Anti-inflammatory alkaloids from the root bark of Hernandia nymphaeifolia

Yu-Wei Lai; Shih-Wei Wang; Ya-Yun Hu; Tsong-Long Hwang; Ming-Jen Cheng; Ih-Sheng Chen; Ping-Jyun Sung; Jih-Jung Chen

doi:10.1016/j.phytochem.2020.112326

Anti-inflammatory alkaloids from the root bark of Hernandia nymphaeifolia

Phytochemistry. 2020 May:173:112326. doi: 10.1016/j.phytochem.2020.112326. Epub 2020 Feb 28.

Authors

Yu-Wei Lai¹, Shih-Wei Wang², Ya-Yun Hu³, Tsong-Long Hwang⁴, Ming-Jen Cheng⁵, Ih-Sheng Chen⁶, Ping-Jyun Sung⁷, Jih-Jung Chen⁸

Affiliations

¹ Division of Urology, Taipei City Hospital Renai Branch, Taipei, Taiwan; Department of Urology, School of Medicine, National Yang-Ming University, Taipei, Taiwan.
² Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung, Taiwan; Department of Medicine, Mackay Medical College, New Taipei City, Taiwan.
³ Graduate Institute of Pharmaceutical Technology, Tajen University, Pingtung, Taiwan.
⁴ Graduate Institute of Natural Products, School of Traditional Chinese Medicine, College of Medicine, Chang Gung University, Taoyuan, Taiwan; Research Center for Chinese Herbal Medicine, Research Center for Food and Cosmetic Safety, Graduate Institute of Health Industry Technology, College of Human Ecology, Chang Gung University of Science and Technology, Taoyuan, Taiwan.
⁵ Bioresource Collection and Research Center (BCRC), Food Industry Research and Development Institute (FIRDI), Hsinchu, Taiwan.
⁶ School of Pharmacy, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan.
⁷ National Museum of Marine Biology and Aquarium, Pingtung, Taiwan; Department of Medicine, Mackay Medical College, New Taipei City, Taiwan.
⁸ Faculty of Pharmacy, School of Pharmaceutical Sciences, National Yang-Ming University, Taipei, Taiwan; Department of Medical Research, China Medical University Hospital, China Medical University, Taichung, Taiwan. Electronic address: chenjj@ym.edu.tw.

PMID: 32120117
DOI: 10.1016/j.phytochem.2020.112326

Abstract

Four undescribed alkaloids, 7-ethoxy-6-methoxy-2-methylisoquinolin-1(2H)-one, 7,8-dihydroxy-6-methoxy-2-methylisoquinolin-1(2H)-one, N-formylhernagine, and 5,6-dihydroxy-N-methylphthalimide, were obtained from the root bark of Hernanadia nymphaeifolia, along with fourteen known compounds. The structures of these compounds were determined through spectroscopic and MS analyses. 7,8-Dihydroxy-6-methoxy-2-methylisoquinolin-1(2H)-one, N-formylhernagine, 5,6-dihydroxy-N-methylphthalimide, oxohernagine, hernandonine, and N-trans-feruloylmethoxytyramine inhibited the superoxide anion (O₂^-) production (IC₅₀ values ≤ 6.23 μg/mL) by neutrophils stimulated with formyl-L-methionyl-L-leuckyl-L-phenyl-alanine/cytochalasin B (fMLP/CB). Furthermore, 7,8-dihydroxy-6-methoxy-2-methylisoquinolin-1(2H)-one, N-formylhernagine, 5,6-dihydroxy-N-methylphthalimide, oxohernagine, and N-trans-feruloylmethoxytyramine inhibited fMLP/CB-induced elastase release with IC₅₀ values ≤ 7.41 μg/mL. In addition, 7,8-dihydroxy-6-methoxy-2-methylisoquinolin-1(2H)-one, N-formylhernagine, oxohernagine, and N-trans-feruloylmethoxytyramine showed potent inhibition with IC₅₀ values ≤ 28.55 μM, against lipopolysaccharide (LPS)-induced nitric oxide (NO) generation.

Keywords: Alkaloid; Anti-inflammatory activity; Hernanadia nymphaeifolia; Hernandiaceae; Root bark; Structure elucidation.

MeSH terms

Alkaloids*
Anti-Inflammatory Agents
Hernandiaceae*
N-Formylmethionine Leucyl-Phenylalanine
Neutrophils
Pancreatic Elastase
Plant Bark
Superoxides

Substances

Alkaloids
Anti-Inflammatory Agents
Superoxides
N-Formylmethionine Leucyl-Phenylalanine
Pancreatic Elastase