- Identification of geranic acid, a tyrosinase inhibitor in lemongrass (Cymbopogon citratus)
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Lemongrass is a popular Asian herb having a lemon-like flavor. Very recently, potent tyrosinase inhibitory activity has been found in lemongrass in addition to various biological activities reported in the literature. The aim of the present study is to identify the active compounds in the lemongrass. An assay-guided purification revealed that one of the active substances was geranic acid. Geranic acid has two stereoisomers, which are responsible for the trans and cis geometry on the conjugated double bond. Both isomers are present in the active ethyl acetate-soluble extract of the lemongrass, and their IC 50 values were calculated to be 0.14 and 2.3 mM, respectively. The structure requirement of geranic acid for the potent tyrosinase inhibitory activity was investigated using geranic acid-related compounds.
- Masuda, Toshiya,Odaka, Yuka,Ogawa, Natsuko,Nakamoto, Katsuo,Kuninaga, Hideki
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- ANTICANCER MICRORNA AND LIPID FORMULATIONS THEREOF
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The present invention relates to a lipid formulation comprising microRNA. The formulation comprises cationic lipids that can form lipid nanoparticles with the microRNA. The formulations are useful in medicine.
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Paragraph 0347; 0349
(2021/02/12)
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- Preparation method of farnesal
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The invention provides a preparation method of farnesal. The preparation method of farnesal comprises the step of carrying out Meyer-Schuster rearrangement reaction on dehydronerolidol under the effect of a catalyst to obtain the farnesal. In isomerous preparation of the farnesal from the dehydronerolidol by catalysis, the catalysis efficiency is high, reaction conditions are gentle, the preparedfarnesal is high in conversion ratio and selectivity, the preparation method is green and pollution-free, the preparation cost is low, and industrialized production can be realized. Experiments show that the yield of the farnesal prepared by the provided method is 93% or above, and the purity is 95% or above.
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Paragraph 0035-0050
(2019/02/26)
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- ADHESION PREVENTING AGENT
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The present invention relates to an adhesion preventing agent comprising an amphipathic compound having the following general formula (I): wherein X and Y each denotes a hydrogen atom or together denote an oxygen atom, n denotes an integer from 0 to 2, m denotes the integer 1 or 2, AA: AA denotes a single bond or double bond, and R denotes a hydrophilic group having two or more hydroxyl groups.
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Paragraph 0368; 0369
(2016/04/20)
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- ADHESION PREVENTING AGENT
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PROBLEM TO BE SOLVED: To provide a compound available as an easily applicable adhesion preventing agent. SOLUTION: The invention provides an amphipathic compound represented by the general formula (II) in the figure. (In the formula, X and Y either each denote a hydrogen atom or together denote an oxygen atom, n denotes an integer from 0 to 2, m denotes the integer 1 or 2, and R denotes a hydrophilic group obtained by removal of one hydroxyl group from any one selected from the group consisting of glycerol, erythritol, pentaerythritol, diglycerol, and glyceric acid.) SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT
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Paragraph 0207-0208
(2016/12/01)
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- METHOD FOR PRODUCING α,β-UNSATURATED CARBONYL COMPOUNDS
