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. 2020 Sep 29;7(10):63. doi: 10.3390/medicines7100063

Table 16.

Chemical structures of flavones isolated from Stachys spp.

graphic file with name medicines-07-00063-i001.jpg

Name R1 R2 R3 R4 R5 R6 R7
R=OH
Apigenin (1) H H OH H H OH H
Apigenin 7-O-β-D-glucoside (cosmoside) (2) H H O-glc H H OH H
Apigenin 7-O-[6′″-O-acetyl]-β-D-allosyl-(1→2)-β-D-glucoside (3) H H O-[6′″-acetyl-allosyl]-(1→2)-glc H H OH H
Apigenin 7-(3″-E-p-coumaroyl)-β-D-glucoside (4) H H O-(3″-E-p-coumaroyl)-glc H H OH H
Apigenin 7-(3″-Z-p-coumaroyl)-β-D-glucoside (5) H H O-(3″-Z-p-coumaroyl)-glc H H OH H
Apigenin 7-(6″-E-p-coumaroyl)-β-D-glucoside (6) H H O-(6″-E-p-coumaroyl)-glc H H OH H
Apigenin 7-(6″-Z-p-coumaroyl)-β-D-glucoside (7) H H O-(6″-Z-p-coumaroyl)-glc H H OH H
Apigenin 7-(3″,6″-p-dicoumaroyl)- β-D-glucoside (Anisofolin A) (8) H H O-(3″,6″-p-dicoumaroyl)-glc H H OH H
Apigenin 8-C-glucoside (9) H H OH C-glc H OH H
Apigenin 6,8-di-C-glucoside (Vicenin-2) (10) H C-glc OH C-glc H OH H
Isoscutellarein (11) H H OH OH H OH H
Isoscutellarein 7-O-glucoside (11a) H H O-glc OH H OH H
4′-Methyl-isoscutellarein (12) H H OH OH H OCH3 H
Isoscutellarein 7-O-allosyl-(1→2)-glucoside (13) H H O-allosyl-(1→2)- glc OH H OH H
3′-Hydroxy-isoscutellarein-7-O-[6′″-O-acetyl]-β-D-glucoside (14) H H O-[6′″-O-acetyl]- glc OH OH OH H
Isoscutellarein 7-O-[6′″-O-acetyl]-β-D-allosyl-(1→2)-β-D-glucoside (15) H H O-[6′″-O-acetyl]-allosyl-(1→2)-glc OH H OH H
Isoscutellarein 7-O-β-D-allosyl-(1→2)-[6″-O-acetyl]-β-D-glucoside (16) H H O-[6″-O-acetyl]-allosyl-(1→2)-glc OH H OH H
Isoscutellarein 7-O-[6′″-O-acetyl]-β-D-allosyl-(1→2)-[6″-O-acetyl]- β-D-glucoside (17) H H O-[6′″-O-acetyl]-allosyl-(1→2)-[6″-O-acetyl]-glc OH H OH H
Isoscutellarein 8-O-(6″-trans-p-coumaroyl)-β-D-glucoside (18) H H OH O-(6”-trans-p-coumaroyl)-glc H OH H
4′-Methyl-isoscutellarein 7-O-β-D-allosyl-(1→2)-β-D-glucoside (19) H H O-allosyl-(1→2)-glc OH H OCH3 H
4′-Methyl- isoscutellarein 7-O-β-D-allosyl-(1→2)-[6″-O-acetyl]-β-D-glucoside (20) H H O-allosyl-(1→2)-[6″-O-acetyl]-glc OH H OCH3 H
4′-Methyl-isoscutellarein 7-O-β-D-[6′″-O-acetyl]-allosyl-(1→2)-β-D-glucoside (21) H H O-[6′″-O-acetyl]-allosyl-(1→2)-glc OH H OCH3 H
4′-Methyl-isoscutellarein 7-O- [2″-O-acetyl]-β-D-allosyl-(1→2)-β-D-glucoside (22) H H O-[2″-O-acetyl]-allosyl-(1→2)-glc OH H OCH3 H
4′-Methyl-isoscutellarein 7-O-β-D-[4′′′-O-acetyl]-allosyl]-(1→2)-β-D-glucoside (annuoside) (23) H H O-[4′′′-O-acetyl]-allosyl-(1→2)-glc OH H OCH3 H
4′-Methyl-isoscutellarein 7-O-[6′′′-O-acetyl]-allosyl-(1→2)-[6″-O-acetyl]-glucoside (24) H H O-[6′′′-O-acetyl]-allosyl-(1→2)-[6″-O-acetyl]-glc OH H OCH3 H
Isostachyflaside (25) H H OH OH H O-mannosyl- (1→2)-glc H
Acetyl-isostachyflaside (26) H H OH OH H O-[acetyl]-mannosyl- (1→2)-glc H
Di-acetyl- isostachyflaside (27) H H OH OH H O-[diacetyl-mannosyl]- (1→2)-glc H
Spectabiflaside (28) H H O-mannosyl- (1→2)-glc OH OCH3 OH H
Scutellarein (29) H OH OH H H OH H
Scutellarein 7-O-β-D-glucoside[5,6, 4′-trihydroxyflavone-7-O-β-D-glucoside] (30) H OH O-glc H H OH H
