• Preventive Nutrition and Food Science
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• 제15권2호
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• pp.92-97
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• 2010

Luteolin and chicoric acid are the most abundant phytochemicals in dandelion (Taraxacum officinale) leaf. In this study, four kinds of extraction methods [hot water, ambient temperature (AT) water, ethanol, and methanol] were applied to analyze the contents of both phytochemicals and verify their anti-inflammatory and antioxidative activities. The methanol extract showed the most potent nitric oxide (NO) inhibitory effect. The luteolin and chicoric acid concentrations were 3.42 and $12.86\;{\mu}g/g$ dandelion leaf in the methanol extract. The NO-suppressive effect of luteolin and chicoric acid was identified in a dose-dependent manner with $IC_{50}$ values of $21.2\;{\mu}M$ and $283.6\;{\mu}M$, respectively, in lipopolysaccharide (LPS)-stimulated RAW 264.7 cells without cytotoxicity. Malondialdehyde (MDA) concentration, as an index for free radical injury on cell membrane, was also dose-dependently inhibited by the two compounds. The suppressive effect was further examined using mRNA and protein expression levels, which were attributable to the inhibition of inducible nitric oxide synthase (iNOS). These results suggest that two phytochemicals in dandelion leaf, luteolin and chicoric acid, may play an important role in the amelioration of LPS-induced oxidative stress and inflammation.

• Natural Product Sciences
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• 제21권1호
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• pp.42-48
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• 2015

Lactuca raddeana (Compositae) is used to treat obesity and complications due to diabetes. The five phenolic compounds including chlorogenic acid, chicoric acid, luteolin 7-O-glucoside, luteolin 7-O-glucuronide, luteolin were qualitatively identified by LC-ESI-MS analysis. The contents were quantitatively determined by HPLC, under the condition of a Capcell Pak C18 column ($5{\mu}m$, $250mm{\times}4.6mm\;i.d.$) and a gradient elution of 0.05% trifluoroacetic acid (TFA) and 0.05% TFA in $MeOH-H_2O$ (60 : 40). The contents of chicoric acid (100.99 mg/g extract) and luteolin 7-O-glucoside (101. 69 mg/g extract) were high, while those of other three phenolic substances were very low. The 3T3-L1 adipocyte cells treated with chicoric acid and luteolin 7-O-glucuronide significantly suppressed the accumulation of fat, suggesting they are effective against obesity. Since high level of peroxynitrite (ONOO) causes cardiovascular disease in obese patients, its scavenging activity was also studied.

• 대한본초학회지
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• 제32권5호
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• pp.27-38
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• 2017

Objective : In the present study, we examined whether Canavalia gladiata D.C. (CG) and Arctium lappa L., Redix (AL) mixture (CGAL), their components, lupeol and chicoric acid, regulate immune system and suppress the tumor in vitro and in vivo. Methods : LPS-induced reactive oxygen species (ROS) and nitric oxide (NO) were measured after treatment with CG extract (CGE), CGAL, lupeol, chicoric acid and lupeol and chicoric acid mixture (lupeol+CA) in Raw264.7 cell. To determine the effect of CGE on immune responses, immune cell population and IgG production were assessed in mice. To investigate the effect of CGAL and their component on anti-tumor activity, tumor volume and weight were measured, cell cycles and immune cell population were analyzed in MC38 injected tumor bearing mice. Also, NK cell activity was determined in splenocyte isolated from tumor bearing mice. Results : CGE, CGAL, lupeol, chicoric acid and lupeol+CA decreased the LPS-induced ROS and NO production without cell toxicity in RAW264.7 cells. CGE increased the immune cell populations of $CD4^+T$, $CD8^+T$ and macrophages in various immune organ of mice. In tumor bearing mice, CGAL, lupeol, chicoric acid and lupeol+CA suppressed tumor volume and weight. In cell cycle analysis, they decreased the percentages of S phase. In addition, CGAL, lupeol, chicoric acid and lupeol+CA immune cell populations of $CD4^+T$, $CD8^+Tcell$, NK cell and macrophage in tumor as well as NK cell activity. Conclusion : CGAL and its compounds may enhance immune responses and suppress tumor growth, and may be capable of developing health functional foods.

