Ochrocephalamines E and F, two new alkaloids from Oxytropis ochrocephala bung. (20th July 2022)

• Record Type: Journal Article
• Authors: 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
• Is Part Of: Tetrahedron letters. Volume 102(2022)
• Publication Date: 2022-07-20
• Subjects: Fabaceae -- Oxytropis ochrocephala Bunge -- Quinolizidine alkaloids -- Anti-HBV activity; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2022.153943
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphic abstracts: 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%). Highlights: 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. Abstract: 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.