Atropisomeric 9, 10-dihydrophenanthrene/bibenzyl trimers with anti-inflammatory and PTP1B inhibitory activities from Bletilla striata. Issue 23 (25th May 2022)

• Record Type: Journal Article
• Authors: Sun, Mohan; Ma, Xianjie; Shao, Siyuan; Jiang, Jianwei; Li, Jiaan; Tian, Jinying; Zhang, Jianjun; Li, Li; Ye, Fei; Li, Shuai
• Is Part Of: Organic & biomolecular chemistry. Volume 20:Issue 23(2022)
• Page Start: 4736
• Page End: 4745
• Publication Date: 2022-05-25
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d2ob00489e
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Two pairs of novel trimeric dihydrophenanthrene–bibenzyl–dihydrophenanthrene enantiomers, together with three rare polymers were isolated from Bletilla striata . Some compounds showed significant anti-inflammatory and PTP1B inhibitory activities. Abstract : Two pairs of novel trimeric dihydrophenanthrene–bibenzyl–dihydrophenanthrene enantiomers (1 and 2 ), the first examples of a dihydrophenanthrene dimer linked to a bibenzyl or dihydrophenanthrene through a C– O –C bond (3 and 4 ), and a pair of rare polymers with a bibenzyl connected to C-8′ of the dihydrophenanthro[ b ]furan moiety via a methylene (5 ), together with four known compounds (6–9 ) were isolated from the tubers of Bletilla striata . Their structures including the absolute configurations were determined using spectroscopic data analysis and ECD and NMR calculations, combined with the exciton chirality method or the reversed helicity rule. The atropisomerism of dihydrophenanthrenes and related polymers was considered based on their chiral optical properties, and QM torsion profile calculations, which revealed the racemic mixture form of the polymers. Compounds 4, 5b, 6a and 7b significantly inhibited the production of NO in LPS-induced BV-2 cells, with IC50 values ranging from 0.78 to 5.52 μM. Further mechanistic study revealed that 7b suppressed the expression of iNOS, and suppressed the phosphorylation of the p65 subunit to regulate the NF-κB signaling pathway. Furthermore, compounds 2b, 5a, 5b, 7a and 7b displayed significant protein tyrosine phosphatase 1B (PTP1B) inhibitory activities with IC50 values of 3.43–12.30 μM.