- Biotransformation of polymethoxylated flavonoids: Access to their 4′-O-demethylated metabolites
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Regioselective O-demethylation of the flavones tangeretin (1) and 3-hydroxytangeretin (6) into their 4′-O-demethylated metabolites was performed by using an Aspergillus niger strain. This method serves as a straightforward alternative to multistep synthes
- Buisson, Didier,Quintin, Jerome,Lewin, Guy
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Read Online
- preparing methods of nobiletin
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The present invention provides a process for preparing nobiletin. The present invention relates to a method for preparing nobiletin by using a specific reagent.
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- Practical Synthesis of Polymethylated Flavones: Nobiletin and Its Desmethyl Derivatives
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We present a practical synthesis of the polymethoxylated citrus flavone nobiletin that is suitable for use on a hundred gram scale. Ready availability of this compound and its derivatives will aid detailed chemical-biological investigations of their biological activities, including activation of signaling via the cAMP-dependent protein kinase A/extracellular signal-related protein kinase/cAMP response element-binding protein pathway.
- Asakawa, Tomohiro,Sagara, Hiroto,Kanakogi, Masaki,Hiza, Aiki,Tsukaguchi, Yuta,Ogawa, Takahiro,Nakayama, Miho,Ouchi, Hitoshi,Inai, Makoto,Kan, Toshiyuki
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p. 595 - 602
(2019/04/01)
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- Synthesis and Antiproliferative Activity of Natural and Non-Natural Polymethoxychalcones and Polymethoxyflavones
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Two series of polymethoxychalcones and polymethoxyflavones, including the natural products 2′-hydroxy-3,4,5,4′,6′-pentamethoxychalcone (8c), 5,6,7,8,3′,4′,5′-heptamethoxyflavone (6), 5,7,3′,4′,5′-pentamethoxyflavone (9c), 3-hydroxy-5,6,7,8,3′,4′,5′-heptam
- Vongdeth, Kingsadingthongkham,Han, Peipei,Li, Wei,Wang, Qiu-An
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- Nobiletin derivative or pharmaceutically acceptable salt thereof as well as preparation method and application thereof
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The invention discloses a nobiletin derivative or a pharmaceutically acceptable salt thereof as well as a preparation method and application thereof. The nobiletin derivative has a structural formula(I) shown in the description, in the formula, R1, R2, R3 and R4 are respectively selected from hydrogen, halogen, hydroxyl, amino, C1-6 substituted or non-substituted alkoxy, a C1-6 substituted or non-substituted ester group, C1-6 substituted or non-substituted alkamino and a C1-6 substituted or non-substituted amide group; R5 is selected from a C3-9 substituted or non-substituted aromatic ring and a C3-9 substituted or non-substituted aromatic heterocyclic ring; and X is selected from O or NR6. The nobiletin derivative or the pharmaceutically acceptable salt thereof, which is disclosed by theinvention, is novel in structure, and in addition, the compound has an excellent inhibition function on P-gp, can be prepared into a P-gp inhibitor, is capable of treating and/or preventing related diseases caused by P-gp, particularly diseases related to tumor drug resistance, or can be mixed and used with other medicines and used as a drug resistance reversal agent, has a high reversion multiple, and is capable of remarkably improving medicine effects of medicines.
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Paragraph 0129-0131; 0133
(2019/12/09)
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- PET imaging of nobiletin based on a practical total synthesis
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A practical synthesis of nobiletin, a polymethoxylated citrus flavone, was accomplished by utilizing our novel flavone synthesis. Synthetic nobiletin was labelled by selective demethylation and rapid incorporation of 11C atom. Positron emission tomography images successfully visualized the brain distribution, which may provide therapeutic benefits in the treatment of Alzheimer's disease. The Royal Society of Chemistry.
- Asakawa, Tomohiro,Hiza, Aiki,Nakayama, Miho,Inai, Makoto,Oyama, Dai,Koide, Hiroyuki,Shimizu, Kosuke,Wakimoto, Toshiyuki,Harada, Norihiro,Tsukada, Hideo,Oku, Naoto,Kan, Toshiyuki
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supporting information; experimental part
p. 2868 - 2870
(2011/04/22)
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- Nobiletin metabolites: Synthesis and inhibitory activity against matrix metalloproteinase-9 production
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A divergent synthesis of nobiletin metabolites was developed through highly oxygenated acetophenone derivative. We used commercially available methyl 3,4,5-trimethoxybenzoate as a starting material for concise preparation of the key intermediate, 2′-hydro
- Oshitari, Tetsuta,Okuyama, Yuji,Miyata, Yoshiki,Kosano, Hiroshi,Takahashi, Hideyo,Natsugari, Hideaki
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p. 4540 - 4544
(2011/09/12)
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- COGNITIVE DISORDER-AMELIORATING AGENT
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A cognitive impairment ameliorant is provided that is useful for the prevention or treatment of cognitive impairment, and particularly Alzheimer's disease. The cognitive impairment ameliorant contains royal jelly as an active ingredient thereof.
