- Modified syntheses of the dietary flavonoid luteolin
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Two novel syntheses of the flavone luteolin are described. In the first, 3,5-dimethoxyphenol was converted to 2-hydroxy-4,6-dimethoxyacetophenone and then by condensation with 3,4-dimethoxybenzaldehyde to 2'-hydroxy-3,4,4',6'-tetramethoxychalcone. In the second, the chalcone step was prepared in which 3,5-dimethoxyphenol was acylated with 3,4-dimethoxycinnamoyl chloride. The chalcone was then cyclised with iodine and demethylated with pyridine hydrochloride to form luteolin in 47% and 40% overall yield, respectively. Several disadvantages of previous syntheses like long reaction time, harsh reaction conditions and low overall yield have been overcome.
- Wang, Qian,Zhang, Ji,Liu, Man,Yang, Jian,Zhang, Xiang-Ming,Zhou, Lei,Cao, Lang,Liao, Xia-Li
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- Synthesis of chlorinated flavonoids with anti-inflammatory and pro-apoptotic activities in human neutrophils
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Neutrophils are considered the central cells of acute inflammation. Flavonoids have been suggested as therapeutic agents to avoid damages induced by inflammatory processes. It is well known the reactivity of flavonoids with hypochlorous acid produced by neutrophils, to form stable mono and dichlorinated products. In this study, we synthesized novel chlorinated flavonoids and investigated their effect in neutrophils' oxidative burst and in its lifespan, in comparison with the parent non-chlorinated flavonoids. The obtained results demonstrate that chlorinated flavonoids were more efficient than their parent compounds in modulating neutrophils' oxidative burst in phorbol myristate acetate-activated neutrophils. Some of the tested flavonoids drive neutrophil apoptosis in a caspase 3-dependent fashion. The present data showed that 8-chloro-3′,4′,5,7-tetrahydroxyflavone (4a) constitute an alternative anti-inflammatory therapy, due to the proven ability to suppress mechanisms engaged at the onset and progression of inflammation.
- Freitas, Marisa,Ribeiro, Daniela,Tomé, Sara M.,Silva, Artur M.S.,Fernandes, Eduarda
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- Identification of methoxylchalcones produced in response to CuCl2 treatment and pathogen infection in barley
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Changes in specialized metabolites were analyzed in barley (Hordeum vulgare) leaves treated with CuCl2 solution as an elicitor. LC-MS analysis of the CuCl2-treated leaves showed the induced accumulation of three compounds. Among them
- Ube, Naoki,Katsuyama, Yuhka,Kariya, Keisuke,Tebayashi, Shin-ichi,Sue, Masayuki,Tohnooka, Takuji,Ueno, Kotomi,Taketa, Shin,Ishihara, Atsushi
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- An improved synthesis of apigenin and luteolin
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Apigenin and luteolin are the antioxidant flavonoids found in foods such as parsley, artichoke, basil and celery. Both of these compounds have shown the ability to protect cells against cancer and also to inhibit DNA oxidative damage. These flavonoids are part of many nutraceutical formulations available in the market. There is a need for the development of cost effective methodologies to produce them in large quantities. The synthetic process developed for both these compounds is general and can be applied for other flavonoids also. An industrially applicable high pure product, cost effective synthesis and general synthetic method has been developed and presented.
- Rambabu,Kumari,Baby Ramana,Ramani,Subbaraju,Hari Babu
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- Anti‐melanogenic properties of velutin and its analogs?
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Velutin, one of the flavones contained in natural plants, has various beneficial activities, such as skin whitening, as well as anti‐inflammatory, anti‐allergic, antioxidant, and antimicrobial activities. However, the relationship between the structure of velutin and its anti‐melanogenesis activity is not yet investigated. In this study, we obtained 12 velutin derivatives substituted at C5, C7, C3′, and C4′ of the flavone backbone with hydrogen, hydroxyl, and methoxy functionalities by chemical synthesis, to perform SAR analysis of velutin structural analogues. The SAR study revealed that the substitution of functional groups at C5, C7, C3′, and C4′ of the flavone backbone affects biological activities related to melanin synthesis. The coexistence of hydroxyl and methoxy at the C5 and C7 position is essential for inhibiting tyrosinase activity. However, 1,2‐diol compounds substituted at C3′ and C4′ of flavone backbone induce apoptosis of melanoma cells. Further, substitution at C3′ and C4′ with methoxy or hydrogen is essential for inhibiting melanogenesis. Thus, this study would be helpful for the development of natural‐derived functional materials to regulate melanin synthesis.
