Fig. 1 Structures of antioxidant flavonoids =R =R =MeO, R =OH 2 R ...

Fig. 1 Structures of antioxidant flavonoids
R 7
R 6
R 5 R 8
R 4 O
R 3
R 2
O
R 1
R 10
R 9
only non-H substituents(R) are indicated
1 R 1 =R 4 =R 8 =MeO, R 2 =OH
2 R 1 =R 8 =MeO, R 2 = R 4 =OH
3 R 2 =R 4 =R 8 =MeO, R 1 =OH
4 R 1 = R 2 =R 4 =R 8 =MeO
5 R 4 = R 8 =OMe, R 1 = R 2 =OH
6 R 2 =R 8 =OH,R 3 =R 4 =R 7 =MeO
7 R 2 =R 5 =R 8 =OH, R 3 =R 4 =R 7 =MeO
8 R 1 =R 4 =MeO, R 2 =R 5 =R 7 =R 8 =R 9 =OH
9 R 1 =R 2 =R 4 =R 8 = OH, R 6 =MeO
10 R 2 = R 4 =R 7 =R 8 = OH
11 R 2 =R 7 =R 8 = OH, R 4 = (β-D-Glc)O
12R 2 =R 4 =R 7 = OH, R 8 = (β-D-Glc)O
13 R 2 =R 7 =R 8 = OH, R 4 = (Rut)O
14 R 2 =R 4 =R 8 = OH, R 7 = (β-D-Glc)O
15 R 1 = (α-L-Rha)O, R 2 =R 4 =R 7 =R 8 = R 9 = OH
16 R 1 =R 2 = R 7 =R 8 = R 9 = OH, R 4 = [β-D-Glc-(16)-β-D-Glc]O
17 R 1 =R 2 = R 7 =R 8 = R 9 = OH, R 4 = [α-L-Rha-(16)-β-D-Glc]O
OH
RO
O
OH O
18 R= β-D-glucopyranosyl
1

R 5 R 6
R 4 O
R 3
R 2
O
R 1
only non-H substituents (R) are indicated
19 R 1 =R 2 =R 4 =R 5 =R 6 =OH
20 R 1 = R 2 =R 6 =OH, R 4 =R 5 =OMe
21 R 1 = R 2 =R 5 =R 6 =OH, R 4 =OMe
22 R 2 =R 4 =R 5 =R 6 =OH
23 R 1 = [α-L-(5''-O-galloyl)Ara(furanose)]O, R 2 =R 4 =R 5 =R 6 =OH
24 R 1 = R 6 = (β-D-Glc)O, R 4 = (α-L-Rha)O, R 2 =R 5 =OH
25 R 1 = (β-D-Glc)O, R 2 =R 4 =R 5 =R 6 =OH
26 R 1 = (α-L-Rha)O, R 2 =R 4 =R 5 =R 6 =OH
27 R 1 = (β-D-Galac)O, R 2 =R 4 =R 5 =R 6 =OH
28 R 1 =[(6''-O-malonyl)Glc]O, R 2 =R 4 =R 5 =R 6 =OH
29 R 1 =[(6''-O-malonyl)Galac]O, R 2 =R 4 =R 5 =R 6 =OH
30 R 1 =(β-D-Glc)O, R 2 = MeO, R 4 =R 5 =R 6 =OH
31 R 1 = (Rut)O, R 2 =R 4 =R 5 =R 6 =OH
32 R 1 =R 2 =R 3 =R 5 =R 6 =OH, R 4 = (β-D-Glc)O
33 R 1 =R 2 =R 3 =R 5 =R 6 =OH, R 4 = [(6''-O-acetyl)Glc]O
34 R 1 =(α-L-Rha)O, R 2 =R 4 =R 5 =R 6 =OH
35 R 1 = [(6''-O-p-coumaroyl)-β-D-Glc-(12)-α-L-Rha]O, R 2 =R 4 = R 6 =OH, R 5 = MeO
36 R 1 =(β-D-Glc)O, R 2 =R 4 =R 5 =R 6 =OH
37 R 1 =R 2 = R 4 =R 5 =R 6 =OH, R 3 = MeO
38 R 1 =R 2 = R 5 =R 6 =OH, R 3 = MeO, R 4 = (β-D-Glc)O
39 R 1 =R 2 = R 5 =R 6 =OH, R 3 = MeO, R 4 = [(6''-isovaleryl)β-D-Glc)]O
40 R 1 =R 2 = R 5 =R 6 =OH, R 3 = MeO, R 4 = [(6''-isobutyryl)β-D-Glc)]O
41 R 1 =R 2 = R 5 =R 6 =OH, R 3 = MeO, R 4 = [{6''- (2-methylbutyryl)}β-D-Glc)]O
42 R 2 = R 5 =R 6 =OH, R 3 = Me, R 4 = (β-D-Glc)O
43 R 1 =R 2 = MeO, R 2 =R 4 = R 5 =R 6 =OH
44 R 1 =R 2 =R 4 =R 6 =OH
45 R 1 = [(6''-O-Z-p-coumaroyl)-β-D-Glc]O, R 2 =R 4 =R 6 =OH
46 R 1 = R 4 =(α-L-Rha)O, R 2 =R 6 =OH
47 R 1 =R 2 =R 3 =R 6 =OH, R 4 = (β-D-Glc)O
48 R 1 =R 2 =R 3 =R 6 =OH, R 4 = [(6''-O-acetyl)Glc]O
49 R 1 = (β-D-Glc)O, R 2 = R 4 =R 6 =OH, R 3 = MeO
50 R 1 = (α-L-Rha)O, R 2 = R 4 =R 6 =OH
51 R 1 = [(6''-O-p-coumaroyl)-β-D-Glc-(12)-α-L-Rha]O, R 2 = R 6 =OH, R 4 = (β-D-Glc)O
2

