• Title/Summary/Keyword: hydroxycinnamic acid

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Isolation and Characterization of 4-hydroxycinnamic Acid with Antimicrobial Activity from Aralia eiata (두릅에서 항미생물활성을 갖는 4-hydroxycinnamic acid의 분리 및 동정)

  • Ma, Seung-Jin;Kuk, Ju-Hee;Ko, Byoung-Seob;Park, Keun-Hyung
    • Applied Biological Chemistry
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    • v.39 no.4
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    • pp.265-267
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    • 1996
  • The methanol extracts of AraIia elata showed antimicrobial activity against bacteria. The antimicrobial active principle was successively purified with solvent fractionation, silica gel adsorption column chromatography, Sephadex LH-20 column chromatography, silica gel partition column chromatography and HPLC. The active substance was isolated by HPLC on $C_{18}$ column with an acetic acid-MeOH system. The active substance was identified as trans-4-hydroxycinnamic acid by MS, $^1H-NMR\;and\;^{13}C-NMR$.

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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.

Stabilization of Ascorbic Acid by Hydroxycinnamic Acid Incorporation and BGsome Encapsulation (Hydroxycinnamic Acid 첨가와 BGsome 포집에 의한 Ascorbic Acid의 안정화)

  • Jeon, Se-Eun;Kim, Seok-Joong;Jin, Byung-Suk
    • Journal of the Korean Applied Science and Technology
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    • v.29 no.2
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    • pp.348-355
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    • 2012
  • Ferulic and caffeic acids are hydroxycinnamic acid derivatives, which are potent plant antioxidants. Their free radical scavenging abilities in aqueous solution exposed to DPPH radical, and chemical stabilities against oxidative stress like high temperature and metal ion, were evaluated. To improve the stability of ascorbic acid solution, ferulic acid or caffeic acid was incorporated into ascorbic acid solution. Stability improvement of ascorbic acid was verified through $SC_{50}$ value change according to storage time. Ascorbic acid in combination with ferulic acid or caffeic acid was encapsulated with high efficiency inside BGsome. In this form, its stability was remarkably enhanced compared to that in free aqueous solution.

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.

Isolation and Identification of 3-Methoxy-4-hydroxybenzoic acid and 3-Methoxy-4-hydroxycinnamic acid from Hot Water Extracts of Hovenia dulcis Thunb and Confirmation of Their Antioxidative and Antimicrobial Activity (헛개나무 열수추출물로부터 항산화 및 항미생물 활성을 갖는 3-methoxy-4-hydroxybenzoic acid 와 3-methyoxy-4-hydroxycinnamic acid의 분리 및 동정)

  • Cho, Jeong-Yong;Moon, Jae-Hak;Park, Keun-Hyung
    • Korean Journal of Food Science and Technology
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    • v.32 no.6
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    • pp.1403-1408
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    • 2000
  • The methanol soluble fraction of the hot water extracts from Hovenia dulcis Thunb showed antioxidative and antimicrobial activity. The methanol fraction was successively purified with solvent fractionation, silica gel adsorption column chromatography, Sephadex LH-20 column chromatography, and octadecylsilane column chromatography. The purified active substances were isolated by high performance liquid chromatography. The isolated substances were identified as 3-methoxy-4-hydroxybenzoic acid (vanillic acid) and 3-methoxy- 4-hydroxycinnamic acid (ferulic acid) by LC-MS and GC-MS. Vanillic acid and ferulic acid showed antimicrobial activity against Gram-positive bacteria, Gram-negative bacteria and yeast. The DPPH-radical scavenging activity of ferulic acid appeared more active than that of vanillic acid. DPPH-radical scavenging concentration of ferulic acid and vanillic acid were $14\;{\mu}g/mL\;(SC_{50})$, $100\;{\mu}g/mL\;(SC_{10})$, respectively.

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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-Thrombosis Activity of Sinapic Acid Isolated from the Lees of Bokbunja Wine

  • Kim, Mi-Sun;Shin, Woo-Chang;Kang, Dong-Kyoon;Sohn, Ho-Yong
    • Journal of Microbiology and Biotechnology
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    • v.26 no.1
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    • pp.61-65
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    • 2016
  • From the lees of bokbunja wine (LBW) made from Rubus coreanus Miquel, we have identified six compounds (1: trans-4-hydroxycinnamic acid; 2: trans-4-hydroxy-3-methoxycinnamic acid; 3: 3,4-dihydroxycinnamic acid; 4: 4-hydroxy-3-methoxybenzoic acid; 5: 3,5-dimethoxy-4-hydroxybenzoic acid; and 6: 3,5-dimethoxy-4-hydroxycinnamic acid (sinapic acid)) through silica gel chromatography and UHPLC-MS. The compounds 1-6 showed strong anticoagulation and platelet aggregation inhibitory activities without hemolytic effect against human red blood cells. To date, this is the first report of the in vitro anti-thrombosis activity of sinapic acid. Our results suggest that different cinnamic and benzoic acid derivatives are closely linked to the anti-thrombosis activity of LBW, and sinapic acid could be developed as a promising anti-thrombosis agent.

Identification of Antioxidative Substances in Allium fistulosum L. by GC-MS (GC-MS에 의한 대파의 항산화 물질 동정)

  • Seo, Gee-Woo;Cho, Jeong-Yong;Kuk, Ju-Hee;Wee, Ji-Hyang;Moon, Jae-Hak;Kim, Sung-Ho;Park, Keun-Hyung
    • Korean Journal of Food Science and Technology
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    • v.35 no.5
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    • pp.988-993
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    • 2003
  • The ethyl acetate-soluble acidic fraction of juice, hot water, and MeOH extract of Allium fistulosum L. showed DPPH radical-scavenging activity. Each fraction was purified through silica gel adsorption column chromatography, and the active substances in the juice and hot water extract were identified as succinic acid, fumaric acid, 4-hydroxybenzoic acid, 4-hydroxy-3-methoxybenzoic acid, 4-hydroxycinnamic acid, and 4-hydroxy-3-methoxycinnamic acid. For the MeOH extract, 4-hydroxybenzoic acid, 4-hydroxy-3-methoxybenzoic acid, 4-hydroxycinnamic acid, and 4-hydroxy-3-methoxycinnmic acid were identified as the active substances by GC-MS. The contents of these compounds were determined by GC analysis, and their anti-oxidative activities were measured using the DPPH radical-scavenging assay. The results obtained showed that 4-hydroxy-3-methoxycinnamic acid was the dominant antioxidant in Allium fistulosum L.

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.