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- Synthesis and biological evaluation of a series of tangeretin-derived chalcones
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A series of chalcones polyoxygenated on the ring A (with pentamethoxy or 2′-hydroxy-3′,4′,5′,6′-tetramethoxy substitution patterns) was synthesized from tangeretin, a natural Citrus flavonoid. These chalcones were evaluated for their antiproliferative, ac
- Quintin, Jerome,Desrivot, Julie,Thoret, Sylviane,Menez, Patrick Le,Cresteil, Thierry,Lewin, Guy
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scheme or table
p. 167 - 169
(2009/04/10)
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- Semisynthesis and antiproliferative evaluation of a series of 3′-aminoflavones
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A series of 3′-aminoflavones 5,6,7,8-tetra- or 5,7-dioxygenated on the A-ring was synthesized from tangeretin or naringin, two natural Citrus flavonoids. These flavones were evaluated for antiproliferative activity, activation of apoptosis, and inhibition
- Quintin, Jerome,Buisson, Didier,Thoret, Sylviane,Cresteil, Thierry,Lewin, Guy
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scheme or table
p. 3502 - 3506
(2010/04/26)
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- Miscrowave-assisted efficient synthesis of polymethoxyacetophenones and natural polymethoxyflavones, and thier inhibitory effects on melanogenesis
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Microwave, assisted Friedel-Crafts acetylation of polymethoxybenzenes with acetic anhydride in the presence of In(CF3SO3)3 under solvent-free conditions was achieved rapidly to give polymethoxyacetophenones in high yields. Microwave-assisted benzoylation of 2'-hydroxypolymethoxyacetophenones with polymethoxybenzoyl chlorides, followed by the rearrangement of the resulting benzoates and the final formation of natural polymethoxyflavones was achieved rapidly and efficiently. The polymethoxyflavones showed inhibitory effects on melanogenesis in human melanoma cells.
- Tsukayama, Masao,Kusunoki, Eiji,Hossain, Mohammad M.,Kawamura, Yasuhiko,Hayashi, Shinji
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p. 1589 - 1600
(2008/09/17)
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- Improved, rapid and efficient synthesis of polymethoxyflavones under microwave irradiation and their inhibitory effects on melanogenesis
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The microwave-assisted methylation of 2,5-dihydroxy-1,3-dimethoxybenzene with (CH3O)2SO2 for 5 min gave easily 1,2,3,5-tetramethoxybenzene, which was converted into pentamethoxybenzene. The microwave-assisted Friedel-Crafts acylation of pentamethoxybenzene in the presence of In(CF3SO3)3 gave pentamethoxyacetophenone for 15 min under solvent-free conditions in high yield. The microwave-assisted cyclization reaction of the diketones, which were synthesized from the acetophenone via three steps under microwave irradiation, gave the desired polymethoxyflavones for 1.5-3 min in high yields. The polymethoxyflavones showed inhibitory effects on melanogenesis in a human melanoma.
- Tsukayama, Masao,Kawamura, Yasuhiko,Ishizuka, Takaaki,Hayashi, Shinji,Torii, Fumihito
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p. 2775 - 2784
(2007/10/03)
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- Studies of the selective O-alkylation and dealkylation of flavonoids. XVI. Demethylation of 2'-methoxyacetophenones with anhydrous aluminum chloride or bromide in acetonitrile
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Demethylation of 2'-methoxyacetophenones with anhydrous aluminum chloride in acetonitrile was studied to survey its scope and limitations. The mechanism which the reaction proceeds via sterically constrained intermediates was proposed from the substituent effects. Additionally, dealkylation of 2'-benzyloxy-, 2'-ethoxy-, and 2'-isopropoxyacetophenones with two demethylating reagents, hydrochloric acid in acetic acid and anhydrous aluminum bromide in acetonitrile, was studied. It was found that the reactivity was greatly affected by the steric factor between the alkoxyl group and reagent. This behavior may have wide application in selection of protecting groups in organic synthesis.
