Isolation and identification of new anthraquinones from Rhamnus alaternus L and evaluation of their free radical scavenging activity

Rebai Ben Ammar, Tomofumi Miyamoto, Leila Chekir-Ghedira, Kamel Ghedira, Marie Aleth Lacaille-Dubois

研究成果: ジャーナルへの寄稿記事

抄録

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.

元の言語英語
ページ(範囲)280-286
ページ数7
ジャーナルNatural Product Research
33
発行部数2
DOI
出版物ステータス出版済み - 1 17 2019

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Rhamnus
Anthraquinones
anthraquinones
Scavenging
Free Radicals
Glycosides
glycosides
sitosterols
Emodin
emodin
kaempferol
rutin
chemical structure
inhibitory concentration 50
bark
Nuclear magnetic resonance
Rhamnus alaternus
extracts
leaves

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Biochemistry
  • Plant Science
  • Organic Chemistry

これを引用

Isolation and identification of new anthraquinones from Rhamnus alaternus L and evaluation of their free radical scavenging activity. / Ben Ammar, Rebai; Miyamoto, Tomofumi; Chekir-Ghedira, Leila; Ghedira, Kamel; Lacaille-Dubois, Marie Aleth.

:: Natural Product Research, 巻 33, 番号 2, 17.01.2019, p. 280-286.

研究成果: ジャーナルへの寄稿記事

Ben Ammar, Rebai ; Miyamoto, Tomofumi ; Chekir-Ghedira, Leila ; Ghedira, Kamel ; Lacaille-Dubois, Marie Aleth. / Isolation and identification of new anthraquinones from Rhamnus alaternus L and evaluation of their free radical scavenging activity. :: Natural Product Research. 2019 ; 巻 33, 番号 2. pp. 280-286.
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abstract = "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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