TY - JOUR
T1 - Isolation and identification of new anthraquinones from Rhamnus alaternus L and evaluation of their free radical scavenging activity
AU - Ben Ammar, Rebai
AU - Miyamoto, Tomofumi
AU - Chekir-Ghedira, Leila
AU - Ghedira, Kamel
AU - Lacaille-Dubois, Marie Aleth
N1 - Funding Information:
This work was supported by the Ministry of Higher Education and Scientific Research in Tunisia [grant number 99/UR/07-03]. The authors would like to thank Professor Marie-Aleth Lacaille-Dubois and Dr. Tomofumi Miyamoto for their precious help in conducting NMR and Mass Spectrometry analysis, and for structure elucidation of the isolated compounds. We are also grateful to the ‘Université de Bourgogne Franche-Comté in France’ and to the ‘Ministry of Higher Education and Scientific Research in Tunisia’, for providing necessary administrative and research facilities.
Publisher Copyright:
© 2018, © 2018 Informa UK Limited, trading as Taylor & Francis Group.
PY - 2019/1/17
Y1 - 2019/1/17
N2 - From the butanolic and the ethyl acetate extracts of Rhamnus alaternus L root bark and leaves, three new anthraquinone glycosides, alaternosides A-C (1,4,6,8 tetrahydroxy-3 methyl anthraquinone 1-O-ß-D-glucopyranosyl-4,6-di-O-α-L-rhamnopyranoside (1); 1,2,6,8 tetrahydroxy-3 methyl anthraquinone 8-O-ß-D-glucopyranoside (2) and 1, 6 dihydroxy-3 methyl 6 [2′-Me (heptoxy)] anthraquinone (3)) were isolated and elucidated together with the two known anthraquinone glycosides, Physcion-8-O-rutinoside (4) and emodin-6-O-α-L-rhamnoside (5) as well as with the known kaempferol-7-methylether (6), β-sitosterol (7) and β-sitosterol-3-O-glycoside (8). Their chemical structures were elucidated using spectroscopic methods (1D-, 2D-NMR and FAB-MS). Free radical scavenging activity of the isolated compounds was evaluated by their ability to scavenge DPPH . free radicals. Compounds (3), (4) and (6) showed the highest activity with IC 50 values of 9.46, 27.68 and 2.35 μg/mL, respectively.
AB - From the butanolic and the ethyl acetate extracts of Rhamnus alaternus L root bark and leaves, three new anthraquinone glycosides, alaternosides A-C (1,4,6,8 tetrahydroxy-3 methyl anthraquinone 1-O-ß-D-glucopyranosyl-4,6-di-O-α-L-rhamnopyranoside (1); 1,2,6,8 tetrahydroxy-3 methyl anthraquinone 8-O-ß-D-glucopyranoside (2) and 1, 6 dihydroxy-3 methyl 6 [2′-Me (heptoxy)] anthraquinone (3)) were isolated and elucidated together with the two known anthraquinone glycosides, Physcion-8-O-rutinoside (4) and emodin-6-O-α-L-rhamnoside (5) as well as with the known kaempferol-7-methylether (6), β-sitosterol (7) and β-sitosterol-3-O-glycoside (8). Their chemical structures were elucidated using spectroscopic methods (1D-, 2D-NMR and FAB-MS). Free radical scavenging activity of the isolated compounds was evaluated by their ability to scavenge DPPH . free radicals. Compounds (3), (4) and (6) showed the highest activity with IC 50 values of 9.46, 27.68 and 2.35 μg/mL, respectively.
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U2 - 10.1080/14786419.2018.1446135
DO - 10.1080/14786419.2018.1446135
M3 - Article
C2 - 29533086
AN - SCOPUS:85043687227
VL - 33
SP - 280
EP - 286
JO - Natural Product Research
JF - Natural Product Research
SN - 1478-6419
IS - 2
ER -