The genus Ammoides (Apiaceae) tribe of Ammineae includes two species in Algeria, one of which is endemic: Ammoides atlantica (Coss. et Dur.) Wolf; the other one, Ammoides pusilla (Brot.) Breistr, is widespread in the Mediterranean region. These species are used in folk medicine as antibacterial, anti-diarrhoea, anti-fever, antiinfluenza and to treat vitiligo in addition of their use as condiments (Bellakhdar J, 1997). Ammoides atlantica is biennal or perennial plant with thick stem fitted with a rosette of basal leaves. Slightly branched stems. Leaves Umbels 3-6 rays. Fruit 2-2.5 mm, it is found in lawns mountains above 1000 m (Quezel and Santa., 1962). In Algerian traditional medicine, the arial parts of Ammoides atlantica are reported to have a wide range of biological activities such as antibacterial, antioxidant, anthidiarrheic and diabetic activies (Ababsa et al., 2013; Laouer et al., 2003). Ammoides atlantica arial parts were subjected to extraction with solvents polarity increased, n-hexane, CHCl3, CHCl3- MeOH (9:1) and MeOH. The study of the extracts was carried out using different chromatographic techniques such as Silica gel, SephadexLH-20, MPLC, and rp-HPLC. Part of chloroform extract (4.5 g) was subjected to column chromatography using silica gel and eluting with CHCl3 followed by increasing concentrations of MeOH in CHCl3 (between 1% and 100%). Fractions of 50 ml were collected and analyzed by TLC. Preliminary study of CHCl3 extract led to isolation of some pure compounds whose structures were elucidated by 1D-and 2D-NMR Spectroscopy (1H, 13C, 13C DEPT, DQF-COSY, HSQC, HMBC, ROESY) and confirmed by mass spectrometry. Seven compounds from CHCl3 extract were isolated: one monoterpene chrysanthenone, two glicosides monoterpenes as l-borneol O-β-D-glucopyranoside (Asano et al., 1993) and (-)-cis-chrysanthenol-β-D-glucopyranoside (Miyakado et al., 1974), three guaianolides as 9α-Acetoxyartecanin, 3α-Chloro-9α-acetoxy-4β,10α-dihydroxy-1β,2β-epoxy-5α,7αH-guai-11(13)-en12,6α-olide and apressin (Trifunovic´ et al., 2006) and a new bisabolene sesquiterpene derivative 1,4-dihydroxybisabol-2,11- diene-10-one.

Sesquiterpenes and monoterpenes from Ammoides atlantica (Coss. Et Dur.) Wolf.

Vassallo A.;
2016

Abstract

The genus Ammoides (Apiaceae) tribe of Ammineae includes two species in Algeria, one of which is endemic: Ammoides atlantica (Coss. et Dur.) Wolf; the other one, Ammoides pusilla (Brot.) Breistr, is widespread in the Mediterranean region. These species are used in folk medicine as antibacterial, anti-diarrhoea, anti-fever, antiinfluenza and to treat vitiligo in addition of their use as condiments (Bellakhdar J, 1997). Ammoides atlantica is biennal or perennial plant with thick stem fitted with a rosette of basal leaves. Slightly branched stems. Leaves Umbels 3-6 rays. Fruit 2-2.5 mm, it is found in lawns mountains above 1000 m (Quezel and Santa., 1962). In Algerian traditional medicine, the arial parts of Ammoides atlantica are reported to have a wide range of biological activities such as antibacterial, antioxidant, anthidiarrheic and diabetic activies (Ababsa et al., 2013; Laouer et al., 2003). Ammoides atlantica arial parts were subjected to extraction with solvents polarity increased, n-hexane, CHCl3, CHCl3- MeOH (9:1) and MeOH. The study of the extracts was carried out using different chromatographic techniques such as Silica gel, SephadexLH-20, MPLC, and rp-HPLC. Part of chloroform extract (4.5 g) was subjected to column chromatography using silica gel and eluting with CHCl3 followed by increasing concentrations of MeOH in CHCl3 (between 1% and 100%). Fractions of 50 ml were collected and analyzed by TLC. Preliminary study of CHCl3 extract led to isolation of some pure compounds whose structures were elucidated by 1D-and 2D-NMR Spectroscopy (1H, 13C, 13C DEPT, DQF-COSY, HSQC, HMBC, ROESY) and confirmed by mass spectrometry. Seven compounds from CHCl3 extract were isolated: one monoterpene chrysanthenone, two glicosides monoterpenes as l-borneol O-β-D-glucopyranoside (Asano et al., 1993) and (-)-cis-chrysanthenol-β-D-glucopyranoside (Miyakado et al., 1974), three guaianolides as 9α-Acetoxyartecanin, 3α-Chloro-9α-acetoxy-4β,10α-dihydroxy-1β,2β-epoxy-5α,7αH-guai-11(13)-en12,6α-olide and apressin (Trifunovic´ et al., 2006) and a new bisabolene sesquiterpene derivative 1,4-dihydroxybisabol-2,11- diene-10-one.
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Descrizione: PhOL 2016 - Supplementary Issue - vol. 1, p. 151.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11563/138824
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