- Choe, Jung-Won,Heo, Hee-Young,Jung, Se-Hui,Kim, Jaehyun,Lee, Kooyeon
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- Hydroxyaurone derivative as well as preparation method and application thereof
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The invention relates to a hydroxyaurone derivative as well as a preparation method and application thereof. A monomeric compound aurone separated from Kunlun chrysanthemum in Xinjiang is used as a mother nucleus compound, hydroxyl is introduced into auro
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Paragraph 0159; 0162
(2021/07/14)
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- Attrition-enhanced deracemization and absolute asymmetric synthesis of flavanones from prochiral precursors
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Seven racemic 5,7-dimethoxyflavanones afforded conglomerate crystals upon recrystallization from a solvent. Three methodologies were investigated to achieve asymmetric transformation based on dynamic crystallization of the chiral conglomerate system. The first was chiral symmetry breaking of racemic flavanones by attrition-enhanced deracemization. Continuous suspension of racemic flavanones in a small amount of propanol in the presence of a base (1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)) and glass beads promoted chiral symmetry breaking and converted the flavanones to crystals of (+)- or (-)-enantiomers with 78 to 99% ee. The second method involved cyclization of the intermediate aldol product to give optically active flavanone with 90% ee involving a reversible oxa-Michael addition reaction with attrition-enhanced deracemization. The third was a reaction starting from prochiral 2-hydroxy-4,6-dimethoxyacetophenone and 2-naphthaldehyde under basic conditions, which gave the corresponding flavanone in 89% ee.
- Kasashima, Yoshio,Mino, Takashi,Sakamoto, Masami,Shimizu, Waku,Uemura, Naohiro,Yoshida, Yasushi
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p. 5676 - 5681
(2020/10/13)
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- Design, synthesis and anti-inflammatory activity of dihydroflavonol derivatives
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Thirty dihydroflavonol derivatives (D1–D30) were designed and synthesized, meanwhile the synthesized compounds were characterized on the basis of spectroscopic analyzes. Their inhibitory activity against the pro-inflammatory inducible interleukin-1β (IL-1β), interleukin-6 (IL-6), and tumor necrosis factor-α (TNF-α) in lipopolysaccharide (LPS)-stimulated murine RAW 264.7 macrophages were evaluated and showed various efficiency. Compounds D1–D30 showed no toxic effects on RAW 264.7 cells at the concentration 20 μM; among them, compounds D9, D13, and D19 exhibited best anti-inflammatory activity through decreasing IL-1β, IL-6, and TNF-α. Furthermore, their structure–activity relationships were discussed preliminarily.
- Hu, Chunling,Zhou, Zongbao,Xiang, Yuanhang,Song, Xiaoying,Wang, Hong,Tao, Kaiqi,Ye, Xiaochuan
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p. 194 - 205
(2018/04/19)
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- Flavokawain derivative or pharmaceutically acceptable salt thereof having inhibitory activity on Hsp90 and medical use thereof
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The present invention relates to a flavokawain derivative or a pharmaceutically acceptable salt thereof having an activity for inhibiting Hsp90 and a medical use thereof wherein the flavokawain derivative comprises good effect of inhibiting Hsp90 and accordingly leads to decomposition of Hsp 90 client protein causing diseases related to cancer or neurodegenerative diseases by inhibiting Hsp90, thereby being used in drug medicine and healthy food products for preventing or treating Hsp 90 which is a mediated disease like diseases related to cancer or neurodegenerative diseases.COPYRIGHT KIPO 2015
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Paragraph 0088-0091
(2016/10/10)
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- Synthesis of flavokawain analogues and their anti-neoplastic effects on drug-resistant cancer cells through Hsp90 inhibition
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Hsp90 is an ubiquitous molecular chaperone protein, which plays an important role in regulating maturation and stabilization of many oncogenic proteins. Due to its potential to simultaneously disable multiple signaling pathways, Hsp90 represents great promise as a therapeutic target of cancer. In this study, we synthesized flavokawain analogues and evaluated their biological activities against drug-resistant cancer cells. The study indicated that compound 1i impaired the growth of gefitinib-resistant non-small cell lung cancer (H1975), down-regulated the expression of Hsp90 client proteins including EGFR, Her2, Met, Akt and Cdk4, and upregulated the expression of Hsp70. The result strongly suggested that compound 1i inhibited the proliferation of cancer cells through Hsp90 inhibition. Overall, compound 1i could serve as a potential lead compound to overcome the drug resistance in cancer chemotherapy.
