Anti-inflammatory butanolides and lignanoids from the root of Machilus zuihoensis var. mushaensis

Shuen-Shin Yang; Ho-Cheng Wu; Tsong-Long Hwang; Ih-Sheng Chen; Chien-Jung Lin; Ming-Jen Cheng; Hsun-Shuo Chang

doi:10.1016/j.bioorg.2022.106166

Anti-inflammatory butanolides and lignanoids from the root of Machilus zuihoensis var. mushaensis

Bioorg Chem. 2022 Dec:129:106166. doi: 10.1016/j.bioorg.2022.106166. Epub 2022 Sep 22.

Authors

Shuen-Shin Yang¹, Ho-Cheng Wu², Tsong-Long Hwang³, Ih-Sheng Chen¹, Chien-Jung Lin⁴, Ming-Jen Cheng⁵, Hsun-Shuo Chang⁶

Affiliations

¹ School of Pharmacy, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan.
² School of Pharmacy, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan; Graduate Institute of Pharmacognosy, College of Pharmacy, Taipei Medical University, Taipei 110, Taiwan.
³ Graduate Institute of Natural Products, College of Medicine, Chang Gung University, Taoyuan 333, Taiwan; Research Center for Chinese Herbal Medicine, Graduate Institute of Health Industry Technology, College of Human Ecology, Chang Gung University of Science and Technology, Taoyuan 333, Taiwan; Department of Anesthesiology, Chang Gung Memorial Hospital, Taoyuan 333, Taiwan.
⁴ Council of Agriculture, Taiwan Forestry Research Institute, Taipei 100, Taiwan.
⁵ Bioresource Collection and Research Center, Food Industry Research and Development Institute, Hsinchu 300, Taiwan; Department of Life Science, Fu Jen Catholic University, New Taipei City 242, Taiwan.
⁶ School of Pharmacy, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan; Department of Medical Research, Kaohsiung Medical University Hospital, Kaohsiung 807, Taiwan; Drug Development and Value Creation Research Center, Kaohsiung Medical University, Kaohsiung 807, Taiwan. Electronic address: hschang@kmu.edu.tw.

PMID: 36191429
DOI: 10.1016/j.bioorg.2022.106166

Abstract

From the anti-inflammatory screening of Formosan Lauraceous plants, the methanolic extract of the root of Machilus zuihoensis var. mushaensis stood out for its potent inhibitory activity toward superoxide anion and elastase release in human neutrophils. Bioassay-guided fractionation of the root of M. zuihoensis var. mushaensis led to eight new compounds, including two butanolides (1-2), five lignanoids (3-7), and one sesquiterpenoid (8), along with 50 known compounds (9-58). Structures of these compounds were elucidated by NMR, UV, IR, CD, and MS analyses. Thirty-two isolates were evaluated for their anti-inflammatory activity. Among them, 9, 20, 27, 28, 30, 31, 35, and 40 exhibited significant superoxide anion generation inhibition selectively (IC₅₀ value < 7.4 μM), 15 and 19 showed selective inhibition toward elastase release (IC₅₀ value < 8.0 μM). Moreover, 3, 16, 21, and 22 simultaneously displayed superoxide anion generation and elastase release inhibition. It is worth mentioning that 21 and 22 showed more potent inhibitory activities (IC₅₀ < 1.0 μM) on superoxide anion than the positive control, LY294002. Further quantitative HPLC analysis indicated the content of 21 and 22 were 0.90 and 3.04 mg/g (w/w) in the ethyl-acetate layer of the root of M. zuihoensis var. mushaensis, respectively. Altogether, M. zuihoensis var. mushaensis revealed a potential for developing the botanical new drug against inflammation-related disease.

Keywords: Anti-inflammation; Butanolide; Lauraceae; Lignanoid; Machilus zuihoensis var. mushaensis.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Anti-Inflammatory Agents / pharmacology
Humans
Lauraceae* / chemistry
Pancreatic Elastase
Superoxides*

Substances

Superoxides
Anti-Inflammatory Agents
Pancreatic Elastase