52 R 1 = [α-L-Rha-(16)-β-D-Glc-(12)-β-D-Glc]O, R 2 =R 4 =R 6 =OH
53 R 1 = [β-D-Glc-(16)-β-D-Glc]O, R 2 = (α-L-Rha)O, R 4 =R 6 =OH
54 R 1 =[{2''-O-(E-6''-O-feruloyl)-β-D-Glc}-β-D- Glac]O
55 R 1 =R 2 =R 6 =OH, R 4 = (α-L-Rha)O
56 R 1 = (α-L-Rha)O, R 2 =R 6 =OH, R 4 = (β-D-Glc)O
57 R 1 = (α-L-Rha)O, R 2 =R 4 =R 6 =OH
O
R 3 R 2
R 4
R 1
O
58 R 1 =R 3 =R 4 =OH (Genistein)
59 R 1 =R 3 =R 4 =OH, R 2 = MeO (Tectorigenin)
R 4 OH
R 3 O
R 1
R 5
HO
O
R 2
OH
60 R 1 =[α-L-Rha]O, R 2 =R 3 = MeO, R 4 =R 5 =H
61R 1 =[(α-D-galac)Cello]O, R 2 =R 4 = MeO, R 5 =OH
OH O
62 Pinocembrin
OH
OH
HO
O
OH
OH
OH
O
63
3

OH
O
OMe
HO
O
O
CH 2 OH
OH
HO
O
64
OH
HOH 2
C
OMe
O
HO
O
OH
HO
O
65
OH
HO
O
OMe
OR
HO
O
66 R= α-L-Rha(1-->6)-β-D-Glc
4

OH
HO
O
OH
HO
O
HO
O
HO
O
Me
67
OH
HO
O
68
OH
R 2 O
O
OH
OH
HO
O
OH
OH
OR 1
HO
HO
72
69R 1 =R 2 =H
70 R=H, R 2 =[β-D- Xylo]O, R=H
71 R=H, R 2 =[β-D- Apiofurano]O
5