• 한국식품저장유통학회지
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• 제18권1호
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• pp.53-58
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• 2011

신선한 울릉도 민들레 뿌리를 70% ethanol로 침지 추출하여 얻어진 추출물을n-hexane, EtOAc, n-BuOH로 순차용매 분획하였다. 이중 상대적으로 높은 pancreatic lipase 저해활성을 나타낸 EtOAc 분획에 대해 Toyopearl 및 $C_{18}$겔을 활용한 column chromatography를 수행하여 5종의 페놀성 화합물을 분리하였다. 각 화합물의 화학구조는 NMR 스펙트럼 데이터 해석 및 표품과의 HPLC 직접 비교를 통하여 3,5-di-O-caffeoylquinic acid, chicoric acid, caffeic acid, protocatechuic aldehyde, luteolin 으로 동정하였다. 이들 화합물중 3,5-di-O-caffeoylquinic acid 는 $IC_{50}$ 값이 $65.1\;{\pm}0.7\; {\mu}M$로 가장 강한 효능을 나타내었으며, 다음으로 tartaric acid의 수산기에 2분자의 caffeic acid가 결합한 chicoric acid 의 IC50 값이 $126.3{\pm}2.3{\mu}M$의 저해능을 나타내었다. 민들레 뿌리의 EtOAc 가용부에에 존재하는 caffeic acid 유도체가 pancreatic lipase 저해활성 물질임을 확인하였으며, 이들 활성은 caffeic acid가 결합한 quinic acid 및 tatrtaric acid 등의 구성화합물에 따라 다름이 시사되었다. 향후 이들 활성물질의 활성 기작에 대한 연구가 필요하며 본 연구결과는 보다 우수한 pancreatic lipase 저해능을 가지는 새로운 선도화합물 발굴을 위한 기초자료로 이용될 수 있을 뿐만 아니라 울릉도에 자생하는 민들레 뿌리의 식물 화학적 성분에 대한 기초자료로 이용될 수 있을 것으로 사료된다.

• 생약학회지
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• 제42권1호
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• pp.38-45
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• 2011

Mountainous vegetables are usually used in the early stage of plant growth. We attempted to identify the quantity of polyphenols (caffoeoylquinic acids (CQs) and flavonoids) and peroxynitrite scavenging effect ($ONOO^-$) of eight Korean mountainous vegetables. The prominent characteristics were as follows: Only the roots of two plants Taraxacum platycarpum and Ixeris dentata contained chicoric acid. Five CQs were identified in the leaves of Cacalia firma whereas only 3-p-coumaroylquinic acid in the petioles of the plant was shown. The quantities of polyphenols such as quinic acid or tartaric acid derivatives in the mountainous vegetables were generally high, though those of flavonoids were very low. The $IC_{50}$ of chlorogenic acid, chicoric acid and kaempferol were 0.31, 0.12 and $0.25\;{\mu}g/ml$, respectively.

• 약학회지
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• 제53권2호
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• pp.89-92
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• 2009

Dicaffeoyltartaric acid has a structural feature consisting of two caffeic acid units separated by tartaric acid linker and has been found to be a potent inhibitor of HIV-1 integrase and an antioxidant. In this study, bis(pyronyl)acrylic acid esters joined through a 5-membered ring as a linker were synthesized as the analogues of dicaffeoyltartaric acid.

• Natural Product Sciences
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• 제21권3호
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• pp.155-161
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• 2015

Peroxynitrite (ONOO⁻)-scavenging activities of nine Compositae herbs consisting of three Ixeris, two Youngia, two Cirsium and one of each Lactuca and Taraxacum species were evaluated. The contents of their ONOO⁻ scavengers in the extracts were also determined on a HPLC using seven standard compounds, chlorogenic acid (CGA), chicoric acid (CA), luteolin 7-glucoside (luteolin-7-glc), luteolin 7-glucuronide (luteolin-7-glcU), luteolin, linarin and pectolinarin. Five of those compounds exhibited potent ONOO⁻-scavenging activities: IC₅₀, CA (0.76 μM), CGA (1.34 μM), luteolin (0.81 μM), luteolin-7-glc (0.86 μM) and luteolin-7-glcU (3.13 μM). Both CA and luteolin-7-glc were highly contained in I. dentata (19.71 mg/g and 13.58 mg/g, respectively), I. dentata var. albiflora (17.58 mg/g and 23.83 mg/g, respectively) and I. sonchifolia (65.71 mg/g and 6.99 mg/g, respectively). Among the nine herbs, those three Ixeris species had very low IC₅₀ values over the range of 0.48 - 1.74 μg/mL, suggesting that they could be potential therapeutic vegetables, particularly for preventing diabetic complications or obesity, which can be caused by an excess production of ONOO⁻.

