• Title/Summary/Keyword: 3,4-Hydroxybenzoic acid

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Comparative Analysis of Antioxidant, Anti Aging and Phenolic Compounds of Different Solvent Extracts from Saccharina japonica and Costaria costata (추출용매에 따른 쇠미역과 다시마의 항산화, 항노화 활성과 페놀화합물 비교분석)

  • Hyun-Hwa Lee;Jin-Sol Kim;Jun-Han Jeong;Chun Sung Kim;Sook Young Lee
    • Korean Journal of Plant Resources
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    • v.36 no.2
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    • pp.107-121
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    • 2023
  • This study analyzed the polyphenol, flavonoid contents, antioxidant activity, anti-aging activity and phenol component contents of Saccharina japonica (SJ), Costaria costata (CC) extracts with hot water, 95% methanol, 95% prethanol for investigating possible utilization of SJ and CC extracts. The result revealed that the SJ and CC methanol extracts showed the highest polyphenol and flavonoid contents, 4.63 mg TAN/g, and 4.19 mg QUE/g respectively. Also, the SJ and CC methanol extracts showed higher antioxidant activity than prethanol and hot water extracts, whereas the ABTS radical scavenging activities were the highest in prethanol extracts (IC50 = 15.4, 10.3 ㎍/µL). In anti-aging activity for evaluating the anti-wrinkle activity and skin whitening activity, the CC methanol extracts had high collagenase inhibitory activity (88.3%), and the SJ prethanol extracts showed higher elastase inhibitory activity (19.0%) compared to other extracts. Then the tyrosinase inhibitory activity was significantly higher in the SJ and CC methanol extracts (41.8, 30.3%, respectively), whereas prethanol extracts were the lowest. To identify the phenol component contents of SJ and CC extracts, 4-hydroxybenzoic acid, naringenin, naringin and nicotinic acid were measured using LC-MS/MS. As a result, the phenol contents were the highest in SJ methanol extract (4-hydroxybenzoic acid), SJ and CC prethanol extract (naringin and naringenin) and CC prethanol extract (nicotinic acid). Lastly, the antioxidant activity of SJ and CC showed high correlations with polyphenol and flavonoid contents (R = -0.946~0.883). These results suggest that prethanol or methanol extracts of SJ and CC have higher antioxidant activities, anti-aging activity and the potential to be used as material for health functional food and cosmetics.

Isolation and Identification of Low Molecular Phenolic Antioxidants from Ethylacetate Layer of Korean Black Raspberry (Rubus coreanus Miquel) Wine (복분자(Rubus coreanus Miquel) 와인의 에틸아세테이트층으로부터 저분자 페놀성 항산화 화합물의 단리·동정)

  • Kim, Seong-Ja;Lee, Hyoung-Jae;Park, Keun-Hyung;Rhee, Chong-Ouk;Lim, Ik-Jae;Chung, Hee-Jong;Moon, Jae-Hak
    • Korean Journal of Food Science and Technology
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    • v.40 no.2
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    • pp.129-134
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    • 2008
  • Five antioxidative active substances were isolated from the EtOAc layer (20 g/56.2 g) of Korean black raspberry (Rubus coreanus Miquel) wine (11 L, black raspberry 15.7 kg fresh wt. eq.) by various column chromatography and high performance liquid chromatography (HPLC). Proton nuclear magnetic resonance ($^1H$-NMR) spectroscopy and gas chromatography Electro Ionization-Mass Spectrometry (GC-EI-MS) identified these as 4-hydroxybenzoic acid (1, 0.1 mg), 3,4-dihydroxybenzoic acid (2, 0.3 mg), 4-(2-hydroxyethyl)-phenol (3, 0.6 mg; tyrosol), pyrocatechol (4, 0.3 mg), 3,4,5-trihydroxybenzoic acid ethyl ester (5, 0.6 mg; ethyl gallate). The presence of 1 and 2 in Korean black raspberry has previously been reported. However, the presence of 3-5 in Korean black raspberry, and the identification of 1-5 from the Korean black raspberry wine have never before been reported.

Identification and Growth Inhibition of Phytotoxic Substances from Tomato Plant (토마토식물의 독성물질 확인과 생장억제작용)

  • 김영식
    • Journal of Plant Biology
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    • v.32 no.1
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    • pp.41-49
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    • 1989
  • Phenolic compounds such as gallic acid, ferulic acid, p-hydroxybenzoic acid, vanillic acid, salicylic acid, tannic acid, and hydroquinone were identified from the aqueous extracts and volatile substances of tomato plant by paper chromatography, high performance liquid chromatography and gas chromatography. The seed germination and seedling growth of the experimental species, lettuce and egg plant, were severely inhibited in 5$\times$10-3M of phenolic reagents identical to those identified from tomato plant. Germination and growth rate of test species in 5$\times$10-4M and 5$\times$10-5M were higher than that of 5$\times$10-3M. Therefore, 5$\times$10-3M of phenolic compounds would be assumed to be threshold concentration for allelopathic effects.