MeO
O O O
MeO
O
HO
OH
OMe
73
HO
O
O
O
O
OH
74
O
OH
75
O
OH
MeO
MeO
HO
+
O
R 1 OH
OH
OH
MeO
OH
76
O
O
R 2
77 R 1 =[(Xylo)galac]O, R 2 =[acetyl Glc]O
78R 1 =[(Xylo)galac]O, R 2 = [β-D-Glc]O
OH
HO
+
O
OH
OR
HO
79 R= [(Glc) Rutin]O
80 R= [Rutin]O
6

OH
OH
HO
OH
O
OH
O
HO
OH
O
OH
O
O
OH
O
OH
OH
HO
OH
HO
OH
O
OH
81
OH
OH
82
R 1 R 2 R 3
O
83 R 1 =R 2 =OH,R 3 =prenyl,R 4 =[β-D-Glc]O
84 R 1 =R 2 =R 3 =OH, R 4 =[β-D-(2''-O-acetyl-6''-cinnamoyl)-Glc]O
85 R 1 =R 2 =R 3 =OH, R 4 =[β-D-(2''-p-Coumaroyl)-Glc]O
86 R 1 =R 2 =R 3 =OH, R 4 =[β-D-(2''-p-Coumaroyl-6''-O-acetyl)-Glc]O
R 4
O
R 2
R 1 R 4
R 3
HO
87 R 1 =R 2 =R 3 =R 4 = OH
88 R 1 =R 3 =R 4 = OH, R 2 = [β-D-Glc]O
89 R 1 =R 3 =R 4 = OH, R 2 = [6''-O-acetyl-β-D-Glc]O
90 R 1 =R 4 = OH, R 3 = MeO, R 2 = [β-D-Glc]O
HO
91
O
O
7

HO
OH
HO
O
RO
O
MeO
HO O
92 R=α-L-Rha
OH
HO
93
O
OH
OH
OH
OH
HO
O
HO
O
Glc
Glc
HO
O
HO
O
94
95
Me
OMe
R
O
Me
HO
O
96 R=OH
97 R=[apfu(1--> 6)-β-D-Glc]O
8

Fig. 2 Structures of antioxidant xanthonoids
O
OH
O
OH
MeO
O
O
HO
O
OMe
OH
98
O
OH
OH
99
O
OH
O
O
OMe
OH 100
HO
OH
O
101
OH
O
OH
MeO
HO
O
102
OH
O
OH
H
HO
O
OH
R
R
OH
O
103 R= H
104 R= OH
H
OH
HO
O
OH
105 R= (2'-O-trans-caffeoyl)-β-D-Glc*
106 R= (2'-O-trans-cinnamoyl)-β-D-Glc*
107 R= (2'-O-trans-coumaroyl)-β-D-Glc*
108 R= (2'-O-benzoyl)-β-D-Glc*
109 R= (2'-O-p-hydroxybenzoyl)-β-D-Glc*
O
OH
OH
O
OH
O
R
HO
R
HO
O
OMe
O
HO
O
OMe
110 R= β-D-Glc*
OH
111
OMe
112 R= (Prim)O
9

Fig. 3 Structures of antioxidant terpenoids
OH
H 3
C
H
AcO
C
H
CH 3
OAc
OAc
CH 3
H
OAc
O
O
H
H
OAc
114
OAc
H 3
Taxusin (113)
H
COOH
GluO
RO
H
H
C 6
H 5
COO
115 R = feruloyl
116 R = E-caffeoyl (117)
O OCOC 6
H 5
O
H
H
H
H
H
RO
H
(119)
HO
H
H
(118)
R = Me(CH 2
) 4
CH=CHCH 2
CH=CH(CH 2
) 7
C
O
10

