• Title/Summary/Keyword: 4-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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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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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-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.

Tertiary Matrices for the Analysis of Polyethylene Glycols Using MALDI-TOF MS

  • Hong, Jangmi;Kim, Taehee;Kim, Jeongkwon
    • Mass Spectrometry Letters
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    • v.5 no.2
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    • pp.49-51
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    • 2014
  • The effectiveness of tertiary matrices composed of the combination of three common matrices (dihydrobenzoic acid (DHB), ${\alpha}$-cyano-4-hydroxycinnamic acid (CHCA), and sinapinic acid (SA)) was compared with that of single or binary matrices in the analysis of polyethylene glycol (PEG) polymers ranging from 1400 to 10000 Da using matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS). A tertiary matrix of 2,5-DHB+CHCA+SA was the most effective in terms of S/N ratios. CHCA and CHCA+SA produced the highest S/N ratios among the single matrices and the binary matrices, respectively. The improvement observed when using a tertiary matrix in analyses of PEG polymers by MALDI-TOF MS is believed to be due to the uniform morphology of the MALDI sample spots and synergistic effects arising from the mixture of the three matrix materials.

Scavenging Effects of Hydroxycinnamic Acids on Paraquat Induced Pulmonary Toxicity (III) (Paraquat 유도 페독성에 대한 Hydroxycinnamic Acid계 화합물의 독성 경감 효과 (III))

  • 최병기;오은정;정세영
    • Environmental Analysis Health and Toxicology
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    • v.14 no.3
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    • pp.95-101
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    • 1999
  • The scavenging effects of two hyaroxycinnamic acids such as caffeic acid and chlorogenic acid on paraquat induced pulmonary toxicity were investigated. The results are summerized as follows: 1. In the 5-lipoxygenase assay, caffeic acid and chlorogenic acid inhibited the enzyme activities whose inhibition concentration (IC$\_$50/) were 4.1 and 9.6 ${\mu}$M respectively. 2. To evaluate the antiinflammatory effects on mediator related to the mechanism of inflammation, ADP-induced platelet aggregation assay and histamine degranulation assay were used. Caffeic acid and chlorogenic acid inhibited on ADP-induced platelet aggregation and histamine release at a concentration dependent manners. 3. Arachidonic acid-induced ear edema were inhibited by administration of caffeic acid and chlorogenic acid. 4. Cytologicad analysis of branchoalveolar lavage fluid (BALF) which was the useful tool for detection of an inflammatory response in the lungs of animals intoxicated with chemicals were used. Alveolar macrophages and neutrophils in BALF, as well as the protein content and the LDH activity in BALF supernatant increased by intoxication of paraquat, but decreased by administration of caffeic acid and chlorogenic acid. Therefore, two hydroxyeinnamic acids tested were the useful candidates for scavenger and antiinflammatory agents on paraquat induced pulmonary toxicity.

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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.