title: Homosecoiridoids from the flower buds of Lonicera japonica.
abstract: 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.
authors.affiliation: State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Ministry of Education, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, People's Republic of China.
authors.forename: Yang
authors.initials: Y
authors.lastname: Yu
authors.forename: Weixia
authors.initials: W
authors.lastname: Song
authors.forename: Chenggen
authors.initials: C
authors.lastname: Zhu
authors.forename: Sheng
authors.initials: S
authors.lastname: Lin
authors.forename: Feng
authors.initials: F
authors.lastname: Zhao
authors.forename: Xiuli
authors.initials: X
authors.lastname: Wu
authors.forename: Zhenggang
authors.initials: Z
authors.lastname: Yue
authors.forename: Bo
authors.initials: B
authors.lastname: Liu
authors.forename: Sujuan
authors.initials: S
authors.lastname: Wang
authors.forename: Shaopeng
authors.initials: S
authors.lastname: Yuan
authors.forename: Qi
authors.initials: Q
authors.lastname: Hou
authors.forename: Jiangong
authors.initials: J
authors.lastname: Shi
mesh_terms: D000818:Animals; D018360:Crystallography, X-Ray; D035264:Flowers / Q000737:chemistry; D005966:Glucuronidase / Q000037:antagonists & inhibitors*; D039823:Iridoids / Q000097:blood / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D031239:Lonicera / Q000737:chemistry*; D015394:Molecular Structure; D009504:Neutrophils / Q000187:drug effects / Q000378:metabolism; D019906:Nuclear Magnetic Resonance, Biomolecular; D010972:Platelet Activating Factor / Q000494:pharmacology; D051381:Rats; D050796:STAT3 Transcription Factor / Q000037:antagonists & inhibitors
chemical_list: D039823:Iridoids; D010972:Platelet Activating Factor; D050796:STAT3 Transcription Factor; D005966:Glucuronidase