• Title/Summary/Keyword: glucopyranosyl

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A Potent Anti-Complementary Acylated Sterol Glucoside from Orostachys japonicus

  • Yoon, Na-Young;Min, Byung-Sun;Lee, Hyeong-Kyu;Park, Jong-Cheol;Choi, Jae-Sue
    • Archives of Pharmacal Research
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    • v.28 no.8
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    • pp.892-896
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    • 2005
  • In order to isolate substances that inhibit the hemolytic activity of human serum against eryth-rocytes, we have evaluated whole plants of the Orostachys japonicus species with regard to its anti-complement activity, and have identified its active principles following activity-guided isolation. A methanol extract of the O. japonicus, as well as its n-hexane soluble fraction, exhibited significant anti-complement activity on the complement system, which was expressed as total hemolytic activity. A bioassay-guided chromatographic separation of the constituents resulted in the isolation of three known compounds 1-3 from the active n-hexane fraction. The structure of these compounds were analyzed, and they were identified as hydroxyhopanone (1), $\beta-sitosteryl-3-O-\beta-D-glucopyranosyl-6'-O-palmitate$ (2), and $\beta-sitosteryl-3-O-\beta-D-glucopyranoside$ (3), respectively. Of these compounds, compound 2 exhibited potent anti-complement activity $(IC_{50}=1.0\pm0.1{\mu}M)$ on the classical pathway of the complement, as compared to tiliroside $(IC_{50}=76.5\pm1.1{\mu}M)$, which was used as a positive control. However, compounds 1 and 3 exhibited no activity in this system.

Constituents of the Herb of Isodon excisus var. coreanus

  • Kim, Ho-Kyoung;Whang, Wan-Kyunn;Kim, Il-Hyuk
    • Archives of Pharmacal Research
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    • v.20 no.3
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    • pp.291-296
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    • 1997
  • The studies were carried out to evaluate the constituents in the aerial part of Isodon excisus var. coreanus (Labiatae). From the aqueous fraction of methanol extract, compound I (${\alpha}$-[[3-(3, 4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-3,4-dihydroxy-benzenepropanoic acid), compound II (9-methyl-dihydroferulic acid-4-O-.betha.-D-glucopyranosyl $(1{\rightarrow}2)$-${\alpha}$-L- rhamnopyranosyl (1.rarw.4)-.betha.-D-glucopyranoside), compound III (ent-7.alpha., 11${\alpha}$,15.betha.-trihydroxy-kaur-16-en-1-O-.betha.-D-glucopyranoside) and compound IV ($2{\alpha}$,3${\beta}$,$7{\alpha}$,23-tetrahydroxy-olean-12 -en-28-oic acid 28-O-${\beta}$-D-glucopyranoside) were isolated and identified on the basis of their physicochemical and spectroscopic evidences[IR, FAB(-)MS,$^{1}H-NMR,$$^{13}C-NMR,$$ HMQC$$^{1}H-^{1}H $COSY and HMBC (Heteronuclear Multiple Bond Connectivity)]. Especially, New compounds II and III were named Isodonin A and Isodonin B respectively.

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Ginsenoside $Rg_5$, A Genuine Dammarane Glycoside from Korean Red Ginseng

  • Kim, Shin-Il;Park, Jeong-Hill;Ryu, Jae-Ha;Park, Jong-Dae;Lee, You-Hui;Park, Jae-Hyun;Kim, Tae-Hee;Kim, Jong-Moon;Baek, Nam-In
    • Archives of Pharmacal Research
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    • v.19 no.6
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    • pp.551-553
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    • 1996
  • A genuine dammarane glycoside, named ginsenoside $Rg_{5}$, has been isolated by repeated column chromatography and preparative HPLC from the MeOH extract of Korean red ginseng (Panax ginseng C.A. Meyer). The chemical structure of ginsenoside$ Rg_{5}$ was determined as $3-O-[{\beta}-D-glucopyranosyl (1{\rightarrow}2)-{\beta}-D-glucopyranosyl]$ dammar-20(22), $24-diene-3{\beta},12{\beta}-diol$ by spectral and chemical methods. The stereostructure of a double bond at C-20(22) of ginsenoside $Rg_{5}$ was characterized as (E) from the chemical shift of C-21 in the $^{13}C-NMR $and a NOESY experiment in the $^{1}H-NMR$.

