• Title/Summary/Keyword: Glycoside compounds

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Analysis and Quantitative Distribution of Glycosided Flavonoids in Citruses and Korean Chung-pi (감귤류와 한국산 청피에 함유된 Glycosided Flavonoids의 분석과 정량적 분포)

  • Baik, S.O.;Bock, J.Y.;Chun, H.J.;Jeong, S.I.;Baek, S.H.;Oh, H.B.;Kim, I.K.
    • Analytical Science and Technology
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    • v.14 no.4
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    • pp.340-348
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    • 2001
  • Glycosided flabonoids (naringenin, naringin, narirutin, hesperidin, and hesperetin) in Citrus and Korea Chung-pi were isolated and analyzed with HPLC, GC-mass, UV and high resolution NMR. Contents of glycosided flavonoids were compared according to kinds of Citrus and fruit ripening periods. Major compound of Korean Chung-pi was hesperidin and minors were narirutin and hesperetin. Major compounds of Gisil were naringin, narirutin, naringenin and were narirutin, hesperidin in Gigak. Major compounds of milgam and orange were narirutin, hesperidin, and the contents of glycoside flavonoids decreased according to the age of maturity.

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Analysis of Essential oil, Quantification of Six Glycosides, and Nitric Oxide Synthase Inhibition Activity in Caryopteris incana

  • Nugroho, Agung;Lee, Sang Kook;Kim, Donghwa;Choi, Jae Sue;Park, Kyoung-Sik;Song, Byong-Min;Park, Hee-Juhn
    • Natural Product Sciences
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    • v.24 no.3
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    • pp.181-188
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    • 2018
  • Caryopteris incana (Verbenaceae) has been used to treat cough, arthritis, and eczema in Oriental medicine. The two fractions ($CHCl_3-$ and BuOH fractions) and the essential oil of the plant material were subjected to the inducible nitric oxide synthase (iNOS) assay. The $IC_{50}$ of the $CHCl_3$ fraction and the essential oil on LPS-induced macrophage RAW 264.7 cells were $16.4{\mu}g/mL$ and $23.08{\mu}g/mL$, respectively. On gas chromatography (GC)-mass spectroscopy (MS) analysis, twenty-five components representing 85.5% amount of total essential oil were identified. On the chromatogram, three main substances, trans-pinocarveol, cis-citral, and pinocarvone, occupied 18.8%, 13.5% and 18.37% of total peak area. Furthermore, by HPLC-UV analysis, six compounds including one iridoid (8-O-acetylharpagide)- and five phenylethanoid glycosides (caryopteroside, acteoside, phlinoside A, 6-O-caffeoylphlinoside, and leucosceptoside A) isolated from the BuOH fraction were quantified. The content of six compounds were shown as the following order: caryopteroside (162.35 mg/g) > 8-O-acetylharpagide (93.28 mg/g) > 6-O-caffeoylphlinoside (28.15 mg/g) > phlinoside (22.60 mg/g) > leucosceptoside A (16.87 mg) > acteoside (7.05 mg/g).

Topical or oral treatment of peach flower extract attenuates UV-induced epidermal thickening, matrix metalloproteinase-13 expression and pro-inflammatory cytokine production in hairless mice skin

