- 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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- 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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