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PROBLEM TO BE SOLVED: To provide a simple and efficient, novel method for producing α,β-unsaturated carbonyl compounds, which can provide α,β-unsaturated carbonyl compounds from allyl alcohols with high yields under a mild reaction condition, and has extremely little influence and toxicity on the environment and the human body. SOLUTION: Provided is a method for producing α,β-unsaturated carbonyl compounds, the method comprising reacting allyl alcohols and hydrogen peroxide to carbonylate alcohol portions to produce corresponding α,β-unsaturated carbonyl compounds. As a reaction catalyst, there are used an Fe(II) or Fe(III) salt soluble in water or an organic solvent, and at least one picolinic acid selected from 2-picolinic acid and 6-C1-4 alkyl-2-picolinic acid in coexistence in a ratio of 1:1 to 1:4. COPYRIGHT: (C)2015,JPOandINPIT
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Paragraph 0037; 0042-0043
(2016/12/26)
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- Characterization of hamster NAD+-dependent 3(17)β-hydroxysteroid dehydrogenase belonging to the aldo-keto reductase 1C subfamily
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The cDNAs for morphine 6-dehydrogenase (AKR1C34) and its homologous aldo-keto reductase (AKR1C35) were cloned from golden hamster liver, and their enzymatic properties and tissue distribution were compared. AKR1C34 and AKR1C35 similarly oxidized various xenobiotic alicyclic alcohols using NAD+, but differed in their substrate specificity for hydroxysteroids and inhibitor sensitivity. While AKR1C34 showed 3α/17β/20α-hydroxysteroid dehydrogenase activities, AKR1C35 efficiently oxidized various 3β- and 17β-hydroxysteroids, including biologically active 3β-hydroxy-5α/β-dihydro-C19/C21-steroids, dehydroepiandrosterone and 17β-estradiol. AKR1C35 also differed from AKR1C34 in its high sensitivity to flavonoids, which inhibited competitively with respect to 17β-estradiol (Ki 0.11-0.69 μM). The mRNA for AKR1C35 was expressed liver-specific in male hamsters and ubiquitously in female hamsters, whereas the expression of the mRNA for AKR1C34 displayed opposite sexual dimorphism. Because AKR1C35 is the first 3(17)β-hydroxysteroid dehydrogenase in the AKR superfamily, we also investigated the molecular determinants for the 3β-hydroxysteroid dehydrogenase activity by replacement of Val54 and Cys310 in AKR1C35 with the corresponding residues in AKR1C34, Ala and Phe, respectively. The mutation of Val54Ala, but not Cys310Phe, significantly impaired this activity, suggesting that Val54 plays a critical role in recognition of the steroidal substrate.
- Endo, Satoshi,Noda, Misato,Ikari, Akira,Tatematsu, Kenjiro,El-Kabbani, Ossama,Hara, Akira,Kitade, Yukio,Matsunaga, Toshiyuki
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p. 425 - 434
(2015/11/27)
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- Rabbit 3-hydroxyhexobarbital dehydrogenase is a NADPH-preferring reductase with broad substrate specificity for ketosteroids, prostaglandin D2, and other endogenous and xenobiotic carbonyl compounds
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3-Hydroxyhexobarbital dehydrogenase (3HBD) catalyzes NAD(P) +-linked oxidation of 3-hydroxyhexobarbital into 3-oxohexobarbital. The enzyme has been thought to act as a dehydrogenase for xenobiotic alcohols and some hydroxysteroids, but its physiological function remains unknown. We have purified rabbit 3HBD, isolated its cDNA, and examined its specificity for coenzymes and substrates, reaction directionality and tissue distribution. 3HBD is a member (AKR1C29) of the aldo-keto reductase (AKR) superfamily, and exhibited high preference for NADP(H) over NAD(H) at a physiological pH of 7.4. In the NADPH-linked reduction, 3HBD showed broad substrate specificity for a variety of quinones, ketones and aldehydes, including 3-, 17- and 20-ketosteroids and prostaglandin D2, which were converted to 3α-, 17β- and 20α-hydroxysteroids and 9α,11β- prostaglandin F2, respectively. Especially, α-diketones (such as isatin and diacetyl) and lipid peroxidation-derived aldehydes (such as 4-oxo- and 4-hydroxy-2-nonenals) were excellent substrates showing low Km values (0.1-5.9 μM). In 3HBD-overexpressed cells, 3-oxohexobarbital and 5β-androstan-3α-ol-17-one were metabolized into 3-hydroxyhexobarbital and 5β-androstane-3α,17β-diol, respectively, but the reverse reactions did not proceed. The overexpression of the enzyme in the cells decreased the cytotoxicity of 4-oxo-2-nonenal. The mRNA for 3HBD was ubiquitously expressed in rabbit tissues. The results suggest that 3HBD is an NADPH-preferring reductase, and plays roles in the metabolisms of steroids, prostaglandin D2, carbohydrates and xenobiotics, as well as a defense system, protecting against reactive carbonyl compounds.
