- Synthesis of Citrus polymethoxyflavonoids and their antiproliferative activities on Hela cells
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Abstract: A series of polymethoxyflavonoids (3–16) were synthesized through dehydrogenation, O-methylation, glycoside hydrolysis, bromination, microwave-assisted aromatic nucleophilic substitution, dimethyldioxirane oxidation and regioselective demethylation, starting from abundant and inexpensive natural sources naringin and hesperidin. All the synthetic compounds were test for antiproliferative activities on human cervical carcinoma Hela cell line by the standard CCK-8 assay, the result showed that most of the target compounds exhibited moderate to potent antiproliferative activities on Hela cells comparable with the positive control cis-Platin. Among them, 5-hydroxypolymethoxy flavonoid 13 showed the strongest activity (IC50 0.791 μM). Graphical Abstract: [InlineMediaObject not available: see fulltext.].
- Nguyen, Van-Son,Li, Wei,Li, Yue,Wang, Qiuan
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p. 1585 - 1592
(2017/06/05)
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- Use of flavone and flavanone derivatives in preparation of sedative and hypnotic drugs
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Disclosed is a use of flavones derivatives and flavanone derivatives in preparation of sedative and hypnotic drugs.
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Page/Page column 48; 49; 50; 51
(2017/07/01)
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- Methoxyflavones from Stachys glutinosa with binding affinity to opioid receptors: In silico, in vitro, and in vivo studies
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Fractionation of the bioactive dichloromethane extract from the aerial parts of Stachys glutinosa led to the isolation of four flavones, xanthomicrol (1), sideritoflavone (2), 8-methoxycirsilineol (3), and eupatilin (4), along with two neo-clerodane diterpenes, roseostachenone (8) and a new compound, 3α,4α-epoxyroseostachenol (7). In order to study structure-activity relationships, two methoxyflavones [5-demethyltangeretin (5) and tangeretin (6)] were synthesized by the methoxylation of xanthomicrol. The isolated compounds (1-4, 7, and 8) as well as the xanthomicrol semisynthetic derivatives (5 and 6) were evaluated for their binding affinity to the μ and δ opioid receptors. Xanthomicrol was the most potent binder to both μ and δ receptors, with a Ki value of 0.83 and 3.6 μM, respectively. Xanthomicrol administered intraperitoneally in mice at a dose of 80 mg/kg significantly reduced morphine-induced antinociception in the tail flick test. Our results suggested that xanthomicrol is a μ opioid receptor antagonist. Docking experiments were carried out to acquire a deeper understanding about important structural aspects of binding of xanthomicrol. In summary, these data suggest that xanthomicrol is a valuable structure for further development into a potential μ opioid receptor antagonist.
- Ruiu, Stefania,Anzani, Nicola,Orrü, Alessandro,Floris, Costantino,Caboni, Pierluigi,Alcaro, Stefano,MacCioni, Elias,Distinto, Simona,Cottiglia, Filippo
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- USE OF FLAVONE AND FLAVANONE DERIVATIVES IN PREPARATION OF SEDATIVE AND HYPNOTIC DRUGS
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Disclosed is a use of flavones derivatives and flavanone derivatives in preparation of sedative and hypnotic drugs.
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Paragraph 0223; 0233
(2015/07/22)
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- Semisynthesis of polymethoxyflavonoids from naringin and hesperidin
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Polymethoxyflavonoids (PMFs) possess important biological activities, notably as anticancer agents. Semisynthesis of a series of PMFs were performed by glycoside hydrolysis, dehydrogenation, bromination, aromatic nucleophilic substitution, O-methylation, dimethyldioxirane oxidation and regioselective demethylation, starting from abundant and inexpensive natural sources naringin and hesperidin. A new synthetic method for selective methylation using CuBr catalysed and microwave-assisted reaction was developed, and the dimethyl dioxirane oxidation of flavones to flavonols was much improved. The new semisynthetic route has the advantages of easy availability of starting materials, simple operation and good yields.
- Li, Yue,Cai, Shuanglian,He, Kailin,Wang, Qiuan
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p. 287 - 290
(2014/06/09)
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- B-Ring-modified and/or 5-demethylated nobiletin congeners: Inhibitory activity against pro-MMP-9 production
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Three metabolites and 12 analogues of nobiletin (1) were synthesized. Whereas nobiletin derivatives 2-4 inhibited pro-MMP-9 production similarly in both PMA- and TNF-α-stimulated human lens epithelial cells, the 2′-hydroxylated analogue 5a exerted marked inhibitory effects (IC 50: 0.4 μM) on PMA-treated cells, which were 170-fold more potent than those on TNF-α-treated cells. This activity may be closely related to PKC-mediated transcriptional regulation of pro-MMP-9.
- Oshitari, Tetsuta,Okuyama, Yuji,Miyata, Yoshiki,Kosano, Hiroshi,Takahashi, Hideyo,Natsugari, Hideaki
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experimental part
p. 7085 - 7092
(2012/01/02)
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- Chemical constituents of Limnophila indica
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Two flavonoids, 5,6-dihydroxy-7,8,4′-trimethoxy flavone 1 and 5,2′-dihydroxy-8,3prime;,4′-trimethoxyflavone 2 together with three known compounds, 5-hydroxy-7,2′-dimethoxyflavone 3, 5,2′-dihydroxy- 7,8-dimethoxyflavone 4 and β-sitosterol 5, have been isolated from the aerial parts and roots of Limnophila indica (Scrophulariaceae). The structures of compounds 1-5 have been elucidated on the basis of spectral and chemical studies.
