Total Synthesis and Anti-inflammatory Activity of Asperjinone and Asperimide C
Issued Date
2024-01-01
Resource Type
ISSN
01633864
eISSN
15206025
Scopus ID
2-s2.0-85200832056
Pubmed ID
39110498
Journal Title
Journal of Natural Products
Rights Holder(s)
SCOPUS
Bibliographic Citation
Journal of Natural Products (2024)
Suggested Citation
Thongpat K., Milehman N., Rojanaverawong W., Holasut P., Soodvilai S., Vaddhanaphuti C.S., Tadpetch K. Total Synthesis and Anti-inflammatory Activity of Asperjinone and Asperimide C. Journal of Natural Products (2024). doi:10.1021/acs.jnatprod.4c00557 Retrieved from: https://repository.li.mahidol.ac.th/handle/123456789/100501
Title
Total Synthesis and Anti-inflammatory Activity of Asperjinone and Asperimide C
Corresponding Author(s)
Other Contributor(s)
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-1β 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.