• Title/Summary/Keyword: Alpha Hydroxy Acid

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The anti-oxidative stress effect of antioxidants in the cell using DCFH-DA (DCFH-DA를 이용한 항산화제의 세포내 oxidative stress 억제 효과에 관한 연구)

  • 유영근;신미희;최종완
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.28 no.1
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    • pp.42-57
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    • 2002
  • 본 연구는 널리 알려져 있는 항산화제들의 세포 수준에서의 anti-oxidative stress 효과 및 그 기작을 알아보기 위한 연구이다. 연구에 사용한 항산화제로는 지용성인 retinol, $\alpha$-tocopherol, propyl gallate(PG) 및 butylated hydroxy toluene(BHT)과 수용성인 ascorbic acid, $\alpha$-glucosyl rutin 및 green tea extract를 사용하였으며 이들 항산화제들의 시간별 세포 생존율을 NR assay 로 측정한 후 적정 농도에서 DCFH-DA(2', 7'-dichlorofluorescin-diacetate) 를 이용하여 항산화제들의 anti-oxidative stress 억제 효과를 시간별로 측정하였다. 또한 이들 항산화제의 항산화 기작을 알아보기 위하여 NBT(Nitro-blue-tetrazolium) 및 DPPH(Diphenyl-picry-hydrazl)도 병행하여 실시하였다. Anti-oxidative stress 실험에서 지용성 항산화제들은 전반적으로 수용성 항산화제에 비하여 세포에 대한 독성이 상대적으로 강하여 retinol 의 경우에는 0.01%에서 oxidative stress 억제 효과를 관할할 수 있었으며 1 시간경과 후 측정시 53.1%의 억제 효과를 보여 주었다. PG 의 경우에는 0.1%에서 2 시간 경과 후 측정시 50%의 oxidative stress 억제 효과를 보여주었다. 수용성 항산화제인 green tea extract 및 $\alpha$-glucosyl rutin의 경우에는 1%에서 1시간 경과 후 측정시 각 각 51.6% 및 69.7%의 oxidative stress 억제 효과를 관찰할 수 있었다. 또한 시료처리 후 자외선 조사시 oxidative stress 억제 효과의 경우 수용성 항산화제인 ascorbic acid, $\alpha$-glucosyl rutin 및 green tea extract 와 지용성 항산화제 중에서는 $\delta$-tocopherol 에서만 oxidative stress 억제 효과가 관찰되었으나 자외선을 조사 하지 않았을 때 보다 약 20%-40%까지 억제 효과가 감소되었다. 그리고 PG 및 retinol 의 경우에는 자외선 조사시 독성이 증가하여 oxidative stress 억제 효과를 측정할 수 없었다. NBT실험에서 $\alpha$-glucosyl rutin, $\alpha$-tocopherol 및 PG 1%에서 70%이상의 superoxide anion 생성 억제 효과를 보였으며 DPPH 실험에서는 ascorbic acid 와 PG 1%에서 98%의 hydroxyl radical 생성 억제 효과를 보여 주었다. 본 실험을 통하여 BHT 를 제외하고 전반적으로 세포 수준에서의 oxidative stress 에 대한 억제 효과를 확인해 볼 수 있었으며 특히 수용성 항산화제들에서 두드러진 효과를 보여 주었다.

A Study on Kinetic Model for the Formation of 5-methyl-4-imidazolecarboxylic Acid Ester (5-methyl-4-imidazolecarboxylic Acid Ester 연속합성의 반응속도론 및 특성 연구)

  • Cho, Wook-Sang;Park, Sang-Jin;Kim, Hak-Hee
    • Applied Chemistry for Engineering
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    • v.5 no.6
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    • pp.1062-1067
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    • 1994
  • The chemistry of 5-methyl-4-imidazolecarboxylic acid ester synthesis involves three distinct reaction steps. Of these the rate of formation of diketone was found to be a function of oxime and HCl concentration and temperature by the batch experiment. The decomposition of diketone was found to be a slow process whereas temperature was the only variable to affect it significantly. An empirical rate expression for the net formation of diketone fits the experminetal data satisfactorily. The principal objectives of this study are to study the kinetics of the diketone formation reaction and to develop the empirical rate expression.