OH
HO
O
OR 2
S 1 =
R
H
1 O
120 R 1 = S 1
, R 2 =S 2
(Modhucoside A)
H
HO
122 OH 121 R 1 = S 1 , R 2 =S 3 (Modhucoside B)
HO
HO
O
O
OH
OH
OH
O
OH
O
O
HO
HO
O
O
HO
S 2 = S 3 =
CH
O
CH 3
3
O
OH
OH
OH O OH
O
O
O
OH OH
OH
O
HO
O
HO
HO
O O
CH O
3
O
CH 3
O
OH OH OH
OH OH
O
OH OH
OH
HO
OH
HO
COOH
HO
Taraxerol (123)
HO
124
11

HO
H
COOMe
O
H
R
R=[β-D-(6'-O-galloyl)Glc]O
125
H
R
R=[β-D-(6'-O-galloyl)Glc]O
126
ROCH H
2
O-β-D-Glc
R= caffeoyl
127
OAc
H
H
OAc
OAc
O
128
H
H
H
COOH
COOH
RO
H
H
129
RO
H
H
130
H
O
COOH
R =
RO
H
H
OH
131 (trans-caffeoyl moiety)
OH
12

O
O
C
O
OH O-β-D-Glc
OH
132
OH
HO
H
COOH
H
COOH
HO
H
H
133
O
H
H
134
OH
HO
O
H CH 3
H
MeO
HOH 2 C
H
O
OH
O
O
135
O
136 137
13

Fig. 4 Structures of antioxidant alkaloids
O
C
OMe
MeO
O
HO
NH
HO
N
O
H
138
OMe
OH
Vitedoamine A (139)
HO
COOH
HO
N
H
N
OGlu
N
H
N
OGlu
MeO
O
RO
O
O
Cordifoline (140)
O
141a R=H (3,4-dehydro-strictosidinic acid)
141b R=Me(3,4-dehydro-strictosidine)
14

Fig. 5 Structures of antioxidant lignans
R 4
R 2
O
OMe
R 1 OH
O
R 3 142 R 1 =R 2 =OH, R 2 =R 4 =H
143 R 1 =R 2 =OH, R 2 = [β-D-Glc]O, R 4 =H
OMe
R 5
R 3
O
OMe
R 1 8
R 2
O
R 4
OMe
144 R 1 = R 2 = R 5 = H, R 3 = R 4 =OH
145 R 1 = R 5 = H, R 2 = R 3 = R 4 =OH
146 R 1 = R 5 = H, R 2 = R 3 = OH, R 4 = [β-D-Glc]O
147 R 1 = R 5 = H, R 2 = [β-D-Glc]O, R 3 = R 4 =OH
148 R 1 = R 2 = R 5 = H, R 3 = OH, R 4 = [β-D-Glc]O
O-β-D-Glc
OH
MeO
HO
O
149
OMe
15

OMe
O-β-D-Glc
O
O
H
H
O
150
O
H
O
R 3
O
O
R 4
H
H
R 1 HO
R 2
OH
R 1
R 2
151 R 1 =OMe,R 2 = [β-D-Glc]O, R 3 =OH, R 4
= OMe
152 R 1 = OMe, R 2 = [β-D-Glc]O, R 3 = OMe, R 4 = OH
153 R 1 = OMe, R 2 = OH, R 3 = OMe, R 4 =[β-D-Glc]O
154 R 1 = OMe, R 2 = [β-D-Glc]O, R 3 = OMe, R 4 =OMe
OMe
OH
155 R 1 = H, R 2 = OMe
156 R 1 = OMe, R 2 = H
O
MeO
O
MeO
H
HO
O
HO
R
OH
157
OMe
OH
158 R = H
159 R = OH
OMe
16

O
O
O
O
OH
160
OH
HO
O
OMe
MeO
OH
161
OH
O
O
H
O
HO
162
OH
MeO
β-D-Glc-O
HO
OH
O
MeO
HO
H
OH
OH
163
OH
OMe
164
OH
OMe
17

18
165
OH
OH
OMe
HO
MeO
OH
OH
OH
OMe
OMe
H
H
166
O
O
OH
167
O
O
H
H
O
O
O
O
168
O
O
H
H
O
O
O
169
O
O
O
O
HO
OH
OMe
MeO
OMe
OMe
(dl-pair)
170
171
O
O
OMe
OMe
O
O