- Brahmachari,Jash,Gangopadhyay,Sarkar,Laskar,Gorai
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experimental part
p. 1898 - 1902
(2009/05/09)
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- 5,8-Dihydroxy-6,7,4′-trimethoxyflavone, a novel flavonoid constituent of Limnophila indica
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The petrol extract of the aerial parts and roots of Limnophila indica (Scrophulariaceae) has yielded a new flavone, 5,8-dihydroxy-6,7,4′- trimethoxyflavone 1 characterized by chemical as well as spectral studies.
- Brahmachari,Gorai,Chatterjee,Mondal,Mistri
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p. 219 - 222
(2007/10/03)
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- Regioselective hydroxylation of 2-hydroxychalcones by dimethyldioxirane towards polymethoxylated flavonoids
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The flavone nucleus is part of a large number of natural products and medicinal compounds. In this presentation the novel regioselective hydroxylation of hydroxyarenes with DMD is described. The results showed further that flavonoids with 5-hydroxy group were selectively oxyfunctionalized at the para-position C8 carbon atom by DMD. Finally, according to this methodology, the naturally occurring isosinensetin, tangeretin, sinensetin, nobiletin, natsudaidain, gardenin B, 3,3′,4′,5,6,7,8- heptamethoxyflavone, quercetin and its derivatives were synthesized.
- Chu, Han-Wei,Wu, Huan-Ting,Lee, Yean-Jang
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p. 2647 - 2655
(2007/10/03)
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- Compositions and methods of treating, reducing and preventing cardiovascular diseases and disorders with polymethoxyflavones
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Compositions and methods for the treatment, reduction and/or prevention of cardiovascular diseases and disorders are described. Individuals at high risk for developing or having cardiovascular disease or disorder may be treated with an effective dose of a polymethoxyflavone including limocitrin derivatives, quercetin derivatives, naturally occurring polymethoxyflavones, tocotrienols, and mixtures of these compounds.
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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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- Taste modifier and a method of modifying taste
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Taste modifier comprising a flavone derivative as an active ingredient of the general formula (I): STR1 wherein R1, R3, R4, R6 and R8 are independently a methoxy group or an hydrogen atom, R2 and R7 are methoxy groups, and R5 is a methoxy group or an hydroxy group, and a method of modifying taste, comprising adding a taste-modifying effective amount of the flavone derivative (I) to a product used in a mouth or an orally ingestible product. Various factors associated with taste can be modified, for example, the derivative can enhance sourness, reduce saltiness, inhibit unpleasant lasting of sweetness, enhance refreshing flavor and its continuity, reduce flavor associated with acetic acid, and enhance body, deliciousness and savor associated with the combination of these tastes.
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- Isolation of 4,4'-Dimethoxy-trans-stilbene and Flavonoids from Leaves and Twigs of Vitex negundo Linn.
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The leaves and twigs of Vitex negundo Linn. afford a stilbene derivative characterised as 4,4'-dimethoxy-trans-stilbene (1), along with five flavones, 5,6,7,8,3',4',5'-heptamethoxy (2), 5-hydroxy-6,7,8,3',4'-pentamethoxy (5-O-desmethylnobiletin) (3), 5-hydroxy-6,7,8,3',4',5'-hexamethoxy (gardenin A) (4), 5-hydroxy-6,7,8,4'-tetramethoxy (gardenin B) (5) and 5-hydroxy-7,3',4',5'-tetramethoxyflavone (corymbosin) (6).This is the first report of 1 as a natural product.Compound 1 has been converted into 3,6-dimethoxyphenanthrene (11).The flavones 2,5 and 6 undergo interesting rearrangements when treated with hydrazine hydrate to generate the pyrazoles 14, 15 and 16 respectively.
- Banerji, J.,Das, B.,Chakrabarty, R.,Jha, H. C.
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p. 597 - 599
(2007/10/02)
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- TLC, UV AND ACIDIC TREATMENT IN THE DIFFERENTIATION OF 5,6- AND 5,8-DIHYDROXYFLAVONES, 3-METHOXYFLAVONES AND FLAVONOLS
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UV and TLC techniques constitute easy procedures to distinguish between 5,6-dihydroxy-7,8-dimethoxy- and 5,8-dihydroxy-6,7-dimethoxyflavonoids, that are difficult to characterize by NMR and classical UV techniques.The acidic treatment of the original products to obtain Wessely-Moser isomers, useful for comparison purposes, yielded novel demethylated products.UV and MS data of 5,8,4' -trihydroxy-6,7,3'-trimethoxyflavone, 5,6,8,3',4'-pentahydroxy-7-methoxyflavone and 5,6,8,4'-tetrahydroxy-7,3'-dimethoxyflavone are presented for the first time.
- Barberan, F.A.T.,Ferreres, F.,Tomas, F.
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p. 5733 - 5740
(2007/10/02)
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- Two New Flavones from Colebrookea oppositifolia
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Components, hitherto unknown from Colebrookea oppositifolia, namely 5-hydroxy-6,7,8,4'-tetramethoxy (I) and 5-hydroxy-6,7,4'-trimethoxy(II)-flavones have been isolated.Flavones 5,6,7-trimethoxy-(III) and 5,6,7,4'-tetramethoxy-(IV) reported earlier have also been isolated.
- Patwardhan, S. A.,Gupta, A. S.
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