• Title/Summary/Keyword: p-Hydroxycinnamic acid

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Anti-hyperglycemic and Antioxidative Activities of Phenolic Acid Concentrates of Rice Bran and Hydroxycinnamic Acids in Cell Assays (미강 페놀산 농축물과 Hydroxycinnamic Acids의 세포내 항당뇨 및 항산화 활성)

  • Jung, Eun-Hee;Ha, Tae-Yeol;Hwang, In-Kyeong
    • The Korean Journal of Food And Nutrition
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    • v.23 no.2
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    • pp.233-239
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    • 2010
  • Phenolic acid concentrates of rice bran(RB-ex) and hydroxycinnamic acids were investigated for their anti-hyperglycemic activities through glucose uptake and glucokinase activity using HepG2 cells and stimulatory effects on insulin secretion using HIT-T15 cells. RB-ex was prepared as an ethylacetate extract after alkaline hydrolysis and hydroxycinnamic acids, found as major compositions of RB-ex, such as ferulic acid(FA), sinapic acid(SA) and p-coumaric acid(p-CA) were investigated to compare with the properties of RB-ex. The properties of glucose uptake in HepG2 cells were examined in the absence of insulin and two different glucose concentrations(5.5 mM and 25 mM). RB-ex and FA showed anti-hyperglycemic activities through the increase of glucose uptake and the stimulation of glucokinase activity in HepG2 cells. RB-ex exhibited higher glucose uptakes with higher glucose concentrations, whereas FA exhibited the same increasing effects on both concentrations of glucose. RB-ex and FA exhibited doubled glucokinase activities relative to control. In the presence of insulin in the 25 mM glucose-containing medium, the levels of glucose uptake were increased in all treatments compared with control. As stimulatory effects of samples on insulin secretion were estimated, RB-ex and FA stimulated insulin secretion at a concentration of 25 ${\mu}g/m{\ell}$ and in particular, FA showed the highest amount of insulin-release in HIT-T15 cells. Antioxidative effects on HIT-T15 cells, RB-ex and hydroxycinnamic acids, excluding p-CA, showed inhibitory activities of 78% to 80% at a concentration of 100 ${\mu}g/m{\ell}$. On the basis of these results, we conclude that RB-ex and FA could help decrease blood glucose levels and prevent the cell damages via antioxidant activity.

The Inhibitory Effect of Hydroxycinnamic Acid Derivatives from Corn (Zea may L.) Bran on Melanogenesis (옥수수겨 유래 하이드록시신나믹애씨드 유도체의 멜라닌 생성 저해 효과)

  • Kim, Mi-Jin;Im, Kyung-Ran;Jeong, Taek-Gyu;Yoon, Kyung-Sup;Choi, Sang-Won
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.35 no.2
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    • pp.143-149
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    • 2009
  • Several hydroxycinnamic acid derivatives, p-coumaric acid, ferulic acid, N,N'-dicoumaroylputrescine (DCP), N-p-coumaroyl-N'-feruloyl-putrescine (CFP), and N,N'-diferuloylputrescine (DFP) were isolated and purified from corn bran. To develop the skin whitening agent, we investigated the effects of hydroxycinnamic acid derivatives from corn bran, on melanogenesis. CFP and DFP inhibited melanin synthesis in a dose dependent manner up to 44.7 ${\pm}$ 6.0 %, and 58.5 ${\pm}$ 3.1 % at a concentration of 50 ${\mu}g/mL$, respectively. The intracellular tyrosinase activity decreased about 42.5 ${\pm}$ 14.6 %, and 9.0 ${\pm}$ 4.4 % at a concentration of 50 ${\mu}g/mL$ of CFP and DFP, respectively. Our results suggest that inhibitory effects of hydroxycinnamic acid derivatives on melanogenesis are due to the inhibition of the intracellular tyrosinase activity. These results indicate that these hydroxycinnamic acid derivatives from corn bran may be potential natural skin whitening agents.

Characterization of phenolic compounds biosynthesized in pink-colored skin of Japanese indigenous Vitis vinifera cv. Koshu grape

  • Kobayashi, Hironori;Suzuki, Yumiko;Ajimura, Kosei;Konno, Tomonori;Suzuki, Shunji;Saito, Hiroshi
    • Plant Biotechnology Reports
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    • v.5 no.1
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    • pp.79-88
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    • 2011
  • Vitis vinifera cv. Koshu is a traditional grape cultivar that has been grown for centuries in Japan. The Koshu grape has pink-colored skin and Koshu wines have slight astringency. We demonstrated for the first time the characterization of hydroxycinnamic acids, flavan-3-ols, and flavonoids in Koshu grape using high-performance liquid chromatography and liquid chromatography-mass spectrometry. The gross weight of phenolic compounds excluding anthocyanins and proanthocyanidins in Koshu grape at harvest was higher than those in Sauvignon Blanc, Chardonnay, and Merlot grapes. In addition, hydroxycinnamic acid and monomeric flavonol contents in Koshu grape were also higher than those in the other grape cultivars. Transcription analysis of cinnamic acid 4-hydroxylase, p-coumarate 3-hydroxylase, caffeate methyltransferase, and flavonol synthase genes indicated high accumulation of hydroxycinnamic acids and flavonols in Koshu grape skin compared with the other cultivars. These findings obtained by chemical and molecular approaches partially explained the phenolic characteristics and the peculiar astringency of Koshu grape.

