• Title/Summary/Keyword: Vanillin

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Synthesis of Dimeric Lignin Model Compounds - Veratrylglycerol-β-vanillylalcohol ether compounds - (리그닌 이양체(二量體) 모델화합물(化合物)의 합성(合成) - Veratrylglycerol-β-vanillylalcohol ether 화합물(化合物) -)

  • Zhao, Julan;Hwang, Byung-Ho
    • Journal of Forest and Environmental Science
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    • v.12 no.1
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    • pp.37-44
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    • 1996
  • Two dilignols composed of ${\beta}$-O-4 structure, a important substructure compound in lignin, was synthesized in high yield in a series of the synthetic studies of lignin model compounds. The dimers were identified with $^1H$ and $^{13}C$-NMR and Mass spectroscopy. The important compound of among them, the final synthetic compound [IV].is called 1-(3,4-dimethoxyphenyl)-2-(2'-methoxy-4'-hydroxymethylphenoxy)-propanediol-l,3. This dimeric lignin model compounds should be usefull for the studies of lignin reactions such as pulping, bleaching, pyrolysis, hydrogenolysis, oxidation, reduction, biodegradation, and chemical utilization.

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Proanthocyanidin Content and Antioxidant Characteristics of Grape Seeds (포도씨의 proanthocyanidin 함량 및 항산화 활성)

  • Hwang, In-Wook;Lee, Hye-Ryun;Kim, Suk-Kyung;Zheng, Hu-Zhe;Choi, Jong-Uck;Lee, Sang-Han;Lee, Suk-Hee;Chung, Shin-Kyo
    • Food Science and Preservation
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    • v.15 no.6
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    • pp.859-863
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    • 2008
  • The proanthocyanidin content and antioxidant characteristics of seeds of grape cultivars were examined. Grape seeds were extracted in 70% acetone solution for 12 hr. The total phenolic content of the extracts ranged from 16.71 to 28.60 mg/100 g. The proanthocyanidin content ranged from 18.36 to 55.30 mg/100 g. The Jaok cultivar had the highest total phenolic and proanthocyanidin content, and showed the strongest antioxidant activity in the FRAP and DPPH assays. The total phenolic and proanthocyanidin content of grape seeds was correlated with their antioxidant capacities (r > 0.92). Acetone extracts of grape seeds could be effective antioxidant materials.

Neuroprotective Effects of Korean Red Pine (Pinus densiflora) Bark Extract and Its Phenolics

  • Kim, Ji-Won;Im, Sungbin;Jeong, Ha-Ram;Jung, Young Sung;Lee, Inil;Kim, Kwan Joong;Park, Seung Kook;Kim, Dae-Ok
    • Journal of Microbiology and Biotechnology
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    • v.28 no.5
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    • pp.679-687
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    • 2018
  • Korean red pine (Pinus densiflora) is one of the major Pinus species in Korea. Red pine bark is removed prior to the chipping process in the wood industry and discarded as waste. However, red pine bark contains a considerable amount of naturally occurring phenolics, including flavonoids, and therefore may have a variety of biological effects. In this study, we investigated if Korean red pine bark extract (KRPBE) could protect neuronal PC-12 cells from oxidative stress and inhibit cholinesterase activity. Analysis of reversed-phase high-performance liquid chromatography results revealed four phenolics in KRPBE: vanillin, protocatechuic acid, catechin, and taxifolin. The total phenolic and flavonoid contents of KRPBE were 397.9 mg gallic acid equivalents/g dry weight (DW) and 248.7 mg catechin equivalents/g DW, respectively. The antioxidant capacities of KRPBE measured using ABTS, DPPH, and ORAC assays were 697.3, 521.8, and 2,627.7 mg vitamin C equivalents/g DW, respectively. KRPBE and its identified phenolics protected against $H_2O_2$-induced oxidative cell death in a dose-dependent manner. Acetylcholinesterase and butyrylcholinesterase, which degrade the neurotransmitter acetylcholine to terminate neurotransmission in synaptic clefts, were inhibited by treatment with KRPBE and its identified phenolics. Taken together, these results suggest that KRPBE and its constituent antioxidative phenolics are potent neuroprotective agents that can maintain cell viability under oxidative stress and inhibit cholinesterase activity.

