title: Homosecoiridoid alkaloids with amino acid units from the flower buds of Lonicera japonica.
abstract: Nine new homosecoiridoid alkaloids, named lonijaposides O-W (1-9), along with 19 known compounds, were isolated from an aqueous extract of the flower buds of Lonicera japonica. Their structures and absolute configurations were determined by spectroscopic data analysis and chemical methods. Lonijaposides O-W have structural features that involve amino acid units sharing the N atom with a pyridinium (1-5) or nicotinic acid (6-9) moiety. The absolute configurations of the amino acid units were determined by oxidation of each pyridinium ring moiety with potassium ferricyanide, hydrolysis of the oxidation product, and Marfey's analysis of the hydrolysate. This procedure was validated by oxidizing and hydrolyzing synthetic model compounds. The phenylalanine units in compounds 4, 5, and 9 have the d-configuration, and the other amino acid units in 1-3 and 6-8 possess the l-configuration. Compounds 1, 4, 6, and 9 and the known compounds 3,4-di-O-caffeoylquinic acid, 3,5-di-O-caffeoylquinic acid, and 5'-O-methyladenosine exhibited antiviral activity against the influenza virus A/Hanfang/359/95 (H3N2) with IC50 values of 3.4-11.6 μM, and 4 inhibited Coxsackie virus B3 replication with an IC50 value of 12.3 μM.
authors.affiliation: State Key Laboratory of Bioactive Substance and Function of Natural Medicines, 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: Chenggen
authors.initials: C
authors.lastname: Zhu
authors.forename: Sujuan
authors.initials: S
authors.lastname: Wang
authors.forename: Weixia
authors.initials: W
authors.lastname: Song
authors.forename: Yongchun
authors.initials: Y
authors.lastname: Yang
authors.forename: Jiangong
authors.initials: J
authors.lastname: Shi
mesh_terms: D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000596:Amino Acids / Q000032:analysis; D000998:Antiviral Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002726:Chlorogenic Acid / Q000031:analogs & derivatives / Q000494:pharmacology; D029822:Enterovirus B, Human / Q000187:drug effects; D035264:Flowers / Q000737:chemistry; D015497:HIV-1 / Q000187:drug effects; D053122:Influenza A Virus, H3N2 Subtype / Q000187:drug effects*; D020128:Inhibitory Concentration 50; D039823:Iridoids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D031239:Lonicera / Q000737:chemistry*; D015394:Molecular Structure; D018139:Simplexvirus / Q000187:drug effects
chemical_list: D000470:Alkaloids; D000596:Amino Acids; D000998:Antiviral Agents; D039823:Iridoids; D002726:Chlorogenic Acid; C478100:3,4-di-O-caffeoylquinic acid