- Endo, Satoshi,Matsunaga, Toshiyuki,Matsumoto, Atsuko,Arai, Yuki,Ohno, Satoshi,El-Kabbani, Ossama,Tajima, Kazuo,Bunai, Yasuo,Yamano, Shigeru,Hara, Akira,Kitade, Yukio
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p. 1366 - 1375
(2013/11/19)
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- Renaissance of traditional organic reactions under microfluidic conditions: A new paradigm for natural products synthesis
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Continuous flow synthesis for bioactive natural products is described. Efficient procedures using the microfluidic system were developed for the large-scale synthesis of important synthetic units of asparagine-linked oligosaccharide in glycoprotein. Advantageous aspects of microfluidic conditions, i.e., efficient mixing, fast heat transfer, and residence time control led to cation-mediated reactions, such as a-sialylation, β-mannosylation, and reductive opening of the benzylidene acetal groups in high yields. Microfluidic dehydration was developed for the industrial-scale synthesis of the immunostimulating natural terpenoid, pristane. The base-mediated aldol condensation in an aqueous biphasic system enabled the multigram synthesis of β-hydroxyketones in high yields. 2009 American Chemical Society.
- Tanaka, Katsunori,Fukase, Koichi
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scheme or table
p. 983 - 990
(2010/04/22)
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- Regioselective alkene carbon-carbon bond cleavage to aldehydes and chemoselective alcohol oxidation of allylic alcohols with hydrogen peroxide catalyzed by [cis-Ru(II)(dmp)2(H2O)2] 2+ (dmp = 2,9-dimethylphenanthroline)
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(Chemical Equation Presented) [cis-Ru(II)(dmp)2(H 2O)2]2+ (dmp = 2,9-dimethylphenanthroline) was found to be a selective oxidation catalyst using hydrogen peroxide as oxidant. Thus, primary alkenes were very efficiently oxidized via direct carbon-carbon bond cleavage to the corresponding aldehydes as an alternative to ozonolysis. Secondary alkenes were much less reactive, leading to regioselective oxidation of substrates such as 4-vinylcyclohexene and 7-methyl-1,6-octadiene at the terminal position. Primary allylic alcohols were chemoselectively oxidized to the corresponding allylic aldehydes, e.g., geraniol to citral.
- Kogan, Vladimir,Quintal, Miriam M.,Neumann, Ronny
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p. 5039 - 5042
(2007/10/03)
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- Niaviolides, new macrocyclic sesquiterpenes secreted by males of the African butterfly Amauris niavius
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The abdominal androconial organs ("hairpencils") of the African butterfly Amauris niavius (Danainae) emit a complex scent bouquet consisting of previously described aromatic compounds, terpenoids, fatty acids, and hydrocarbons. This work reports the identification of two major sesquiterpenes, each possessing a unique 13-membered macrolide ring, originating from an α,ω-oxidation pattern of the sesquiterpene backbone. To the best of our knowledge, sesquiterpene macrolides have not been found before in nature. The structure elucidation of the two compounds, which we propose to call niaviolide (3) and epoxyniaviolide (4), by NMR and GC/MS experiments is presented, together with their subsequent synthesis. Finally, the absolute configuration of natural 4 was determined to be (S,S) by stereoselective synthesis and chiral gas chromatography. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
- Stritzke, Katja,Schulz, Stefan,Boppre, Michael
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p. 1337 - 1342
(2007/10/03)
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- Inactivation of protein farnesyltransferase by active-site-targeted dicarbonyl compounds
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Upon farnesylation by protein farnesyltransferase (FTase), key proteins become compartmentalized in cells. For example, cell membrane localization is essential for the mitogenic role of mutant Ras protein, which acts as a switch for cancer cell proliferation. We report that α-dicarbonyl compounds derived from the isoprenoid skeleton or other hydrophobic groups potently obstruct farnesylation of a Ras model peptide by human recombinant FTase in vitro. A geranyl-derived isoprenoid diketone, 5,9-dimethyl-8-decene-2,3-dione, at 17 μM caused a 62% reduction in FTase activity after 30 minutes. A farnesyl-derived isoprenoid diketone, 5,9,13-trimethyl-8,12-tetradecadiene-2,3-dione, at 93 μM caused a 94% reduction after 30 minutes. Other dicarbonyl compounds found to be effective against FTase in vitro were (±)-6-(camphorquinone-10-sulfonamido)-hexanoic acid, 4,4′-biphenyldiglyoxaldehyde, dehydroascorbic acid 6-palmitate, 2-oxododecanal, and phenylglyoxal. Higher concentrations of the α-dicarbonyl compound resulted in more rapid and more extensive inactivation. These findings demonstrate that α-dicarbonyl compounds targeted to FTase interfere with protein farnesylation in vitro and may lead to derivatives that have utility as chemotherapeutic agents.