Fig. 6 Structures of antioxidant miscellaneous compounds
CH 3
CH 2 OH
OH
O
CH 3
H
H 3
C
CH 3
H
H
H
O
O
CH 2
-CH 2
-CH-CH 2
-CH-(CH 2
) 13
-CH 3
H
172
OH
OH
H
OH
O
173
R 1 O
COOR
R 4 O
OR 2
OR 3
174 R 4 = caffeoyl, R=R 1 =R 2 =R 3 =H
175 R 4 = p-(O-galloyl)caffeoyl, R=Me, R 1 =R 2 =R 3 =H
176 R 4 = p-(O-galloyl)caffeoyl, R=R 1 =R 2 =R 3 =H
177 R 4 = caffeoyl, R= Me, R 1 =R 2 =R 3 =H
178 R 3 = galloyl, R=R 1 =R 2 =R 4 =H
179 R 2 = 3-methylcaffeoyl, R=R 1 =R 3 =R 4 =H
180 R 4 = caffeoyl, R 3 = Me, R=R 1 =R 2 =H
181 R 2 = caffeoyl, R 1 = Me, R=R 3 =R 4 =H
182 R=R 1 = Me, R 2 =R 4 = caffeoyl, R 3 =H
183 R 4 = methylcaffeoyl, R= n-butyl, R 1 =R 2 =R 3 =H
184 R 2 =R 4 = caffeoyl, R=R 1 =R 3 =H
185 R 3 = succinyl, R 2 =R 4 = caffeoyl, R=R 1 =H
19

OR 1
HO
OH
OR 1
HO
COOR
186 R=R 1 =H
187 R=H, R 1 =β-D-Glc
188 R=Me, R 1 =H
HO
H 3
C
RO
O
OH
O
O
O
OH
189
OH
O
OH
O
(R=β-D-apiose)
H
R 1 O
O H
OR 1 H
OR
H OR 1
190 R=R 1 =gallose
OH
COONa
OH
H OH
CH 2
Ph
191
O
O
OH
O
O
O
HO
OMe
HO
HO
192
O
O
COOR
OH
193 R=H
194 R=Me
195 R=Et
OH
20

HO CH 2
CH 2 OR
HO
196 R=sugar
OH
CH 2
CH2 CH CH (CH 2
CH
2
) 13
CH 3
OH
OH
197
R 2
R 1
N
R
198 R=-CH 2 CN,
199 R=-CH 2 CN, R 1 = H, R 2 =OH
200 R=-CH(Ph)CN, R 1 = H, R 2 =OH
201 R=R 2 =H, R 1 =COOH,
21

CH 2
OH
MeO
N
202
H
R 2 R 3
R 1 CH=CHCOCH 2
COCH=CH
R 4
203 R 1 =R 4 =OH, R 2 =R 3 =MeO
204 R 1 =R 4 =OH, R 2 =R 3 =H
205 R 1 =R 2 =R 3 =R 4 =MeO
206 R 1 =R 4 =OH, R 2 =R 3 =H
MeO
OMe
HO
CH=CHCOCH 2
COCH=CH
OH
207
OMe
OH
OMe
OH
MeO
R
CHO
208 R=Me
209 R=H
OMe
210
HO
211
22

R 4 R 5 R 6
CH 2
CH 2
R 3
R 2
R 1
212 R 1 =R 3 =R 5 =OH, R 2 =R 6 = i-pentenyl, R 4 =H
213 R 1 =R 3 =R 4 =R 5 =OH, R 6 = i-pentenyl,R 2 =H
214 R 1 =R 3 =R 4 =OH, R 5 =MeO,R 6 = i-pentenyl,R 2 =H
O
COO
OH
OH
HO
O
C 13
H 27
(n)
CHO
215
O
216
CHO
RO
OMe
217 R=H
218 R=Me
CHO
CHO
COOH
OH
219
OMe
OMe
220
OH
OH
221
23