• 한국식품영양학회지
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• 제32권6호
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• pp.717-729
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• 2019

The chemical informs about 70 individual phenolic compounds were constructed from various lettuce samples based on literature sources and analytical data. A total of 30 phenolic compounds including quercetin 3-O-glucuronide, quercetin 3-O-(6''-O- malonyl) glucoside, cyanidin 3-O-(6''-O-malonyl)glucoside, chlorogenic acid and chicoric acid as major components were identified in 6 lettuce samples from Korea using UPLC-DAD-QToF/MS on the basis of constructed library. Among these, quercetin 3,7-di-O-glucoside(m/z 627 [M+H]⁺), quercetin 3-O-(2''-O-malonyl)glucoside(morkotin C, m/z 551 [M+H]⁺), quercetin 3-O-(6''- O-malonyl)glucoside methyl ester(m/z 565 [M+H]⁺), 5-O-cis-p-coumaroylquinic acid(m/z 339 [M+H]⁺) and 5-O-caffeoylquinic acid methyl ester(m/z 369 [M+H]⁺) were newly confirmed from the lettuce samples. In total content of phenolic compounds, 4 red lettuce samples(2,947.7~7,535.6 mg/100 g, dry weight) showed higher than green lettuce(2,687.3 mg) and head lettuce(320.1 mg).

• 한국식품영양과학회지
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• 제44권8호
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• pp.1157-1164
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• 2015

본 연구는 민들레 지상부와 지하부의 혼합 추출에 따라 항산화 활성에 상승 효과가 있는지 확인하기 위해 민들레 지상부와 지하부를 9:1 또는 8:2 중량 비로 혼합한 혼합 추출분말과 지상부, 지하부 단독 추출분말의 생리활성 성분을 분석하고 항산화 활성을 비교하였다. 민들레의 대표적인 성분으로 알려진 luteolin, chicoric acid를 분석한 결과 지상부의 함량이 지하부보다 월등히 높았으며 혼합 추출분말의 함량은 지상부보다 낮고 지하부보다 높았다. HepG2 cell에서의 산화적 스트레스 방어 효과 및 CAT 활성을 확인하여 효소적 항산화 시스템에 대한 영향을 평가한 결과 민들레 지상부와 지하부 간에 CAT 활성의 차이는 없었으나 혼합 추출분말의 활성이 현저히 증가하여 혼합 추출을 통한 상호작용이 영향을 미쳤을 것으로 보였다. DPPH 라디칼 소거활성 및 지질과 산화 억제에 대한 $EC_{50}$ 분석 결과에서도 지상부보다 혼합 추출분말의 항산화능이 유의적으로 높은 것으로 나타났다. 항산화능 평가 항목에 따라 8:2 혼합과 9:1 혼합의 활성에 차이가 있었는데 DPPH 라디칼 소거활성에서는 9:1 혼합의 $EC_{50}$이 더 낮고 지질과산화 억제 활성에서는 8:2 혼합의 $EC_{50}$이 더 낮았다. 이와 같이 민들레 지상부와 지하부를 혼합하여 추출할 때 지상부, 지하부 단독 추출물보다 항산화 활성이 상승한 것은 청미래 덩굴잎 열수추출물과 토복령 열 수추출물을 혼합하였을 때 EDA 및 FRAP와 같은 항산화 활성이 높아진다는 연구 및 로스팅 커피와 홍삼 혼합 추출물의 항산화 효과 평가에서 커피와 홍삼의 함량 조절을 통해 항산화력을 변화시킬 수 있다는 연구에서 2개 이상의 식품 또는 천연물을 혼합할 때 항산화 활성에 상승효과를 나타낸다는 결과와 유사한 것으로서 민들레 지상부와 지하부에 함유된 각기 다른 화합물들의 상호 작용으로 인해 항산화 활성이 상승한 것으로 보였다. 그러나 혼합 추출을 통한 생리활성 물질의 변화 및 상호 작용에 대해서는 추가적인 연구를 통해 확인이 필요하겠다. 본 연구는 기존의 민들레 전초 또는 각 부위별 항산화능을 평가한 연구와는 달리 민들레 지상부와 지하부를 9:1 또는 8:2로 혼합한 추출분말이 단독 추출 분말보다 항산화 활성이 높은 것을 확인함으로써 지상부, 지하부의 혼합을 통해 항산화 활성에 시너지 효과가 있는 것을 확인하였다. 지질과산화 억제 활성, HepG2 cell에서의 산화적 스트레스 방어 효과 및 catalase 활성에서 지상부와 지하부 혼합 비율에 따른 유의적인 차이 없이 모두 지상부보다 높은 활성을 보였고 DPPH 라디칼 소거활성과 같은 총 항산화능 평가에서는 8:2 혼합보다 9:1 혼합 추출분말의 활성이 유의적으로 높으며 수율도 9:1 혼합 추출분말이 8:2 혼합보다 약 1.5배 가량 높게 나타나 9:1 혼합 추출분말이 상업적인 항산화 활성 소재로써의 가치가 더 높을 것으로 기대된다.