Six rare naturally occurring indazole-type alkaloids including two new compounds, 17-O-(β-d-glucopyranosyl)-4-O-methylnigellidine (1) and nigelanoid (2), and four known compounds (3-6) were isolated from a defatted extract of Nigella sativa (black cumin) seeds. 17-O-(β-d-Glucopyranosyl)-4-O-methylnigellidine (1) increased glucose consumption by liver hepatocytes (HepG2 cells) through activation of AMP-activated protein kinase (AMPK). Also, this is the first report of compounds 4 and 6 from a natural source.
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| http://dx.doi.org/10.1021/np500398m | DOI Listing |
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Indazole-type alkaloids from Nigella sativa seeds exhibit antihyperglycemic effects via AMPK activation in vitro.
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The Key Laboratory of Plant Resources and Chemistry of Arid Zone, and State Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences , Urumqi 830011, People's Republic of China.
Six rare naturally occurring indazole-type alkaloids including two new compounds, 17-O-(β-d-glucopyranosyl)-4-O-methylnigellidine (1) and nigelanoid (2), and four known compounds (3-6) were isolated from a defatted extract of Nigella sativa (black cumin) seeds. 17-O-(β-d-Glucopyranosyl)-4-O-methylnigellidine (1) increased glucose consumption by liver hepatocytes (HepG2 cells) through activation of AMP-activated protein kinase (AMPK). Also, this is the first report of compounds 4 and 6 from a natural source.
View Article and Find Full Text PDFNigellidine-4-O-sulfite, the first sulfated indazole-type alkaloid from the seeds of Nigella sativa.
J Nat Prod
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National Center for Natural Products Research, University of Mississippi, Mississippi, USA.
The rare indazole-type alkaloid nigellidine (2) is accompanied by its 4-O-sulfite (4) in the seeds of Nigella sativa. Compound 4 may represent the true natural product leading to nigellidine (2) via hydrolysis of the sulfate functionality during the isolation process. The structure of nigellidine-4-O-sulfite (4) is confirmed by NMR, MS, and X-ray crystallographic data.
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