  • Kwak, Chung Shil;Yang, Jiwon;Shin, Chang-Yup;Chung, Jin Ho
    • Nutrition Research and Practice
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    • v.12 no.1
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    • pp.29-40
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    • 2018
  • BACKGROUND/OBJECTIVES: Ultraviolet radiation (UV) is a major cause of skin photoaging. Previous studies reported that ethanol extract (PET) of Prunus persica (L.) Batsch flowers (PPF, peach flowers) and its subfractions, particularly the ethylacetate (PEA) and n-butanol extracts (PBT), have potent antioxidant activity and attenuate the UV-induced matrix metalloproteinase (MMP) expression in human skin cells. In this study, we investigated the protective activity of PPF extract against UV-induced photoaging in a mouse model. MATERIALS/METHODS: Hairless mice were treated with PET or a mixture of PEA and PBT either topically or orally along with UV irradiation. Histological changes and biochemical alterations of mouse skin were examined. Major phenolic compounds in PPF extract were analyzed using an ACQUITY UPLC system. RESULTS: The overall effects of topical and oral treatments with PPF extract on the UV-induced skin responses exhibited similar patterns. In both experiments, the mixture of PEA and PBT significantly inhibited the UV-induced skin and epidermal thickening, while PET inhibited only the UV-induced epidermal thickening. Treatment of PET or the mixture of PEA and PBT significantly inhibited the UV-induced MMP-13 expression, but not type I collagen expression. Topical treatment of the mixture of PEA and PBT with UV irradiation significantly elevated catalase, superoxide dismutase (SOD) and glutathione-peroxidase (GPx) activities in the skin compared to those in the UV irradiated control group, while oral treatment of the mixture of PEA and PBT or PET elevated only catalase and SOD activities, but not GPx. Thirteen phytochemical compounds including 4-O-caffeoylquinic acid, cimicifugic acid E and B, quercetin-3-O-rhamnoside and kaempferol glycoside derivatives were identified in the PPF extract. CONCLUSIONS: These results demonstrate that treatment with PET or the mixture of PEA and PBT, both topically or orally, attenuates UV-induced photoaging via the cooperative interactions of phenolic components having anti-oxidative and collagen-protective activities.

Simultaneous Determination of Asperosaponins and Iridoid Glycosides from Dipsaci Radix by Using LC-ESI-MS Spectrometry (속단(Dipsaci Radix) 중 Asperosaponins 및 Iridoid glycosides의 LC-ESI-MS에 의한 동시분석)

  • Cho, Hwang-Eui;Son, In-Seop;Kim, Sun-Cheun;Son, Kun-Ho;Woo, Mi-Hee;Moon, Dong-Cheul
    • Korean Journal of Pharmacognosy
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    • v.43 no.2
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    • pp.137-146
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    • 2012
  • Dipsaci Radix (Dipsacaceae) has been used as a tonic, an analgesic, anti-inflammatory and anti-complement agents in traditional herbal medicine for the therapy of low back pain, knee pain, rheumatic arthritis, traumatic hematoma, and bone fractures. A high-performance liquid chromatography-electrospray ionization-mass spectrometric method (HPLC-ESI-MS) was developed for the simultaneous quantitation method of the five compounds from the herbal drug: asperosaponin VI and asperosaponin XII (terpene glycosides), sweroside, loganin and dipsacus A(iridoid glycosides). HPLC separation of the analytes was achieved on a C18 column ($150{\times}2.0$ mm i.d., 5 ${\mu}m$) using the aqueous methanol containing 5 mM ammonium acetate with gradient flow of the mobile phase. Detection of the analytes was performed by positive ion electrospray ionization, and selected ion monitoring was used for data acquisition using m/z corresponding molecular adduct ion, $[M+NH_4]^+$ and $[M+H]^+$. Calibration graphs showed good linearity ($r^2$=0.9997) over the wide range of the analytes; intra- and inter-day precisions (RSD, %) were within 9.1% and the accuracy between 94.0-111.0%. Recoveries of the analytes through the assay procedure were in the range of 93.7-110.8%. Analytical results of the herbal drugs of Dipsaci Radix (17 samples) show wide distribution of the five marker compounds and clear difference of the species from Phlomidis Radix (4 samples). The developed method would provide a practical guide for the quality control of the herbal drug.

