- Hexahydrocurcumin ameliorates hypertensive and vascular remodeling in L-NAME-induced rats
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Hexahydrocurcumin (HHC), a major metabolite of curcumin, possesses several biological activities such as antioxidant, anti-inflammation, and cardioprotective properties. This study aimed to investigate the effect of HHC on high blood pressure, vascular dy
- Panthiya, Luckika,Tocharus, Jiraporn,Onsa-ard, Amnart,Chaichompoo, Waraluck,Suksamrarn, Apichart,Tocharus, Chainarong
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- Pharmacokinetics-driven evaluation of the antioxidant activity of curcuminoids and their major reduced metabolites—a medicinal chemistry approach
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Curcuminoids are the main bioactive components of the well-known Asian spice and traditional medicine turmeric. Curcuminoids have poor chemical stability and bioavailability; in vivo they are rapidly metabolized to a set of bioreduced derivatives and/or glucuronide and sulfate conjugates. The reduced curcuminoid metabolites were also reported to exert various bioactivities in vitro and in vivo. In this work, we aimed to perform a comparative evaluation of curcuminoids and their hydrogenated metabolites from a medicinal chemistry point of view, by determining a set of key pharmacokinetic parameters and evaluating antioxidant potential in relation to such properties.Reduced metabolites were prepared from curcumin and demethoxycurcumin through continuous-flow hydrogenation. As selected pharmacokinetic parameters, kinetic solubility, chemical stability, metabolic stability in human liver microsomes, and parallel artificial membrane permeability assay (PAMPA)-based gastrointestinal and blood-brain barrier permeability were determined. Experimentally determined logP for hydrocurcumins in octanol-water and toluene-water systems provided valuable data on the tendency for intramolecular hydrogen bonding by these compounds. Drug likeness of the compounds were further evaluated by a in silico calculations. Antioxidant properties in diphenyl-2-picrylhydrazyl (DPPH) radical scavenging and oxygen radical absorbance capacity (ORAC) assays were comparatively evaluated through the determination of ligand lipophilic efficiency (LLE). Our results showed dramatically increased water solubility and chemical stability for the reduced metabolites as compared to their corresponding parent compound. Hexahydrocurcumin was found the best candidate for drug development based on a complex pharmacokinetical comparison and high LLE values for its antioxidant properties. Development of tetrahydrocurcumin and tetrahydro-demethoxycurcumin would be limited by their very poor metabolic stability, therefore such an effort would rely on formulations bypassing first-pass metabolism.
- ?tv?s, Sándor B.,Balogh, Gy?rgy T.,Fül?p, Ferenc,Girst, Gábor,Hunyadi, Attila
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- Use of curcumin derivative
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The invention provides the use of a curcumin derivative. The use of the curcumin derivative shown in a formula I (please see the specification for the formula), or salts of the curcumin derivative inthe preparation of drugs of anti-inflammatory diseases and/or a COX inhibitor is particularly provided. The curcumin derivative has good COX inhibitory activity and anti-inflammatory activity and canbe used for preparing the COX inhibitor and anti-inflammatory drugs. Compound 6 and compound 7 have the best effects on COX-2 inhibitory activity and anti-inflammatory activity and can be used for preparing a COX-2 inhibitor and the anti-inflammatory drugs.
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Paragraph 0039; 0054-0056; 0067
(2019/10/23)
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- FOOD COMPOSITION FOR PREVENTING OBESITY, PHARMACEUTICAL COMPOSITION FOR TREATING OBESITY, AND ANIMAL MEDICINE FOR TREATING OBESITY, CONTAINING GINGERNONE A
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Disclosed is a composition comprising gingerenone A as an active ingredient. The composition includes a food composition for preventing obesity, a pharmaceutical composition for treating obesity and a medicine for treating animal obesity. Since the composition includes gingerenone A, which inhibits expression of the important transcriptional factors C/EBPα and PPARγ, expressed upon adipocyte differentiation, as well as FAS protein expression, the composition has superior potential for obesity prevention or treatment.