- Kawamura,Takatsuki,Torii,Horie
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p. 511 - 515
(2007/10/02)
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- OCTASUBSTITUTED FLAVONES FROM AGERATUM HOUSTONIANUM
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Ageratum houstonianum; Asteraceae; Eupatorieae; octasubstituted flavones; 3'-hydroxy-5,6,7,8,2',4',5'-heptamethoxyflavone; 5,3'-dihydroxy-6,7,8,2',4',5'-hexamethoxyflavone.Two new highly oxygenated flavones, were isolated from aerial parts of Ageratum houstonianum.Their structures were established as 3'-hydroxy-5,6,7,8,2',4',5'-heptamethoxyflavone and 5,3'-dihydroxy-6,7,8,2',4',5'-hexamethoxyflavone on the basis of spectral data and chemical degradation.The structure of the latter compound was confirmed by X-ray analysis.
- Quijano, Leovigildo,Calderon, Jose S.,Gomez, G., Federico,Escobar, Edgar,Rios, Tirso
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p. 1085 - 1088
(2007/10/02)
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- Structure Reinvestigation of Conyzorigun, a New Chromone from Ageratum conyzoides
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A highly oxygenated chromone, conyzorigun (1), from Ageratum conyzoides plants was earlier reported to contain a novel stable ketene acetal system by virtue of an oxygen linkage between the benzopyrone and phenyl moieties.A reinvestigation of this structure in the light of biosynthetic experiments followed by chemical degradation is now described.The results obtained indicate that conyzorigun does not contain the above-described oxygen linkage, being a flavone of a known structure, viz. eupalestin (4).
- Vyas, Ashok V.,Mulchandani, Mewand B.
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p. 2945 - 2947
(2007/10/02)
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- Synthetic studies on the flavone derivatives. XIII. Synthesis of flavones with tetramethoxyl groups in ring B
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2',3',4',5,5',6,7,8-Octamethoxy- (Ia) and 2',3',4',5,5',6,7-heptamethoxyflavone (IIa) and their position isomers substituted with tetramethoxyl groups in ring B were synthesized to confirm the structures of agehoustin A and agehoustin B isolated from Ageratum houstonianum. The characteristics of the synthesized flavones were investigated by spectroscopic methods.
- Iinuma,Tanaka,Matsuura
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p. 3354 - 3360
(2007/10/02)
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- TWO POLYMETHOXYFLAVONES FROM AGERATUM HOUSTONIANUM
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Besides agecorynin C, eupalestin and lucidin dimethyl ether, two new highly oxygenated flavones were isolated from Ageratum houstonianum.Their structures were established by spectroscopic and degradative evidence as 5,6,7,8,2',3',4',5'-octamethoxyflavone and 5,6,7,2',3',4',5'-heptamethoxyflavone. - Key Word Index: Ageratum houstonianum; Asteraceae; Eupatorieae; new octasubstituted and heptasubstituted flavones.
- Quijano, L.,Calderon, J. S.,Gomez, F.,Rios, T.
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p. 2965 - 2968
(2007/10/02)
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- 13C-Nuclear Magnetic Resonance (NMR) Spectral Studies on Polysubstituted Flavonoids. I. 13C-NMR Spectra of Flavones
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The 13C-NMR spectra of 61 flavone derivatives were measured in dimethyl sulfoxide.By consideration of the chemical shifts of skeletal carbons, the parameters (α and β values) and correction factor (o value) necessary for calculating their carbon shifts were deduced.The skeletal carbons of polysubstituted flavones and flavonols could easily be assigned by the use of these values and SCS of OMe or OH.The 13C-NMR spectra were confirmed to give useful information that could not be obtained from other spectral data.The data were applied for the structure elucidation of unknown polysubstituted flavones.Keywords - 13C-NMR spectra; polysubstituted flavones; α value; β value; o value; extensive additivity rule
- Iinuma, Munekazu,Matsuura, Shin,Kusuda, Kousuke
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p. 708 - 716
(2007/10/02)
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- Highly oxygenated flavonoids from Ageratum corymbosum
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The investigation of Ageratum corymbosum resulted in the isolation of four new highly oxygenated flavonoids, and their structures established by spectroscopic and degradative evidence as 5,6,7,5′-tetramethoxy-3′,4′-methylenedioxyflavanone; 5,6,7,8,5′-pentamethoxy-3′,4′-methylenedioxyflavanone; 5,6,7,8,2′,4′,5′-heptamethoxy-flavone and 5,2′,4′-trihydroxy-6,7,8,5′-tetramethoxyflavone. The recently reported gardenin A monomethyl ether and 5′-methoxylucidin dimethyl ether (eupalestin) were also isolated.
- Quijano,Calderon,G, F.Gomez,Soria,Rios
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p. 2439 - 2442
(2007/10/02)
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