Polymethoxyflavones in Citrus Regulate Lipopolysaccharide-Induced Oscillating Decay of Circadian Rhythm Genes by Inhibiting Nlrp3 Expression

Table 1

The citrus flavonoids used in this study and their substituents. Numbered columns indicate the position number of the substituents.

Flavonoids	Chemical name	2 and 3	5	6	7	8	3	4
Nobiletin	5,6,7,8,3,4-Hexamethoxyflavone	Double	OCH3	OCH3	OCH3	OCH3	OCH3	OCH3
Sinensetin	5,6,7,3,4-Pentamethoxyflavone	Double	OCH3	OCH3	OCH3	H	OCH3	OCH3
Isosinensetin	5,7,8,3,4-Pentamethoxyflavone	Double	OCH3	H	OCH3	OCH3	OCH3	OCH3
Tangeretin	5,6,7,8,4-Pentamethoxyflavone	Double	OCH3	OCH3	OCH3	OCH3	H	OCH3
Gardenin B	5-Hydroxy-6,7,8,4-tetramethoxyflavone	Double	OH	OCH3	OCH3	OCH3	H	OCH3
5-Demethylnobiletin	5-Hydroxy-6,7,8,3,4-pentamethoxyflavone	Double	OH	OCH3	OCH3	OCH3	OCH3	OCH3
Hesperetin	5,7,3-Trihydroxy-4-methoxyflavanone	Single	OH	H	OH	H	OH	OCH3
Apigenin	5,7,4-Trihydroxyflavone	Double	OH	H	OH	H	H	OH
Naringenin	5,7,4-Trihydroxyflavanone	Single	OH	H	OH	H	H	OH
Diosmetin	5,7,3-Trihydroxy-4-methoxyflavone	Double	OH	H	OH	H	OH	OCH3
Isovitexin	5,7,4-Trihydroxyflavone-6-C-glucoside	Double	OH	Glu^1	OH	H	H	OH
Vitexin	5,7,4-Trihydroxyflavone-8-C-glucoside	Double	OH	H	OH	Glu	H	OH
Vicenin-2	5,7,4-Trihydroxyflavone-6,8-di-C-glucoside	Double	OH	Glu	OH	Glu	H	OH
Hesperidin	5,7,3-Trihydroxy-4-methoxyflavanone-7-O-rutinoside	Single	OH	H	O-Rut^2	H	OH	OCH3
Neohesperidin	5,7,3-Trihydroxy-4-methoxyflavanone-7-O-neohesperidoside	Single	OH	H	O-Nhp^3	H	OH	OCH3
Diosmin	5,7,3-Trihydroxy-4-methoxyflavone-7-O-rutinoside	Double	OH	H	O-Rut	H	OH	OCH3
Neodiosmin	5,7,3-Trihydroxy-4-methoxyflavone-7-O-neohesperidoside	Double	OH	H	O-Nhp	H	OH	OCH3
Didymin	5,7-Dihydroxy-4-methoxyflavanone-7-O-rutinoside	Single	OH	H	O-Rut	H	H	OCH3
Poncirin	5,7-Dihydroxy-4-methoxyflavanone-7-O-neohesperidoside	Single	OH	H	O-Nhp	H	H	OCH3
Narirutin	5,7,4-Trihydroxyflavanone-7-O-rutinoside	Single	OH	H	O-Rut	H	H	OH
Naringin	5,7,4-Trihydroxyflavanone-7-O-neohesperidoside	Single	OH	H	O-Nhp	H	H	OH
Isorhoifolin	5,7,4-Trimethoxyflavone-7-O-rutinoside	Double	OH	H	O-Rut	H	H	OH
Rhoifolin	5,7,4-Trihydroxyflavone-7-O-neohesperidoside	Double	OH	H	O-Nhp	H	H	OH
Eriocitrin	5,7,3,4-Tetrahydroxyflavanone-7-O-rutinoside	Single	OH	H	O-Rut	H	OH	OH
Neoeriocitrin	5,7,3,4-Tetrahydroxyflavanone-7-O-neohesperidoside	Single	OH	H	O-Nhp	H	OH	OH

¹Glu: glucoside; ²Rut: rutinoside; ³Nhp: neohesperidoside.