title: Parvifloranines A and B, two 11-carbon alkaloids from Geijera parviflora.
abstract: Two novel alkaloids (parvifloranines A and B), possessing an unusual 11-carbon skeleton linked with amino acids, were isolated from Geijera parviflora, an endemic Australian Rutaceae. Their structures were elucidated by extensive spectroscopic measurements including 2D NMR analyses. Parvifloranine A was found to be a mixture of two enantiomers, (S)-1 and (R)-1, in a ratio of 1:4, based on their separation using a chiral column. Parvifloranine B is also believed to be a mixture of enantiomers. Proposed biosynthetic pathways are discussed. Parvifloranine A inhibited the synthesis of nitric oxide in LPS-stimulated RAW 264.7 macrophages with an IC50 value of 23.4 μM.
authors.affiliation: Southern Cross Plant Science, Southern Cross University, PO Box 157, Lismore NSW 2480, Australia. qingyao.shou@scu.edu.au
authors.forename: Qingyao
authors.initials: Q
authors.lastname: Shou
authors.forename: Linda K
authors.initials: LK
authors.lastname: Banbury
authors.forename: Dane E
authors.initials: DE
authors.lastname: Renshaw
authors.forename: Joshua E
authors.initials: JE
authors.lastname: Smith
authors.forename: Xiaoxiang
authors.initials: X
authors.lastname: He
authors.forename: Ashley
authors.initials: A
authors.lastname: Dowell
authors.forename: Hans J
authors.initials: HJ
authors.lastname: Griesser
authors.forename: Michael
authors.initials: M
authors.lastname: Heinrich
authors.forename: Hans
authors.initials: H
authors.lastname: Wohlmuth
mesh_terms: D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000818:Animals; D001315:Australia; D020128:Inhibitory Concentration 50; D008070:Lipopolysaccharides / Q000494:pharmacology; D008264:Macrophages / Q000187:drug effects; D051379:Mice; D015394:Molecular Structure; D009569:Nitric Oxide / Q000096:biosynthesis; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D008070:Lipopolysaccharides; C584069:parvifloranine A; C584070:parvifloranine B; D009569:Nitric Oxide