Extractives from Epimedium koreanum Nakai (삼지구엽초(Epimedium koreanum Nakai)의 추출성분)

  • Lee, Tae-Seong;Cho, Jae-Hyun;Hwang, Byung-Ho
    • Journal of Korea Foresty Energy
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    • v.24 no.2
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    • pp.16-23
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    • 2005
  • The air dried of Epimedium koreanum Nakai was extracted with MeOH and its extractives were concentrated with a vacuum evaporator. The extractives were fractionated with a series of n-hexane, chloroform (${CHCl}_3$), butanol (BuOH), ethyl acetate (EtOAc) and water on a separately funnel. Each fraction was freeze dried to give some dark brown powder. The EtOAc and BuOH soluble fractions were chromatographed on a Sephadex LH-20 column using a series of aqueous methanol and ethanol-n-hexane mixture as eluents. The isolated compounds were tested with a cellulose TLC developed with TBA and 6% acetic acid and then visualized on UV lamp or sprayed with vanillin-HCl-EtOH. The purified compounds were flavonoids and their glycosides, and organic acid as follows : (+)-catechin, icariin, hyperoside, Ikarisoside A and caffeic acid. The structures of each compounds were confirmed by $^1H-NMR,\;^{13}C-NMR$ and Mass spectra. Also, executed qualitative analysis as use GC/MS(Libraries search) about ${CHCl}_3$ soluble compounds of each part.

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Antioxidant activity of phalaenopsis Sogo Yukidian 'V3' plant parts

  • Truong, Ngoc Minh;Phung, Thi Tuyen;Do, Tan Khang;Nguyen, Van Quan;Pham, Thi Thu Ha;Nguyen, Thanh Quan;Andriana, Yusuf;Truong, Mai Van;Tran, Dang Xuan
    • Proceedings of the Korean Society of Crop Science Conference
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    • 2017.06a
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    • pp.34-34
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    • 2017
  • Various extracts of roots, stems, and leaves of Phalaenopsis Sogo Yukidian 'V3' were evaluated for total phenolics, total flavonoids, and antioxidant capacity. The conjugate form of stem samples contained the highest total phenolics ($5.092{\pm}0.739mg$ gallic acid equivalent per g dry weight) and the highest total flavonoids ($2.218{\pm}0.021mg$ rutin equivalent per g dry weight) was found in the hexane extract of leaves. The ethyl acetate extract of roots showed the maximum antioxidant activity as compared to other extracts. Of which, the $IC_{50}$ value of this sample were 0.070 mg/mL and 0.450 mg/mL in the 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging assay and reducing power, respectively, while the lipid peroxidation inhibition (LPI) value was as 94.2% by ${\beta}$-carotene bleaching method. Five phenolic compounds including caffeic acid, syringic acid, vanillin, ellagic acid, and cinnamic acid were quantified by high-performance liquid chromatography (HPLC). It is suggested that roots of the hybrid Phalaenopsis Sogo Yukidian 'V3' can be explodited as an effective source of antioxidants.

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Bioassay-Guided Isolation and Identification of Compounds from Arecae Pericarpium with Anti-inflammatory, Anti-oxidative, and Melanogenesis Inhibition Activities

