Issue 45, 2021

Pentacyclic spermidine alkaloids with radioprotective and anti-inflammatory activities from Orychophragmus violaceus

Abstract

Two pairs of novel pentacyclic spermidine alkaloid enantiomers, (±)-orychoviolines A and B ((±)-1 and (±)-2), were isolated from the seeds of Orychophragmus violaceus and represented the first example of a 2-piperidinone-fused hydrodibenzofuran skeleton, constructed from a 6/5/6/6 tetracyclic system and an 18 atomic ring. The most unexpected novelty was the formation of one more piperidinone ring by a connection between C-6 and N-7. Their structures and absolute configurations were determined by spectroscopic analyses, X-ray crystallography, and ECD analysis. Compared to Ex-RAD (sodium salt of 4-carboxystyryl-4-chlorobenzylsulfone), (−)-1 exhibited a significant radioprotective effect on cell survival and DNA damage. (−)-1 also exhibited remarkable anti-inflammatory activity by inhibiting the production of NO in RAW 264.7 cells activated by lipopolysaccharide with an IC50 value of 20.3 ± 1.58 μM, which was equivalent to that of dexamethasone.

Graphical abstract: Pentacyclic spermidine alkaloids with radioprotective and anti-inflammatory activities from Orychophragmus violaceus

Associated articles

Supplementary files

Article information

Article type
Communication
Submitted
08 oct. 2021
Accepted
29 oct. 2021
First published
30 oct. 2021

Org. Biomol. Chem., 2021,19, 9844-9848

Pentacyclic spermidine alkaloids with radioprotective and anti-inflammatory activities from Orychophragmus violaceus

Z. Xu, B. Li, Y. Tian, M. Li, J. Dong and G. Zhang, Org. Biomol. Chem., 2021, 19, 9844 DOI: 10.1039/D1OB01973B

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