Structural Modification and Characteristics of Lappaconitine Alkaloid for the Discovery of Bioactive Components by Hypervalent Iodine Reagent

Chang Sang Moon, Heung Mo Kang, Yunchan Nam, Jiwoong Lim, Jiewan Kim, Tae Hee Lee, Junho Lee, Mun Seog Chang, Jae Yeol Lee

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

Lappaconitine, a diterpene alkaloid isolated from Aconitum sinomontanum Nakai, exhibits a wide range of biological activities, making it a promising candidate for the development of novel derivatives with therapeutic potential. In our research, we executed a two-step transformation via oxidative cleavage of lappaconitine’s vicinal diol using the hypervalent iodine reagent PhI(OAc)2, followed by strong alkaline hydrolysis. This approach yielded four new unanticipated compounds, whose structures were identified by spectroscopic methods and/or X-ray crystallography. Thus, we proposed plausible reaction mechanisms for their formations and particularly investigated the remarkable diastereoselectivity for the formation of single stereoisomer 8 observed during the alkaline hydrolysis step. Among them, compound 8 (code name: QG3030) demonstrated both enhanced osteogenic differentiation of human mesenchymal stem cells and significant osteogenic effect in an ovariectomized rat model with no acute oral toxicity.

Original languageEnglish
Pages (from-to)6535-6539
Number of pages5
JournalOrganic Letters
Volume26
Issue number31
DOIs
Publication statusPublished - 9 Aug 2024

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© 2024 American Chemical Society

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