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

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...

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Published inJournal of natural medicines Vol. 78; no. 4; pp. 901 - 907
Main Authors Tan, Lingjian, Otsuki, Kouharu, Kikuchi, Takashi, Zhou, Di, Li, Ning, Huang, Li, Chen, Chin-Ho, Li, Wei
Format Journal Article
LanguageEnglish
Published Singapore Springer Nature Singapore 01.09.2024
Springer Nature B.V
Subjects
Anti-HIV Agents - chemistry
Anti-HIV Agents - isolation & purification
Anti-HIV Agents - pharmacology
antiretroviral properties
Antiviral activity
Biomedical and Life Sciences
Biomedicine
Cell Line
Complementary & Alternative Medicine
Daphne
Daphne - chemistry
Diterpenes
Diterpenes - chemistry
Diterpenes - isolation & purification
Diterpenes - pharmacology
diterpenoids
Esters - chemistry
HIV
HIV infections
HIV-1 - drug effects
Human immunodeficiency virus
Humans
Medicinal Chemistry
Molecular Structure
Original Paper
ortho esters
Orthoesters
Pharmacology/Toxicology
Pharmacy
phytochemicals
Plant Extracts - chemistry
Plant Extracts - pharmacology
Plant Sciences
spectroscopy
Tandem Mass Spectrometry
Anti-HIV
Odd-numbered aliphatic side chain
Thymelaeaceae
Daphnane
Daphne pedunculata
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Summary: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
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Methodology, LJT, KO, TK, NL, CHC, and WL; investigation, LJT, DZ, NL, LH, and CHC; formal analysis, LJT and KO; writing–original draft, LJT; funding acquisition, LJT, KO, CHC, and WL; project administration, KO and WL; writing, review and editing, KO, TK, NL, CHC, and WL; conceptualization, supervision, WL. All authors have read and approved the published version of the manuscript.
Author contributions
ISSN:1340-3443
1861-0293
1861-0293
DOI:10.1007/s11418-024-01826-x