Cytotoxic and anti-inflammatory effects of lignans and diterpenes from Cupressus macrocarpa

Eman Al-Sayed; Tzu-Yi Ke; Tsong-Long Hwang; Shu-Rong Chen; Michal Korinek; Shu-Li Chen; Yuan-Bin Cheng

doi:10.1016/j.bmcl.2020.127127

Cytotoxic and anti-inflammatory effects of lignans and diterpenes from Cupressus macrocarpa

Bioorg Med Chem Lett. 2020 May 15;30(10):127127. doi: 10.1016/j.bmcl.2020.127127. Epub 2020 Mar 20.

Authors

Eman Al-Sayed¹, Tzu-Yi Ke², Tsong-Long Hwang³, Shu-Rong Chen², Michal Korinek⁴, Shu-Li Chen², Yuan-Bin Cheng⁵

Affiliations

¹ Department of Pharmacognosy, Faculty of Pharmacy, Ain-Shams University, Cairo 11566, Egypt.
² Graduate Institute of Natural Products, Center for Natural Product Research and Development, College of Pharmacy, Drug Development and Value Creation Research Center, Kaohsiung Medical University, Kaohsiung 80708, Taiwan.
³ Graduate Institute of Natural Products, College of Medicine, Chang Gung University, Taoyuan 33302, Taiwan; Research Center for Chinese Herbal Medicine, Research Center for Food and Cosmetic Safety, and Graduate Institute of Health Industry Technology, College of Human Ecology, Chang Gung University of Science and Technology, Taoyuan 33302, Taiwan; Department of Anesthesiology, Chang Gung Memorial Hospital, Taoyuan 33302, Taiwan; Chinese Herbal Medicine Research Team, Healthy Aging Research Center, Chang Gung University, Taoyuan 33302, Taiwan.
⁴ Graduate Institute of Natural Products, College of Medicine, Chang Gung University, Taoyuan 33302, Taiwan; Research Center for Chinese Herbal Medicine, Research Center for Food and Cosmetic Safety, and Graduate Institute of Health Industry Technology, College of Human Ecology, Chang Gung University of Science and Technology, Taoyuan 33302, Taiwan; Department of Biotechnology, College of Life Science, Kaohsiung Medical University, Kaohsiung 80708, Taiwan.
⁵ Graduate Institute of Natural Products, Center for Natural Product Research and Development, College of Pharmacy, Drug Development and Value Creation Research Center, Kaohsiung Medical University, Kaohsiung 80708, Taiwan; Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 80424, Taiwan; Department of Medical Research, Kaohsiung Medical University Hospital, Kaohsiung 80708, Taiwan. Electronic address: jmb@kmu.edu.tw.

PMID: 32223924
DOI: 10.1016/j.bmcl.2020.127127

Abstract

Cupressus macrocarpa is a windbreak tree and is reported to have various cytotoxic effects. A natural product study on the leaves of C. macrocarpa has yielded ten secondary metabolites, including three new diterpenoids (1-3), four known diterpenoids (4-7), and three known lignans (8-10). The structures of all isolated compounds were elucidated via the interpretation of spectroscopic methods, especially 2D NMR and mass analyses. In the cytotoxic assays, compounds 1-3 and 7-10 showed inhibition effect against HepG2, MDA-MB-231, and A549 cells with IC₅₀ values ranging from 0.004 to 19.9 μg/mL. Moreover, the anti-inflammatory assays revealed that (-)-matairesinol (8) had significant inhibitory activities on superoxide anion generation (IC₅₀ = 2.7 ± 0.3 μM) and elastase release (IC₅₀ = 6.6 ± 0.7 μM).

Keywords: Anti-inflammatory; Cupressus macrocarpa; Cytotoxicity; Diterpenes; Elastase; Lignans; Superoxide anion.

Publication types

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

MeSH terms

Anti-Inflammatory Agents / chemistry*
Anti-Inflammatory Agents / isolation & purification
Anti-Inflammatory Agents / pharmacology
Cell Line, Tumor
Cell Survival / drug effects
Cupressus / chemistry*
Cupressus / metabolism
Diterpenes / chemistry*
Diterpenes / isolation & purification
Diterpenes / pharmacology
Humans
Lignans / chemistry*
Lignans / isolation & purification
Lignans / pharmacology
Magnetic Resonance Spectroscopy
Molecular Conformation
Neutrophils / cytology
Neutrophils / drug effects
Neutrophils / metabolism
Pancreatic Elastase / metabolism
Plant Leaves / chemistry
Plant Leaves / metabolism
Superoxides / metabolism

Substances

Anti-Inflammatory Agents
Diterpenes
Lignans
Superoxides
Pancreatic Elastase