• Title/Summary/Keyword: ethyl vanillin

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Enzymatic Synthesis of Vanillin-a -Glucoside and Ethyl Vanillin-a -Glucoside (효소적 방법에 의한 Vanillin-$\alpha$ -Glucoside 및 Ethyl Vanillin-$\alpha$ -Glucoside의 합성)

  • 김삼곤;김근수;나도영;김영회
    • Journal of the Korean Society of Tobacco Science
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    • v.25 no.2
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    • pp.120-127
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    • 2003
  • Cyclodextrin glucanotransferase (CGTase) from Bacillus stearothermophilus synthesized vanillin and ethyl vanillin monoglucoside, with a series of its maltooligoglucosides by transglycosylation with dextrin as a donor, and vanillin or ethyl vanillin as an acceptor. The monoglucoside formed from reaction mixture of vanillin or ethyl vanillin by the successive actions of CGTase and Rhizopus glucoamylase was isolated by extraction with n-butanol saturated with water and silica gel column chromatography. The structure of the isolated monoglucoside was identified as vanillin- $\alpha$ -D-glucoside and ethyl vanillin- $\alpha$ -D-glucoside, respectively, by FAB-MS, UV, IR, 1H-NMR, 13C-NMR spectra and products by hydrolysis with acid, $\alpha$ - and $\beta$ -glucosidases.

Analysis of volatile aroma compounds from vanilla perfume using headspace disk type monolithic material sorptive extraction (시료상층부 원판 형태 단일 다공성 물질을 이용한 바닐라 향수의 휘발성 아로마 성분 추출 분석)

  • Son, Hyun-Hwa;Lee, Dong-Sun
    • Analytical Science and Technology
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    • v.24 no.6
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    • pp.421-428
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    • 2011
  • In this study, headspace disk type monolithic material sorptive extraction (HS-MMSE) was developed, validated and applied to the analysis of volatile aroma compounds from vanilla perfume by gas chromatography -mass spectrometry (GC/MS). HS-MMSE uses monolithic material (MonoTrap) based on silica bonded with octadecyl silane (ODS) and activated carbon as a sorbent. Aroma compounds was adsorbed onto the MonoTrap in headspace and extracted by only 100 ${\mu}L$ of solvent. Total 12 volatile compounds from vanilla perfume were successfully analyzed using HS-MMSE. The influence of extractive parameters was investigated and optimized, using benzyl acetate, linalyl acetate, vanillin, ethyl vanillin as target compounds. Under the optimum condition, the limit of detection (S/N = 3) and the limit of quantification (S/N = 10) of proposed method for the target compounds were obtained within the range of 8.35~13.76 ng and 27.82~45.88 ng, respectively. The method showed good linearity with correlation coefficient more than 0.9888, satisfactory recovery and reproducibility. These results showed that HS-MMSE using disk type MonoTrap is a new promising technique for the analysis of volatile aroma compounds from vanilla perfume.

Isolation and Identification of 3 Low-molecular Compounds from Pear (Pyrus pyrifolia Nakai cv. Chuhwangbae) Fruit Peel (추황배(Pyrus pyrifolia Nakai cv. Chuhwangbae) 과피로부터 3종의 저분자 화합물의 단리·동정)

  • Lee, Yu Geon;Cho, Jeong-Yong;Kim, Chan-Mi;Jeong, Hang-Yeon;Lee, DongI;Kim, Soo Ro;Lee, Sang-Hyen;Kim, Wol-Soo;Park, Keun-Hyung;Moon, Jae-Hak
    • Korean Journal of Food Science and Technology
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    • v.45 no.2
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    • pp.174-179
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    • 2013
  • Three low-molecular compounds were isolated from methanol extracts of pear (Pyrus pyrifolia N. cv. Chuhwangbae) fruit peels using solvent fractionation, various types of column chromatogrphy (Diaion HP-20, Sephadex LH-20, and silica gel), and high performance liquid chromatography with an assay guided by 1,1-diphenyl-2-picrylhydrazyl radical-scavenging activity. The isolated compounds were identified as 2-carboxyl-4(1H)-quinolinone (kynurenic acid, 1) from butanol fraction, cis-p-coumaric acid (2) from ethyl acetate-acidic fraction, and vanillin (3) from the ethyl acetate-phenolic fraction, respectively. These isolated compounds were confirmed on the basis of the spectroscopic data of electrospray ionization mass spectrometry and nuclear magnetic resonance. This is the first time that compounds 1-3 were isolated and identified in pear.