- Seo, Young Ho,Park, Sun You
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p. 1154 - 1158
(2014/05/06)
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- Synthesis and anticholinesterase inhibitory activity of mannich base derivatives of flavonoids
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Hesperidin-derived 2'-hydroxy-3,4,4',6'-tetramethoxy-chalcone and 5-hydroxy-7,3',4'-trimethoxy-flavone underwent reaction with formaldehyde and a series of secondary amines producing 11 new Mannich base derivatives of flavonoids. The aminomethylation occurred preferentially at the C-3' position of the chalcone and at the C-6 position of flavone. These aminated derivatives of flavonoids were evaluated as inhibitors of acetylcholinesterase (AChE) and the results showed that two of them exhibited excellent AChE inhibitory activity.
- Duan, Keke,Liu, Haoran,Fan, Haoqun,Zhang, Jing,Wang, Qiuan
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p. 443 - 446
(2014/08/05)
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- Oxidative dimerisation of isoflavones: Synthesis of kudzuisoflavone a and related compounds
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Kudzuisoflavone-A was successfully synthesised via oxidative dimerisation of daidzein in the presence of cuprous chloride. Appropriately substituted isoflavones also undergo regioselective oxidative dimerisation when treated with thallium trifluoroacetate to give novel 6′,6′″-biisoflavones in good yield. A rationale for the regioselectivity is proposed.
- Deodhar, Mandar,Wood, Kasey,Black, David Stclair,Kumar, Naresh
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p. 1377 - 1383,7
(2020/09/02)
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- Isolation and synthesis of flavonols and comparison of their antioxidant activity
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Phytochemical investigation of the leaves of Astragalus beckari yielded four flavonol aglycones, namely kaempferol, quercetin, 5-deoxy kaempferol and fisitin. These isolated compounds were then synthesised in the laboratory using the Algar-Flyn-Oyamad reaction. Antioxidant activity of both the isolated and synthesised flavonoids was compared using the 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay method. The isolated flavonoids were found to be more active.
- Hasan, Aurangzeb,Sadiq,Abbas,Mughal,Khan, Khalid M.,Ali, Muhammad
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experimental part
p. 995 - 1003
(2010/09/05)
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- Structure - Activity relationship studies of chalcone leading to 3-hydroxy-4,3′,4′,5′-tetramethoxychalcone and its analogues as potent nuclear factor κB inhibitors and their anticancer activities
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Chalcone is a privileged structure, demonstrating promising anti-inflammatory and anticancer activities. One potential mechanism is to suppress nuclear factor kappa B (NF-κB) activation. The structures of chalcone-based NF-κB inhibitors vary significantly that there is minimum information about their structure-activity relationships (SAR). This study aims to establish SAR of chalcone-based compounds to NF-κB inhibition, to explore the feasibility of developing simple chalcone-based potent NF-κB inhibitors, and to evaluate their anticancer activities. Three series of chalcones were synthesized in one to three steps with the key step being aldol condensation. These candidates demonstrated a wide range of NF-κB inhibitory activities, some of low micromolar potency, establishing that structural complexity is not required for NF-κB inhibition. Lead compounds also demonstrate potent cytotoxicity against lung cancer cells. Their cytotoxicities correlate moderately well with their NF-κB inhibitory activities, suggesting that suppressing NF-κB activation is likely responsible for at least some of the cytotoxicities. One lead compound effectively inhibits lung tumor growth with no signs of adverse side effects.
- Srinivasan, Balasubramanian,Johnson, Thomas E.,Lad, Rahul,Xing, Chengguo
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experimental part
p. 7228 - 7235
(2010/08/19)
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- Synthesis of a Typical Chalkone and a Flavanone of Wyethia glabra
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The constitution of a new chalkone as 2',4',6'-trihydroxy-4-methoxychalkone (1), isolated from Wyethia glabra has now been confirmed by its synthesis using 2'-hydroxy-4',6'-dibenzoyloxy-4-methoxychalkone (1a) as an essential intermediate.The structure of another compound as 5,3',4'-trihydroxy-7-methoxyflavanone (2) (eriodictyol-7-methyl ether) isolated from the same source, has also been confirmed by its synthesis using vanillin as the starting material.
- Babber, Sunanda,Chandra, S.,Aggarwal, Anil K.
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p. 797 - 798
(2007/10/02)
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