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- Synthesis and evaluation of curcumin derivatives toward an inhibitor of beta-site amyloid precursor protein cleaving enzyme 1
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To research a new non-peptidyl inhibitor of beta-site amyloid precursor protein cleaving enzyme 1, we focused on the curcumin framework, two phenolic groups combined with an sp2 carbon spacer for low-molecular and high lipophilicity. The structure-activity relationship study of curcumin derivatives is described. Our results indicate that phenolic hydroxy groups and an alkenyl spacer are important structural factors for the inhibition of beta-site amyloid precursor protein cleaving enzyme 1 and, furthermore, non-competitive inhibition of enzyme activity is anticipated from an inhibitory kinetics experiment and docking simulation.
- Konno, Hiroyuki,Endo, Hitoshi,Ise, Satomi,Miyazaki, Keiki,Aoki, Hideo,Sanjoh, Akira,Kobayashi, Kazuya,Hattori, Yasunao,Akaji, Kenichi
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p. 685 - 690
(2014/01/23)
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- Curcuminoid analogs inhibit nitric oxide production from LPS-activated microglial cells
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The chemically modified analogs, the demethy-lated analogs 4-6, the tetrahydro analogs 7-9 and the hexahydro analogs 10-12, of curcumin (1), demethoxycurcumin (2) and bisdemethoxycurcumin (3) were evaluated for their inhibitory activity on lipopolysaccharide activated nitric oxide (NO) production in HAPI microglial cells. Di-O-demethylcurcumin (5) and O- demethyldemethoxycurcumin (6) are the two most potent compounds that inhibited NO production. The analogs 5 and 6 were twofold and almost twofold more active than the parent curcuminoids 1 and 2, respectively. Moreover, the mRNA expression level of inducible NO synthase was inhibited by these two compounds. The strong neuroprotective activity of analogs 5 and 6 provide potential alternative compounds to be developed as therapeutics for neurological disorders associated with activated microglia. The Japanese Society of Pharmacognosy and Springer 2011.
- Tocharus, Jiraporn,Jamsuwan, Sataporn,Tocharus, Chainarong,Changtam, Chatchawan,Suksamrarn, Apichart
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body text
p. 400 - 405
(2012/09/10)
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- Synthesis of gingerol and diarylheptanoids
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The synthesis of gingerol 1 and related compounds 2-5 along with diarylheptanoids 6-8 has been accomplished using a Keck allylation, Crimmins' aldol reaction, aldehyde coupling with acetylene, and chelation controlled reductions as the key reactions. The absolute configuration of these molecules was confirmed by preparing their acetonide derivatives and by comparison of the NMR data with natural compounds.
- Sabitha, Gowravaram,Srinivas, Chitti,Reddy, Teega Rammohan,Yadagiri, Kurra,Yadav, Jhillu Singh
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p. 2124 - 2133
(2012/03/27)
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- Autoxidative and cyclooxygenase-2 catalyzed transformation of the dietary chemopreventive agent curcumin
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The efficacy of the diphenol curcumin as a cancer chemopreventive agent is limited by its chemical and metabolic instability. Non-enzymatic degradation has been described to yield vanillin, ferulic acid, and feruloylmethane through cleavage of the heptadienone chain connecting the phenolic rings. Here we provide evidence for an alternative mechanism, resulting in autoxidative cyclization of the heptadienone moiety as a major pathway of degradation. Autoxidative transformation of curcumin was pH-dependent with the highest rate at pH 8 (2.2 μM/min) and associated with stoichiometric uptake of O 2. Oxidation was also catalyzed by recombinant cyclooxygenase-2 (COX-2) (50 nM; 7.5 μM/min), and the rate was increased ≈10-fold by the addition of 300 μM H2O2. The COX-2 catalyzed transformation was inhibited by acetaminophen but not indomethacin, suggesting catalysis occurred by the peroxidase activity. We propose a mechanism of enzymatic or autoxidative hydrogen abstraction from a phenolic hydroxyl to give a quinone methide and a delocalized radical in the heptadienone chain that undergoes 5-exo cyclization and oxygenation. Hydration of the quinone methide (measured by the incorporation of O-18 from H218O) and rearrangement under loss of water gives the final dioxygenated bicyclopentadione product. When curcumin was added to RAW264.7 cells, the bicyclopentadione was increased 1.8-fold in cells activated by LPS; vanillin and other putative cleavage products were negligible. Oxidation to a reactive quinone methide is the mechanistic basis of many phenolic anti-cancer drugs. It is possible, therefore, that oxidative transformation of curcumin, a prominent but previously unrecognized reaction, contributes to its cancer chemopreventive activity.
