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The oxidized macrocyclic dimer eugeniflorin D 2 ( 86 , Lee et al. ,
1997) also deserves special mention, for it features a dehydrovaloneoyl
group. It was isolated from Eugenia uniflora together with eugeniflorin
D 1 , a regular macrocyclic dimer (see Chapter 1). Similarly, oenotherin T 1
( 87 ), isolated from Oenothera tetraptera , is a dehydro-derivative of
trimer oenothein A found in Oenothera erythrosepala and Oenothera
biennis (Yoshida et al. , 1991c). Interestingly, the cyclohexenetrione
moiety in 87 can be reduced to a valoneoyl group under mild conditions
to give oenothein A (Taniguchi et al. , 2002).
GO
GO
O
O
GO
GO
OG
OG
OH
GO
GO
OH
O
O
OH
OH
O
O
OH
OH
O
OH
HO
OH
O
HO
OH
HO
HO
OH
HO
OH
O
O
O
O
OG
O
O
OG
O
O
O
O
Euphorbin B ( 88 )
Euphorbin I ( 89 )
O
O
O
O
O
O
O
O
H
H
O
HO
OH
OH
O
HO
OH
OH
OH
OH
HO
O
HO
O
OH
G =
OH
R'O
OH
O
O
O
OH
RO
O
OH
GO
OH
O
OH
O
HO
OH
O
( S )-HHDP =
O
O
HO
OH
O
O
O
HO
OH
HO
OH
OG
HO
OH HO
OH
O
O
O
Euphorbin C ( 90 ): R,R' = ( S )-HHDP
Euphorbin D ( 91 ): R = R' = G
O
O
O
O
H
O
HO
OH
OH
OH
HO
O
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