Ursolic acid from Plantago major, a selective inhibitor of cyclooxygenase-2 catalyzed prostaglandin biosynthesis.

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Ringbom T, Segura L, Noreen Y, Perera P, Bohlin L

Ursolic acid from Plantago major, a selective inhibitor of cyclooxygenase-2 catalyzed prostaglandin biosynthesis.

J Nat Prod. 1998 Oct;61(10):1212-5.

PubMed ID
9784154 [ View in PubMed
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Abstract

A hexane extract of Plantago major was investigated by bioactivity-directed fractionation, using an in vitro cyclooxygenase-2 (COX-2) catalyzed prostaglandin biosynthesis inhibition assay, and resulted in the isolation of ursolic acid (1). This triterpenoid showed a significant COX-2 inhibitory effect, directly on the enzyme activity, with an IC50 value of 130 microM and a COX-2/COX-1 selectivity ratio of 0.6. The structural isomer oleanolic acid (2) was found to be less active than 1, with an IC50 value of 295 microM, but showed a similar selectivity ratio (0.8). Furthermore, no significant inhibition on COX-2 or COX-1 was observed by the triterpenoid, 18beta-glycyrrhetinic acid (3). The direct inhibitory effect of 1 and 2 on COX-2 catalyzed prostaglandin biosynthesis increased with preincubation, indicating a time-dependent inhibition, while the effect on COX-1 was found to be independent of preincubation time.

DrugBank Data that Cites this Article

Binding Properties
DrugTargetPropertyMeasurementpHTemperature (°C)
IbuprofenProstaglandin G/H synthase 1IC 50 (nM)18000N/AN/ADetails
IbuprofenProstaglandin G/H synthase 2IC 50 (nM)1030000N/AN/ADetails
IndomethacinProstaglandin G/H synthase 1IC 50 (nM)1400N/AN/ADetails
IndomethacinProstaglandin G/H synthase 2IC 50 (nM)165000N/AN/ADetails
NaproxenProstaglandin G/H synthase 1IC 50 (nM)11000N/AN/ADetails
NaproxenProstaglandin G/H synthase 2IC 50 (nM)1010000N/AN/ADetails