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OH
OR
1
O
R
2
O
H
3
CO
O
12
R
3
H
H
13
14
11
H
H
3
CO
H
3
CO
CH
3
H
3
CO
H
3
CO
CH
3
10
RO
9
CH
3
8
CH
3
H
3
CO
H
3
CO
CH
3
10a
R
H
6
5a
OH
H
H
5
7
1
2
CH
3
H
H
3
CO
O
4
R
3
OH
O
O
3
O
130
R=O-benzoyl, R
3
=H
131
R=O-angeloyl, R
3
=H
132
R=H, R
3
=H
142
R=H, R
3
=Br
133
R
1
+R
2
=CH
2
, R=benzoyl
134
R
1
+R
2
=CH
2
, R=angeloyl
135
R
1
=R
2
=CH
3
, R=benzoyl
136
O
angeloyl =
benzoyl =
O
O
OR
1
OCH
3
O
R
3
R
2
O
H
3
CO
R
3
OR
H
H
H
O
O
CH
3
H
3
CO
H
3
CO
CH
3
H
H
H
3
CO
H
3
CO
CH
3
OH
H
CH
3
CH
3
CH
3
O
R
3
H
3
CO
R
3
H
3
CO
R
2
O
O
OCH
3
OH
OR
1
137
R
1
+R
2
=CH
2
138
R
1
=R
2
=CH
3
143
R
1
+R
2
=CH
2
, R
3
=Br
144
R
1
=R
2
=CH
3
, R
3
=Br
139
R
1
+R
2
=CH
2
140
R
1
=R
2
=CH
3
145
R
1
+R
2
=CH
2
, R
3
=Br
146
R
1
=R
2
=CH
3
, R
3
=Br
141
R=angeloyl
Figure
9-8. Structures
of
dibenzocyclooctadiene
lignans
130-141
and
dibrominated
derivatives 142-146.
show anti-HIV activity; however, compounds with Bz at C-6b, 130, 133, and 135,
did exhibit anti-HIV activity with EC
50
values of 5.9, 0.96, and 0.011 mM. The most
potent compound, gomisin G (135), has S-biphenyl configuration and 6b-benzoyl-
7b-methyl-7a-hydroxy substitutions. In contrast, a 7b-hydroxy substituent (139 and
140) diminished the activity. Compounds 132, 136, 137, and 138 have different sub-
stituents on the aromatic rings, but no substituents on C-6. Although these four
compounds showed similar EC
50
values, 136 and 138, without a methylenedioxy
group, showed much lower IC
50
values than 132 and 137, which contain one or
more methylenedioxy groups on the aromatic rings. These results showed that a
C-6b benzoyl group, a C-7b hydroxy substituent, and methylenedioxy substitutions
on the aromatic rings are important for enhanced anti-HIV activity.
50
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