Journal
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
Volume 31, Issue -, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmcl.2020.127682
Keywords
Myanmar; Piper betle; Piperaceae; Neolignans; Anti-inflammatory
Categories
Funding
- NSFC [31670338, 31960480]
- Southeast Asia Biodiversity Research Institute, Chinese Academy of Sciences [2015CASE-ABRIRG001, Y4ZK111B01]
- International Partnership Program of Chinese Academy of Sciences [153631KYSB20160004]
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This study isolated several sesquineolignan and neolignan compounds from Piper betle leaves collected from Myanmar, some of which showed anti-inflammatory activity, with hydroxychavicol being essential for this activity.
One new sesquineolignan, piperneolignan A (1), four new neolignans, piperneolignans B-E (2-5), and eight known compounds were isolated from the leaves of Piper betle (Piperaceae) collected from Myanmar. These new structures were determined by analysis of MS and NMR data, and the absolute configuration of piperneolignan A was elucidated by electronic circular dichroism (ECD) calculations. Piperneolignan A (1), piperneolignan B (2), hydroxychavicol (6), p-hydroxycinnamaldehyde (10), and diallylcatechol (13) possessed anti-inflammatory activity against nitric oxide (NO) production in lipopolysaccharide (LPS)-activated murine macrophage RAW 264.7 cells with IC50 values of 9.87, 45.94, 4.80, 26.40, and 40.45 mu M, respectively, compared with the positive control NG-monomethyl-L-arginine (L-NMMA, IC50 = 33.84 mu M). The two hydroxy groups in the structure of hydroxychavicol are essential for activity, and dimerization or trimerization of hydroxychavicol decreases activity.
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