- Griesser, Markus,Pistis, Valentina,Suzuki, Takashi,Tejera, Noemi,Pratt, Derek A.,Schneider, Claus
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experimental part
p. 1114 - 1124
(2012/01/06)
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- Microbial transformation of curcumin by Rhizopus chinensis
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Curcumin (1) is a potent antioxidant and antitumor natural product. In spite of its efficacy and safety, its clinical use is hindered mainly by poor water solubility and bioavailability. Structural modification to introduce hydrophilic functions is a promising approach to resolve this problem. In the present study we first found that curcumin could be efficiently converted into glucosides by filamentous fungi including Rhizopus chinensis IFFI 03043, Absidia coerulea AS 3.3389 and Cunninghamella elegans AS 3.1207. Curcumin 4′-O-β-d-glucoside (2), together with hexahydrocurcumin (3), was isolated from a preparative-scale biotransformation with R. chinensis IFFI 03043 and characterized fully by NMR and MS. A time-course study revealed that curcumin could be efficiently converted into curcumin 4′-O-β-d- glucoside within 8 h when administered at 0.05 mmol L-1 and the productivity was 57%. Additionally, the biotransformation products of curcumin by different fungal strains were analyzed by LC/MS. At least 15 metabolites were detected, and the predominant biotransformation reaction was glucosylation. This study provides a simple, efficient and less expensive approach for the preparation of curcumin glucosides. The introduction of the glucosyl function might be able to enhance the bioavailability of curcumin.
- Zhang, Xing,Ye, Min,Li, Rui,Yin, Jun,Guo, De-An
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experimental part
p. 380 - 386
(2011/10/08)
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- Curcuminoid analogs with potent activity against Trypanosoma and Leishmania species
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The natural curcuminoids curcumin (1), demethoxycurcumin (2) and bisdemethoxycurcumin (3) have been chemically modified to give 46 analogs and 8 pairs of 1:1 mixture of curcuminoid analogs and these parent curcuminoids and their analogs were assessed against protozoa of the Trypanosoma and Leishmania species. The parent curcuminoids exhibited low antitrypanosomal activity (EC50 for our drug-sensitive Trypanosoma brucei brucei line (WT) of compounds 1, 2 and 3 are 2.5, 4.6 and 7.7 μM, respectively). Among 43 curcuminoid analogs and 8 pairs of 1:1 mixture of curcuminoid analogs tested, 8 pure analogs and 5 isomeric mixtures of analogs exhibited high antitrypanosomal activity in submicromolar order of magnitude. Among these highly active analogs, 1,7-bis(4-hydroxy-3-methoxyphenyl)hept-4-en-3-one (40) was the most active compound, with an EC50 value of 0.053 ± 0.007 μM; it was about 2-fold more active than the standard veterinary drug diminazene aceturate (EC50 0.12 ± 0.01 μM). Using a previously characterized diminazene-resistant T. b. brucei (TbAT1-KO) and a derived multi-drug resistant line (B48), no cross-resistance of curcuminoids was observed to the diamidine and melaminophenyl arsenical drugs that are the current treatments. Indeed, curcuminoids carrying a conjugated keto (enone) motif, including 40, were significantly more active against T. b. brucei B48. This enone motif was found to contribute to particularly high trypanocidal activity against all Trypanosoma species and strains tested. The parent curcuminoids showed low antileishmanial activity (EC50 values of compounds 1 and 2 for Leishmania mexicana amastigotes are 16 ± 3 and 37 ± 6 μM, respectively) while the control drug, pentamidine, displayed an EC50 of 16 ± 2 μM. Among the active curcuminoid analogs, four compounds exhibited EC50 values of less than 5 μM against Leishmania major promastigotes and four against L. mexicana amastigotes. No significant difference in sensitivity to curcuminoids between L. major promastigotes and L. mexicana amastigotes was observed. The parent curcuminoids and most of their analogs were also tested for their toxicity against human embryonic kidney (HEK) cells. All the curcuminoids exhibited lower toxicity to HEK cells than to T. b. brucei bloodstream forms and only one of the tested compounds showed significantly higher activity against HEK cells than curcumin (1). The selectivity index for T. b. brucei ranged from 3-fold to 1500-fold. The selectivity index for the most active analog, the enone 40, was 453-fold.