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Stereospecific Synthesis of the (2R,3S)- and (2R,3R)-3-Amino-2-hydroxy-4-phenylbutanoic Acids from D-Glucono-δ-lactone

  • Lee, Jin Hwan;Kim, Jin Hyo;Lee, Byong Won;Seo, Woo Duck;Yang, Min Suk;Park, Ki Hun
    • Bulletin of the Korean Chemical Society
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    • v.27 no.8
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    • pp.1211-1218
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    • 2006
  • The enantiomerically pure (2R,3S)- and (2R,3R)-3-amino-2-hydroxy-4-phenylbutanoic acids (AHPBA) 1 and 3 are readily obtained from D-glucono-a-lactone. Both AHPBAs are the structural key units of KMI derivatives which are the potent inhibitors of BACE 1 ($\beta$-secretase) and HIV protease. Additionally, the obtained AHPBAs 1 and 3 are converted to dipeptides of bestatin stereoisomers 2 and 4.

Anticoagulation and Anticancer Constituents from Eugenia caryophyllata Thunb

  • Han, Kyung-Min;Kim, Dong-Hyun;Ahn, Eun-Mi;Lee, Youn-Hyung;Chung, In-Sik;Kim, Dae-Keun;Kwon, Byoung-Mog;Kim, Sung-Hoon;Baek, Nam-In
    • Korean Journal of Medicinal Crop Science
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    • v.15 no.2
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    • pp.82-88
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    • 2007
  • From the EtOAc fraction of Eugenia caryophyllata, four compounds were isolated through activity-guided silica gel column chromatography, From the result of spectroscopic data including NMR, MS and IR, the chemical structures of the compounds were determined as 1-allyl-4-hydroxy-3-methoxybezene acetate (eugenol acetate, 1), 1-allyl-4-hydroxy-3-methoxybezene (eugenol, 2), $3{\beta}-hydroxyolean-12-en-28-oic$ acid (oleanolic acid, 3) and $2{\alpha}$, $3{\beta}-dihydroxyolean-12-en-28-oic$ acid (maslinic acid, 4). Compounds 3 and 4 were isolated for the first time from this plant. Also, compounds 1, 2 and 3 exhibited relatively high platelet aggregation inhibitory activity with the $IC_{50}$ values of 0.24, 0.09 and 0.07 mM, respectively. Compound 2 significantly prolonged activated partial thromboplastin time (aPTT) with the value of $124{\pm}11.2$ seconds as compared to the control with the value of $37.5{\pm}2.2$ seconds at the concentration of 50 ${\mu}g/ml$. Compounds 1 and 3 revealed inhibitory activity on farnesyl protein transferase (FPTase) with the $IC_{50}$ values of 0.49 and 0.24 mM and compounds 1 and 2 highly inhibited the growth of rat-H-ras cells with the $Gl_{50}$ values of 6.63 and 5.70 ${\mu}M$, respectively.

Skin Irriation Effect of Glycolic Acid and UVB in Guinea Pig (Guinea pid를 이용한 Glycolic acid 및 UVB의 피부 자극성 평가)

  • 조대현;홍진태
    • Toxicological Research
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    • v.16 no.1
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    • pp.89-94
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    • 2000
  • Alpha-hydroxy acid(AHA) are used in cosmetic products as a pH adjuster, mild exfoliant and humectant-skin conditioner. Cosmetics containing higher concentration (30%) and lower pH (3.0) of AHA can cause side effects if it is applied without the prescription. For providing information on the safety of AHA and on human risk assessments we studied skin irritation effect of glycolic acid, one of the most commonly used AHA in guinea pigs. The skin irritation by glycolic acid was increased in a dose(10% to 70%), acidity (pH 2.5 to 5.5.) and length of exposure dependent manner (for up to 14 days), respectively. The combination treatment with UVB (0.4 or 3.0 J/$cm^2$) increased glycolic acid-induced skin irritation. Histological examination showed that hyperplasia of non-inflammatory cells in the epidermis of skin treated with high dose of glycolic acid (pH 3.0). There results show that glycolic acid increased skin irritation in a dose, length of exposure and pH dependent manner, respectively, in guinea pig, and the combination with UVB increased glycolic acid-induced skin irritation. The cell proliferation of non-inflammatory cell may be involved in high doses of glycolic acid-induced skin irritation. Long-term application of more than 30% of glycolic acid (pH 3.0) may cause skin irritation.

