Ochrocephalamines E and F, two new alkaloids from Oxytropis ochrocephala bung
Two new quinolizidine-based alkaloids, ochrocephalamines E (1) and F (2), were isolated from Oxytropis ochrocephala Bunge. Compound 1 represented the first 14-nor matrine-type alkaloid with 6/6/6/5 ring system. Compound 2 shared the aloperine-type scaffold including the C-10 location of carbonyl gro...
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Veröffentlicht in: | Tetrahedron letters 2022-07, Vol.102, p.153943, Article 153943 |
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Zusammenfassung: | Two new quinolizidine-based alkaloids, ochrocephalamines E (1) and F (2), were isolated from Oxytropis ochrocephala Bunge. Compound 1 represented the first 14-nor matrine-type alkaloid with 6/6/6/5 ring system. Compound 2 shared the aloperine-type scaffold including the C-10 location of carbonyl group. The inhibitory activities of 2 against the secretion of HBsAg and HBeAg were respectively 22.34 ± 4.38% and 18.00 ± 5.01% at the noncytotoxic concentration of 1×10-5 mol/L, which was more active than the positive control hyperoside (16.09% and 12.23%).
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•Two new quinolizidine-based alkaloids were isolated from Oxytropis ochrocephala Bunge.•Compound 1 represented the first 14-nor matrine-type alkaloid with 6/6/6/5 ring system.•Compound 2 exhibited potential activity in inhibiting HBsAg and HBeAg secretion.
Two new quinolizidine-based alkaloids, ochrocephalamines E (1) and F (2) were isolated from Oxytropis ochrocephala Bunge (Fabaceae). Their structures were elucidated by extensive spectroscopic analysis and electronic circular dichroism (ECD) calculations. Compound 1 represented the first 14-nor matrine with 6/6/6/5 ring system, while compound 2 shared the aloperine-type scaffold including the carbonyl group at C-10 postition. The inhibitory activities of 2 against the secretion of HBsAg and HBeAg were respectively 22.34 ± 4.38% and 18.00 ± 5.01% at the noncytotoxic concentration of 1 × 10-5 mol/L, which were more active than the positive control hyperoside (16.09% and 12.23%). The binding mode between compound 2 and HBV core protein was illustrated by molecular docking. |
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ISSN: | 0040-4039 1873-3581 |
DOI: | 10.1016/j.tetlet.2022.153943 |