- Okolotowicz, Karl J.,Lee, Wei-Jen,Hartman, Rosemarie F.,Kim, Ann Y.,Ottersberg, Steven R.,Robinson Jr., Dale E.,Lefler, Scott R.,Rose, Seth D.
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p. 194 - 202
(2007/10/03)
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- Mixed superbase LICKOR as a key reagent for the synthesis of conjugate dienes from citral and farnesal - A new route to a potential mimic agent of juvenile hormones by Diels-Alder cycloaddition
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Treatment of the dimethyl acetals of citral (1) and farnesal (2) with the superbase 'LICKOR' in THF at low temperatures reduces regioselective metallation at the allylic methyl group at C(3). The metal-hydrogen exchange promotes immediate 1,4-elimination, yielding an (E)-configured conjugate alkyloxy-functionalized diene. The elimination product can be subjected to a Diels-Alder reaction, which allows further synthetic elaboration. In particular, in the case of farnesal dimethyl acetal the cycloaddition process leads to a derivative that can be transformed into a potential mimic agent of Juvenile hormones.
- Tivola, Paolo Balma,Deagostino, Annamaria,Fenoglio, Claudia,Mella, Mariella,Prandi, Cristina,Venturello, Paolo
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p. 2143 - 2147
(2007/10/03)
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- Organic Oxoammonium Salts. 3. A New Convenient Method for the Oxidation of Alcohols to Aldehydes and Ketones
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A new method for the selective oxidation of alcohols using organic oxoammonium salts generated by acid-promoted disproportionation of nitroxides in solution has been developed.Major advantages are high yields, ease of product isolation, and a high degree of selectivity in the presence of other functional groups.
- Ma, Zhenkun,Bobbitt, James M.
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p. 6110 - 6114
(2007/10/02)
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- Ring D Expansion and Aromatisation in the Biosynthesis of Nic-1, an Antifeedant Steroid from Nicandra physaloides
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Isotope administration experiments with Nicandra physaloides plants using 2H3>- and 14C3>-mevalonic acid, analysed by 2H NMR and by degradation, respectively, show that the aromatic ring-D of Nic-1 (2) is formed by ring-D expansion in a steroid precursor with oxidative inclusion of the C/D angular methyl.
- Gill, Harjit K.,Smith, Roland W.,Whiting, Donald A.
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p. 2989 - 2993
(2007/10/02)
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- Electrochemical Oxidation of Primary Alcohols to Aldehydes at the Nickel Hydroxide Electrode
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Primary alcohols were oxidized to aldehydes at the nickel hydroxide electrode in an emulsion of water and a nonpolar organic solvent.Benzylic and allylic primary alcohols afforded good yields, whereas the oxidation of saturated primary alcohols was less satisfactory.
- Schneider, Roy,Schaefer, Hans-J.
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p. 742 - 743
(2007/10/02)
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- (E)-4,8-DIMETHYL-1,3,7-NONATRIENE AND (E,E)-4,8,12-TRIMETHYL-1,3,7,11-TRIDECATETRAENE, TWO UNUSUAL HYDROCARBONS FROM CARDAMOM OIL
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The identification of two new natural products, (E)-4,8-dimethyl-1,3,7-nonatriene 1 and (E,E)-4,8,12-trimethyl-1,3,7,11-tridecatetraene 3 is reported.These unusual C11 and C16 hydrocarbons were isolated from essential oil of Elettaria cardamomum Maton var. miniscula Burkhill (Zingiberaceae) and their structures confirmed by synthesis.
- Maurer, Bruno,Hauser, Arnold,Froidevaux, Jean-Claude
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p. 2111 - 2112
(2007/10/02)
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- 2-HYDROXYMETHYL-4-PHENYLTHIO-1-BUTENE AS A KEY COMPOUND FOR TOTAL SYNTHESIS OF ACYCLIC TERPENOIDS
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A new total synthesis of myrcene, citral, squalane, and isophytol employing 2-hydroxymethyl-4-phenylthio-1-butene as a starting material is described.
- Mandai, Tadakatsu,Yamaguchi, Hirofumi,Nishikawa, Kengo,Kawada, Mikio,Otera, Junzo
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p. 763 - 764
(2007/10/02)
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