Homosecoiridoids from the Flower Buds of Lonicera japonica

Homosecoiridoids (1–15) were isolated from the flower buds of Lonicera japonica. Compounds 1–4, designated as loniphenyruviridosides A–D, possess unprecedented skeletons featuring phenylpyruvic acid derived moieties coupled with an iridoid or a secoiridoid nucleus. Compounds 5–15 (lonijaposides D–N)...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2011-10, Vol.74 (10), p.2151-2160
Main Authors: Yu, Yang, Song, Weixia, Zhu, Chenggen, Lin, Sheng, Zhao, Feng, Wu, Xiuli, Yue, Zhenggang, Liu, Bo, Wang, Sujuan, Yuan, Shaopeng, Hou, Qi, Shi, Jiangong
Format: Article
Language:English
Subjects:
Animals
Biological and medical sciences
Crystallography, X-Ray
Flowers - chemistry
General pharmacology
Glucuronidase - antagonists & inhibitors
Iridoids - blood
Iridoids - chemistry
Iridoids - isolation & purification
Iridoids - pharmacology
Lonicera - chemistry
Medical sciences
Molecular Structure
Neutrophils - drug effects
Neutrophils - metabolism
Nuclear Magnetic Resonance, Biomolecular
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
Platelet Activating Factor - pharmacology
Rats
STAT3 Transcription Factor - antagonists & inhibitors
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Summary:Homosecoiridoids (1–15) were isolated from the flower buds of Lonicera japonica. Compounds 1–4, designated as loniphenyruviridosides A–D, possess unprecedented skeletons featuring phenylpyruvic acid derived moieties coupled with an iridoid or a secoiridoid nucleus. Compounds 5–15 (lonijaposides D–N) are additional examples of the unusual pyridinium alkaloid-coupled secoiridoids (lonijaposides A–C). The validity of the CD data to determine the configuration of the secoiridoid derivatives is discussed on the basis of detailed CD data analysis and semisynthesis of 2 and 3 with the co-occurring secologanic acid. The configuration of secologanic acid was determined by a single-crystal X-ray crystallographic analysis using anomalous scattering of Cu Kα radiation. Biosynthetic pathways of the homosecoiridoids were postulated. Compounds 1–4 inhibited STAT-3 activity of HELF cells, and lonijaposides F (7), H (9), I (10), and K (12) showed activity against the release of glucuronidase in rat polymorphonuclear leukocytes induced by platelet-activating factor.
ISSN:0163-3864
1520-6025
DOI:10.1021/np2004566