- Changtam, Chatchawan,de Koning, Harry P.,Ibrahim, Hasan,Sajid, M. Sohail,Gould, Matthew K.,Suksamrarn, Apichart
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experimental part
p. 941 - 956
(2010/04/24)
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- Isoxazole analogs of curcuminoids with highly potent multidrug-resistant antimycobacterial activity
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Curcumin (1), demethoxycurcumin (2) and bisdemethoxycurcumin (3), the curcuminoid constituents of the medicinal plant Curcuma longa L., have been structurally modified to 55 analogs and antimycobacterial activity against Mycobacterium tuberculosis has been evaluated. Among the highly active curcuminoids, the isoxazole analogs are the most active group, with mono-O-methylcurcumin isoxazole (53) being the most active compound (MIC 0.09 μg/mL). It was 1131-fold more active than curcumin (1), the parent compound, and was approximately 18 and 2-fold more active than the standard drugs kanamycin and isoniazid, respectively. Compound 53 also exhibited high activity against the multidrug-resistant M. tuberculosis clinical isolates, with the MICs of 0.195-3.125 μg/mL. The structural requirements for a curcuminoid analog to exhibit antimycobacterial activity are the presence of an isoxazole ring and two unsaturated bonds on the heptyl chain. The presence of a suitable para-alkoxyl group on the aromatic ring which is attached in close proximity to the nitrogen function of the isoxazole ring and a free para-hydroxyl group on another aromatic ring enhances the biological activity.
- Changtam, Chatchawan,Hongmanee, Poonpilas,Suksamrarn, Apichart
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scheme or table
p. 4446 - 4457
(2010/10/19)
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- Different curcuminoids inhibit T-lymphocyte proliferation independently of their radical scavenging activities
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Purpose. We investigated the inhibitory effects of curcumin, curcumin derivatives and degradation products on OKT3-induced human peripheral blood mononuclear cell (PBMC) proliferation and the role of their radical scavenging activity. Methods. OKT3-induced human PBMC proliferation was determined by measuring 3H-thymidine incorporation. Radical scavenging activity was evaluated by using an in vitro DPPH assay. Results. OKT3-induced PBMC proliferation was inhibited by curcumin, isocurcumin, bisdesmethoxy-, diacetyl-, tetrahydro-, hexahydro-, and octahydrocurcumin as well as by vanillin, ferulic acid, and dihydroferulic acid with IC50-values of 2.8, 2.8, 6.4, 1.0, 25, 38, 82, 729, 457, and >1,000 μM, respectively. The investigated substances with the strongest effect on radical scavenging were tetrahydro-, hexahydro-, and octahydrocurcumin with IC50 values of 10.0, 11.7, and 12.3 μM, respectively. IC50-values of dihydroferulic acid, ferulic acid, and curcumin were 19.5, 37, and 40 μM. The substances with the lowest radical scavenging activities were vanillin, isocurcumin, diacetylcurcumin, and bisdesmethoxycurcumin with IC50 values higher than 100 μM each. Conclusions. Curcuminoid-induced inhibition of OKT3-induced PBMC proliferation depends on the number of carbon atoms and double bonds of the 1,6-heptadiene-3,5-dione structure as well as on the phenolic ring substitutes of the curcuminoids but is not correlated to their respective radical scavenging activity.
