- Inhibitory mechanisms and interaction of tangeretin, 5-demethyltangeretin, nobiletin, and 5-demethylnobiletin from citrus peels on pancreatic lipase: Kinetics, spectroscopies, and molecular dynamics simulation
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This study aimed to reveal the interaction and inhibitory mechanisms of tangeretin (TAN), nobiletin (NBT), and their acidic hydroxylated forms, 5-demethyltangeretin (5-DT) and 5-demethylnobiletin (5-DN) on porcine pancreatic lipase (PPL) using spectroscop
- Huang, Xin,Jing, Huijuan,Kou, Xingran,Ma, Chaoyang,Wang, Hongxin,Wang, Li,Zhu, Junxiang
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- Synthesis and antiproliferative activities of polymethoxyflavones aminoalkyl and amino acid derivatives
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Twelve novel aminoalkyl derivatives 3a-3f, 4a-4f and four novel amino acid derivatives 5a, 5b, 6a and 6b of polymethoxyflavones 1 and 2 were synthesized through regioselective demethylation, etherification, amination, EDCl-mediated amide condensation and
- Li, Xue-Li,Liu, Man-Hui,Ran, Li-Qiong,Wang, Qiu-An
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- 5-Demethylnobiletin and 5-Acetoxy-6,7,8,3′,4′-pentamethoxyflavone Suppress Lipid Accumulation by Activating the LKB1-AMPK Pathway in 3T3-L1 Preadipocytes and High Fat Diet-Fed C57BL/6 Mice
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Polymethoxyflavones (PMFs) and hydroxylated polymethoxyflavones (HPMFs), such as nobiletin (Nob) and 5-demethylnobiletin (5-OH-Nob), are unique flavonoids that are found exclusively in citrus peels. Nobiletin has been shown to suppress adipogenesis in vit
- Tung, Yen-Chen,Li, Shiming,Huang, Qingrong,Hung, Wei-Lun,Ho, Chi-Tang,Wei, Guor-Jien,Pan, Min-Hsiung
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Read Online
- Synthesis of Polymethoxyflavonoids from Hesperidin and Naringin and their Antiproliferative Activity
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[Figure not available: see fulltext.] A series of polymethoxyflavonoids were synthesized via cleavage of the glycosidic bond, dehydrogenation, selective methylation, bromination, nucleophilic aromatic substitution, O-prenylation, Claisen–Schmidt aldol condensation, cyclization, and oxidation from very abundant and inexpensive natural flavonoids hesperidin and naringin. The in vitro antiproliferative activity of the synthesized compounds was evaluated against a panel of four human cancer cell lines (Aspc-1, HCT-116, HepG-2, and SUN-5) by the CellTiter-Glo assay. The results showed that some of synthesized compounds exhibited moderate to high antiproliferative activity. Among them, (2E)-1-(2-hydroxy-3,4,5,6-tetramethoxyphenyl)-3-(7-methoxy-1,3-benzodioxol-5-yl)prop-2-en-1-one was revealed to be the most active with IC50 values ranging from 10.35 to 13.89 μM against all four cancer cell lines, the IC50 value (10.35 μM) being below positive control cisplatin (12.36 μM) against HepG-2 cells.
- Su, Liang,Jin, Zhizhong,Liu, Kexiong,Wang, Qiuan
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p. 100 - 105
(2022/03/27)
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- Hydroxylated polymethoxylated flavone and preparation method thereof
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The invention provides hydroxylated polymethoxylated flavone and a preparation method thereof. The chemical structure of a compound is shown as a formula (I). The method comprises the following steps: synthesizing an intermediate product 2a by using an in
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Paragraph 0030-0036
(2021/05/26)
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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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- Concise synthesis of polymethoxyflavone sudachitin and its derivatives, and biological evaluations
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We accomplished a divergent synthesis of sudachitin (2), a polymethoxyflavone isolated from citrus fruits, and six derivatives from acetophenone 9, which was an intermediate in our previous synthesis of nobiletin (1). Compound 2 enhanced glucose-induced i
- Sagara, Hiroto,Kanakogi, Masaki,Tara, Yuki,Ouchi, Hitoshi,Kimura, Junko,Kaneko, Yukiko,Inai, Makoto,Asakawa, Tomohiro,Ishikawa, Tomohisa,Kan, Toshiyuki
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p. 1816 - 1818
(2018/04/11)
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- 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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- Method of preparing demethylation form of polymethoxylated flavone from citrus skin
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The present invention provides a method of using citrus skin to prepare demethylation form of polymethoxylated flavone, comprising steps of acid treatment, heating, cooling, neutralization and extraction, and using microwave heating and high temperature/p
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Paragraph 0018; 0019
(2017/01/26)
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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; 0236
(2015/07/22)
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- Synthetic studies of fisetin, myricetin and nobiletin analogs and related probe molecules
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We synthesized a series of analogs of fisetin, myricetin and nobiletin, as well as related fluorescein- and biotin-based flavone-probe molecules, on a suitable scale for biological and structure-activity relationship studies.
- Hiza, Aiki,Tsukaguchi, Yuta,Ogawa, Takahiro,Inai, Makoto,Asakawa, Tomohiro,Hamashima, Yoshitaka,Kan, Toshiyuki
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p. 1371 - 1396
(2016/10/12)
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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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- 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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p. 2868 - 2870
(2011/04/22)
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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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- PROCESS TO PREPARE FLAVONES
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The present invention relates to the field of flavor ingredients. More particularly it provides, a process for making 5- hydroxy -polyitιethoxy-f lavones (5-OH-PMF) (I) or improving the organoleptic properties of natural polymethoxy-f lavones (PMF) . The invention's process comprises treating flavones (II) in the presence of a HCl solution in a non-acidic and non -aqueous solvent. (I) (II).
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Page/Page column 6-8
(2008/06/13)
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- HYDROXYLATED POLYMETHOXYFLAVONE COMPOSITIONS
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Provided herein are compositions enriched in polyhydroxylated polymethoxyflavones useful as dietary supplements, food additives, pharmaceutical compositions, nutraceutical compositions and cosmetic compositions.
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Page/Page column 41
(2008/06/13)
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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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