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

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...

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Published inOrganic & biomolecular chemistry Vol. 19; no. 45; pp. 9844 - 9848
Main Authors Xu, Zan-Xin, Li, Bin, Tian, Ying, Li, Min, Dong, Jun-Xing, Zhang, Guang-Jie
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 25.11.2021
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SEEDS
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Summary: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 mu M, which was equivalent to that of dexamethasone.
ISSN:1477-0520
1477-0539
DOI:10.1039/d1ob01973b