Phytochemical Investigation and Anti-Inflammatory Activity of the Leaves of Machilus japonica var. kusanoi.

Shiou-Ling Li,Hsun-Shuo Chang,Ho-Cheng Wu,Shuen-Shin Yang,Chu-Hung Lin,Tsong-Long Hwang

doi:10.3390/molecules25184149

Abstract

In a series of anti-inflammatory screenings of lauraceous plants, the methanolic extract of the leaves of Machilus japonica var. kusanoi (Hayata) J.C. Liao showed potent inhibition on both superoxide anion generation and elastase release in human neutrophils. Bioassay-guided fractionation of the leaves of M. japonica var. kusanoi led to the isolation of twenty compounds, including six new butanolides, machinolides A–F (1–6), and fourteen known compounds (7–20). Their structures were characterized by 1D and 2D NMR, UV, IR, CD, and MS data. The absolute configuration of the new compounds were unambiguously confirmed by single-crystal X-ray diffraction analyses (1, 2, and 3) and Mosher’s method (4, 5, and 6). In addition, lignans, (+)-eudesmin (11), (+)-methylpiperitol (12), (+)-pinoresinol (13), and (+)-galbelgin (16) exhibited inhibitory effects on N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLP/CB)-induced superoxide anion generation in human neutrophils with IC50 values of 8.71 ± 0.74 μM, 2.23 ± 0.92 μM, 6.81 ± 1.07 μM, and 7.15 ± 2.26 μM, respectively. The results revealed the anti-inflammatory potentials of Formosan Machilus japonica var. kusanoi.

Highlights

IntroductionIn response to immune stimulation, activated neutrophils generate a series of cytotoxic substances, such as the superoxide anion (O2 − ), a precursor of other ROS, granule proteases, and bioactive lipids
Neutrophils play an important role in the human body against infections [1]
The results proved that the stereochemistry stereochemistry of 1 should be shown as 2R,3S,4S,11R-form in the Oak Ridge thermal ellipsoid plot of 1 should be shown as 2R,3S,4S,11R-form in the Oak Ridge thermal ellipsoid plot program (ORTEP)

Summary

Introduction

In response to immune stimulation, activated neutrophils generate a series of cytotoxic substances, such as the superoxide anion (O2 − ), a precursor of other ROS, granule proteases, and bioactive lipids. The superoxide anion is known to cause damage to cells and tissues, stimulate macrophages, and trigger a cascade of inflammatory pathways [2]. Neutrophil elastase is one of the serine proteases stored in large amounts in neutrophil granules and is involved in the nonoxidative pathway of the intracellular. Molecules 2020, 25, 4149 and extracellular immune response [3]. Neutrophil elastase is stimulated by neutrophils and causes the destruction of tissue in chronic inflammatory disease [2]. The persistent overexpression of neutrophils is involved in various conditions, such as rheumatoid arthritis, asthma, psoriasis, and ischemic heart disease

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