Norprzewalsone A, a Rearranged Polycyclic Polyprenylated Acylphloroglucinol with a Spiro[cyclopentane-1,3'-tricyclo[7.4.0.0 1,6 ]tridecane] Core from Hypericum przewalskii .
Yulin DuanYi GuoYanfang DengPengfei BuZhengyi ShiYunfang CaoYeting ZhangHong HuWeiguang SunChangxing QiYong-Hui ZhangPublished in: The Journal of organic chemistry (2022)
Norprzewalsone A ( 1 ), a rearranged polyprenylated polycyclic acylphloroglucinol (PPAP) with a new carbon skeleton, along with a new congener, norprzewalsone B ( 2 ), were isolated from Hypericum przewalskii . Compound 1 possessed a new 5/6/5/6/6 pentacyclic ring system based on a spiro[cyclopentane-1,3'-tricyclo[7.4.0.0 1,6 ]tridecane] core, which might be derived from the common [3.3.1]-type bicyclic polyprenylated acylphloroglucinol (BPAP) via the key retro-Claisen, intramolecular cyclization, and Diels-Alder cyclization reactions. Their structures and absolute configurations were confirmed by spectroscopic data, calculated 1D NMR data with DP4+ probability analyses, and electronic circular dichroism calculations and comparison. More significantly, compound 1 exhibited a moderate inhibitory effect on NO production in lipopolysaccharide-stimulated RAW264.7 cells.
Keyphrases
- electronic health record
- induced apoptosis
- high resolution
- big data
- magnetic resonance
- molecular docking
- cell cycle arrest
- molecular dynamics simulations
- toll like receptor
- molecular dynamics
- density functional theory
- endoplasmic reticulum stress
- signaling pathway
- cell proliferation
- mass spectrometry
- oxidative stress
- artificial intelligence
- cell death
- energy transfer