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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.

In silico Analysis of Natural Compounds as Modulators of Type I Collagen

  • Narayanaswamy, Radhakrishnan;Wai, Lam Kok;Esa, Norhaizan Mohd;Ismail, Intan Safinar
    • Journal of Integrative Natural Science
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    • v.9 no.3
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    • pp.166-170
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    • 2016
  • Collagen plays a vital role in the maintenance of structure and function of a human body. It has been widely applied in various fields including biomedical, cosmeceutical, food, pharmaceutical and tissue engineering. In the present study, the docking behaviour of type I collagen with 15 different ligands namely hydroxymethylfurfural, methylglyoxal, methylsyringate, O-methoxyacetophenone, 3-phenyllactic acid, 4-hydroxybenzoic acid, kojic acid, lumichrome, galangin, artoindonesianin F, caffeic acid, 4-coumaric acid, origanol A, thymoquinone and quercetin was evaluated along with their putative binding sites using Discovery Studio Version 3.1. Docking studies and binding free energy calculations revealed that origanol A has maximum interaction energy (-40.48 kcal/mol) and quercetin with the least interaction energy (-15.44 kcal/mol) as compared to the other investigated ligands. Three ligands which are galangin, methylsyringate and origanol A were shown to interact with Asp21 amino acid residue of chain B (type I collagen). Therefore, it is strongly suggested that the outcomes from the present study might provide new insight in understanding these 15 ligands as potential type I collagen modulators for the prevention of collagen associate disorders.

Composition of Phenolic Compounds in Hypochaeris radica L. Extracts and their Allelopathic Effects on Gramineous Forage Crops (서양금혼초(Hypochaeris radicata L.) 추출물의 화본과 사료작물에 대한 타감작용 효과 및 phenole 화합물의 조성)

  • Kim, Og-Yim;Park, Sun-Ill;Jung, Ill-Min;Ha, Sang-Young
    • Korean Journal of Environmental Agriculture
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    • v.24 no.4
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    • pp.391-397
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    • 2005
  • This study was carried out to examine the allelopathic effect of the aqueous extract of Hypochaeris radicata L. on growth of three gramineous forage crops, tall fescue, perennial ryegrass and italian ryegrass. The result on relative elongation ration (RER) of gramineous forage crops treated with the aqueous extract of Hypochaeris radicata L. and the change of quantity generally indicated the inhibitory effect. The inhibitory effect was increased as its concentration was increased. As a result, it is ascertained that the aqueous extract of Hypochaeris radicata L. has allelopathy effect. According to the chemical experiment of the allelochemical substances in Hypochaeris radicata L. by HPLC, there are the differences at each part of plants. However, it is ascertained that there are eleven phenolic compounds, ${\rho}-hydroxybenzoic$ acid, chlorogenic acid, catechin, caffeic acid, syringic acid, salicylic acid, ${\rho}-coumaric$ acid, ferulic acid, hesperidin, trans-cinnamic acid and naringenin. Especially three phenolic acids such as caffeic acid, ferulic acid and naringenin were detected from all part of the plant.

Various Properties and Phenolic Acid Contents of Rices and Rice Brans with Different Milling Fractions (품종 및 도정도별 백미와 미강의 특성 및 페놀산 함량)

  • Kim, Sung-Ran;Ahn, Ji-Yun;Lee, Hyun-Yu;Ha, Tae-Youl
    • Korean Journal of Food Science and Technology
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    • v.36 no.6
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    • pp.930-936
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    • 2004
  • Effects of rice cultivars and degree of milling (DM) on composition, pasting properties, total phenolic contents, and distribution of phenolic acids were investigated. Rice and bran fractions with 94.4, 92.0, and 90.4% milling yields from brown rice of four cultivars (Odae, Nampyung, Chucheong, and Ilmi) were used. Fat and ash contents of milled rices decreased with increasing DM, whereas protein contents were not affected. In rice bran, differences in fat and ash contents by cultivars were higher than those caused by DM. With increasing DM, gelatinization temperature of rice flour decreased, whereas peak viscosity and hold viscosity at $95^{\circ}C$ increased. While cold viscosity, final viscosity, and setback varied among cultivars, DM had little effect. Total polyphenolic contents in brown rice, milled rice, and rice bran were 93.9-88.8, 30.3-71.9, and 310.0-541.6 mg catechin eq/100g, respectively. Major phenolic compounds were identified as ferulic and p-coumaric acids. Total phenolic content of brown rice (65.9-27.9 mg%) decreased with increasing DM, whereas ratio of ferulic acid composition increased. Chucheong and Ilmi varieties showed biggest reduction of phenolic acid contents by milling. In rice bran, ferulic and p-coumaric acids were 157.8-240.2 and 31.8-90.4 mg%, respectively. Contents of sinapinic, benzoic, and m-hydroxybenzoic acids in rice bran were higher than those of brown and milled rices.