Formation of Fruit Aroma Compounds from Whey by Kluyverumyces lactis (Kluyveromyces lactis에 의한 유청으로부터 과일향 성분의 생성)

  • 김소미;이형주
    • Microbiology and Biotechnology Letters
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    • v.19 no.5
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    • pp.536-541
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    • 1991
  • To enhance the productivity of fruit flavor compounds from whey by the lactose fermenting yeast, Kluyveromyces lactzs ATCC 8585 was treated with N-methyI-N'-nitro-N-nitrosoguanidine (NTG). After the NTG treatments, a mutant showing resistance to antifungal activity of geraniol, and strong fruity but low yeasty flavor was selected and named as K. lactis 450 K. Flavor compounds from 3-day culture broth were extracted with pentane-dichloromethane (2:l) and the concentrated oleoresins were analyzed by gas chromatography. The mutant strain produced more classes and larger amount of flavor compounds than the parent stlain. Tentatively identified volatile compounds from the culture of the mutant were: terpenes such as myrcenol; alcohols such as cis-3-hexenol, n-hexanol; esters such as ethyl isovalerate, cis- 3-hexenyl n-butyrate, n-amyl-n-hexanoate, phenyl ethyl n-propioate; ketones such as methyl vinyl ketones; other compounds such as vanillin, 3-methylcoumarin.

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New Methods for Isolation of Sesquiterpene from Panax ginseng (인삼 Sesquiterpene의 새로운 분리방법)

  • 위재준;신지영
    • Journal of Ginseng Research
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    • v.21 no.3
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    • pp.214-218
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    • 1997
  • New simple methods for the Isolation of sesquiterpenes from Panax ginseng were developed. First, volatile compounds were isolated by simultaneous distillation and extraction (SDE) with 30% methanol and $\alpha$-hexane instead of water and ethyl ether/pentane (1:1). Secondly, head space volatiles in U-shaped tube at 7$0^{\circ}C$ were passed through C18 Sep-Pak by nitrogen gas streaming and the adsorbed volatiles were fluted by $\alpha$-hexane. TLC analysis showed that the volatile concentrates consisted mainly of terpenes when colored by vanillin-sulfuric and. GC/MS data revealed that approximately 30 sesquiterpenes of molecular weight 204 occupied 81.1% or more of the volatile concentrates isolated by those two newly developed methods. Among these, alloaromadendrene, germacrene B, isocaryophyllene, $\alpha$-neoclovene, ${\gamma}$-muurolene, $\beta$-panaslnsene, and $\alpha$-humulene were identified as being major sesqulterpenes by authentic samples or literatme search Key words : Panax ginseng, volatile compound, sesquiterpene, isolation, new method, GC/MS.

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Antioxidant Properties of Proanthocyanidin Fraction Isolated from Wild Grape (Vitis amurensis) Peel (산머루 과피에서 분리한 proanthocyanidin 획분의 항산화 특성)

  • Lee, Hye-Ryun;Hwang, In-Wook;Zheng, Hu-Zhe;Jeong, Woo-Sik;Kim, Young-Chan;Chung, Shin-Kyo
    • Korean Journal of Food Science and Technology
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    • v.42 no.4
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    • pp.420-423
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    • 2010
  • The proanthocyanidin fraction was isolated from the wild grape (Vitis amurensis) peel and its antioxidant capacities were examined to promote the utilization of wild grape by-products. The 70% acetone crude extract of the wild grape peel was fractionated with hexane, ethyl acetate, and water. The ethyl acetate fraction was applied to a Sephadex LH-20 column chromatograph, which was eluted with 50% methanol, 75% methanol, and 75% acetone. The proanthocyanidin characteristics and contents of the isolated fractions were investigated by the vanillin-$H_2SO_4$ and BuOH-HCl methods. Fraction 6 had the highest proanthocyanidin content ($49.35{\pm}2.75\;g%$) among the isolated fractions. The antioxidant activities of the proanthocyanidin fraction were examined by DPPH radical scavenging, FRAP assay, and total phenolic contents. The FRAP values and total phenolic contents of the fractions ranged from 3.54 to 32.25 mmol/kg and from 4.48 to 50.80 g/100 g, respectively. The proanthocyanidin contents was strongly correlated with DPPH radical scavenging activities, FRAP values, and total phenolic contents.

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.

Quantitative Analysis of The Fruit Flesh of Prunus mume Siebold & Zuccarni. (매실 과육성분의 분석)

