Total Synthesis and Anti-inflammatory Activity of Asperjinone and Asperimide C.
J Nat Prod
; 87(8): 2045-2054, 2024 Aug 23.
Article
in En
| MEDLINE
| ID: mdl-39110498
ABSTRACT
Total syntheses of two γ-butenolide natural products, asperjinone (1) and asperimide C (2) in both racemic and chiral forms have been accomplished utilizing Basavaiah's one-pot Friedel-Crafts/maleic anhydride formation protocol as a key strategy. Our syntheses verified the revised structure of 1 proposed by Williams et al. and the structure and absolute configuration of 2 reported by the Li group. This work also discloses the unprecedented anti-inflammatory activity of 1. Synthetic 1 exhibited significant anti-inflammatory activity in renal proximal tubular epithelial cells (RPTEC) by suppression of gene expression of pro-inflammatory cytokines TNF-α, IL-1ß and IL-6 under LPS-induced renal inflammation condition and was superior to (S)-1, rac-2, 2, and a positive drug control, indomethacin. Moreover, compound 1 inhibited downstream signaling of inflammation by significantly reducing iNOS and COX-2 gene expression and total NO production. The anti-inflammatory activity of asperjinone (1) renders it a potential and promising candidate for developing novel anti-inflammatory agents against inflammation worsening acute kidney injury.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Anti-Inflammatory Agents
Limits:
Animals
Language:
En
Journal:
J Nat Prod
Year:
2024
Document type:
Article
Affiliation country:
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