Ginsenoside, Phenolic Acid Composition and Physiological Significances of Fermented Ginseng Leaf (발효처리가 인삼잎의 진세노사이드 및 페놀산 조성 변화와 생리활성에 미치는 영향)

  • Lee, Ka-Soon;Seong, Bong-Jae;Kim, Gwan-Hou;Kim, Sun-Ick;Han, Seung-Ho;Kim, Hyun-Ho;Baik, Nam-Doo
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.39 no.8
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    • pp.1194-1200
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    • 2010
  • This study was carried out to investigate the compositional changes of ginsenosides and phenolic acids of ginseng leaf by fermentation in order to promote the utilization of ginseng leaf. The chief ginsenosides in non-fermented ginseng leaf (NFGL) were ginsenoside-Rg1 (26.0 mg/g), -Re (47.3 mg/g) and -Rd (23.9 mg/g). By fermentation, ginsenoside-Rg1, -Rb1, -Rb2, -Rb3, -Rc and -Re were decreased tremendously and new ginsenoside-Rh2, -Rh1, -Rg2 and -Rg3 appeared. Especially, ginsenoside-Rg3 (3.7 mg/g) on FGL was increased 15-fold compared to that of NFGL (0.2 mg/g). Total phenolic compound content of NFGL and FGL measured by colorimetric analysis was 350.4 and 312.5 mg%, respectively. There were 8 free and 6 ester forms of phenolic acids in NFGL. Among them, content of ferulic acid was the highest, comprised of 12.6 and 50.7 mg%, respectively. In FGL, total content of protocatechuic acid, p-hydroxybenzoic acid, and vanillic acid were increased by 28, 5 and 7.8 fold and ferulic acid was decreased greatly. Tyrosinase inhibitory activity of FGL was stronger than NFGL, while electron donating abilities of FGL were similar to NFGL.

Phenolic constituents of Nelumbinis Semen and Their Tyrosinase Inhibitory Activity (연자육의 페놀성 성분 및 Tyrosinase 저해 활성)

  • Jeong, Ji Yeon;Mo, Eun Jin;Hwang, Bang Yeon;Lee, Mi Kyeong
    • Korean Journal of Pharmacognosy
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    • v.46 no.1
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    • pp.1-5
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    • 2015
  • In the course of screening tyrosinase inhibitory activity, EtOAc-soluble fraction of Nelumbinis Semen (Seeds of Nelumbo nucifera) showed significant inhibition. Further fractionation of the EtOAc-soluble fraction resulted in 12 compounds, which were identified as 4-(hydroxymethyl)phenol (1), tyrosol (2), 4-(hydroxymethyl)benzaldehyde (3), 4-hydroxybenzoic acid (4), 4-(2-methoxyvinyl)benzene-1,2-diol (5), 2,6-dihydroxybenzoic acid (6), (2R-trans)-2,3-dihydro-3,5,7,8-tetrahydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one (7), (+)-catechin (8), elephantorrhizol (9), (+)-dehydrovomifoliol (10), (-)-boscialin (11) and uridine (12). Compounds 5 and 7 were first reported from this plant. Among the isolated compounds, compound 7 showed strong inhibition on tyrosinase activity with mixed mechanism of competitive and noncompetitive inhibition.

Determination of Phenolic Compounds Responsible for Allelopathy in Upland Weeds (밭 잡초(雜草)중에 존재(存在)하는 Allelopathy 관련(關聯) Phenol 화합물(化合物)의 검색(檢索))

  • Chon, J.C.;Han, K.W.;Jang, B.C.;Shin, H.S.
    • Korean Journal of Weed Science
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    • v.8 no.3
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    • pp.258-264
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    • 1988
  • Phenolic compounds present in upland weeds (Artemisia asiatica Nakai, Capsella bursa-pastoris (L.) Medik, Portulaca orleracea L. and Trifolium repens L.) which have shown allelopathic activity were determined using paper chromatography (PC) and high performance liquid chromatography (HPLC). Effect of the determined phenolic compounds on germination and post-germination growth of test plants was also investigated. Kinds of phenolic compounds determined by PC in the four weed species were greater in the aqueous extract than in the methanol extract. Ferulic acid was found in both extracts of the weeds studied, whereas benzoic acid was that the weeds commonly contained hydroquinone, p-hydroxybenzoic, ferulic and cinnamic acids. Out of the phenolic compounds determined by PC and HPLC p-hydroxybenzoic, cinnamic and ferulic acids inhibited germination and post-germination growth of radish and sesame. Inhibition of the phenolic compounds on the radicle growth was greater than on the germination of the test plants.

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