• Title/Summary/Keyword: Glycoside

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Antimelanogenic Effect of Isomaltol Glycoside from Red Ginseng Extract (홍삼추출물에 함유된 이소말톨 글리토시드의 멜라닌 생성저해 효과)

  • Lee, Sang Myung
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.45 no.3
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    • pp.255-263
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    • 2019
  • Isomaltol glycoside is a hydrophilic furanic glycoside in which the amino acids and sugars of ginseng are thermally denatured during red ginseng production. Various skin whitening tests were conducted on isomaltol glycoside containing a lot of red ginseng extract in order to investigate the skin whitening effect as a cosmetic raw material. We have tested melanin content assay in B16-F10 cells, zebrafish embryo pigmentation assay, mushroom tyrosinase inhibitory activity, western blot analysis to determine skin whitening activity of isomaltol glycosides. In the zebrafish melanin content assay, isomaltol glycoside decreased total melanin content by about 20% and zebrafish tyrosinase activity by about 10% after treatment with 50 and $100{\mu}g/mL$ compared to the untreated control group. Isomaltol glycoside also showed a concentration-dependent decrease in melanin content in B16-F10 melanoma. Furthermore, it increased the expression of MITF phosphorylation factors p-AKT and p-ERK in B16-F10 melanoma and decreased the concentration of MITF. It also inhibited tyrosinase, TRP-1 and TRP-2 expression. The content of isomaltol glycoside was about 3% in the ginseng extract and about 1% in the ginseng root. Thus, isomaltol glycoside is considered as one of the main components that exhibit the whitening activity of ginseng when considered quantitatively as whitening activity.

Synthesis of Glycoside by Transglycosylation of Amyloglucosidase from Starch. (전분으로부터 Amyloglucosidase의 당전이반응에 의한 배당체의 합성)

  • 박종이;이희정;이태호
    • Microbiology and Biotechnology Letters
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    • v.26 no.2
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    • pp.187-194
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    • 1998
  • Glycosides were synthesized using transglycosylation reaction of amylase in water system. Starch as a glycosyl donor and benzylalcohol as an acceptor were selected as substrates of transglycosylation reaction. Among tested 9 commercial amylase, amyloglucosidase from Rhizopus sp. had high activity for transglycosylation from starch. The glycoside synthesized in water phase by amyloglucosidase was identified as benzylalcohol-${alpha}$-glucoside (BG) of which one molecule of benzylalcohol was bound to 1-OH of glucose. The transglycosylation reaction by amyloglucosidase were carried out in reaction system containing 50 mg starch, 50 mg benzylalcohol, and 10 units enzyme in pH 5.0 at 45$^{\circ}C$. The synthesized BG was hydrolyzed by ${alpha}$-glucosidase to produce glucose and benzylalcohol.

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Enzymatic Glycosylation of Fatty Acids by Methyl Glycosides (메틸글리코시드에 의한 지방산의 효소적 배당화)

  • SunWoo, Hwan;Kim, Chong-Tai;Kim, Hae-Sung
    • Journal of the Korean Applied Science and Technology
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    • v.16 no.1
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    • pp.83-94
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    • 1999
  • Glycoside fatty acid esters were synthesized by lipase-catalyzed glycosylation of fatty acids with methyl glycoside in solvent and solvent free process. Optimum condition of solvent process using 2-methyl-2-propanol were : moral ratio of methyl glycoside to fatty acid 1:3: initial concentration of methyl glycoside 50g/l:enzyme(immodilized lipase Novozym 435 from Candidia antarctica) content 1%(w/v) : desiccant content 9%(w/v); reaction temperature $60^{\circ}C$: reaction time 10hrs. The yield of 99% was obtained. Solvent-free process was carried out in total absence of solvent at $70^{\circ}C$ under reduced pressure, 5-20mmHg. To give meximum yield of 99% at the optimum condition of molar ratio of methyl glycoside to fatty acid 1:3, enzyme content 10%(w/w), and reaction time 10hrs. The glycosylation reactivity of different glycosylation agents were sequent to $Methyl-{\beta}-D-fructofuranoside$. $Methyl-{\beta}-D-glucopyranoside$. $Methyl-{\beta}-D-fructofuranosi$ de, and $Methyl-{\alpha}-D-glucopyranoside$.

Comparative Studies on the Composition of Polar Lipids in Japonica and Indica Rice Bran Oils (일반계 및 다수계 미강유의 극성지방질 조성)

  • 권경순;최광수;김현구
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.25 no.5
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    • pp.735-740
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    • 1996
  • This study was carried out to determine the composition of glycolipids and phospholipids in Japonica and Indica rice bran oils. The ratio of glycolipids and phospholipids was 4.1 : 6.5% in Japonica rice bran oils and 2.6 : 3.7% in Indica rice bran oils. Polar lipid content was significantly higher in Japonica rice bran oils. The main components of glycolipids were esterified steryl glycoside, monogalactosyl diglyceride steryl glycoside, cerebroside and digalactosyl diglyceride. The content of esterified steryl glycoside was the highest, resulting in 48.8~52.1% of total glycolipids. Phospholipids in rice bran oils consisted of diphosphatidyl glycerol, phosphatidyl ethanolamines, phosphatidyl inositol, phosphatidyl serines, phosphatidyl choline and lysophosphotidyl choline. Major fatty acids of the glycolipids and phospholipids fractions were oleic, linoleic and palmitic acids in Japonica and Indica rice bran oils.

