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
Hauptverfasser: Xue, Zhan, Zhang, Ya-Kun, Yi, Ping, Yang, Fu-Mei, Huo, Xiao-Min, Wang, Ting-Ting, Zhang, Hong-Yan, Zhao, Bao-Yu, Zeng, Yan-Rong, Wang, Yue-Hu, Tan, Cheng-Jian
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Sprache:eng
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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%). [Display omitted] •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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2022.153943