Major Constituents and Cytotoxic Effects of Ajuga chamaecistus ssp. tomentella

Abstract

The n-butanolic fraction of a methanolic extract (80%) from aerial parts of Ajuga chamaecistus ssp. tomentella was analysed using different chromatographic methods. Column (CC) and high-performance liquid chromatography (HPLC) were used for isolation and purifi cation. 13C, 1H NMR, H-H COSY, HSQC, HMBC, and ESI-MS were employed for identifi cation of the compounds isolated from this fraction. The structures of the compounds were determined to be cis-melilotoside (1), trans-melilotoside (2), lavandulifolioside (3), 20-hydroxyecdysone (4), leonoside B (5), martynoside (6), ajugalactone (7), makisterone A (8), and 24-dehydroprecyasterone (9). This is the fi rst report on the presence of cis- and transmelilotoside in Ajuga species. Cytotoxic evaluation of the n-butanolic fraction, cis- and transmelilotoside against cancer (T47D, HT-29, and Caco-2) and normal (NIH 3T3) cell lines by the mitochondrial tetrazolium test (MTT) showed no cytotoxic effects up to 400 μg/mL. The results of this study suggest that melilotoside, phenylethyl glycosides, and phytoecdysteroids are the main constituents of the n-butanolic fraction of Ajuga chamaecistus ssp. tomentella

Evaluation of in vitro antiprotozoal activity of Ajuga laxmannii and its secondary metabolites

“…The genus Ajuga has been reported to contain iridoids, phenylethanoid glycosides, flavonoids, anthocyanins and o-coumaric acid derivatives (De la Torre et al 1997;Takasaki et al 1998;Akbay et al 2002Akbay et al , 2003Sadati et al 2012;Inomata et al 2013). Among the isolated compounds in this study, harpagide or its acetyl derivative 8-O-acetylharpagide were also reported from other genera of Lamiaceae including Stachys (Calis et al 1992), Lamium (Alipieva et al 2003) and Galeopsis (Venditti et al 2013).…”

“…Among the isolates, cis-and transmellitoside (3 and 4) have previously been reported from only one Ajuga species, namely Ajuga chamaecistus ssp. tomentella (Sadati et al 2012). This is the second report of the presence of mellitoside from a member of the Ajuga genus.…”

“…Some of these species are consumed for the treatment of haemorrhoids and as a wound-healing agent in Anatolian folk medicine (Sezik et al 1992;Yesilada et al 1995). Previous phytochemical studies on Ajuga species have shown the presence of diterpenes, phytoecdysteroids, iridoids, sterol glycosides, flavonoids and phenylethanoid glycosides as the secondary metabolites of the genus (De la Torre et al 1997;Takasaki et al 1998;Akbay et al 2002Akbay et al , 2003Sadati et al 2012;Inomata et al 2013). There is only one report on A. laxmannii (L.) Bentham collected from Bulgaria stating the isolation of a diterpene, a coumarin, a phytoecdysteroid, two iridoid glycosides and an ocoumaric acid derivative (Malakov et al 1998).…”

Phytochemical studies of Melilotus officinalis

“…The glucose moiety, which can be assigned a β-configuration on the basis of the coupling constant of the anomeric proton at δ 5.05 (d, J = 7.2 Hz, 1H, H-1′) [33] is attached to the C-2 (δ 153.81) position. Based on the analysis of the spectroscopic data and literature data, it can be concluded that compound 1 is cis-coumaric acid-2-O-β-D-glucopyranoside (cis-melilotoside, Figure 2) [30,31]. This is the first report on the isolation of cis-melilotoside (1) from M. officinalis.…”

“…cis-Melilotoside has previously been reported from several other plants such as Ajuga chamaecistus ssp. Tomentella and Mikania laevigata [30,34]. Compound 2 was isolated from the MeOH extract of the seeds of M. officinalis as a white powder and has a melting point of 70-71 o C. The UV-Vis spectrum of 2 in MeOH revealed an absorption maximum (λ max ) at 274 and the IR spectrum in KBr showed absorption bands at 1729, 1288, 1124 cm -1 due to the presence of an aromatic ring and an α,β-unsaturated carbonyl carbon.…”