Pentacyclic spermidine alkaloids with radioprotective and anti-inflammatory activities from Orychophragmus violaceus. Issue 45 (9th November 2021)

• Record Type: Journal Article
• Authors: Xu, Zan-Xin; Li, Bin; Tian, Ying; Li, Min; Dong, Jun-Xing; Zhang, Guang-Jie
• Is Part Of: Organic & biomolecular chemistry. Volume 19:Issue 45(2021)
• Page Start: 9844
• Page End: 9848
• Publication Date: 2021-11-09
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d1ob01973b
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Two pairs of novel pentacyclic spermidine alkaloid enantiomers, (±)-orychoviolines A and B, were isolated from the seeds of Orychophragmus violaceus and represented the first example of a 2-piperidinone-fused hydrodibenzofuran skeleton. 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.