Chemistry Reference
In-Depth Information
Scheme 6.19
Structure of dehydroabietic acid derivatives (
77
-
79
)
6.2.7 Other Activities
As natural products, rosin acids exhibit a wide range of other biological activities
which have not been mentioned above. The common diterpenoid abietic acid
(1)
was
found to be an inhibitor of soybean 5-lipoxygenase with an IC
50
value of 29.5±1.29
μM. Because of this result, it is considered that abietic acid may inhibit human
5-lipoxygenase and may potentially be used in the treatment of allergy, asthma,
arthritis and psoriasis [55]. Abietic acid
(1)
exhibited potent testosterone 5-alpha
reductase inhibitory activity with an IC
50
value of 56±22 μM. Methyl abietate was
substantially inactive against testosterone 5-alpha reductase, whereas other diterpene
resin acids, pimaric acid and neoabietic acid (
6
), were as active as abietic acid against
testosterone 5-alpha-reductase with IC
50
values of 750±120 μM and 120±50 μM,
respectively. This indicated that the negatively-charged anionic carboxyl group on the
molecule is an important structural moiety for the inhibitory activity. These findings
suggest that a nonsteroidal anionic diterpene compound of natural origin may have
the potential to act as a transition state analogue inhibitor of testosterone 5-alpha
reductase in the treatment of androgen-dependent diseases [56]. Dehydroabietic
acid (
2
) improves the levels of plasma glucose, plasma insulin, plasma triglyceride
TG, and hepatic TG by decreasing the macrophage infiltration into adipose tissues,
which suggests that dehydroabietic acid is a useful natural compound for treating
obesity-related diseases [57]. Mono-, di-, and linear triglycosides of a diterpene
alcohol, derived from abietic acid and glucose (
80
-
82
), have been synthesised
employing peracetylbromo-α-D-glucose and maltose derivatives as glycosyl donors.
The triglycoside (
82
) (
Scheme 6.20
) exhibits slight haemolytic activity [58].