Antioxidative and anti-inflammatory activities of Phaseolus aureus

  • Hong, In-Taik;Kim, Beom-Jun;Yu, Duck-Cho;Kim, Jung-Haeng;Kim, Jung-Han;Heo, Moon-Young;Lee, Song-Jin;Kim, Hyun-Pyo
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.22 no.2
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    • pp.41-51
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    • 1996
  • Phaseolus aureus (mung bean), Leguminosae, has been used as an antidote from the ancient time. Especially, it has been widely used for cleaning face and skin in oriental countries. Although several constituents such as fatty acids, phytoallexin and phaseol derivatives were reported in P. aureus and related species including seedlings, there has been a few report to describe its biological activity. Therefore, in this investigation, the ethanol extract from P. aureus was obtained and its biological activities including the antioxidative and anti-inflammatory activities were studied. The 70% ethanol extract from P. aureus showed dose-dependent antioxidative activity (52.3% inhibition at 4 mg/ml) against lipid peroxidation assay, while the extract did not show the inhibitory activity of superoxide radical formation. The extract also showed the topical anti-inflammatory activity against croton-oil and arachidonic acid induced mouse ear edema test (18-19% inhibition at 7.5 mg/ear) as well as mild inhibitory activity against picryl chloride induced delayed hypersensitivity in mouse. For investigating active principles, vitexin and isovitexin (apigenin C-glycoside) as flavonoids, and adenosine were isolated from the extract using silica gel chromatography. The actual contents of vitexin and isovitexin were found to be 3.7 and 2.4 mg/g extract, respectively. Vitexin and isovitexin showed the antioxidative activity. They showed the topical anti-inflammatory activity, although the activities were not potent compared to the reference compounds. These results suggested that vitexin and isovitexin may be, at least in part, the compounds contributing the antioxidative activity in vitro and the topical anti-inflammatory activity of P. aureus in vivo. All results of present study might be one of the scientific rationale in using mung bean for skin care from the ancient time.

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Isolation of Daucosterol and Naphthalene glucoside from Seeds of Cassia mimosoides var. nomame Makino (차풀 종자로부터 Daucosterol과 Naphthalene glucoside의 분리)

  • Park, Jun-Hong;Kwon, Sun-Jin
    • Korean Journal of Plant Resources
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    • v.22 no.1
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    • pp.26-30
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    • 2009
  • Daucosterol and naphthalene glycoside were isolated from the seeds of Cassia mimosoides var. nomame Makino. The isolated compounds were identified by spectral means including 1D, 2D-NMR and FAB-MS experiments. Daucosterol was characterized as ${\beta}$-sitosterol-3-O-${\beta}$-D-glucoside and naphthalene glucoside was done as 2-acetyl-3-methyl-6-methoxynaphthalene-1,8-diol 8-O-glucosyl-(1${\rightarrow}$6)-glucoside. These compounds were isolated for the first time from Cassia mimosoides var. nomame Makino.

Evaluation of Skin Sebosuppression by Components of Total Green Tea (Camellia sinensis) Extracts

  • Kim, Jeong-Kee;Shin, Hyun-Jung;Lee, Byeong-Gon;Lee, Sang-Jun
    • Food Science and Biotechnology
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    • v.17 no.3
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    • pp.464-469
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    • 2008
  • In human beings, it is known that there is a correlation between the occurrence of acne and the ability to suppress sebum. Sebosuppression may be related to the inhibition of sebocyte proliferation, differentiation, and lipogenesis in sebaceous glands. To investigate the skin sebosuppressive activity of green tea extract, the in vivo effects of its flavonoid compounds on the androgen-dependent stimulation of pigmented macules in hamsters and performed in vitro experiments with human primary sebocytes were examined. Our results imply a dual activity of skin sebosuppression by green tea flavonoids; some catechins including epigallocatechin-3-gallate (EGCG) and gallocatechin-3-gallate (GCG) may reduce the differentiation of sebocytes by inhibiting PPAR-${\gamma}1$ mRNA expression, whereas some flavonol glycosides including kaempferol may inhibit lipogenesis in sebaceous glands by decreasing levels of the mature form of sterol-sensitive response elements binding protein-1c (SREBP-1c). Therefore, green tea is a potentially effective material for use in the development of health foods or cosmetics for skin sebosuppression.

