Piperlongosides A–C, Three New Phenolic Constituents From Piper longum L

• Published in: Natural product communications 2023-01, Vol.18 (1)
• Main Authors: Huyen, Le Thi, Thu Hau, Nguyen Thi, Kiem, Phan Van
• Format: Article
• Language: English
• ISSN: 1934-578X; 1555-9475
• DOI: 10.1177/1934578X221150367

Phytochemical study on the methanolic extract of the aerial parts of this plant led to the isolation of 7 phenolic compounds (1-7), including 3 new ones (1-3). Their chemical structures were determined to be (7,8-threo)-1-O-β-D-[6′-O-syringoylglucopyranosyl]-2-methoxy-7,8,9-trihydroxyphenylpropane (1), (7,8-threo)-8-O-(2′′-methoxyacetophenone-1′′-yl)-1-O-β-D-glucopyranosyl-2-methoxy-7,9-dihydroxyphenylpropane (2), 1-O-β-D-glucopyranosyl-2-O-(2′′-methoxy-4′′-acetylphenyl)-3-hydroxypropane (3), (−)-isolariciresinol 4-O-β-D-glucopyranoside (4), (−)-isolarisiresinol 9′-O-β-D-glucopyranoside (5), (+ )-lyoniresinol 9′-O-β-D-glucopyranoside (6), (+ )-isolarisiresinol 9′-O-β-D-glucopyranoside (7) by the spectroscopic data and in comparison with those reported in the literature. Compounds 3 to 7 significantly inhibited NO production in LPS-activated RAW264.7 cells with IC50 values ranging from 32.09 ± 3.34 to 38.16 ± 1.35 µM, similar to those of the positive control, NG-monomethyl-L-arginine acetate (IC50 32.51 ± 3.70 µM).