하고자 하였다. 즉, 추출용매로 Water-EtOH 비율을 조절하여 추출하여 추출물의 함량, HPLC를 이용한 caffeoylquinic acid(CQ) 화합물의 함량분석 및 peroxynitrite 소거효과를 비교하였다. Water-EtOH (7:3)으로 추출한 섬쑥부쟁이 추출물은 CQ 함량이 높고, 높은 peroxynitrite 소거효과, 항경련효과, 진정효과 및 항비만효과 등이 나타났다. 건강기능식품을 위한 추출물 제조시 한국에서는 물과 에탄올만이 허용되기 때문에 CQ 함량이 높은 추출물의 제조가 가능하고 높은 peroxynitrite 소거효과를 유지할 수 있는가에 관한 실험 이외에 마우스에서 선택된 추출물의 진정효과 및 항경련효과 실험을 수행하였다. 진정효과와 항경련효과를 위하여 마우스에서 각각 pentobarbital로 유도한 수면연장효과와 PTZ로 유도한 경련에 대한 효과를 측정하여 유의성있는 활성이 확인되었으므로 이 추출물을 이용한 건강기능식품으로의 이용이 가능하다고 생각된다.

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백출 지상부의 항산화 성분 (Anti-oxidative Compounds from The Aerial Parts of Atractylodes macrocephala Koidzumi)

  • 한정훈;김진효;김성건;정성희;김도훈;김기은;황완균
    • 약학회지
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    • 제51권2호
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    • pp.88-95
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    • 2007
  • Atractylodes macrocephala has been used for renal anorexia, gastroenteritis, cold, dyspepsia in Korean folk medicine. Specially aerial parts has been eaten as edible mountain herbs. In order to investigate the efficacy of antioxidant activity the activity guided fractionation and isolation of physiologically active substance were peformed. For the investigation of the active components from Atractylodes macrocephala MeOH extracts of aerial parts of Atractylodes macrocephala Koidzumi L. were suspended with H$_2$O, partitioned by CHCl$_3$. In order to investigate the efficacy of antioxidative activity the activity guided fractionation and isolation of physiologically active substance were peformed. CHCl$_3$, H$_2$O, 30% MeOH, 60% MeOH, MeOH fractions were examined antioxidative activity by DPPH method. It was revealed that 30% MeOH and 60% MeOH fractions have significantly antioxidant activity. From 30% MeOH and 60% MeOH fraction, six flavonoids (7-methoxy-pinocembrin-7-O-${\beta}$-D-glucopyranoside, apige nin-8-C-${\beta}$-D-glucopyranoside, 4'-caffeoyl-luteolin-6-glucopyranoside, luteloin-6-C-${\beta}$-D-glucopyranoside, apigenin-6-C-${\beta}$-D-glucopyranoside, luteolin) and four phenylpropanoids (3-feruloylquinic acid, 4,5-di-O-caffeoylquinic acid, feruloyl acid, 3,5-di-O-caffeoylquinic acid) were isolated. To investigate the antioxidant activities of each compounds, we measured radical scavening activity with DPPH method and anti-lipid peroxidative efficacy on low density lipoprotein (LDL) with TBARS assay. Six compounds (III, IV, V, VI, IX, X) which have antioxidant factor showed significant activities.

망초(Conyza canadensis) Ethyl Acetate 추출물의 항산화성 물질의 분리와 동정 (Isolation and Structural Identification of Antioxidant Substances from Ethyl Acetate Extract of Conyza canadensis)

  • 송현숙
    • 한국자연치유학회지
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    • 제12권1호
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    • pp.7-15
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    • 2023
  • 배경: 야생 망초(줄기와 잎)의 성분을 분석한 결과에서 생리활성 성분의 함유가 확인되어 화합물의 규명이 필요하다. 목적: 망초에는 항산화성 물질이 함유되었다는 선행연구 결과가 있어서 화합물의 분자적 구조를 연구하는 것이 목적이었다. 방법: 망초(줄기와 잎) 초음파 분쇄물을 1차로 90% 메탄올로, 다음에 유기 용매로 추출하였다. 다음에 HPLC, LC/MS 크로마토그래피 등으로 분획하였고, 분핵물을 NMR 분광기로 정밀 분석하여 분자의 구조를 동정하였다. 결과: 망초 100 g을 초음파기로 파쇄하여 90% methanol로 추출하고, 감압 농축하여 조 추출물 11.96 g을 얻었다. 조추출물을 유기용매로 재추출하여 n-hexane으로 123.8 mg, dichloromethane으로 448.2 mg, ethyl acetate(EA)로는 1047.7 mg, butanol로는 2563.8 mg, water로는 7.04 g을 얻었다. EA 추출물을 LC-MS 크로마토그래피로 분획하고, 정밀 분획하여 F1~F20의 20개를 얻었다. F15 분획을 다시 분획하여 9개를 얻었다. F17 분획을 재분획하여 10개의 분획을 얻었다. F15-7 분획물을 LC-MS 분석과 NMR 분광기로 분석한 결과는 이 화합물의 구조가 3,5-di-caffeoylquinic acid로 확인되었다. F17-4와 F17-5의 구조를 조사한 결과는 Quercetin-3-o-β-galactose로 동정 되었다. F17-10의 구조를 확인한 결과는 1,3,4-tri-caffeoylquinic acid로 확인되었다. 결론: 본 연구에서 망초 성분에도 항산화성 물질이 있었으며, 이의 활용성을 기대하며, 식물에는 항산화성 물질인 phenol 성분을 다양하게 함유하였다.