- Deters, Michael,Knochenwefel, Heiko,Lindhorst, Daniel,Koal, Therese,Meyer, Hartmut H.,Haensel, Wolfram,Resch, Klaus,Kaever, Volkhard
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p. 1822 - 1827
(2008/09/21)
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- Curcuminoids form reactive glucuronides in vitro
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Curcumin is of current interest because of its putative anti-inflammatory, anticarcinogenic, and anti-Alzheimer's activity, but its pharmacokinetic and metabolic fate is poorly understood. The present in vitro study has therefore been conducted on the glucuronidation of curcumin and its major phase I metabolite, hexahydro-curcumin, as well as of various natural and artificial analogs. The predominant glucuronide generated by rat and human liver microsomes from curcumin, hexahydro-curcumin, and other analogs with a phenolic hydroxyl group was a phenolic glucuronide according to LC-MS/MS analysis. However, a second glucuronide carrying the glucuronic acid moiety at the alcoholic hydroxyl group was formed from the same curcuminoids, but not hexahydro-curcuminoids, by human microsomes. Curcuminoids without a phenolic hydroxyl group gave rise to the aliphatic glucuronide only. The phenolic glucuronides of curcuminoids, but not of hexahydro-curcuminoids, were rather lipophilic and, in part, unstable in aqueous solution, their stability depending strongly on the type of aromatic substitution. The phenolic glucuronide of curcumin and of its natural congeners, but not the parent compounds, clearly inhibited the assembly of microtubule proteins under cell-free conditions, implying chemical reactivity of the glucuronides. These novel properties of the major phase II metabolites of curcuminoids deserve further investigation.
- Pfeiffer, Erika,Hoehle, Simone I.,Walch, Stephan G.,Riess, Alexander,Solyom, Aniko M.,Metzler, Manfred
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p. 538 - 544
(2008/02/09)
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- Metabolism of curcuminoids in tissue slices and subcellular fractions from rat liver
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Curcumin and its natural congeners are of current interest because of their putative anti-inflammatory and anticarcinogenic activities, but knowledge about their metabolic fate is scant. In the present study conducted with precision-cut liver slices from
- Hoehle, Simone I.,Pfeiffer, Erika,Solyom, Aniko M.,Metzler, Manfred
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p. 756 - 764
(2007/10/03)
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- Preparation and anti-inflammatory activities of diarylheptanoid and diarylheptylamine analogs
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Seven diarylheptylamine (12a-g) and four diarylheptanoid analogs (3-5, 9), structurally related to the natural anti-inflammatory agent oregonin (1), have been prepared from curcumin (2) for evaluation of their activity against the expression of iNOS and COX-2. Diarylheptylamine 12b and diarylheptanoid analogs can inhibit iNOS and COX-2 responses of LPS, although less potently than 1. These compounds, however, possess stronger potency than 1 against COX-2-derived PGE2 formation, of which hexahydrocurcumin (4) is the most potent one with an IC50 value of 0.7 μM.
- Lee, Su-Lin,Huang, Wei-Jan,Lin, Wan Wan,Lee, Shoei-Sheng,Chen, Chung-Hsiung
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p. 6175 - 6181
(2007/10/03)
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- Anti-allergic principles from Thai zedoary: Structural requirements of curcuminoids for inhibition of degranulation and effect on the release of TNF-α and IL-4 in RBL-2H3 cells
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The 80% aqueous acetone extract of the rhizomes of Curcuma zedoaria cultivated in Thailand (Thai zedoary) was found to inhibit release of β-hexosaminidase, as a marker of antigen-IgE-mediated degranulation, in RBL-2H3 cells and passive cutaneous anaphylaxis reaction in mice. Effects of four curcuminoids from Thai zedoary and several related compounds on the degranulation were examined. Among them, curcumin showed the highest activity against β-hexosaminidase release with IC50 of 5.3 μM, followed by bisdemethoxycurcumin (IC50 = 11 μM). With regard to the structural requirements of curcuminoids for the activity, the conjugated olefins at the 1-7 positions and the 4′- or 4″-hydroxyl groups of curcuminoids were suggested to be essential for the strong activity, whereas the 3′- or 3″-methoxyl group only enhanced the activity. Furthermore, effects of curcumin and bisdemethoxycurcumin on calcium ionophores (A23187 and ionomycin)-induced degranulation and antigen-induced release of TNF-α and IL-4 were examined. The 80% aqueous acetone extract of the rhizomes of Curcuma zedoaria cultivated in Thailand (Thai zedoary) was found to inhibit release of β-hexosaminidase, as a marker of antigen-IgE-mediated degranulation, in RBL-2H3 cells and passive cutaneous anaphylaxis reaction in mice. From the active fraction, four curcuminoids (curcumin, dihydrocurcumin, tetrahydrodemethoxycurcumin, and tetrahydrobisdemethoxycurcumin) were isolated together with two bisabolane-type sesquiterpenes, and the effects of four curcuminoids from Thai zedoary and several related compounds on the degranulation were examined. Among them, curcumin showed the highest activity against β-hexosaminidase release with IC50 of 5.3 μM, followed by bisdemethoxycurcumin (IC50 = 11 μM). With regard to the structural requirements of curcuminoids for the activity, the conjugated olefins at the 1-7 positions and the 4′- or 4″-hydroxyl groups of curcuminoids were suggested to be essential for the strong activity, whereas the 3′- or 3″-methoxyl group only enhanced the activity. Furthermore, effects of curcumin and bisdemethoxycurcumin on calcium ionophores (A23187 and ionomycin)-induced degranulation and antigen-induced release of TNF-α and IL-4 were examined.
