np8b00182_si_001.pdf (1.23 MB)
Chemical Constituents of Apios americana Tubers and Their Inhibitory Activities on Nitric Oxide Production in Lipopolysaccharide-Stimulated RAW 264.7 Macrophages
journal contribution
posted on 2018-06-22, 19:15 authored by Young
Hye Seo, Ju-Hyun Jeon, Miran Jeong, Seung Mok Ryu, Won Kyung Jeon, Dae Sik Jang, Sang Hee Shim, Dongho Lee, Jung-Hye Choi, Jun LeeApios americana is
an important food crop producing
edible tubers with high nutritional and medicinal values and is widely
cultivated in many countries. Despite its usefulness, research on
its secondary metabolites and biological activities has been limited.
In the present study, a new coumaronochromone, (2R,3S)-3,7,4′-trihydroxy-5-methoxycoumaronochromone
(1), and two new isoflavone glucosides, 7,2′,4′-trihydroxy-5-methoxyisoflavone-4′-O-β-d-glucopyranoside (3) and
5,7,4′-trihydroxyisoflavone-7-O-β-d-gentiotrioside (5), were isolated from the tubers
of A. americana via chromatographic separation. Seventeen
known compounds (2, 4, and 6–20) were also obtained from this plant part.
The chemical structures of 1, 3, and 5 were determined by the interpretation of spectroscopic data.
The absolute structure of the new compound 1 was established
from experimental and calculated electronic circular dichroism spectra.
This is the first study to determine the absolute configuration of
a 3-hydroxycoumaronochromone derivative. The potential anti-inflammatory
activity of the 20 isolates obtained was evaluated by measuring their
inhibitory effects on nitric oxide production in lipopolysaccharide-stimulated
RAW 264.7 macrophages. Among the isolates, seven compounds (1, 3, 6–8, 15, and 20) showed substantial inhibition of
nitric oxide production in RAW 264.7 cells, with the most active being
compound 1 (IC50 value of 0.38 ± 0.04
μM).