Anti-inflammatory Effect of p-Hydroxycinnamic Acid on HT-29 Intestinal Cells and Its Therapeutic Effect of Immune Bowel Disease (대장 상피세포에서 p-Hydroxycinnamic Acid의 항염증 효과와 염증성 장질환에 대한 치료 효과)

  • Lee, Hyun-Su;Lee, Seung-Ho;Choi, Hyukjae;Jeong, Gil-Saeng
    • Korean Journal of Pharmacognosy
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    • v.51 no.2
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    • pp.107-114
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    • 2020
  • Inflammatory bowel disease (IBD) is a chronic inflammatory disorder on the large intestine that has been considered as an incurable not only in Western society but also in Eastern Asia in recent years. Despite enormous efforts to develop novel therapeutics for this disease, strategy using bioactive compounds from natural product is still considered as important. p-hydroxycinnamic acid (HCA) is an intermediate substance found in several plants and has been known to possess anti-inflammation but little evidence is reported whether HCA has an inhibitory effect on intestinal inflammation. In the present study, we observed HCA does not show cytotoxic and apoptotic in HT-29 cells. Quantitative PCR analysis revealed that HCA effectively blocks the activity of HT-29 cells stimulated with TNF-α treatment. HCA inhibits translocation of p65 and MAPK pathways in activated HT-29 cells by TNF-α treatment. Besides, oral administration of HCA attenuates manifestation of DSS-induced inflammatory disease in vivo. Histological analysis exhibited that oral administration of HCA recovers IBD symptoms. The expression of pro-inflammatory cytokines were reduced by oral administration of HCA on intestinal tissues. Therefore, these results suggest that HCA has a potent anti-inflammatory effect on intestinal cells as well as show a therapeutic potential for treating IBD in vivo.

Research Trend about the Development of White Biotech-Based Aromatic Compounds (화이트바이오텍기반 방향족화합물 개발에 관한 연구동향)

  • Lee, Jin-Ho
    • Microbiology and Biotechnology Letters
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    • v.37 no.4
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    • pp.306-315
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    • 2009
  • Due to the depleting petroleum reserve, recurring energy crisis, and global warming, it is necessary to study the development of white biotech-based aromatic chemical feedstock from renewable biomass for replacing petroleum-based one. In particular, the production of aromatic intermediates and derivatives in biosynthetic pathway of aromatic amino acids from glucose might be replaced by the production of petrochemical-based aromatic chemical feedstock including benzene-derived aromatic compounds. In this review, I briefly described the production technology for hydroquinone, catechol, adipic acid, shikimic acid, gallic acid, pyrogallol, vanillin, p-hydroxycinnamic acid, p-hydroxystyrene, p-hydroxybenzoic acid, indigo, and indole 3-acetic acid using metabolic engineering, bioconversion, and chemical process. The problems and possible solutions regarding development of production technology for competitive white biotech-based aromatic compounds were also discussed.

Simultaneous determination and acute toxicity study of Fructus mume extracts in ICR mice (오매(烏梅)의 다성분동시분석 및 마우스를 이용한 경구 단회투여 급성독성시험)

  • Lee, In-Sun;Han, Chang-Hyun;Lee, Chul;Hwang, Bang-Yeon;Jung, Sang-Hyeok;Lee, Young-Joon;Jeon, Won-Kyung
    • Journal of Society of Preventive Korean Medicine
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    • v.15 no.1
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    • pp.37-47
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    • 2011
  • Objectives : Previous studies have shown that Fructus mume (FM) has anti-platelet effects. The present study was performed to determine the acute oral toxicity and quality control of a crude extract of FM in ICR mice. Methods : We investigated the in vivo single dose acute toxicity of FM 95% ethanol extract. This test was orally administered once by gavage to 20 male and 20 female mice at dose levels of 0 (control group), 1250, 2500 and 5000mg/kg body weight, respectively. Mortalities, clinical findings, autopsy findings and body weight changes were monitored daily for the 14 days following the administration. HPLC analysis was performed for the simultaneous determination of ursolic acid and p-hydroxycinnamic acid in FM. Reverse-phase chromatography using a C18 column and photodiode array detection at 211 nm was used for quantification of the two maker components. The mobile phase for gradient elution consists of water and acetonitrile. Results : We observed survival rates, general toxicity, change of body weight, and autopsy. The mice did not die after single oral administration of maximum dose of FM. Autopsy of animal revealed no abnormal gross finding. Therefore, $LD_{50}$ value of FM for ICR mice was more than 5000mg/kg on oral route. The HPLC analysis showed that ursolic acid and p-hydroxycinnamic acid amounts to 9.75- and 0.12% in the extract with the retention times of 47.99- and 15.38 minutes, respectively. Conclusions : These results suggest that no toxic dose level of FM in mice is considered to be more than 5000mg/kg. Consequently, it was concluded that FM have no effect on acute toxicity and side effect in ICR mice. For the quality control of FM extract, simultaneous determination of ursolic acid and p-hydroxycinnamic acid was established.

