Cyclooxygenase-2 Inhibitory 1,4-Naphthoquinones from Impatiens balsamina L.

Abstract

Significant selective cyclooxygenase-2 (COX-2) inhibitory activities were observed for two new 1,4-naphthoquinone sodium salts, sodium 3-hydroxide-2{[sodium 3-hydroxide-1,4-dioxo(2-naphthyl)]ethyl}naphthalene-1,4-dione (impatienolate) (1) and sodium 2-hydroxide-3-(2-hydroxyethyl)naphthalene-1,4-dione (balsaminolate) (2), which were isolated from the corolla of Impatiens balsamina L. (Balsaminaceae). Their structures were elucidated by spectral techniques. Our results offer evidence supporting the use of I. balsamina L. to treat articular rheumatism, pain, and swelling.

Validation of cyclooxygenase-2 as a direct anti-inflammatory target of 4-O-methylhonokiol in zymosan-induced animal models

“…The substrate arachidonic acid was then added, and the test tubes were incubated for 2 min at 37°C. The concentration of PGF 2a (final product) was measured using enzyme immunoassay (EIA) provided in the same kit, and was calculated from a standard curve (Oku and Ishiguro, 2002).…”

Antinociceptive activity of methanol extract of flowers of Impatiens balsamina

“…The potent antinociceptive effect of MIB in the acetic acid-induced model, therefore, suggests that MIB may be involved in the inhibition of COX, LOX and other inflammatory mediators resulting interrupted signal transduction in primary afferent nociceptors. The COX-2 inhibitory effect of 1,4-naphthoquinones isolated from I. balsamina has already been reported by Oku and Ishiguro (2002), that justifies the use of the corolla in articular rheumatism, pain, and swelling. Our findings also provide evidences supporting the use of I. balsamina in such painful and inflammatory conditions.…”

“…The aerial parts of the plant contain 2-methoxy-1, 4-naphthoquinone (Mori et al, 2011) and bisnaphthoquinone derivative called impatienol (Ishiguro et al, 2000). The flowers have been reported to contain flavonols (Clevenger, 1958), flavonoid pigments (Hargen, 1966), phenolic compounds (Bohm and Towers, 1962), lawsone methyl ether, a naphthoquinone (Little et al, 1948), kaempferol 3-rutinoside, 2-hydroxy 1,4-naphthoquinone Fukumoto et al, 1995), impatienolate, balsaminolate (Oku and Ishiguro, 2002), a flavonoid-3-b-D-glucosidase (Boylen et al, 1969), p-coumaric and ferulic acids (Mansell and Kemerer, 1970), kaempferol 3-[2 00 -rhamnosyl-3 00 -glucosyl] glucoside . Antimicrobial polypeptides (Thevissen et al, 2005), baccharane glycosides called hosenkosides, a viscous oil, alpha-amyrin, beta-sitosterol, alpha-spinasterol, balsaminasterol and an anthraquinone glycoside (Ghani, 2003) have been isolated from seeds (Shoji et al, 1994).…”

“…Pharmacological studies have proven the antianaphylactic (Ishiguro et al, 1992), antipruritic, and antidermatitic effect of petal extract, kaempferol 3-rutinoside and 2-hydroxy-1,4-naphthoquinone (lawsone) (Oku and Ishiguro, 2001) and antimicrobial activity (Sakunphueak and Panichayupakaranant, 2011) cyclooxygenase-2 inhibitory effect of isolated naphthoquinones (Oku and Ishiguro, 2002). Polypeptides isolated from seeds have been reported to possess antimicrobial activity (Thevissen et al, 2005).…”

Antioxidant, Antibacterial and Antifungal Activity of Impatiens sulcata Wallich in Roxb. Extracts

“…The secondary metabolites isolated from Impatiens species include phenolics, flavonols, anthocyanin pigments, quinones and saponins [2][3]. Impatiens species are reported to be useful as antifungal [4], antibacterial [5], anti-anaphylactic [6], anti-inflammatory [7], anti-pruritic/anti-dermatitis [8], anti-tumour [9], antibacterial [10], anti-helminthic [11] and anti-histaminic [12]. The present paper for first time reports the antioxidant potential and antimicrobial activity of Impatiens sulcata from the high altitude regions of North West (Garhwal) Himalayas, Uttarakhand, India.…”