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Synthesis of trifluoromethylated dihydro-1,4-dithiin carboxamides and their antifungal activities (Trifluoromethylated Dihydro-1,4-dithiin carboxanilide 유도체의 합성 및 살균활성)

  • Hahn, Hoh-Gyu;Nam, Kee-Dal;Chang, Kee-Hyuk;Lee, Seon-Woo;Cho, Kwang-Yun
    • The Korean Journal of Pesticide Science
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    • v.5 no.2
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    • pp.26-32
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    • 2001
  • [ ${\alpha},{\beta}$ ]-Unsaturated carboxamides 12 with trifluromethylated dihydro-1,4-dithiins were synthesized for the purpose of development of new agrochemical fungicide. Chlorination of trifluoromethylated ${\beta}$-ketoester 4 followed by tile reaction with 1,2-ethanedithiol gave intermediate 1,4-dithiane 9. Without purification of 9 substitution of hydroxy by chlorine followed by dehydrochlorination in the presence of triethylamine afforded trifluoromethylated dihydro-1,4-dithiin ethyl ester 7. Activation of the hydroxy of the carboxylic acid 10 obtained from the hydrolysis of 7 and then reacted with various amines gave the corresponding trifluoromethylated dihydro-1,4-dithiin carboxamides. Antifungal screening (in vivo) against typical plant diseases, Rice Blast, Rice Sheath Blight, Cucumber Gray Mold, Tomato Late Blight, Wheat Leaf Rust, and Barley Powdery Mildew of the synthesized compounds was carried out. As a result, most of the compounds shlowed weak antifungal activities and some compounds in which isopropyl group was substituted in meta of the phenyl showed antifungal activity (99%) at 250 ppm against the disease Wheat Leaf Rust.

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Phenolic Compounds from Leaves of Spiraea salicifolia (꼬리조팝나무 잎의 페놀성 화합물)

  • Ahn, Byung-Tae;Oh, Kap-Jin;Park, Si-Kyung;Chung, Sun-Gan;Cho, Eui-Hwan;Kim, Jae-Gil;Ro, Jai-Seup;Lee, Kyong-Soon
    • Korean Journal of Pharmacognosy
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    • v.27 no.3
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    • pp.178-183
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    • 1996
  • Seven phenolic compounds were isolated from the leaves of Spiraea salicifolia. Their structures were characterized as cinnamic acid, ${\rho}-hydroxy$ cinnamic acid, ${\rho}-methoxy$ cinnamic acid, $1-O-coumaroyl-{\beta}-D-glucopyranose$, $1-O-caffeoyl-{\beta}-D-glucopyranose$, hyperoside and quercetin $3-O-(6'-O-{\alpha}-L-arbinopyranosyl)-{\beta}-D-galactopyranoside$ by chemical and spectroscopic evidence.

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Aromatase Inhibitors from Isodon excisus var. coreanus

  • Jeong, Hyeh-Jean;Chang, Leng-Chee;Kim, Ho-Kyoung;Kim, Il-Hyuk;A.Douglas Kinghorn;John M.Pezzuto
    • Archives of Pharmacal Research
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    • v.23 no.3
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    • pp.243-245
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    • 2000
  • The diethyl ether extract of isodon excisus var. coreanus exhibited significant inhibitory activity in aromatase assay. Bioactivity-guided fractionation of the extract led to the isolation of three active compounds: inflexin(ent-1${\alpha}$-hydroxy-3${\beta}$,6a-diacetoxykau r-16-en-11,15-dione) (1), ursolic acid (2), and ursolic acid 3-O-acetate (3).