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Phytochemical Constituents Isolated from the Stems of Chaenomeles sinensis Koehne (모과나무 줄기의 화학성분)

  • Shin, Ji-Eun;Jin, Qing-Long;Jin, Hong-Guang;Woo, Eun-Rhan
    • Korean Journal of Pharmacognosy
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    • v.42 no.3
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    • pp.223-228
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    • 2011
  • Chaenomeles sinensis Koehne (Rosaceae) is a deciduous tree and is distributed in China, Korea and Japan. In previous studies on the fruits of C. sinensis, some triterpenoid compouds such as oleanolic acid, tormentic acid were reported. In an ongoing investigation into biologically active compounds from natural products, the methanol extract of the stems of C. sinensis was investigated. By means of the repeated column chromatography using silica gel, Sephadex LH-20, LiChroprep RP-18, betulin (1), tormentic acid (2), 1-${\beta}$-D-glucopyranosyl-3,4,5-trimethoxybenzene (3), lyoniresinol-2a-O-${\alpha}$-L-rhamnopyranoside (4) were isolated. The chemical structures of compounds 1-4 were determined by the basis of physico-chemical properties and spectroscopic methods such as 1D and 2D NMR. For the isolated compounds (1-4), the inhibitory activity of IL-6 production in TNF-${\alpha}$ stimulated MG-63 cell was examined. Among the isolates, betulin (1), 1-${\beta}$-D-glucopyranosyl-3,4,5-trimethoxybenzene (3), lyoniresinol-2a-O-${\alpha}$-L-rhamnopyranoside (4) showed inhibitory effects on IL-6 production in TNF-${\alpha}$ stimulated MG-63 cell.

Antioxidant Effect of Hederagenin 3-O-b-D-Glucopyranosyl(1→3)-a-L-Rhamnopyranosyl(1→2)-a-L-Arabinopyranoside (HDL) Isolated from Root Bark of Ulmus davidiana (유근피로부터 분리한 hederagenin 3-O-b-D-glucopyranosyl(1→3)-a-L-rhamnopyranosyl(1→2)-a-L-arabinopyranoside (HDL)의 항산화 효과)

  • Bong, Jin-Gu;Park, Yoon-Yub
    • Journal of Life Science
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    • v.20 no.2
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    • pp.281-291
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    • 2010
  • We investigated the antioxidant effects of hederagenin 3-O-b-D-glucopyranosyl($1{\rightarrow}3$)-a-L-rhamnopyranosyl($1{\rightarrow}2$)-a-L-arabinopyranoside (HDL) isolated from root bark of Ulmus davidiana on the activity of enzymes related to reactive oxygen species (ROS) in human osteosarcoma U2OS cells. Cobalt chloride ($CoCl_2$), a transition metal, was used as an inducer of oxidative stress, generating hydrogen peroxide ($H_2O_2$) via increasing xanthine oxidase (XO) activity. The increased levels of $H_2O_2$, XO, ferritin, and ferritin iron by $CoCl_2$ were diminished effectively by co-treatment with HDL in U2OS cells. Furthermore, decreased levels of antioxidant enzymes such as superoxide dismutase (SOD), catalase (CAT) by $CoCl_2$ were highly increased by co-treatment with HDL in U2OS cells; however, the levels of glutathione peroxidase (GPx) did not change. The increased contents of TBARS related to lipid peroxidation were significantly reduced by HDL in U2OS cells. The concentration of GSH changed in a pattern that went against regulated TBARS by $CoCl_2$ and HDL. We examined the expression of p53, $p21^{CIP1/WAF1}$, and $p27^{KIP1}$ proteins related to oxidative stress and cell cycle regulation. As a result, the expression of $p27^{KIP1}$ modulated by $CoCl_2$ was not changed by HDL. However, the expression of p53 and $p21^{CIP1/WAF}$ increased by $CoCl_2$ was reduced by HDL in U2OS cells. Together with alteration of p53 and $p21^{CIP1/WAF1}$ proteins, the accumulated cells at G1 phase by $CoCl_2$ was decreased by HDL in U2OS cells. Our data suggests that HDL inhibits $CoCl_2$-generated ROS in U2OS cells, providing potentially new antioxidant compounds that are isolated from natural products.

Effect of Steviol β-Glucopyranosyl Ester on The Production of Nitric Oxide and Inflammatory Cytokines in RAW 264.7 Cells (Steviol β-Glucopyranosyl Ester가 RAW 264.7 세포의 산화질소 및 염증성 사이토카인 생성에 미치는 영향)