HO
O
OH
OMe
OMe
OH
OH
O
222
223
CH 2
CH CH 2
HO
R 1 CH CH CH 2
OR
MeO
224 R=β-D-apfu(1-->6)-O-β-D-Glc , R 1 =H
225 R=β-D-apfu(1-->6)-O-β-D-Glc , R 1 =OMe
OH
Me
OMe
226
CH 2
CH
COOH
SHCH 2
CH(NH 2
)COOH
227
N
NH 2
H
228
OH
OMe
HO
OH
OH
CH(OH)(CH 2
) 3
CH 3
COOH
H
OH
MeO
CH 2
CH
CH 2
HO
H
229
CH 2
Cl
230
231
24

O
OR
HO
OH
HO
232 R=β-D-xyl
233 R=H
OH
O
HO
OH
HO
234
OH
OH
HO
OH
HO
R
235 R= [β-D-xyl]O
236 R= [β-D-Glc]O
OH
OCOCH=CH
OH
COOH
R 2
R 1
OH
237 R 1 =H, R 2 =OH
238 R 1 =OH, R 2 =H
OH
239
OH
OH
OH
CH 2
CH(OH)COOH
240
HO
OH
HO
R
R 1
241 R=[β-D-Glc(1->3)-β-D-xyl]O, R 1 =H
242 R=[β-D-apfu(1->6)-β-D-Glc]O, R 1 =H
243 R=H, R 1 =[β-D-Glc]O
244 R=H, R 1 =OH
245 R=[β-D-xyl]O, R 1 =OH
25

O-β-D-Glc
HO
OH
O
246
R 1
HO
R 4 O
H 3
C
HO
R 2 O
O
R 3 O
O
OH
O
OH
247 R 1 =R 2 =R 3 =H, R 4 =Rha
248 R 1 =R 3 =H, R 2 =caffeoyl, R 4 =Rha
249 R 1 =R 3 =R 4 =H, R 2 =coumaroyl
250 R 1 =R 2 =R 4 =H, R 3 =coumaroyl
251 R 1 =OH, R 2 =caffeoyl, R 3 =R 4 =H
252 R 1 =OH, R 2 =caffeoyl, R 3 =H, R 4 =Rha
253 R 1 =R 3 =H, R 2 =coumaroyl, R 4 =Rha
O
RO
HO
HO
OH
H 3
C
HO
HO
O
OH
O
O
RO
O
OH
255 R=H
256 R=Rha
O O
OH
254 R= coumaroyl
O
OH O
CH 3
H 3
C
OH
CH 3
OH
OH
RO
O
OH
257 R=H
258 R=Glc
O
MeO
NHCO
OH
HO
HO
NHCO
MeO
259
OGlc
260
26

MeO
HO
NHCO
261
OH
O
OH
O
OMe
CHO
CH 2
OH
OH
OH
O
O
262
O
O
263
OH
HOH 2
C
OH
O 264
O
265
HO R1 R 2 R 3
HO
O
HO
O
O
266 R 1 =H, R 2 =OH,R 3 =H
267 R 1 =OH, R 2 =OMe, R 3 =OH
OH
27

R 2
R 1 R
HO
3
OH
HO
O
HO
O
O
OH
HO
O
O
OH
OH
HO
OH
R 4
268 R 1 =H, R 2 =OH, R 3 =H,R 4 =H
269 R 1 =OH, R 2 =OMe, R 3 =OH, R 4 =H
270 R 1 =OH, R 2 =H, R 3 =OH, R 4 =OMe
HO
271
HO
OH
OH
HO
O
O
OH
HO
O
O
OH
272 HO RO
273 R= H
274 R=(6''-galloyl)-O-β-D-Glc
275 R=(4''-acetyl)-O-β-D-Xyl
HO
OH
RO
273 R= H
274 R=(6''-galloyl)-O-β-D-glucopyranosyl
275 R=(4''-acetyl)-O-β-D-xylopyranosyl
28