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Effects of ${\alpha}-ketol$ type oxylipin (KODA) on flowering and its application as a growth regulater

  • Yokoyama, Mineyuki
    • Proceedings of the Korean Society of Plant Biotechnology Conference
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    • 2005.11a
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    • pp.27-39
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    • 2005
  • a-Ketol linolenic acid [KODA, 9,10-ketol-octadecadienoic acid, or 9-hydroxy-10 -oxo-12(Z), 15(Z)-octadecadienoic acid] was found as a stress-induced factor in Lemna paucicostata. KODA reacts with catecholamines to generate many products that strongly induce flowering in L. paucicostata, although KODA itself was inactive. KODA contains an asymmetric carbon at the 9-position in the molecule; the 9-hydroxyl group is predominantly 9R, with an enantiomeric excess of 40% (70% 9R and 30% 9S). We analyzed two major products of the reaction between KODA and norepinephrine, named FN1 and FN2. FN1 was identified as a tricyclic a-ketol fatty acid, 9(R)-11-{(2'R,8’R,10'S,11'S)-2',8'-dihydroxy-7'-oxo-11'-[(Z)-2-pentenyl]-9'-oxa-4'-azatricyclo[6.3.1.01.5]dodec-5'en-10'-yl}-9-hydroxy-10-oxoundecanoic acid. FN2 was the C-9 epimer of FN1. FN1 was derived from 9R-type KODA and FN2 from 9S-type. FN1 showed strong flower-inducing activity, but FN2 was inactive. Pharbitis nil (violet) is a typical short-day plant; flowering can be induced by exposing a seedling cultivated under continuous light to a single 16-h dark period. We analyzed endogenous KODA levels and showed that they were closely related to flower induction: KODA sharply increased in the later part of a 16-h dark period, on the other hand, it failed to increase in the night-break experiment. In addition to it, KODA increased transiently in immature flower buds in all the plants we examined, including P. nil. No such increase of KODA was seen in foliar buds of P. nil. When KODA was sprayed on seedlings of Pharbitis, flower induction was promoted only by the (R)-form of KODA. We also found that KODA enhances flowering in garden plants such as carnations and impatienses. These phenomena indicate that KODA may be involved in flowering formationg of plants and it is potentially useful for a regulating agent for commercial plant flowering.

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The Involvement of AMPA Receptor in the Antidepressant-like Effects of the Portulaca Oleracea L. Extract in Mice

  • Park, Soo-Jin;Choi, Min-Ji;Chung, Sun-Yong;Kim, Jong-Woo;Cho, Seung-Hun
    • Journal of Oriental Neuropsychiatry
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    • v.24 no.3
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    • pp.271-280
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    • 2013
  • Objectives : The development of natural drugs with antidepressant effects is important and needed. This study was performed to investigate the antidepressant-like effects of the distilled water extract of Portulaca oleracea L. (POL) in a mouse model and to investigate the role of ${\alpha}$-amino-3-hydroxy-5-methyl-4-isoxazole-propionic acid (AMPA) receptors in producing these antidepressant-like effects. Methods : The forced swim test (FST) and tail suspension test (TST) were used to investigate the behavioral anti-depressive-like effects of POL in mice. Additional behavioral experiments with 2,3-dihydroxy-6-nitro-7-sulfamoyl-benzo[f]quinoxaline-2,3-dione, an AMPA receptor antagonist, were undertaken to determine the involvement of the antidepressant-like properties of POL in AMPA receptor throughput. Results : Oral administration of the POL extract (100 mg/kg) 1 h prior to testing significantly reduced the immobility times in the FST and TST. The antidepressant-like effects of the POL extract were not increased in a dose-dependent manner. Pre-treatment with NBQX significantly attenuated the reduction in immobility time induced by the POL extract in the FST. Conclusions : The distilled water extract of POL has antidepressant-like effects, which may be related to AMPA receptor. Pre-treatment with NBQX significantly attenuates the reduction in immobility time induced by the POL extract in the FST.