Chemical constituents of the root bark of Ulmus davidiana var. japonica and their potential biological activities

• Published in: Bioorganic chemistry Vol. 91; p. 103145
• Main Authors: So, Hae Min, Yu, Jae Sik, Khan, Zarha, Subedi, Lalita, Ko, Yoon-Joo, Lee, Il Kyun, Park, Woo Sung, Chung, Sang J., Ahn, Mi-Jeong, Kim, Sun Yeou, Kim, Ki Hyun
• Format: Journal Article
• Language: English
• Published: SAN DIEGO Elsevier Inc 01.10.2019; Elsevier
• Subjects: Anti-Helicobacter pylori activity; Anti-neuroinflammation; Biochemistry & Molecular Biology; Chemistry; Chemistry, Organic; Life Sciences & Biomedicine; Nerve growth factor (NGF); Physical Sciences; Science & Technology; Ulmaceae; Ulmus davidiana var. japonica; Nerve growth factor (NGF); Anti-Helicobacter pylori activity; Ulmaceae; Ulmus davidiana var. japonica; Anti-neuroinflammation; GLYCOSIDES; BIOACTIVE COMPOUNDS; INDUCED APOPTOSIS; LEAVES; LIGNAN GLUCOSIDES; INHIBITION; GROWTH; EXTRACTS; ADIPOCYTE
• ISSN: 0045-2068; 1090-2120
• DOI: 10.1016/j.bioorg.2019.103145

[Display omitted] •A new chromane derivative (1) was identified from Ulmus davidiana var. japonica root bark.•The structure were determined by 2D NMR data and NMR chemical shifts calculations.•Compounds 1, 8, and 20 displayed neuroprotective effect by the secretion of NGF in C6 glioma cells.•Compounds 11, 14, and 19 inhibited NO production in LPS-stimulated murine microglial cells.•Compounds 1, 11, 18, and 20 showed significant anti-H. pylori activity. The root bark of Ulmus davidiana var. japonica (Ulmaceae), commonly known as yugeunpi, has been used as a traditional Korean medicine for the treatment of gastroenteric and inflammatory disorders. As part of continuing projects to discover bioactive natural products from traditional medicinal plants with pharmacological potential, phytochemical investigation of the root bark of this plant was carried out. This led to the successful isolation of a new chromane derivative (1) and 22 known compounds: catechin derivatives (2–5), megastigmane glycoside (6), dihydrochalcone glycosides (7 and 8), flavanone glycosides (9 and 10), coumarins (11 and 12), lignan derivatives (13–17), and phenolic compounds (18–23). The structure of the new compound (1) was determined with 1D and 2D NMR spectroscopy and HR-ESIMS, and its absolute configurations were achieved by chemical reactions and the gauge-including atomic orbital (GIAO) NMR chemical shifts calculations. All the isolated compounds were evaluated for their potential biological activities including neuro-protective, anti-neuroinflammatory, and anti-Helicobacter pylori activities. Among the isolates, compounds 1, 8, and 20 displayed stronger potency by causing a greater increase in the production and the activity of nerve growth factor (NGF) in C6 glioma cells (147.04 ± 4.87, 206.27 ± 6.70, and 143.70 ± 0.88%, respectively), whereas compounds 11, 14, and 19 inhibited nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated murine microglial cells (IC50 of 18.72, 12.31, and, 21.40 µM, respectively). In addition, compounds 1, 11, 18, and 20 showed anti-H. pylori activity with MIC values of 25 or 50 µM against two strains of H. pylori 51 and 43504. These findings provide scientific evidence that supports the traditional usage of U. davidiana var. japonica root bark in the treatment of gastroenteric and inflammatory disorders.