Glaulactams A–C, daphniphyllum alkaloids from Daphniphyllum glaucescens

• Published in: Scientific reports Vol. 8; no. 1; pp. 15417 - 9
• Main Authors: Chao, Chih-Hua, Cheng, Ju-Chien, Gonçalves, Théo P., Huang, Kuo-Wei, Lin, Chi-Chien, Huang, Hui-Chi, Hwang, Syh-Yuan, Wu, Yang-Chang
• Format: Journal Article
• Language: English
• Published: London Nature Publishing Group UK 18.10.2018; Nature Publishing Group
• Subjects: 119/118; 140/131; 631/1647/2258/878/1263; 631/92/349; Alkaloids; 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; Carbon; Chromatography; Chromatography, Ion Exchange; Circular Dichroism; Cytokines - metabolism; Daphniphyllum - chemistry; Data processing; Dendritic Cells - drug effects; Dogs; Drug Evaluation, Preclinical; Female; Fingerprinting; Humanities and Social Sciences; Immunosuppression; Influenza A Virus, H1N1 Subtype - drug effects; Influenza A Virus, H1N1 Subtype - physiology; Ion-exchange chromatography; Medical research; Mice; Mice, Inbred C57BL; Molecular Structure; multidisciplinary; Natural products; Nitric Oxide - metabolism; NMR; Nuclear magnetic resonance; Nuclear Magnetic Resonance, Biomolecular; Plant Extracts - chemistry; Plant Leaves - chemistry; R&D; Research & development; Science; Science (multidisciplinary); Virus Replication - drug effects; HMBC Correlations; Daphniphyllum Glaucescens; Medium Pressure Liquid Chromatography (MPLC); High-resolution Electrospray-ionization Mass Spectrometry (HRESIMS); Experimental Electronic Circular Dichroism (ECD)
• ISSN: 2045-2322; 2045-2322
• DOI: 10.1038/s41598-018-33748-6

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.