• Title/Summary/Keyword: beta-hydroxy acid

Search Result 145, Processing Time 0.022 seconds

Chemical Constituents from the Stems of Lagerstroemia indica and Their Anti-oxidant Effect (배롱나무의 항산화 활성 성분)

  • Woo, Kyeong Wan;Sim, Mi Ok;Park, Eel Jong;Kim, Min Suk;Suh, Won Se;Cho, Hyun Woo;Kwon, Hak Cheol;Park, Jong Cheol;Lee, Kang Ro
    • Korean Journal of Pharmacognosy
    • /
    • v.47 no.3
    • /
    • pp.204-210
    • /
    • 2016
  • Phytochemical investigation of the 80% MeOH extract from the stems of Lagerstroemia indica resulted in the isolation of eighteen compounds; four norsesquiterpenes, fourteen phenolic derivatives. Their chemical structures were characterized by spectroscopic methods to be tachioside (1), isotachioside (2), 2,4,6-trimethoxyphenyl ${\beta}$-D-glucopyranoside (3), gallic acid 4-methyl ether (4), protocatechuic acid (5), gallic acid (6), vanillic acid (7), vanillin (8), 2-methoxy-5-hydroxymethyl-phenyl-1-O-(6"-galloyl)-${\beta}$-D-glucopyranoside (9), 2,4,6-trimethoxyphenol-1-O-${\beta}$-D-(6'-O-galloyl)-glucopyranoside (10), 4-hydroxy-3-methoxyphenyl-1-O-(6'-O-galloyl)-${\beta}$-D-glucopyranoside (11), vomifoliol (12), vomifoliol 9-O-${\beta}$-D-glucopyranoside (13), 6R,9R-3-oxo-${\alpha}$-ionol-9-O-${\beta}$-D-glucopyranoside (14), dihydrophaseic acid 4'-O-${\beta}$-D-glucopyranoside (15), ${\beta}$-hydroxypropiovanillone 3-O-${\beta}$-D-glucopyranoside (16), myrciaphenone A (17), and coumaric acid (18). Compounds 1-5 and 7-18 were isolated for the first time from this plant. Compounds 1-18 were investigated for their antioxidant properties using DPPH and ABTS radical scavenging capacity assay, $Fe^{2+}$ chelating, and FRAP assay. It was found that 4, 6, and 11 possessed the highest antioxidant capacities.

Antisteroidogenic activity of Raphanus sativus seed extract in female albino mice

  • Haldar, P.K.;Mazumder, U.K.;Bhattacharya, Sanjib;Manikandan, L.;Bhattacharya, Siladitya
    • Advances in Traditional Medicine
    • /
    • v.9 no.4
    • /
    • pp.303-306
    • /
    • 2009
  • The defatted methanol extract of Raphanus sativus Linn. (Cruciferae) seed (MERS) was evaluated for its antisteroidogenic potential in mature female Swiss albino mice. The methanol extract at the doses of 100 and 200 mg/kg body weight significantly elevated the levels of cholesterol and ascorbic acid contents which serve as a precursor for the synthesis of steroid hormones in ovaries. The extract also significantly inhibited glucose-6-phosphate dehydrogenase and ${\Delta}^5-3{\beta}$-hydroxy steroid dehydrogenase, the two key enzymes involved in ovarian steroidogenesis. Hence the extract (MERS) exhibited significant antisteroidogenic activity.

Phytochemical Constituents of Allium victorialis var. platyphyllum

  • Woo, Kyeong Wan;Lee, Kang Ro
    • Natural Product Sciences
    • /
    • v.19 no.3
    • /
    • pp.221-226
    • /
    • 2013
  • Phytochemical investigation of the 80% MeOH extract from the leaves of Allium victorialis var. platyphyllum resulted in the isolation of seventeen compounds; two terpenes, three norsesquiterpenes, one furofuran lignan, and eleven phenolic derivatives. Their chemical structures were characterized by spectroscopic methods to be trans-phytol (1), phytene-1,2-diol (2), icariside B2 (3), (6S,9S)-roseoside (4), sedumoside G (5), pinoresinol-4-O-glucoside (6), 2-methoxy-2-(4'-hydroxyphenyl)ethanol (7), 2-hydroxy-2-(4'-hydroxyphenyl)ethanol (8), Benzyl ${\beta}$-D-glucopyranoside (9), methyl ferulate (10), trans-ferulic acid (11), methyl-p-hydroxycinnamate (12), glucosyl methyl ferulate (13), linocaffein (14), siringin (15), 2-(4-hydroxy-3-methoxyphenyl)-ethyl-O-${\beta}$-Dglucopyranoside (16), and pseudolaroside C (17). All compounds were isolated for the first time from this plant.

Synthesis and $5{\alpha}$-Reductase Inhibitory Activity of $3{\beta}$-Substituted 5-Androstene-17-Carboxamides ($3{\beta}$-치환 5-Androstene-17-Carboxamides 합성과 $5{\alpha}$-Reductase 저해 활성)

  • Jo, Ik-Sung;Ma, Eun-Sook
    • YAKHAK HOEJI
    • /
    • v.54 no.6
    • /
    • pp.466-473
    • /
    • 2010
  • A series of $3{\beta}$-substituted 5-androstene-$17{\beta}$-carboxamides were synthesized from analogs of $3{\beta}$-hydroxy-5-androstene-$17{\beta}$-carboxylic acid (1) with tert-butylamine, N,N-diethylamine and 3-aminopyridine and some compounds were epoxidized with mCPBA. A rat prostate testosterone $5{\alpha}$-reductase inhibitory activity of synthesized compounds was assessed by radioimmunoassay using [1,2,6,7-3H]-testosterone as substrate. All synthesized compounds showed lower activity than finasteride and the N-(3-pyridino)-$3{\beta}$-carboxycarbonyloxy-5-androstene-$17{\beta}$-carboxamide (12) showed weak inhibitory activity ($IC_{50}$: $2.4{\times}10^{-7}M$).