옥수수 수염에서 Maysin 및 유사물질의 동정 (Identification of Maysin and Related Flavonid Analogues in Corn Silks)

  • 김선림;;김이훈;박철호
    • 한국작물학회지
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    • 제45권3호
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    • pp.151-157
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    • 2000
  • 옥수수수염에 함유되어 있는 maysin 및 유사 flavonoid 물질의 분리 및 정제법을 확립하여 신품종 육성의 기초적인 자료를 제공하고자 본 시험을 수행하였으며 얻어진 결과를 요약하면 다음과 같다. 1. Preparative $C_{18}$ 컬럼에서 10% MeOH에 용출된 물질은 neochlorogenic acid, chlorogenic acid 및 4-caffeoylquinic acid였으며 30% MeOH로 용출된 물질은 rhamnosyl isoorientin이었고 maysin은 50%의 MeOH에서 용출되었다. 2. Silicic acid 컬럼으로 maysin 조추출물의 1차 정제시 100% ethyl acetate 500$m\ell$로 컬럼에 흡착되어 있는 maysin을 용출시켰으며, 이때 수거된 maysin의 순도는 75% 이상에 해당하였고, $C_{18}$ 컬럼($\frac{1}{2}$$\times$43")으로 maysin의 2차 정제시 maysin의 순도는 95% 이상에 달하였다. 3. FAB-MS에 의한 maysin의 분자량은 577M+H m/z이고, fragmentation으로 보아 431M+H m/z은 rhamnose에 해당하였고, $^1$H 및 $^{13}$C NMR에 의한 spectrum을 확인한 결과 분리한 물질이 maysin임을 확인할 수 있었다. 있었다.

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Chemical Constituents from the Aerial Parts of Bupleurum falcatum L. and Biological Evidences

  • Tung, Nguyen Huu;Uto, Takuhiro;Morinaga, Osamu;Shoyama, Yukihiro
    • Natural Product Sciences
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    • 제21권2호
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    • pp.71-75
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    • 2015
  • In this study, phytochemical investigation on the aerial parts of Bupleurum falcatum resulted in the isolation of fourteen compounds including three quinic acid derivatives (1 - 3), five flavonoids (4 - 8), three monoterpene glycosides (9 - 11), and three saikosaponins (12 - 14). Compound 1 was first isolated from nature and unambiguously determined to be 3-O-feruloyl 5-O-caffeoylquinic acid on the basis of the extensive spectroscopic evidence. Biological testing revealed that saikosaponin A (12) and saikosaponin D (13) showed moderate antiproliferative effects on HL-60 and HepG2 cancer cell lines.

Isolation and Antioxidative Activities of Caffeoylquinic Acid Derivatives and Flavonoid Glycosides from Leaves of Sweet Potato (Ipomoea batatas L.)

  • Kim, Hyoung-Ja;Jin, Chang-Bae;Lee, Yong-Sup
    • Biomolecules & Therapeutics
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    • 제15권1호
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    • pp.46-51
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    • 2007
  • Bioassay-directed chromatographic fractionation of an ethyl acetate extract from leaves of sweet potato (Ipomoea batatas L.) afforded six quinic acid derivatives: 3,5-epi-dicaffeoylquinic acid (1), 3,5-dicaffeoylquinic acid (2), methyl 3,5-O-dicaffeoylquinate (3), methyl 3,4-dicaffeoylquinate (4), methyl 4,5-dicaffeoylquinic acid (5),4,5-dicaffeoylquinate (6), and two phenolic compounds: caffeic acid (7) and caffeic acid methyl ester (8) together with three flavonoids: quercetin 3-O-${\beta}$-D-glucopyranoside (9), quercetin 3-O-${\beta}$-D-glucopyranoside, isoquercitrin (10) and kaempferol 3-O-${\beta}$-D-glucopyranoside (11). The structures of these compounds were elucidated by the aid of spectroscopic methods. These compounds were assessed for antioxidant activities using three different cell-free bioassay systems. All isolates except 11 showed potent DPPH and superoxide anion radicals scavenging, and lipid peroxidation inhibitory activities. 3,5-epi-DCQA (1) and methyl quinates (3-5) along with flavonoide 9 were isolated for the first time from this plant.

Gymnaster koraiensis and its major components, 3,5-di-O-caffeoylquinic acid and gymnasterkoreayne B, reduce oxidative damage induced by tert-butyl hydroperoxide or acetaminophen in HepG2 cells

  • Jho, Eun Hye;Kang, Kyungsu;Oidovsambuu, Sarangerel;Lee, Eun Ha;Jung, Sang Hoon;Shin, Il-Shik;Nho, Chu Won
    • BMB Reports
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    • 제46권10호
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    • pp.513-518
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    • 2013
  • We investigated the protective effects of Gymnaster koraiensis against oxidative stress-induced hepatic cell damage. We used two different cytotoxicity models, i.e., the administration of tert-butyl hydroperoxide (t-BHP) and acetaminophen, in HepG2 cells to evaluate the protective effects of G. koraiensis. The ethyl acetate (EA) fraction of G. koraiensis and its major compound, 3,5-di-O-caffeoylquinic acid (DCQA), exerted protective effects in the t-BHP-induced liver cytotoxicity model. The EA fraction and DCQA ameliorated t-BHP-induced reductions in GSH levels and exhibited free radical scavenging activity. The EA fraction and DCQA also significantly reduced t-BHP-induced DNA damage in HepG2 cells. Furthermore, the hexane fraction of G. koraiensis and its major compound, gymnasterkoreayne B (GKB), exerted strong hepatoprotection in the acetaminophen-induced cytotoxicity model. CYP 3A4 enzyme activity was strongly inhibited by the extract, hexane fraction, and GKB. The hexane fraction and GKB ameliorated acetaminophen-induced reductions in GSH levels and protected against cell death.