Isolation and biomimetic synthesis of phenylpropionyl phenylethylamines from Chloranthus henryi.
Phytochemistry
; 222: 114090, 2024 Jun.
Article
in En
| MEDLINE
| ID: mdl-38599509
ABSTRACT
In this study, ten phenylpropionyl phenylethylamines, including five previously undescribed ones (1a/b, 2a/b, and 3), five known analogues (4-8), and two established phenylpropanoids precursors (9, 10) were isolated from the aerial parts of Chloranthus henryi Hemsl. Their structures, including absolute configurations, were determined by high-resolution mass spectrometry, enantio-separation, electronic circular dichroism calculation, and single crystal diffraction. Compounds 1a and 1b were the first examples of natural hetero-[2 + 2] cycloaddition products between phenylpropionyl phenylethylamine and phenylpropene. The plausible hetero-[2 + 2] biosynthesis pathway was confirmed by a photocatalytic biomimetic synthesis in eight steps, which also led to the production of three other potential natural homo-[2 + 2] adducts (1'a/b, 2', and 3'). Bioactivity screening indicated that these adducts bear medium inhibitory activity on nitric oxide generation, with IC50 values of 6-35 µM in RAW 264.7 macrophages.
Key words
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Phenethylamines
/
Nitric Oxide
Limits:
Animals
Language:
En
Journal:
Phytochemistry
Year:
2024
Document type:
Article
Affiliation country:
China
Country of publication:
Reino Unido