Solvent Extracted Volatile Components of Mushroom Mycelia Cultivated with Citrus Juice Processing Wastes (감귤 주스 착즙박을 이용하여 재배된 버섯균사체의 용매추출에 의한 휘발성 성분)

  • Lee, Chang-Hwan;Yang, Min-Ho;Park, Seung-Rim;Kang, Young-Joo
    • Food Science and Preservation
    • /
    • v.14 no.4
    • /
    • pp.351-355
    • /
    • 2007
  • Solvent-extracted volatile components from dry powder prepared from Citrus unshiu products such as immature Citrus unshiu (PCU), mature Citrus unshiu (MCU), Citrus unshiu peel (CUP), and citrus juice processing wastes (CJPW), were examined. Also, solvent-extracted volatile components from mushroom mycelia of Pycnoporus coccineus (PC), Lentinus edodes (LE), Pleurotus eryngii (PE), Hericium coralloides (HC), Panellus serotinus (PS), and Ganoderma lucidum(GL), all cultivated using citrus pulp solid media, were assayed. Twenty-nine volatile components were identified in dry powder prepared Citrus unshiu and 18 volatile components were characterized from mushroom mycelia. Of these, ${\beta}-elemene$, germacrene-D, and ${\delta}-cadinene$, were derived from CJPW, but caryophyllene, hexadecanoic acid, decanoic acid, and tetradecanoic acid were synthesized by mushroom mycelia.

Synthesis of 6-Exomethylenepenams as $\beta-Lactamase$ Inhibitors

  • Im, Cha-Euk;Oh, Jung-Suk;Yim, Chul-Bu
    • Archives of Pharmacal Research
    • /
    • v.22 no.1
    • /
    • pp.68-71
    • /
    • 1999
  • The 6,6-dibromopenam (6) was treated with CH3MgBr and carbaldehyde 5 to afford the hydroxy compound 7, which was reacted with acetic anhydride to give acetoxy compound 8. The deacetobromination of 8 with zinc and acetic acid gave 6-exomethylenepenams, E-isomer 10 and Z-isomer 9, which was oxidized to sulfone 11 by m-CPBA. The p-methoxybenzyl compounds were deprotected by AlCl3 and neutralized to give the sodium salts 12, 13, and 14.

  • PDF

A New 24-Nor-Lupane-Glycoside of Acanthopanax trifoliatus

  • Kiem, Phan-Van;Minh, Chau-Van;Cai, Xing-Fu;Lee, Jung-Joon;Kim, Young-Ho
    • Archives of Pharmacal Research
    • /
    • v.26 no.9
    • /
    • pp.706-708
    • /
    • 2003
  • A new 24-nor-lupaneglycoside was isolated from the leaves of Acanthopanax trifoliatus. Based on spectroscopic data its chemical structure was determined as 24-nor-11$\alpha$-hydroxy-3-oxo-lup-20(29)-en-28-oic acid 28-Ο-$\alpha$-L-rhamnopyranosyl-(1$\rightarrow4)-\beta-D-glucopyranosyl-(1\rightarrow6)-\beta$-D-glucopyranosyl ester.

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
    • /
    • v.27 no.8
    • /
    • pp.1211-1218
    • /
    • 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.

Di- and Sesqui-Terpenoids Isolated from the Pods of Sindora sumatrana and Their Potential to Inhibit Lipopolysaccharide-Induced Nitric Oxide Production

  • Jang, Dae-Sik;Min, Hye-Young;Jeong, Yeon-Hee;Lee, Sang-Kook;Seo, Eun-Kyoung
    • Archives of Pharmacal Research
    • /
    • v.27 no.3
    • /
    • pp.291-294
    • /
    • 2004
  • Activity-guided fractionation of the n-hexane and ${CHCl_3}-soluble$ fractions of Sindora sumatrana using a bioassay based on the inhibition of lipopolysaccharide (LPS)-induced nitric oxide (NO) production by inducible nitric oxide synthase (iNOS) in murine macrophage RAW 264.7 cells led to the isolation of the known compound, $(+)-7{\beta}-acetoxy-15,16-epoxy-3$, 13(16), 14-clero-datriene-18-oic acid (2) as an active constituent. In addition, a new trans-clerodane diterpenoid, (+)-2-oxokolavenic acid (1), together with six known compounds, (+)-3, 13-clerodadiene-16,15-olide-18-oic acid (3), $(+)-7{\beta}-acetoxy-3$,13-clerodadiene-16,15-olide-18-oic acid (4), $(+)-7{\beta}-acetoxy-16-hydroxy-3$,13-clerodadiene-16, 15-olide-18-oic acid (5), ${\beta}-caryophyllene$ oxide (6), $clovane-2{\beta},9{\beta}-diol (7),{\;}and{\;}caryolane-1,9{\beta}-diol$ (8) were isolated and found to be inactive. The structure of compound 1 was determined using physical and spectroscopic methods such as 1D and 2D-NMR experiments. The known compounds 2-8 were identified by the spectroscopic data and by comparison with the published values. Of eight isolates (1-8), only compound 2 exhibited an iNOS inhibitory activity with $IC_{50}$/ value of $51.6{\;}\mu\textrm{m}M$.

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
    • /
    • v.15 no.2
    • /
    • pp.82-88
    • /
    • 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.