Tyrosinase Inhibitory Phenolic Constituents of Smilax china Leaves (청미래덩굴 잎의 페놀성 성분 및 Tyrosinase 저해 활성)

  • Kim, Sang Hyun;Ahn, Jong Hoon;Jeong, Ji Yeon;Kim, Seon Beom;Jo, Yang Hee;Hwang, Bang Yeon;Lee, Mi Kyeong
    • Korean Journal of Pharmacognosy
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    • v.44 no.3
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    • pp.220-223
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    • 2013
  • In the course of screening tyrosinase inhibitory activity, total methanolic extract and EtOAc-soluble fraction of Smilax china leaves showed significant inhibitory activity. Further fractionation and isolation of the EtOAc-soluble fraction resulted in 12 phenolic compounds, which were identified as 4-hydroxybenzoic acid (1), 3,4-dihydroxybenzaldehyde (2), 3,4-dihydroxybenzoic acid (3), 3,4-dihydroxyacetophenone (4), 3-hydroxy-4-methoxy benzoic acid (5), trans-p-hydroxycinnamic acid (6), cis-p-hydroxycinnamic acid (7), trans-resveratrol (8), cis-resveratrol (9), dihydroresveratrol (10), moracin M (11) and kaempferol (12). Compounds 1-11 were first reported from this plant. Among the isolated compounds, compounds 2, 8, 9 and 12 showed strong inhibition on tyrosinase activity.

Studies on the antioxidant components of Korean ginseng 3

  • Han, Byung-Hoon;Park, Myung-Hwan;Nam, Han-Yong
    • Archives of Pharmacal Research
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    • v.4 no.1
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    • pp.53-58
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    • 1981
  • The effective components of Korean ginseng showing the lipid-peroxide depressing activity were isolated. From the ether-soluble acidic fraction of fresh ginseng three phenolic acids were obtained. Salicylic acid and vanilic acid exhibited the potent antioxidant activity, where p-hydroxycinnamic acid did not.

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Quantitative Changes of Hydroxycinnamic Acid Derivatives and Anthocyanin in Corn (Zea mays L.) According to Cultivars and Heat Processes (옥수수의 품종별 및 가공별 Hydroxycinnamic Acid 유도체 및 Anthocyanin 색소의 함량 변화)

  • Yu, Myeong-Hwa;Kim, Eun-Ok;Choi, Sang-Won
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.39 no.6
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    • pp.843-852
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    • 2010
  • Hydroxycinnamic acid derivatives (HADs) and anthocyanins in corn (Zea mays L.) have recently been reported to have anticarcinogenic, anti-hypertensive, antidiabetic, antifungal, antioxidant, and anti-melanogenic activities. Five HADs and anthocyanins in corn were quantified by HPLC according to cultivars and heat processes. In addition, major anthocyanin of a black waxy corn was isolated and identified by several instrumental analysis, and its content was also quantified by HPLC according to heat processes. Of the ten corn cultivars, five waxy corn cultivars had moderate five HADs contents except "Baksa" waxy corn with higher two free cinnamic acids (FCAs), p-coumaric and ferulic acids. In contrast, three dent corn cultivars contained higher levels of three polyamine conjugates (PCs), CFP, DCP and DFP, and especially "P3394" had the highest amount of the three PCs. Two sweet corn cultivars had generally intermediate HADs levels between waxy and dent corn cultivars. Of the three colored-waxy corns, a black Mibaek waxy corn had the highest anthocyanin content. During heat processes, levels of two FCAs in the black waxy corn generally increased, whereas no significant change on three PCs contents was observed except the puffing process. Roasting, retort and puffing processes significantly increased two FCAs and especially, the puffed black waxy corn had the highest amount of FCAs. Meanwhile, most heat treatments except retort process, considerably decreased total anthocyanin contents, and especially the puffed black waxy corn had nearly no anthocyanin. Level of one major anthocyanin, pelargonidin 3-glucoside (P3G) isolated from a black waxy corn was appreciably decreased by heat treatments except retort process, which greatly increased P3G content. These results suggest that the retorted black waxy corn may be a promising high quality functional corn product.