Isolations of Flavonoids and a Higher Alcohol from the Aerial Parts of Brassica juncea (갓 지상부에서 플라보노이드와 고급 알콜 화합물의 분리)

  • Ahn, Byoung-Gwan;Hur, Jong-Moon;Park, Jong-Cheol
    • Korean Journal of Pharmacognosy
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    • v.38 no.3 s.150
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    • pp.254-257
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    • 2007
  • The aerial parts of Brassica juncea (Cruciferae) called by brown or oriental mustard have been widely used as a spice in food and also traditional folk medicine as stimulant, diuretic and expectorant agent. And Gatkimchi made of the aerial parts of this plant are very popular in Korea. The aerial parts of this plant was refluxed with MeOH and then fractionationed with $CH_2Cl_2$, EtOAc, n-BuOH and $H_2O$, successively. One higher alcohol compound and three flavonoids were isolated from the EtOAc fraction through silica gel and Sephadex LH-20 column chromatographies. Their structures were elucidated as n-hexacosanol(1), kaempferol(2), isorhamnetin $3-O-{\beta}-D-glucopyranoside(3)$ and isorhamnetin $3-O-(6'-O-acetyl)-{\beta}-D-glucopyranoside(4)$ by comparison of spectral data with those in references. And compounds 1 and 4 were firstly isolated from this plant.

Flavonoids from the Stem of Rhamnus taquetii (좀 갈매나무 줄기의 플라보노이드)

  • Hwang, Wan-Gyun;Jeong, Hye-Jin;Go, Seong-Gwon;Lee, Mu-Taek;Kim, Il-Hyeok
    • YAKHAK HOEJI
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    • v.40 no.4
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    • pp.394-399
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    • 1996
  • As a series of the studies on the specific and indigenous plants of Mt. Halla, the constituents from stem of Rhamnus taquetii (Rhamnaceae) were investigated. From the water fraction of the MeOH extract, a new flavonol glycoside, kaempferide-3-O-${\alpha}$-L-rhamnopyranosyl(1->3)-${\alpha}$-L-rhamnopyranosyl(1-6)-${\beta}$-D-galactopyranoside, was isolated with three known compounds, quercetin, quercetin-3-methylether, kaempferol, by column chromatographic separation using Amberlite XAD-2, ODS-gel and Sephadex LH-20 and elucidated physico-chemical evidences($^1H-NMR,\;^{13}C-NMR$,IR, EI-Mass, FAB-Mass, and G.C.),respectively.

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Structure-Activity Relationship of Triterpenoids Isolated from Mitragyna stipulosa on Cytotoxicity

  • Tapondjou, Leon Azefack;Lontsi, David;Sondengam, Beiham Luc;Choudhary, Muhammad Iqbal;Park, Hee-Juhn;Choi, Jong-Won;Lee, Kyung-Tae
    • Archives of Pharmacal Research
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    • v.25 no.3
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    • pp.270-274
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    • 2002
  • Chromatographic separation of the stem bark extract of Mitragyna stipulosa afforded triterpene derivatives ursolic acid (1), quinovic acid (2), quinivic acid $3-O-{\beta}-D-glucopyranoside$ (3, quinovin glycoside C), quinovic acid 3-O-[$(2-O-sulfo)-{\beta}-D-quinovopyranoside$] (4, zygophyloside D) and quinovic acid $3-O-{\beta}-D-quinovopyranosyl-27-O-{\beta}-D-glucopyranosyl$ ester (5, zygophyloside B). These five compounds were subjected to the cytotoxicity on MTT assay system. Compound 1 among tested showed the most potent cytotoxicity. Quinovic acid showed less potent cytotoxicity than ursolic acid and sugar linkages to 2 decreased the cytotoxicity. Compound 4 more potent than 3 with indicate that the sulfonyl group significantly enhances the activity. This indicates that the glycosidic linkage in ursane-type triterpenoids has mainly negative effect on cytotoxicity unlike in oleanane-type glycosides.