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Methyl Jasmonate-mediated Enhancement of Phenylethanoid Glycoside in Callus from Abeliophyllum distichum (cultivar Okhwang1)

  • Tae-Won Jang;So-Yeon Han;Da-Yoon Lee;Seo-Yoon Park;Woo-Jin Oh;Jae-Ho Park
    • Proceedings of the Plant Resources Society of Korea Conference
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    • 2023.04a
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    • pp.53-53
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    • 2023
  • Abeliophyllum distichum, one of the Korean endemic plant, is a significant pharmaceutical plant resource. A. distichum with phenylethanoid glycoside can use to regulate the development of cancer, DNA damage with radicals, and the generation of inflammatory mediators. In this study, we investigated whether the biomass, content of phenylethanoid glycoside, and growth rate of callus derived from A. distichum (cultivar Okhwang1, CAD) change in the absence or presence of plant hormones (2,4-Dichlorophenoxyacetic acid; 2, 4-D and 1-Naphthaleneacetic acid; NAA). The results showed that the best biomass, the growth rate of callus, and the contents of phenylethanoid glycoside were cultivated on Murashige and Skoog (MS) growth medium fortified with 1 ppm 2,4-D + 2 ppm NAA after 4 weeks. In a further study, CAD was cultivated on MS growth medium fortified with an elicitor (Methyl Jasmonate, MeJA). The results showed that CAD turned to brown color and fragile form with the elicitor. HPLC-PDA analysis revealed that the contents of phenylethanoid glycoside in the elicitor-treated group were higher than in the elicitor-non-treated group. These results are consistent with the findings of Arano-Varela H et al.,'s study which is that acteoside production can increase after the treatment of MeJA. Therefore, this study can be used to develop an effective and sustainable production of useful substances as an alternative to plant cultivation.

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Flavanone Glycoside from the Fruits of Chaenomeles sinensis

  • Kim, Ho-Kyoung;Jeon, Won-Kyung;Ko, Byoung-Seob
    • Natural Product Sciences
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    • v.6 no.2
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    • pp.79-81
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    • 2000
  • Investigation of the fruits of Chaenomeles sinensis (Rosaceae) resulted in the isolation of a minor flavonoid. The structure of flavanone glycoside was determined to be as $2-hydroxynaringenin-7-O-{\beta}-glucoside$ on the basis of FAB-MS and spectral evidence, especially by 2D-NMR $(^1H-^1H\;COSY,\;HMQC,\;HMBC\;and\;NOESY)$.

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Antitumor and Antiinflammatory Constituents from Celtis sinensis

  • Kim Dae Keun;Lim Jong Pil;Kim Jin Wook;Park Hee Wook;Eun Jae Soon
    • Archives of Pharmacal Research
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    • v.28 no.1
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    • pp.39-43
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    • 2005
  • Eight compounds were isolated from the methanolic extract of the twigs of Celtis sinensis through repeated silica gel and Sephadex LH-20 column chromatography. Their chemical structures were elucidated as two triterpenoids, germanicol and epifriedelanol, two amide compounds, trans-N-caffeoyltyramine and cis-N-coumaroyltyramine, two lignan glycoside, pinoresinol glycoside and pinoresinol rutinoside, and two steroids by spectroscopic analysis.

Catechin Glycoside from Ulmus davidiana

  • Son, Byeng-Wha;Park, Jong-Hee;Zee, Ok-Pyo
    • Archives of Pharmacal Research
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    • v.12 no.3
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    • pp.219-222
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    • 1989
  • Cartechin and catechin glycoside named uldavioside A were isolated from the Korean folk medicine Ulmus davidiana. Based on chemical and physicochemical evidences, their structure have been determined as (+) catechin (1) and (+)-catechin-5-0-$\betha$ D-apiofuranoside (2).

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Diterpene Glycoside from Acanthopanax koreanum

  • Kim, Young-Ho;Ryu, Jong-Hyeon;Chung, Bo-Sup
    • Korean Journal of Pharmacognosy
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    • v.21 no.1
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    • pp.49-51
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    • 1990
  • From tire root bark of Accnthopanax koreanum a new diterpene glycoside, mp $212{\sim}214^{\circ}$, was isolated. The structure was established as 15(R),16-dihydroxypimar-9(11)-ene-19-oic acid ${\beta}$-D-glucopyranosyl ester (sumogaside) oil the basis of spectroscopic methods and chemical transformation.

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Iridoid Compounds from the Whole Plant of Galium verum var. asiaticum

  • Lee, Tae Gwan;Kim, Dae Keun
    • Natural Product Sciences
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    • v.19 no.3
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    • pp.227-230
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    • 2013
  • One new iridoid glycoside, 10-p-dihydrocoumaroyl-6-${\alpha}$-hydroxygeniposide (1), and six known iridoid glycoside derivatives, 10-p-dihydrocoumaroyl deacetylasperuloside (2), asperulosidic acid methylester (3), asperuloside (4), asperulosidic acid (5), deacetylasperuloside (6), and scandoside (7) were isolated from the methanolic extract of the whole plant of Galium verum var. asiaticum Nakai (Rubiaceae) through repeated column chromatography. Their chemical structures were characterized by spectroscopic analysis. This is the first report of the characterization of compounds 1 - 7 from this plant.