Isolation of (S)-(+)-Naproxene from Musa acuminata. Inhibitory Effect of Naproxene and its 7-Methoxy Isomer on Constitutive COX-1 and Inducible COX-2

Abstract

The isolation and characterisation of (S)-(+)-6-methoxy-α-methyl-2-naphthaleneacetic acid, a well known synthetic non-steroidal anti-inflammatory drug (naproxene), from a natural source is described for the first time. We evaluated the ability of naproxene and its 7-methoxy isomer to abrogate constitutive COX-1 and inducible COX-2 activity in human A549 cells. Naproxene inhibited COX-1 (IC₅₀ = 3.42 μM) and COX-2 (IC₅₀ = 1.53 μM), whereas the 7-methoxy isomer had no appreciable effect on COX-1 (IC₅₀ >> 100 μM) but also abrogated the activity of COX-2 enzyme (IC₅₀ = 14.42 μM).

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