Two new chlorinated iridoids, named bungosides A (1) and B (2), were isolated from the seeds of Catalpa bungei (family Bignoniaceae). Their structures were elucidated on the basis of NMR analysis. Twenty known compounds (3-22) were also characterized, including in one case (6-O-p-hydroxybenzoylglutinoside, 3) the assignment of the absolute configuration by employing electronic circular dichroism (CD) and time-dependent density functional theory (TDDFT) calculations. Compounds 1-3 were unusual cage-like iridoids with an oxygen bridge between C-3 and C-10. Among the isolates, ursolic acid lactone (14) was the most active soluble epoxide hydrolase (sEH) inhibitor with an IC50 19.1 ± 0.8 μM. In addition, d-pinoresinol (19) and ladanein (21) displayed selectively inhibitory effects on butyrylcholinesterase (BChE) with IC50 of 31.5 ± 0.4 μM and 33.0 ± 2.3 μM, respectively, but not acetylcholinesterase (AChE) activity, and only compound 18 suppressed NF-κB activity in HepG2 cells (IC50 21.53 ± 2.37 μM).

Chemical components from the seeds of: Catalpa bungei and their inhibitions of soluble epoxide hydrolase, cholinesterase and nuclear factor kappa B activities

PESCITELLI, GENNARO;
2016

Abstract

Two new chlorinated iridoids, named bungosides A (1) and B (2), were isolated from the seeds of Catalpa bungei (family Bignoniaceae). Their structures were elucidated on the basis of NMR analysis. Twenty known compounds (3-22) were also characterized, including in one case (6-O-p-hydroxybenzoylglutinoside, 3) the assignment of the absolute configuration by employing electronic circular dichroism (CD) and time-dependent density functional theory (TDDFT) calculations. Compounds 1-3 were unusual cage-like iridoids with an oxygen bridge between C-3 and C-10. Among the isolates, ursolic acid lactone (14) was the most active soluble epoxide hydrolase (sEH) inhibitor with an IC50 19.1 ± 0.8 μM. In addition, d-pinoresinol (19) and ladanein (21) displayed selectively inhibitory effects on butyrylcholinesterase (BChE) with IC50 of 31.5 ± 0.4 μM and 33.0 ± 2.3 μM, respectively, but not acetylcholinesterase (AChE) activity, and only compound 18 suppressed NF-κB activity in HepG2 cells (IC50 21.53 ± 2.37 μM).
Tang, Hao Yu; Bai, Meng Meng; Tian, Jun Mian; Pescitelli, Gennaro; Ivšić, Trpimir; Huang, Xiao Hua; Lee, Hyunwoo; Son, Ya Nan; Kim, Jang Hoon; Kim, Young Ho; Gao, Jin Ming
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11568/803873
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