Daphnane diterpenoid orthoesters with an odd-numbered aliphatic side chain from Daphne pedunculata

• Published in: Journal of natural medicines 2024-09, Vol.78 (4), p.901-907
• Main Authors: Tan, Lingjian, Otsuki, Kouharu, Kikuchi, Takashi, Zhou, Di, Li, Ning, Huang, Li, Chen, Chin-Ho, Li, Wei
• Format: Article
• Language: English
• Subjects: Anti-HIV Agents - chemistry; Anti-HIV Agents - isolation & purification; Anti-HIV Agents - pharmacology; Antiviral activity; Biomedical and Life Sciences; Biomedicine; Cell Line; Complementary & Alternative Medicine; Daphne - chemistry; Diterpenes; Diterpenes - chemistry; Diterpenes - isolation & purification; Diterpenes - pharmacology; Esters - chemistry; HIV; HIV-1 - drug effects; Human immunodeficiency virus; Humans; Medicinal Chemistry; Molecular Structure; Original Paper; Orthoesters; Pharmacology/Toxicology; Pharmacy; Plant Extracts - chemistry; Plant Extracts - pharmacology; Plant Sciences; Tandem Mass Spectrometry
• ISSN: 1340-3443; 1861-0293; 1861-0293
• DOI: 10.1007/s11418-024-01826-x

Daphnane diterpenoids were recognized for their extensive range of potent biological activities. In the present study, phytochemical investigation including LC–MS/MS analysis resulted in the identification of five daphnane diterpenoid orthoesters ( 1 – 5 ). Among the five daphnane diterpenoids, two previously unreported compounds, daphnepedunins I and J ( 2 and 4 ) were isolated from Daphne pedunculata . The structure of new compounds was elucidated with extensive physicochemical and spectroscopic analyses. Their structure was characterized by the presence of an unusual odd-numbered aliphatic chain connected to an orthoester. The isolated compounds were evaluated for their anti-HIV activity against HIV-1 infection of MT4 cells, and the results indicated that compound 1 showed the most potent anti-HIV activity with an IC 50 value of 0.82 nM. Graphical Abstract