Glaulactams A-C, daphniphyllum alkaloids from Daphniphyllum glaucescens

Chih-Hua Chao; Ju-Chien Cheng; Théo P Gonçalves; Kuo-Wei Huang; Chi-Chien Lin; Hui-Chi Huang; Syh-Yuan Hwang; Yang-Chang Wu

doi:10.1038/s41598-018-33748-6

Glaulactams A-C, daphniphyllum alkaloids from Daphniphyllum glaucescens

Sci Rep. 2018 Oct 18;8(1):15417. doi: 10.1038/s41598-018-33748-6.

Authors

Chih-Hua Chao^{1

2}, Ju-Chien Cheng³, Théo P Gonçalves⁴, Kuo-Wei Huang⁴, Chi-Chien Lin^{5

6}, Hui-Chi Huang⁷, Syh-Yuan Hwang⁸, Yang-Chang Wu^{9

10

11}

Affiliations

¹ School of Pharmacy, China Medical University, Taichung, 404, Taiwan. [email protected].
² Chinese Medicine Research and Development Center and Department of Medical Research, China Medical University Hospital, Taichung, 404, Taiwan. [email protected].
³ Department of Medical Laboratory Science and Biotechnology, China Medical University, Taichung, 404, Taiwan.
⁴ Division of Physical Sciences and Engineering and KAUST Catalysis Center, King Abdullah University of Science and Technology, Thuwal, 23955-6900, Saudi Arabia.
⁵ Institute of Biomedical Science, National Chung-Hsing University, Taichung, 402, Taiwan.
⁶ Department of Health and Nutrition, Asia University, Taichung, 413, Taiwan.
⁷ Department of Chinese Pharmaceutical Sciences and Chinese Medicine Resources, China Medical University, Taichung, 404, Taiwan.
⁸ Endemic Species Research Institute, Council of Agriculture, Nantou, 552, Taiwan.
⁹ Chinese Medicine Research and Development Center and Department of Medical Research, China Medical University Hospital, Taichung, 404, Taiwan. [email protected].
¹⁰ Graduate Institute of Natural Products and Research Center for Natural Products & Drug Development, Kaohsiung Medical University, Kaohsiung, 807, Taiwan. [email protected].
¹¹ Department of Medical Research, Kaohsiung Medical University Hospital, Kaohsiung, 807, Taiwan. [email protected].

Abstract

Glaulactams A-C (1-3), which possess a novel skeleton, as well as the known compound daphmanidin B (4), were isolated from the leaves of Daphniphyllum glaucescens and separated using ion-exchange chromatography aided by NMR fingerprinting. Their structures, including their absolute configurations, were elucidated by spectroscopic analyses and time-dependent density-functional-theory-calculated electronic circular dichroism spectra; the data were subsequently analyzed to gain insight into the respective biogenetic relationships between the isolates, which exhibited anti-H1N1 and immunosuppressive activities.

Publication types

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

MeSH terms

Alkaloids / chemistry
Alkaloids / isolation & purification*
Alkaloids / pharmacology
Alkaloids / therapeutic use
Animals
Antiviral Agents / chemistry
Antiviral Agents / isolation & purification
Antiviral Agents / pharmacology
Antiviral Agents / therapeutic use
Chromatography, Ion Exchange
Circular Dichroism
Cytokines / metabolism
Daphniphyllum / chemistry*
Dendritic Cells / drug effects
Dogs
Drug Evaluation, Preclinical
Female
Influenza A Virus, H1N1 Subtype / drug effects
Influenza A Virus, H1N1 Subtype / physiology
Mice
Mice, Inbred C57BL
Molecular Structure
Nitric Oxide / metabolism
Nuclear Magnetic Resonance, Biomolecular
Plant Extracts / chemistry
Plant Leaves / chemistry
Virus Replication / drug effects

Substances

Alkaloids
Antiviral Agents
Cytokines
Plant Extracts
Nitric Oxide