Aconapelsulfonines A and B, seco C20-diterpenoid alkaloids deriving via Criegee rearrangements of napelline skeleton from Aconitum carmichaelii

• Published in: Chinese chemical letters Vol. 32; no. 1; pp. 33 - 36
• Main Authors: Liu, Hui, Wu, Yuzhuo, Guo, Qinglan, Shao, Shuai, Xu, Chengbo, Zhang, Tiantai, Shi, Jiangong
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 01-01-2021; State Key Laboratory of Bioactive Substance and Function of Natural Medicines,Institute of Materia Medica,Chinese Academy of Medical Sciences and Peking Union Medical College,Beijing 100050,China
• Subjects: Aconapelsulfonine; Aconitum carmichaelii; Analgesic activity; C20-Diterpenoid alkaloid; Ranunculaceae; Aconapelsulfonine; Aconitum carmichaelii; C20-Diterpenoid alkaloid; Ranunculaceae; Analgesic activity
• ISSN: 1001-8417; 1878-5964
• DOI: 10.1016/j.cclet.2020.09.062

Two sulfonated seco C20-diterpenoid alkaloids, having analgesic activities and unprecedented carbon skeletons biogenetically derived via Criegee rearrangements of the napelline-type architecture, were isolated from an aqueous extract of the raw material of “Fu Zi”.
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Two sulfonated seco C20-diterpenoid alkaloids, aconapelsulfonines A (1) and B (2), were isolated from an aqueous extract of the raw material of “Fu Zi” (the Aconitum carmichaelii lateral roots), of which the structures were elucidated by various spectroscopic data, combined with X-ray crystallographic analysis. The unprecedented skeletons are biogenetically proposed to be derived via Criegee rearrangements of the napelline-type architecture. The two compounds exhibited dose-depended analgesic activities on an acetic acid-induced mice writhing test.