Anti-inflammatory alkaloids from the root bark of Hernandia nymphaeifolia. (May 2020)

• Record Type: Journal Article
• Authors: Lai, Yu-Wei; Wang, Shih-Wei; Hu, Ya-Yun; Hwang, Tsong-Long; Cheng, Ming-Jen; Chen, Ih-Sheng; Sung, Ping-Jyun; Chen, Jih-Jung
• Is Part Of: Phytochemistry. Volume 173(2020)
• Publication Date: 2020-05
• Subjects: Hernanadia nymphaeifolia -- Hernandiaceae -- Root bark -- Structure elucidation -- Alkaloid -- Anti-inflammatory activity; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2020.112326
• Languages: English
• ISSNs: 0031-9422

Abstract

Abstract: Four undescribed alkaloids, 7-ethoxy-6-methoxy-2-methylisoquinolin-1(2 H )-one, 7, 8-dihydroxy-6-methoxy-2-methylisoquinolin-1(2 H )-one, N -formylhernagine, and 5, 6-dihydroxy- N -methylphthalimide, were obtained from the root bark of Hernanadia nymphaeifolia, along with fourteen known compounds. The structures of these compounds were determined through spectroscopic and MS analyses. 7, 8-Dihydroxy-6-methoxy-2-methylisoquinolin-1(2 H )-one, N -formylhernagine, 5, 6-dihydroxy- N -methylphthalimide, oxohernagine, hernandonine, and N - trans -feruloylmethoxytyramine inhibited the superoxide anion (O2 – ) production (IC50 values ≤ 6.23 μg/mL) by neutrophils stimulated with formyl-L-methionyl-L-leuckyl-L-phenyl-alanine/cytochalasin B (fMLP/CB). Furthermore, 7, 8-dihydroxy-6-methoxy-2-methylisoquinolin-1(2 H )-one, N -formylhernagine, 5, 6-dihydroxy- N -methylphthalimide, oxohernagine, and N - trans -feruloylmethoxytyramine inhibited fMLP/CB-induced elastase release with IC50 values ≤ 7.41 μg/mL. In addition, 7, 8-dihydroxy-6-methoxy-2-methylisoquinolin-1(2 H )-one, N -formylhernagine, oxohernagine, and N - trans -feruloylmethoxytyramine showed potent inhibition with IC50 values ≤ 28.55 μM, against lipopolysaccharide (LPS)-induced nitric oxide (NO) generation. Graphical abstract: Four previously undescribed alkaloids and fourteen known compounds were isolated from the root bark of Hernandia nymphaeifolia . Several of them showed potent anti-inflammatory activity in vitro . Image 10806 Highlights: Four undescribed alkaloids were isolated from Hernanadia nymphaeifolia. Their chemical structures were determined on the basis of extensive spectroscopic analyses. The isolated compounds were evaluated for anti-inflammatory activities.