  • Lee, Oh-Kyu;Lee, Hak-Ju;Shin, Yu-Su;Ahn, Yun-Gyong;Jo, Hyun-Jin;Shin, Hyeon-Cheol;Kang, Ha-Young
    • Korean Journal of Medicinal Crop Science
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    • v.15 no.3
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    • pp.143-147
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    • 2007
  • The fruit flesh of four Prunus mume cultivated varieties, P. mume 'Nanko', P. mume 'Viridicalyx', P. mume 'Baigo', P. mume var, microcarpa 'Koshusaisho' Siebold & Zuccarni, were ground and extracted with ethyl acetate and their chemical components were analyzed by GC/MS-SIM. In the ten compounds which was used fer the calibration, maleic anhydride, citraconic anhydride, 5-hydroxymethylfurfural, vanillin, linoleic acid, ethyl linoleate, and squalene were determined in all the four cultivated varieties. However, palmitic acid was detected only in P. mume var. microcarpa 'Koshusaisho'. Isopropyl palmitate was found only in P. mume 'Baigo' and var, microcarpa 'Koshusaisho', while stearic acid was determined in P. mume 'Nanko', 'Viridicalyx', and var, microcarpa 'Koshusaisho'. In the variation of quantities, maleic anhydride was contained 245.4, 153.6, 20.1, and 2.7 ppm in P. mume 'Baigo', 'Nanko', var. microcarpa 'Koshusaisho', and 'Viridicalyx', respectively. Citraconic anhydride was also contained 637.4, 543.1, 150.7, and 38.7 ppm in P. mume 'Baigo', 'Nanko', var. microcarpa 'Koshusaisho', and 'Viridicalyx', respectively. The amounts of stearic acid were 105.5, 64.4, and 32.3 ppm in P. mume var. microcarpa 'Koshusaisho', 'Viridicalyx', and 'Nanko', respectively. Squalene was found in amounts of 7.6, 1.7, 1.0, and 0.5 ppm in P. mume var. microcarpa 'Koshusaisho', 'Baigo', 'Nanko', and 'Viridicalyx', respectively. The amounts of other minor compounds also were varied in the P. mume cultivated varieties.

Radical Scavenging Activity of Kemenyan Resin Produced by an Indonesian Native Plant, Styrax sumatrana

  • Hidayat, Asep;Iswanto, Apri Heri;Susilowati, Arida;Rachmat, Henti Hendalastuti
    • Journal of the Korean Wood Science and Technology
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    • v.46 no.4
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    • pp.346-354
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    • 2018
  • Kemenyan resin from Styrax sumatrana is a unique non-timber forest product (NTFP) native from Sumatera Island, Indonesia. It possesses a wide range of applications in the pharmaceutical, perfume, and cosmetics industries. In this paper, six kemenyan resin samples were investigated to evaluate their free radical scavenging activity using 1,1-diphenyl-2-picrylhydrazyl (DPPH) reagent. The kemenyan resin samples, which originated from North Tapanuli, Pakpak Bharat, and Humbang Hasundutan, showed high antioxidant activity with $IC_{50}$ < 16 mg/L. The antioxidant activity of common kemenyan resin constituents, i.e., cinnamic acid, ethyl cinnamate, gallic acid, and vanillin was also investigated as positive control, although they exhibited lower antioxidant activity ($IC_{50}$ < 1000 mg/L), except for gallic acid ($IC_{50}$ = 5,23 mg/L). The total phenolic and flavonoid contents (TPC and TFC) for all samples were 44-66 mg gallic acid equivalents (GAE)/g sample and 143-160 mg quarcetin equivalents (QE)/g sample. The results revealed that kemenyan resin has high potency as an antioxidant and could be used as a natural antioxidant resource.

Structure Determination of the Extractives from the Taxus Cuspidata Fruits (주목열매 추출물 구조분석)

  • Park, Se-Yeong;Choi, In-Gyu;Bae, Young-Soo
    • Journal of the Korean Wood Science and Technology
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    • v.41 no.6
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    • pp.566-575
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    • 2013
  • The fruits of Taxus cuspidata were collected, divided into seeds and fruits, and extracted with 95% EtOH. The extracts were evaporated under the reduced vacuum pressure, concentrated, then successively fractionated with a series of n-hexane, dichloromethane, ethyl acetate and water on a separatory funnel to get some freeze dried samples. A portion of the EtOAc (arils:1.65 g, seeds:1.04 g) and $H_2O$ (arils:7 g, seeds:10 g) soluble samples were chromatographed on a Sephadex column using MeOH-$H_2O$ (1:1, 1:3, 1:5, v/v), EtOH-hexane (3:1, v/v) mixture and 100% $H_2O$ as eluting solvents to isolate pure compounds from the fractions. The isolates were developed by cellulose TLC using t-BuOH-HOAc-$H_2O$ (TBA; 3:1:1, v/v/v) and 6% aqueous HOAc. Visualization was done under ultraviolet light and by spraying the vanillin-HCl-EtOH reagent (4.8:12:480, v/v/v). followed by heating. The structures of the isolates were characterized by $^1H$- and $^{13}C$-NMR, DEPT, 2D-NMR, LC/MS and EI-MS spectra. In addition to the NMR and MS spectra, acid hydrolysis and permethylation were used to determine the correct structure of the isolated sugar compound. Their structures were elucidated as (+)-catechin (1), (-)-epicatechin (2), (+)-gallocatechin (3), (-)-epigallocatechin (4) and ${\beta}$-D-fructofuranose-($2{\rightarrow}4$)-O-${\beta}$-D-glucopyranose($1{\rightarrow}4$)-O-${\alpha}$-D-glucopyranose ($1{\rightarrow}2$)-O-${\beta}$-D-fructofuranose (5) on the basis of the above experimental evidences.