  • Jung, Heehoon;Cho, Uk Min;Hwang, Hyung Seo;Cho, Kun;Lee, Sang Rin;Kim, Moo Sung
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.44 no.3
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    • pp.239-247
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    • 2018
  • Chronic inflammation is known to have effects on various diseases such as gout, cancer, dementia, atopic disease, and obesity. In addition, since some signal cascades involved in the development of inflammation are known to affect the damage and aging of the skin tissue, studies are being conducted actively to control the inflammation mechanism. In order to mitigate or prevent inflammatory response, a number of researches have been made to develop anti-inflammatory materials from some plants. In particular, Stevia rebaudiana produces steviol glycosides (SG), a natural sweetener with a distinctive flavor. Studies on some of SG have been shown to have anti-inflammatory activity. Researchers of this study expected that more SG also possess anti-inflammatory activity, besides stevioside, rebaudioside A, and steviol. In order to confirm this possibility, the researchers screened inhibition activity of various steviol glucosides for NO production in RAW 264.7 cell lines. As a result, steviol ${\beta}-glucopyranosyl$ ester (SGE) showed the highest inhibitory activity among steviol derivatives treated at the same molar concentration. In addition, we found that mRNA expression level of $interleukin-1{\alpha}$ ($IL-1{\alpha}$), $interleukin-1{\beta}$ ($IL-1{\beta}$), cyclooxygenase-2 (COX-2), nuclear factor kappa-light chain-enhancer of activated B cells ($NF-{\kappa}B$) and inducible nitric oxide synthase (iNOS) was also decreased in a dose-dependent manner. These results show that SGE inhibits anti-inflammatory activity and NO production in mouse macrophage RAW 264.7 cells. It was confirmed that SGE has potential to be applied as an anti-inflammatory material.

Development of an Alcoholic Drink Using Onion Extract. (양파즙을 사용한 알코올 음료의 개발)

  • Kim, Sam-Woong;Oh, Eun-Hye;Jun, Hong-Ki
    • Journal of Life Science
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    • v.18 no.7
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    • pp.980-985
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    • 2008
  • This study was carried out to develope an alcoholic drink by fermentation of onion extract using Saccharomyces cerevisiae. The optimal conditions for ethanol production were obtained by standing culture at $25^{\circ}C$ for 5 days with 5% inoculum volume. At the results by flask culture, the growth curve of used S. cerevisiae reached to the stantionary phase at 48 hr and the death phase at 90 hr, whereas ethanol production reached maximum at 114 hr. Under the above conditions, a large scale production was carried out. A standing culture in 5 l fermenter showed the similar results to its flask culture, but progressed 24 hr rapidly more than that of the flask culture. A fed-batch culture was performed by addition of the onionic medium supplemented with 10% (v/v) sucrose after 72 hr from the fermenting start. The fed-batch culture could prevent S. cerevisiae from entering into the death phase and maintain constant level of alcohol production. A continuous culture was able to carry out by adding per every 24 hr the onionic medium supplemented with 10% (v/v) sucrose after 72 hr from the fermenting start. Although S. cerevisiae used showed a little decreased growth, alcohol production maintained roughly the constant level at the maximum yield. To enhance the quality of this alcoholic drink, $2-O-{\alpha}-D-glucopyranosyl$ L-ascorbic acid (AA-2G) was supplemented into the onion extract of the substrate for fermentation. As resulted at this study, this alcoholic drink containing AA-2G should be used as a functional fermented alcohol drink strengthened with vitamin C.

Development of Cosmeceutical Cosmetics Using Enzyme Bio-Conversion System (효소 생전환 시스템을 이용한 기능성 화장품 개발)

  • Lee Ghang Tai;Kwon Ji Youn;Bae Dong Jun;Yu Chang Seon;Lee Myoung Hee;Oh Sei Ryang;Jang Dong Il
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.31 no.1 s.49
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    • pp.111-114
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    • 2005
  • This study is about the cosmeceutical products using enzyme induced bio-conversion system. In general, ascorbic acid (AA) has the higher reducing activity and can be used for various purpose in the cosmetics. But it is very unstable in the aqueous system and difficult to maintain its stability in the cosmetics product. 2-O-$\alpha$-D-Glucopyranosyl-L-ascorbic acid (AA2G) is the stabilized form of AA and showed the less whitening activity than AA. In this study, we developed bio-conversion system improving the stability and efficacy of AA2G and AA, respectively. In this system, AA2G (over $80\%$) can be converted to AA and glucose within 30 min. The converted product showed higher anti-tyrosinase activity like AA (AA2G showed no anti tyrosinase activity) and depigmenting activity in the artificial tanning test. From these results, we could conclude this system is a brand new method to increase the activity of AA and maintain its stability.

Verticilloside, a New Daucosteryl Derivative from the Seeds of Malva verticillata

  • Kim, Jeong-Ah;Yang, Seo-Young;Kang, Sang-Jin;Kim, Young-Ho
    • Natural Product Sciences
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    • v.17 no.4
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    • pp.350-353
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    • 2011
  • A new daucosteryl derivative, verticilloside (1), was isolated from the seeds of Malva verticillata L. (Malvaceae). The structure was determined to be 3-O-[${\beta}$-D-(6'-linoleoyl)glucopyranosyl]-${\beta}$-sitosterol based on spectroscopic analyses ($^1H$ and $^{13}C$-NMR, DEPT, COSY, HMQC, and HMBC) and chemical reactions.