- Matsuda, Hisashi,Tewtrakul, Supinya,Morikawa, Toshio,Nakamura, Akihiko,Yoshikawa, Masayuki
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p. 5891 - 5898
(2007/10/03)
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- Pharmacognostic studies on ginger and related drugs - Part 1: Five sulfonated compounds from Zingiberis rhizome (Shokyo)
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Five sulfonated compounds, namely 4-gingesulfonic acid and shogasulfonic acids A, B, C and D, were isolated together with seven known compounds including 6-gingesulfonic acid from Zingiberis rhizome (Japanese name: Shokyo) made out of ginger. Their struct
- Hori, Yumiko,Miura, Tsuyoshi,Hirai, Yasuaki,Fukumura, Motonori,Nemoto, Yukio,Toriizuka, Kazuo,Ida, Yoshiteru
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p. 613 - 617
(2007/10/03)
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- Antitumor agents. Part 214: Synthesis and evaluation of curcumin analogues as cytotoxic agents
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Fifty-eight curcumin analogues were prepared and evaluated for in vitro cytotoxicity against a panel of human tumor cell lines. Compound 50 was the most potent analogue against several cell lines, including HOS (bone cancer) and 1A9 (breast cancer), with ED50 values of 0.97 and 0.63 μg/mL, respectively.
- Ishida, Junko,Ohtsu, Hironori,Tachibana, Yoko,Nakanishi, Yuka,Bastow, Kenneth F,Nagai, Masahiro,Wang, Hui-Kang,Itokawa, Hideji,Lee, Kuo-Hsiung
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p. 3481 - 3487
(2007/10/03)
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- Antitumor agents. 217. Curcumin analogues as novel androgen receptor antagonists with potential as anti-prostate cancer agents
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A number of curcumin analogues were prepared and evaluated as potential androgen receptor antagonists against two human prostate cancer cell lines, PC-3 and DU-145, in the presence of androgen receptor (AR) and androgen receptor coactivator, ARA70. Compounds 4 [5-hydroxy-1,7-bis(3,4-dimethoxyphenyl)-1,4,6-heptatrien-3-one], 20 [5-hydroxy-1,7-bis[3-methoxy-4-(methoxycarbonylmethoxy)phenyl]-1, 4,6-heptatrien-3-one], 22 [7-(4-hydroxy-3-methoxyphenyl)-4-[3(4-hydroxy-3-methoxyphenyl) acryloyl]-5-oxohepta-4,6-dienoic acid ethyl ester], 23 [7-(4-hydroxy-3-methoxyphenyl)-4-[3-(4-hydroxy-3-methoxyphenyl)acryloyl] 5-oxohepta-4,6-dienoic acid], and 39 [bis(3,4-dimethoxyphenyl)-1,3-propanedione] showed potent antiandrogenic activities and were superior to hydroxyflutamide, which is the currently available antiandrogen for the treatment of prostate cancer. Structure-activity relationship (SAR) studies indicated that the bis(3,4-dimethoxyphenyl) moieties, the conjugated β-diketone moiety, and the intramolecular symmetry of the molecules seem to be important factors related to antiandrogenic activity. The data further suggest that the coplanarity of the β-diketone moiety and the presence of a strong hydrogen bond donor group were also crucial for the antiandrogenic activity, which is consistent with previous SAR results for hydroxyflutamide analogues. When the pharmacophoric elements of dihydrotestosterone (DHT) and compound 4 are superposed, the resulting construct implies that the curcumin analogues may function as a 17α-substituted DHT. Compounds 4, 20, 22, 23, and 39 have been identified as a new class of antiandrogen agents, and these compounds or their new synthetic analogues could be developed into clinical trial candidates to control androgen receptor-mediated prostate cancer growth.