R 1 R 2
R 6 R
R 5 3
O
Me
R 1
H
R 4
non-hydrogen substituents (R) are indicated
278 R
R 2
(CH 2
) 12
CH 1 = MeO, R 3 =R 5 =OH
3
279 R 1 =R 3 = OH, R 5 =MeO
O
280 R 1 =R 3 =R 4 =R 6 =OH, R 2 =MeO
276 R 1 =AcO, R 2 = OH
277 R 1 = OH, R 2 =AcO
H
O
R2 O
R
R 3
1 O
R4
O
281 R 1 =R 2 =R 3 =R 4 =OH
282 R 1 =R 3 =MeO, R 2 =R 4 =OH
283 R 1 =R 3 =R 4 =MeO, R 2 =OH
284 R 1 =MeO, R 3 = [α-L-(3''-O-acetyl)Rha]O, R 2 =R 4 =OH
285 R 1 =MeO, R 3 = [α-L-(2''-O-acetyl)Rha]O, R 2 =R 4 =OH
286 R 1 =MeO, R 3 = [α-L-(4''-O-acetyl)Rha]O, R 2 =R 4 =OH
O
O
O
O
O
OH
OH
O
MeO
MeO
H
C CH 3
CH 3
OH
O
287
288
HO
OMe
289
29

OR 1 H
COOMe
H
O
ROH 2
C
H
OGlc
HO
-CH=CH-COOH
290 R=caffeoyl, R 1 = H
291 R= H, R 1 =Me
292 R=R 1 =H
HO
293
COOMe
HO
CH=CH-CHO
R
OH
HO
HO
294
295 R=H
296 R=OH
OH
HO
OH
O
O
297 298
COOR
OH
O
299
OH
O
300 R= H
301 R= β-D-Glc
30

OH
HO
OH
O
O
H
R
HO
OH
O
OH
H
R=[β-D-Glc]O
302
303
OR
O
H
HO
O H
OH
H
O
H
OH
304 R= feruloyl
OH
OH
OH
O
305
OH
MeO
HO
OH
O
O
R
O OH
306 R= OH
307 R= [β-D-(6'-O-galloyl)Glc]O 308
31

HO
OH
HO
O
R 2 R 3
O
O
H
R 1
O
O
309
O
310 R 1 =H, R 2 =R 3 =OH
311 R 1 =R 3 =OH, R 2 =OMe
O
OH
O
O
HO
OH
OH
OH
COOCH 2
CH 3
CH 2
COOH
312 313
HO
HO
OH
O
HO
O
O
O
O
OH
HO
OH OH
OH
H
COOH
314
R 1 R 2 R 3
O
H
O
H
H
OH
O
O
R 4 O
OH
OH
315 R 1 =H, R 2 =OH, R 3 =CH 3
, R 4 =trans-feruloyl
316 R 1 =OH, R 2 ,R 3 : =CH 2
, R 4 =trans-feruloyl
O
32

Abbreviations: Glc = glucopyranosyl (* denotes C-glycoside); Ara = arabinopyranosyl; Galac =
galactopyranosyl;Gent = gentiobiosyl; Prim = primverosyl; Rha = rhamnopyranosyl; Xyl =
xylopyranosyl; cell = cellobiosyl.
Systematic name: Primverosyl = (O-{[5-methoxy-2-(methoxycarbonyl)]phenyl}-β-Dglucopyranosyl)-(61)-xylopyranosyl;
Gentiobiosyl = 6-O-(β-D-glucopyranosyl)-β-Dglucopyranosyl;
Feruloyl= 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl; p-Coumaroyl= 3-(4-
hydroxyphenyl)prop-2-enoyl
Prenyl =
(3-methyl-but-2-enyl)
Isoprenyl =
(1,1-dimetylyallyl)
O
O
Cinnamoyl =
p-Coumaroyl =
OH
O
OH
O
OMe
trans-Caffeoyl =
OH
Feruloyl =
(E)/(Z)
OH
O
OH
Galloyl =
OH
OH
33