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Molecules 2019, 24(1), 197; https://doi.org/10.3390/molecules24010197

Separation of Five Iridoid Glycosides from Lonicerae Japonicae Flos Using High-Speed Counter-Current Chromatography and Their Anti-Inflammatory and Antibacterial Activities

1,†
,
1,2,†
,
1
,
1
,
2,* and 1,*
1
Key Laboratory of Natural Pharmaceutical Chemistry, Shandong University of Traditional Chinese Medicine, Jinan 250200, China
2
School of Biological Science and Technology, University of Jinan, Jinan 250022, China
These authors contributed equally to this work.
*
Authors to whom correspondence should be addressed.
Received: 12 December 2018 / Revised: 27 December 2018 / Accepted: 28 December 2018 / Published: 7 January 2019
(This article belongs to the Section Natural Products Chemistry)
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Abstract

A high-speed counter-current chromatography (HSCCC) method, using a two-phase solvent system composed of ethyl acetate/n-butanol/methanol/water (5:1:1:5, v/v/v/v), was successfully established to separate the five iridoid glucosides 7-O-ethyl sweroside (1), secologanin dimethylacetal (2), adinoside F (3), (7R)-secologain n-butyl methyl acetal (4) and adinoside G (5) from Lonicerae Japonicae Flos. Their purities were 96.8%, 98.5%, 93.3%, 98.0% and 99.9%, respectively. All the iridoid glucosides were identified by HR-ESI-MS, 1D and 2D NMR. Compounds 3 and 5 are new iridoid glucosides. The anti-inflammatory tests showed that compounds 15 all expressed moderate inhibitory effects on β-glucuronidase release in rat polymorphonuclear leukocytes (PMNs) induced by platelet-activating factor (PAF) with IC50 values ranging from 4.52 to 6.50 µM, while the antibacterial assays demonstrated that all the compounds displayed mild inhibitory activities against Staphylococcus aureus ATCC 25923 with MIC values ranging from 13.7 to 26.0 µg/mL. View Full-Text
Keywords: Lonicerae Japonicae Flos; high-speed counter-current chromatography; iridoid glucosides; anti-inflammatory activity; antibacterial activity Lonicerae Japonicae Flos; high-speed counter-current chromatography; iridoid glucosides; anti-inflammatory activity; antibacterial activity
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Yang, R.; Fang, L.; Li, J.; Zhao, Z.; Zhang, H.; Zhang, Y. Separation of Five Iridoid Glycosides from Lonicerae Japonicae Flos Using High-Speed Counter-Current Chromatography and Their Anti-Inflammatory and Antibacterial Activities. Molecules 2019, 24, 197.

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