  • Indriana, Amelia;Lee, Kyoung Jin;Kim, Yeong Shik
    • Natural Product Sciences
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    • v.22 no.3
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    • pp.193-200
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    • 2016
  • This study describes the anti-inflammatory, anti-oxidant, and melanogenesis inhibition activities of methanol extract and various organic solvent fractions of Arecae Pericarpium. We examined the inhibition of lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW 264.7 cells, 1,1-diphenyl-2-picrylhydrazine (DPPH) scavenging activity, mushroom tyrosinase inhibition activity and melanin contents. The study showed that, among all tested fractions, methylene chloride fraction showed the strongest inhibition of LPS-induced NO production in RAW 264.7 cells ($IC_{50}$ value $8.89{\mu}g/mL$) and DPPH radical scavenging activity ($EC_{50}$ value $21.39{\mu}g/mL$). Methylene chloride and ethyl acetate fractions similarly inhibited mushroom tyrosinase activity. Methanol extract exhibited strongest reduction of melanin content in B16F10 melanoma cells. Based on the bioactivity assay results, methylene chloride and ethyl acetate fractions were further separated. Eight phenolic compounds were isolated, which are dimeric syringol (1), catechol (2), 4-hydroxybenzaldehyde (3), vanillin (4), 4-hydroxyacetophenone (5), apocynin (6), protocatechuic acid (7) and 4-hydroxybenzoic acid (8). Among the isolated compounds tested, catechol showed the strongest inhibition of LPS-induced NO production in RAW 264.7 cells. Catechol also showed the concentration-dependent NF-${\kappa}B$ inhibition activity. Arecae Pericarpium might have potentials to be developed as anti-inflammatory agent or dermatological product for skin-whitening agent.

Chemical Constituents from the Stems of Lagerstroemia indica and Their Anti-oxidant Effect (배롱나무의 항산화 활성 성분)

  • Woo, Kyeong Wan;Sim, Mi Ok;Park, Eel Jong;Kim, Min Suk;Suh, Won Se;Cho, Hyun Woo;Kwon, Hak Cheol;Park, Jong Cheol;Lee, Kang Ro
    • Korean Journal of Pharmacognosy
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    • v.47 no.3
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    • pp.204-210
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    • 2016
  • Phytochemical investigation of the 80% MeOH extract from the stems of Lagerstroemia indica resulted in the isolation of eighteen compounds; four norsesquiterpenes, fourteen phenolic derivatives. Their chemical structures were characterized by spectroscopic methods to be tachioside (1), isotachioside (2), 2,4,6-trimethoxyphenyl ${\beta}$-D-glucopyranoside (3), gallic acid 4-methyl ether (4), protocatechuic acid (5), gallic acid (6), vanillic acid (7), vanillin (8), 2-methoxy-5-hydroxymethyl-phenyl-1-O-(6"-galloyl)-${\beta}$-D-glucopyranoside (9), 2,4,6-trimethoxyphenol-1-O-${\beta}$-D-(6'-O-galloyl)-glucopyranoside (10), 4-hydroxy-3-methoxyphenyl-1-O-(6'-O-galloyl)-${\beta}$-D-glucopyranoside (11), vomifoliol (12), vomifoliol 9-O-${\beta}$-D-glucopyranoside (13), 6R,9R-3-oxo-${\alpha}$-ionol-9-O-${\beta}$-D-glucopyranoside (14), dihydrophaseic acid 4'-O-${\beta}$-D-glucopyranoside (15), ${\beta}$-hydroxypropiovanillone 3-O-${\beta}$-D-glucopyranoside (16), myrciaphenone A (17), and coumaric acid (18). Compounds 1-5 and 7-18 were isolated for the first time from this plant. Compounds 1-18 were investigated for their antioxidant properties using DPPH and ABTS radical scavenging capacity assay, $Fe^{2+}$ chelating, and FRAP assay. It was found that 4, 6, and 11 possessed the highest antioxidant capacities.

