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. 2010 Apr 29;15(5):3135–3170. doi: 10.3390/molecules15053135

Table 1.

Major phenolics reported from Artemisia annua and the general structure of flavonoids. The number refers to the number given to each compound in Figure 2. Compounds with a 3-OH group attached to the 2,3-double bond, and adjacent to the 4-carbonyl group in the C ring are predicted to have major antioxidant activity [29]. Substituents (R) are numbered according to the ring position (A, C, and B).

graphic file with name molecules-15-03135-i001.jpg

Structure Phenolic type Ring and substituent position
No. Flavones C(R3) A(R5) A(R6) A(R7) A(R8) B(R2’) B(R3’) B(R4’) B(R5’) B(R6’)
7 Apigenin H OH H OH H H H OH H H
8 Luteolin (5,7,3’,4’-Tetrahydroxy flavone) H OH H OH H H OH OH H H
9 Luteolin-7-methylether H OH H OCH3 H H OH OH H H
10 Acacetin (apigenin-4’-methyl ether) or 5,7-dihydroxy-4-methoxy flavone H OH H OH H H H OCH3 H H
11 Chrysoeriol (Lutoelin-3’-methyl ether) or5,7,4’-Trihydroxy-3’-methoxy flavone H OH H OH H H OCH3 OH H H
12 Chrysin (5,7-Dihydroxy flavone) H OH H OH H H H H H H
13 Cirsilineol (6-Hydroxyluteolin-6,7,3’-trimethyl ether or 5,4’-dihydroxy-6,7,3’-trimethoxyflavone, Fastigenin, Anisomelin, Eupatrin) H OH OCH3 OCH3 H OH OCH3 OH H H
15 Cynaroside (Luteolin-7-glucoside or 5,7,3’,4’-Tetrahydroxyflavone-7-glucoside or Glucoluteolin or Luteoloside or Cinaroside) H OH H OGlu H H OH OH H H
16 Eupatorin (6-Hydroxyluteolin-6,7,4’-trimethyl ether or 5,3’-Dihydroxy-6,7,4’-trimethoxyflavone) H OH OCH3 OCH3 H H OH OCH3 H H
17 Cirsimaritin (Scutellarin-6,7-dimethyl ether or 6-Hydroxyapigenin-6,7-dimethyl ether or 5,4’-Dihydroxy-6,7-Dimethoxyflavone or Scorphulein or Cirsumaritin or Cirsitakaogenin) H OH OCH3 OCH3 H H H OH H H
18 Artemetin OCH3 OH OCH3 OCH3 H H OCH3 OCH3 H H
19 Chrysosplenol-C OCH3 OH OH OCH3 H H OCH3 OH H H
20 Chrysosplenol-D OCH3 OH OCH3 OCH3 H H OH OH H H
21 Mikanin OH OH OCH3 OCH3 H H H OCH3 H H
22 Astragalin (Kaempferol-3-α-D-glucoside) O-glu OH H OH H H H OH H H
23 Axillarin (5,7,3’,4’-Tetrahydroxy-3,6-dimethoxyflavone or quercetagetin -3,6- dimethyl ether) OCH3 OH OCH3 OH H H OH OH H H
24 Casticin (5,3’-dihydroxy-3,6,7,4’-tetramethyl ether flavone or Quercetagetin -3,6-7,4’-tetramethyl ether) OCH3 OH OCH3 OCH3 H H OH OCH3 H H
25 Eupatin (3,5,3’-Trihydroxy-6,7,4’-trimethoxyflavone or Quercetagetin -3,6- dimethyl ether) OH OH OCH3 OCH3 H H OH OCH3 H H
26 Kaempferol (3,5,7,4’-Tetrahydroxy flavone) OH OH H OH H H H OH H H
27 Kaempferol-6-methox-3-O-β-D-glucoside OGlu OH OCH3 OH H H H OH H H
28 Tamarixetin OH OH H OH H H OH OCH3 H H
29 Myricetin (3,5,7,3’,4’,5’-Hexahydroxy flavone) OH OH H OH H H OH OH OH H
30 Gossypetin- 3,8-dimethylether OCH3 OH H OH OH H OH OCH3 H H
31 Laricitrin (3,5,7,3’,4’, -Pentahydroxy 5’-methoxyflavone) OH OH H OH H H OH OH OCH3 H
32 Mearnsetin (3,5,7,3’,5’, -Pentahydroxy 4’-methoxyflavone or Myricetin-4-methyl ether) OH OH H OH H H OH OCH3 OH H
33 Quercetin (3,5,7,3’,4’-Pentahydroxy flavone) OH OH H OH H H OH OH H H
34 Quercetin-3’- O-β-D-glucoside OH OH H OH H H O-Glu OH H H
35 Quercetin-3- methylether OCH3 OH H OH H H OH OH H H
36 Quercimeritrin (Quercetin-7-glucoside) OH OH H O-Glu H H OH OH H H
37 Retusin (5-Hydroxy-3,7,3’4’-tetramethoxy flavone or Quercetin3,7,3’,4’-tetramethylether) OCH3 OH H OCH3 H H OCH3 OCH3 H H
38 Rhamnetin (Quercetin-7-methylether or 3,5,7,3’-Tetrahydroxy-4’-methoxy flavone) OH OH H OCH3 H H OH OH H H
39 Isorhamnetin (Quercetin-3’-methylether or 3,5,7,4’-Tetrahydroxy-3’-methoxy flavone) OH OH H OH H H OCH3 OH H H
40 Rutin (Quercetin-3-rutinoside) O-Diglyc. OH H OH H H OH OH H H
41 Mearncetin glucoside OH OH H OGlu H H OH OCH3 OH H
42 Chrysosplenetin (5,4’-Dihydroxy-3,6,7,3’-tetramethoxy flavone or Quercetagetin-3,6-7,3’-tetramethyl ether) OCH3 OH OCH3 OCH3 H H OCH3 OH H H
43 3,5-Dihydroxy-3’,4’,6,7,-Tetramethoxyflavone OH OH OCH3 OCH3 H H OCH3 OCH3 H H
44 Syringetin (Myricetin-3’,5’-dimethyl ether) OH OH H OH H H OCH3 OH OCH3 H
45 Isokaempferide (5,7,4’-Trihydroxy-3-methoxyflavone or Kaemferol-3-methyl ether) OCH3 OH H OH H H H OH H H
46 Quercetagetin 3,4’-dimethyl ether OCH3 OH OH OH H H OH OCH3 H H