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-alpha-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 microM) and COX-2 (IC50 = 1.53 microM), whereas the 7-methoxy isomer had no appreciable effect on COX-1 (IC50 >> 100 microM) but also abrogated the activity of COX-2 enzyme (IC50 = 14.42 microM).

Anti-inflammatory, Cyclooxygenase (COX)-2, COX-1 Inhibitory, and Free Radical Scavenging Effects ofRumex nepalensis

“…Emodin exhibited an anti-inflammatory effect by inhibiting the TPA-induced degradation of IkBα, the nuclear translocation of p65, and the NF-κB DNA-binding activity [26], and knipholone, a binary compound composed of anthraquinone chrysophanol and an acetylphloroglucinol, showed an anti-inflammatory effect by inhibiting leukotriene metabolism through selective inhibition of 5-LOX [27]. Naproxen [(S)-(+)-6methoxy-α-methyl-2-naphthaleneacetic acid] and its 7-methoxy isomer isolated from a natural source are reported to possess COX-1 and COX-2 inhibitory activity [28]. Emodin (3), endocrocin (6), and nepodin (7) were also evaluated for acute topical anti-inflammatory activity in TPA-induced inflammation in the mouse ear; they exhibited a 65.3 %, 57.7 %, and 43.2 % reduction in ear edema, respectively (l " Table 1).…”

A Review of Malaysian Medicinal Plants with Potential Anti-Inflammatory Activity

“…Interestingly, some of them exerted significant inhibition on inflammation. In 2000, Abad et al [ 93 ] evaluated the common anti-inflammatory drug naproxene isolated from Musa acuminate (pisang abu nipah) which exhibited good inhibition in COX-1 and COX-2 activities. Besides, in Carica papaya leaves, coumarin was isolated and exerted anti-inflammatory activity by suppressing the cytokine TNF- α production [ 94 , 95 ].…”

In vitro functional properties of crude extracts and isolated compounds from banana pseudostem and rhizome

“…Few reports using crude extracts of aerial parts of banana showed the antimicrobial, antidiabetic, antihypertensive, wound healing, antimalarial and anti‐snake venom activity . Very few reports have implicated sterylacylglucosides, naphthaleneacetic acid and methylisochroman derivative compounds as anti‐ulcerogenic, anti‐inflammatory and antihypertensive, respectively . We have also previously reported the antioxidant activity of polyphenols from pseudostem and rhizome of different banana cultivars and nutraceutical beverage from pseudostem and rhizome juice .…”