Characterization and distribution of phenolics in carrot cell walls

  • Kang, Yoon-Han
    • Proceedings of the Korean Society of Postharvest Science and Technology of Agricultural Products Conference
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    • 2003.10a
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    • pp.134.1-134
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    • 2003
  • The purpose of this study was to investigate the release of p-hydroxybenzoic acid and other compounds from cell wall materials(CWM) and their cellulose fraction from carrot with chemical and enzymatic hydrolysis. To investigate this effect on cell wall chemistry of carrot, alcohol insoluble residue(AIR) of CWM were prepared and were extracted sequentially with water, imidazole, CDTA(-1, -2), Na$_2$CO$_3$(-1, -2), KOH(0.5, 1.0 and 4M), to leave a residue. These were analysed for their carbohydrate and phenolic acids composition. Arabinose and galactose were the main noncellulosic sugars. Phenolics esterified to cell walls in carrot were found to consist primarily of p-hydroxybenzoic acid with minor contribution from vanillin, ferulic acid and p-hydroxybenzaldehyde. p-Hydroxybenzoic acid was quite strongly bound to the cell wall. The contents of p-hydroxybenzoic acid in 0.5M KOH, Na$_2$CO$_3$-2, IM KOH, and ${\alpha}$-cellulose were 2,097, 1,360, 1,140, and 717 $\mu\textrm{g}$/g AIR from CWM, respectively. Alkali labile unknown aromatic compound(C$\sub$7/H$\sub$10/O$_2$) was found in ${\alpha}$ -cellulose hydrolyzate digested with driselase and cellulase. This compound was also found in hydrolyzate of 2 M trifluoroacetic acid at 120$^{\circ}C$ for 2 hours. Driselase treatment solubilized only 46.6 $\mu\textrm{g}$/g of the p-hydroxybenzoic acid from carrot AIR. These results indicate that p-hydroxybenzoic acid was associated with neutral polysaccharides, long chain galactose and branched arabinan from graded alcohol precipitation.

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Characterization of North American Ginseng Rust-Spot and the Effects of Ethephon

  • Campeau, Cindy;Proctor, John T.A.;Murr, Dennis P.;Schooley, Jan
    • Journal of Ginseng Research
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    • v.27 no.4
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    • pp.188-194
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    • 2003
  • Rust-spot on North American ginseng roots (Panax quinquefolius L.) is considered a physiological, not a pathological disorder. Ginseng rust-spot starts as an orange spot on the surface of the root and may spread forming a sunken, round to irregular lesion. 5 mm in diameter. Pieces of root, 7 mm in length and containing a rust-spotted lesion, were embedded in agar and sectioned using a vibratome. These sections and hand sections, cut with a two-sided razor blade, were examined using fluorescence microscopy. The 4-5 cell layers of the periderm were destroyed in the area of the lesion and orange substance:, were deposited in and around the lesion. Sections stained with vanillin-HCI and viewed using bright field microscopy confirmed that the orange substances were phenolic compounds. Scanning electron micros-copy showed that the periderm had pulled away from the root, or was completely destroyed, in the area of the lesion. The smooth surface of the lesion indicates the deposition of phenolic compounds in surrounding cells as a wound response. Roots sprayed or dipped in ethephon (1500 mgㆍL$^{-1}$ ) developed rust-spots, more so at 21$\pm$2$^{\circ}C$ than at 3$\pm$0.2$^{\circ}C$. Roots held at 21$\pm$2$^{\circ}C$ were yellowish and developed white cell proliferations. Comparable control roots also developed rust-spots likely due to the high undecomposed organic matter content of the incubation soilless mix.

Phenolic Compounds from the Flower Buds of Camellia japonica

  • Cho, Jeong-Yong;Ryu, Hyun-Jung;Ji, Soo-Hyun;Moon, Jae-Hak;Jung, Kyung-Hee;Park, Keun-Hyung
    • Food Science and Biotechnology
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    • v.18 no.3
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    • pp.766-770
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    • 2009
  • Hot water extracts of Camellia japonica flower buds were found to have the higher 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity than the other solvent extracts. Five phenolic compounds were isolated and purified from the ethyl acetate soluble-neutral fraction of hot water extracts by Sephadex LH-20 column chromatography and octadecyl silane-high performance liquid chromatography using the guided assay of DPPH radical scavenging. Based on mass spectrometer and nuclear magnetic resonance, the isolated compounds were identified as p-hydroxybenzaldehyde (1), vanillin (2), dehydroxysynapyl alcohol (3), 7S,7'S,8R,8'R-icariol $A_2$ (4), and (-)-epicatechin (5). Four compounds (1-4) except for 5 were newly identified in this plant. Their DPPH radical scavenging activities as 50% scavenging concentration decreased in order to 5 $(20\;{\mu}M)>{\alpha}-tocopherol$ $(29\;{\mu}M)>4$ $(67\;{\mu}M)>3$ $(72\;{\mu}M)>1=2$ ($>250\;{\mu}M$). These results indicate that the antioxidant effect of the hot water extract of C. japonica flower buds may partially due to 5 isolated phenolic compounds.