Scutellarein 7-O-β-D-mannnosyl- (1→2)-β-D-glucoside (stachyflaside) (31) H OH O-mannosyl- (1→2)-glc H H OH H
7-O-β-D-glucopyranosyl-5,6-dihydroxy-4′-methoxyflavone (Stachannin A) (32) H OH O-glc H H OCH3 H
4′-Methoxy-scutellarein 7-[O-β-D-mannosyl-(1→2)-β-D-glucoside (Stachannoside B) (33) H OH O-mannosyl- (1→2)-glc H H OCH3 H
Luteolin (34) H H OH H OH OH H
Luteolin 7-methyl ether (35) H H OCH3 H OH OH H
Luteolin 7-O-β-D-glucuronide (36) H H O-glcA H OH OH H
Luteolin 7-O-β-D-glucoside (37) H H O-glc H OH OH H
Luteolin 6-C-glucoside (isoorientin) (38) H -C-glc OH H OH OH H
Luteolin 7-O-[6′′′-O-acetyl]-allosyl-(1→2)-glucoside (39) H H O-[6′′′-O-acetyl]-allosyl-(1→2)-glc H OH OH H
6,8 Di-C-β-D-glucopyranosyl luteolin (Lucenin-2) (40) H C-glc OH C-glc OH OH H
3′,4′-Dimethyl-luteolin-7-O-β-D-glucoside (41) H H O-glc H OCH3 OCH3 H
Chrysoeriol (42) H H OH H OCH3 OH H
Chrysoeriol 7-O-β-D-glucoside (43) H H O-glc H OCH3 OH H
Chrysoeriol 7-O-[6′′′-O-acetyl]-β-D-allosyl-(1→2)-glucoside (Stachyspinoside) (44) H H O-[6′′′-O-acetyl]- allosyl-(1→2)-glc H OCH3 OH H
Chrysoeriol 7-O-[6″-O-acetyl]-β-D-allosyl-(1→2)-glucoside (Isostachyspinoside) (45) H H O-[6″-O-acetyl]- allosyl-(1→2)-glc H OCH3 OH H
Chrysoeriol 7-(3″-E-p-coumaroyl)-β-D-glucoside (46) H H O-(3″-E-p-coumaroyl)-glc H OCH3 OH H
Chrysoeriol 7-(6″-E-p-coumaroyl)-β-D-glucoside (47) H H O-(6″-E-p-coumaroyl)-glc H OCH3 OH H
Hypolaetin (48) H H OH OH OH OH H
Hypolaetin-7-O-glucoside (49) H H O-glc OH OH OH H
Hypolaetin-7-O-glucuronide (49a) H H O-glcA OH OH OH H
Hypolaetin 7-O-allosyl-(1→2)-glucoside (50) H H O-allosyl-(1→2)-glc OH OH OH H
Hypolaetin 7-O-[6′′′-O-acetyl]-β-D-allosyl-(1→2)-β-D-glucoside (51) H H O-[6′′′-O-acetyl]- allosyl-(1→2)- glc OH OH OH H
Hypolaetin 7-O-[6″-O-acetyl]-allosyl-(1→2)glucoside (52) H H O-[6″-O-acetyl]- allossyl-(1→2)- glc OH OH OH H
Hypolaetin 7-O-[6′′′-O-acetyl]-allosyl-(1→2)-[6″-O-acetyl]-glucoside (53) H H O-[6′′′-O-acetyl]-allosyl-(1→2)-[6″-O-acetyl]- glc OH OH OH H
Hypolaetin 7-O-[6′′′-O-acetyl]-allosyl-(1→2)-[3″-O-acetyl]-glucoside (54) H H O-[6′′′-O-acetyl]-allosyl-(1→2)-[3″-O-acetyl]- glc OH OH OH H
4′-Methyl-hypolaetin-7-O-allosyl-(1→2)-glucoside (55) H H O-allosyl-(1→2)-glc OH OH OCH3 H
4′-Methyl-hypolaetin-7-O-[6′′′-O-acetyl]-β-D-allopyranosyl-(1→2)-β-D-glucopyranoside (56) H H O-[6′′′-O-acetyl]-allosyl-(1→2)- glc OH OH OCH3 H
4′-Methyl-hypolaetin-7-O-[6″-O-acetyl]-β-D-allopyranosyl-(1→2)-β-D-glucopyranoside (57) H H O-[6″-O-acetyl]-allosyl-(1→2)- glc OH OH OCH3 H
4′-Methyl-hypolaetin-7-O-[6′′′-O-acetyl]-allosyl-(1→2)-[6″-O-acetyl]-glucoside (58) H H O-[6′′′-O-acetyl]-allosyl-(1→2)-[6″-O-acetyl]- glc OH OH OCH3 H
Selgin 7-O-glucoside (59) H H O-glc H OCH3 OH OH
Tricin 7-O-glucuronide (60) H H O-glcA H OCH3 OH OCH3
Tricin 7-O-glucoside (61) H H O-glc H OCH3 OH OCH3
Tricetin 3′,4′,5′-trimethyl-7-O-glucoside (62) H H O-glc H OCH3 OCH3 OCH3
R= O-glcA-glc (2 → 1)
Palustrin (63) H OH OCH3 H H H H
R= O-glcA
Palustrinoside (64) H OH OCH3 H H H H

glc: glucose, glcA: glucuronide.