Chemical constituents and their anti-neuroinflammatory activities from the bark of Taiwan incense cedar, Calocedrus formosana

Ho-Cheng Wu; Yu-Chang Chen; Chin-Lin Hsieh; George Hsiao; Shih-Wei Wang; Ming-Jen Cheng; Che-Yi Chao; Tzong-Huei Lee; Yueh-Hsiung Kuo

doi:10.1016/j.phytochem.2022.113347

Chemical constituents and their anti-neuroinflammatory activities from the bark of Taiwan incense cedar, Calocedrus formosana

Phytochemistry. 2022 Dec:204:113347. doi: 10.1016/j.phytochem.2022.113347. Epub 2022 Aug 24.

Authors

Ho-Cheng Wu¹, Yu-Chang Chen², Chin-Lin Hsieh³, George Hsiao⁴, Shih-Wei Wang⁵, Ming-Jen Cheng⁶, Che-Yi Chao⁷, Tzong-Huei Lee⁸, Yueh-Hsiung Kuo⁹

Affiliations

¹ Graduate Institute of Pharmacognosy, College of Pharmacy, Taipei Medical University, Taipei, 110, Taiwan; Traditional Herbal Medicine Research Center, Taipei Medical University Hospital, Taipei, 110, Taiwan.
² School of Pharmacy, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, 807, Taiwan.
³ Department of Chemistry, National Taiwan University, Taipei, 106, Taiwan; Department of Disaster Management, Taiwan Police College, Taipei, 116, Taiwan.
⁴ Graduate Institute of Medical Sciences, College of Medicine, Taipei Medical University, Taipei, 110, Taiwan.
⁵ Institute of Biomedical Sciences, MacKay Medical College, New Taipei City, 252, Taiwan; Department of Medicine, Mackay Medical College, New Taipei City, 252, Taiwan; Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan.
⁶ Bioresource Collection and Research Center (BCRC), Food Industry Research and Development Institute (FIRDI), Hsinchu, 300, Taiwan.
⁷ Department of Food Nutrition and Health Biotechnology, Asia University, Taichung, 413, Taiwan.
⁸ Institute of Fisheries Science, National Taiwan University, Taipei, 106, Taiwan.
⁹ Department of Chinese Pharmaceutical Sciences and Chinese Medicine Resources, China Medical University, Taichung, 404, Taiwan; Chinese Medicine Research Center, China Medical University, Taichung, 404, Taiwan; Department of Biotechnology, Asia University, Taichung, 413, Taiwan. Electronic address: kuoyh@mail.cmu.edu.tw.

PMID: 36027968
DOI: 10.1016/j.phytochem.2022.113347

Abstract

One undescribed C₄₀ terpenoid, calomacroquinoic acid; four undescribed diterpenes, 5α,6α-epoxy-7α-hydroxyferruginol, 15-ethoxysugiol, 7-methoxy-6,7-secoabieta-8,11,13-triene-6,12-diol, and ethyl 7,8-secoabieta-11,14-dioxo-7-ate; two compounds isolated from Nature for the first time, 6β,7α-dihydroxyferruginol and 12-O-methyltaxochinon; and six known compounds were successfully identified from the bark of Taiwan incense cedar Calocedrus formosana. Structures of all isolates were elucidated by physical data (appearance, ultraviolet, infrared, specific rotation, and X-ray) and spectroscopic data (1D and 2D nuclear magnetic resonance, and high-resolution electron ionization mass spectrometry). The biosynthetic pathway of calomacroquinoic acid is also described in the current study. Nitric oxide production in lipopolysaccharide (LPS)-stimulated BV-2 microglia cells was inhibited by 6,7-dehydroferruginol, 7α,11-dihydroxy-12-methoxy-8,11,13-abietriene, and trans-communic acid. Altogether, the bark of C. formosana possessed several potential natural therapeutics against inflammation-related neuronal diseases.

Keywords: Anti-inflammatory activity; BV-2 microglial cells; Calocedrus formosana; Cupressaceae; Diterpenes; Taiwan incense cedar; Tetraterpene.