- Ohtsu, Hironori,Xiao, Zhiyan,Ishida, Junko,Nagai, Masahiro,Wang, Hui-Kang,Itokawa, Hideji,Su, Ching-Yuan,Shih, Charles,Chiang, Tzuying,Chang, Eugene,Lee, YiFen,Tsai, Meng-Yin,Chang, Chawnshang,Lee, Kuo-Hsiung
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p. 5037 - 5042
(2007/10/03)
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- Synthesis of gingerenone-A and hirsutenone
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Gingerenone-A 5, a diarylheptenone from Zingiber officinale, has been synthesized from vanillin 1 in four steps with an overall yield of 15%. Demethylation of 5 with AlCl3 gives hirsutenone 6, a metabolite of Alnus hirsute, in 36% yield. The spectral data of 5 and 6 are in agreement with those of natural metabolites 5 and 6 and both the compounds exhibited weak antibacterial activity.
- Venkateswarlu,Ramachandra,Rambabu,Subbaraju
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p. 495 - 497
(2007/10/03)
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- STRUCTURES OF ANTIFUNGAL DIARYLHEPTENONES, GINGERENONES A, B, C AND ISOGINGERENONE B, ISOLATED FROM THE RHIZOMES OF ZINGIBER OFFICINALE
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Four new diarylheptenones, 1,7-bis(4-hydroxy-3-methoxyphenyl)hept-4-en-3-one (gingerenone A), 7-(3,5-dimethoxy-4-hydroxyphenyl)-1-(4-hydroxy-3-methoxyphenyl) hept-4-en-3-one (gingerenone B), 1- gingerol -> shogaol) of zingiberaceous plants.Gingerenone A exhibited a moderate anticoccidium activity in vitro and a strong antifungal effect to Pyricularia oryzae.
- Endo, Katsuya,Kanno, Emi,Oshima, Yoshiteru
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p. 797 - 799
(2007/10/02)
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- Diarylheptanoids from the Rhizomes of Curcuma xanthorrhiza and Alpinia officinarum
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Five diarylheptanoids including two new compounds were isolated from the rhizomes of Curcuma xanthorrhiza (Zingiberaceae).The structures of the new compounds were determined to be octahydrocurcumin ((3S, 5S)-1,7-bis(4-hydroxy-3-methoxyphenyl)-heptane-3,5-diol) (Ia) and (1ξ)-1-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-6-heptene-3,5-dione (II) on the basis of spectral and chemical evidence.The absolute configurations of Ia and a new similar diarylheptanoid, (3R, 5R)-1-(4-hydroxyphenyl)-7-phenylheptane-3,5-diol (VIa), isolated from the rhizomes of Alpinia officinarum (Zingiberaceae), were established by application of the exciton chirality rule.Keywords--diarylheptanoid; Curcuma xanthorrhiza; Alpinia officinarum; Zingiberaceae; (3S, 5S)-1,7-bis(4-hydroxy-3-methoxyphenyl)-heptane-3,5-diol; (1ξ)-1-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-6-heptene-3,5-dione; (3R, 5R)-1-(4-hydroxyphenyl)-7-phenylheptane-3,5-diol; exciton chirality rule; CD
- Uehara, Shin-ichi,Yasuda, Ichiro,Akiyama, Kazuyuki,Morita, Hiroshi,Takeya, Koichi,Itokawa, Hideji
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p. 3298 - 3304
(2007/10/02)
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- NEW METHODS AND REAGENTS IN ORGANIC SYNTHESIS. 47. A GENERAL, EFFICIENT, AND CONVENIENT SYNTHESIS OF DIARYLHEPTANOIDS
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An efficient synthesis of physiologically interesting diarylheptanoids has been carried out through direct C-acylation using diethyl phosphorocyanidate (DEPC) followed by Grignard reactions with aldehydes.Keywords - diarylheptanoid; C-acylation; diethyl p
- Kato, Nobuharu,Hamada, Yasumasa,Shioiri, Takayuki
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p. 3323 - 3326
(2007/10/02)
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