TABLE 1.

Core structures and names of flavonoid compounds used in this study

Thirty-seven flavonoid compounds from four different subclasses: flavones, flavanones, isoflavones, and chalcones were previously tested.

Compound	Number	Nomenclature	R1	R2	R3	Molecular Weight
Flavone	1	Flavone	H	H	H	222.24
	2	5-Hydroxyflavone	H	5-OH	H	238.24
	3	2′,3′-Dihydroxyflavone	H	H	2′,3′-Di-OH	254.24
	4	2′,3′-Dimethoxyflavone	H	H	2′,3′-Di-OCH3	282.29
	5	4′-Hydroxy-3′methoxyflavone	H	H	4′-OH-3′-OCH3	268.26
	6	3′,5-Dihydroxyflavone	H	5-OH	3′-OH	254.24
	7	4′-Hydroxy-5-methoxyflavone	H	5-OCH3	3′-OH	268.26
	8	5-Methoxyflavone	H	5-OCH3	H	252.26
	9	4′,5,7-Trimethoxyflavone	H	5,7-Di-OCH	4′-OCH3	312.32
	10	8-Carboxyl-3-methylflavone	CH3	8-COOH	H	280.27
	11	5,6-Benzoflavone	H	5,6-Benzo	H	272.3
	12	7,8-Benzoflavone	H	7,8-Benzo	H	272.3
	13	2′-Methoxy-ᾳ-naphthoflavone	H	7,8-Benzo	2′-OCH3	302.32
	14	3,3′,4′,5,7-Pentahydroxyflavone-8-O-glucoside (Gossypin)	OH	5,7-Di-OH-8-O-Glucoside	3′,4′-Di-OH	480.38
	15	3,4′,5,7-Tetrahydroxyflavone (Kaempferol)	OH	5,7-Di-OH	4′-OH	286.24
	16	5,7-Dihydroxyflavone (Luteolin)	H	5,7-Di-OH	H	286.24
	17	3,7-Dihydroxyflavone	H	3,7-Di-OH	H	254.24
Flavanone	18	4′,5,7′-Trihydroxyflavanone (Naringenin)	H	5,7-Di-OH	4′-OH	272.25
	19	5-Methoxyflavanone	H	5-OCH3	H	254.28
	20	5,7-Dimethoxyflavanone	H	5,7-OCH3	H	284.31
	21	3′,4′,5′,7-Tetramethoxyflavanone	H	7-OCH3	3′,4′,5′-Tri-OCH3	344.36
	22	Flavanone	H	H	H	224.08
	23	7-Hydroxyflavanone	H	7-OH	H	240.25
	24	4-Hydroxyflavanone	H	4-OH	H	254.24
Isoflavone	25	7-Methoxyisoflavone	H	7-OCH3	H	252.26
	26	4′,6,7-Trihydroxyisoflavone (Demethyltexasin)	H	6,7-OH	4′-OH	270.24
	27	4′-Hydroxy-6-methoxyisoflavone-7-D-guloside (Glycitin)	H	6-OCH3-7-D-Glucoside	4′-OH	446.4
	28	5,7,4′-Trihydroxyisoflavone (Genistein)	H	5,7-Di-OH	4′-OH	270.24
	29	5,7-Dihydroxy-4′-methoxyisoflavone(Biochanin A)	H	5,7-Di-OH	4′-OCH3	284.26
	30	5,7,3′,4′-Tetramethoxyisoflavone (Orobol)	H	5,7-Di-OCH3	3′,4′-Di-OCH3	342.34
Chalcone	31	2′,3′′,5′′-Trimethoxychalcone	—	2′-OCH3	3′′,5′′-Di-OCH3	298.33
	32	3′,3′′,5′′-Trimethoxychalcone	—	3′-OCH3	3′′,5′′-Di-OCH3	298.33
	33	3′,3′′,5′-Trimethoxychalcone	—	3′5′-Di-OCH3	3′′-OCH3	298.33
	34	2′′,3′,5′-Trimethoxychalcone	—	3′5′-Di-OCH3	2′OCH3	314.33
	35	3′,3′′,5′,5′′-Tetramethoxychalcone	—	3′5′-Di-OCH3	3′′,5′′-Di-OCH3	328.36
	36	2′-Hydroxy-4′,4′′-dimethoxychalcone	—	2′-OH-4′-OCH3	4′′-OCH3	284.31
	37	2′-Hydroxy-3′′,4′,5′′-trimethoxychalcone	—	2′-OH-4′-OCH3	3′′,5′′-Di-OCH3	298.33

^—, no chemical group considered.