title: Isolation, Structural Elucidation, and Synthesis of Lepteridine From Ma̅nuka (Leptospermum scoparium) Honey.
abstract: Ma̅nuka honey, made from the nectar of Leptospermum scoparium, has garnered scientific and economical interest due to its nonperoxide antibacterial activity. Biomarkers for genuine ma̅nuka honey are increasingly in demand due to the presence of counterfeit ma̅nuka honey. This work reports the identification of a compound previously unreported in ma̅nuka honey by HPLC, and determination of the structure of the as 3,6,7-trimethyllumazine using NMR, MS, IR, and UV/vis spectroscopy. This assignment was confirmed by total synthesis. The natural product, renamed lepteridine, was only observed in ma̅nuka honeys and could potentially serve as a biomarker for genuine ma̅nuka honey.
authors.affiliation: School of Chemical Sciences, The University of Auckland , 23 Symonds Street, Auckland 1010, New Zealand.
authors.forename: Benjamin J
authors.initials: BJ
authors.lastname: Daniels
authors.affiliation: Comvita NZ Limited , 23 Wilson South Road, Te Puke 3189, New Zealand.|School of Biological Sciences and Institute for Innovation in Biotechnology, The University of Auckland , 3A Symonds Street, Auckland 1010, New Zealand.
authors.forename: Gordana
authors.initials: G
authors.lastname: Prijic
authors.affiliation: School of Biological Sciences and Institute for Innovation in Biotechnology, The University of Auckland , 3A Symonds Street, Auckland 1010, New Zealand.
authors.forename: Sarah
authors.initials: S
authors.lastname: Meidinger
authors.affiliation: School of Biological Sciences and Institute for Innovation in Biotechnology, The University of Auckland , 3A Symonds Street, Auckland 1010, New Zealand.|Maurice Wilkins Centre for Molecular Biodiscovery, The University of Auckland , 3 Symonds Street, Auckland 1010, New Zealand.
authors.forename: Kerry M
authors.initials: KM
authors.lastname: Loomes
authors.affiliation: Comvita NZ Limited , 23 Wilson South Road, Te Puke 3189, New Zealand.|School of Biological Sciences and Institute for Innovation in Biotechnology, The University of Auckland , 3A Symonds Street, Auckland 1010, New Zealand.
authors.forename: Jonathan M
authors.initials: JM
authors.lastname: Stephens
authors.affiliation: Comvita NZ Limited , 23 Wilson South Road, Te Puke 3189, New Zealand.
authors.forename: Ralf C
authors.initials: RC
authors.lastname: Schlothauer
authors.affiliation: School of Chemical Sciences, The University of Auckland , 23 Symonds Street, Auckland 1010, New Zealand.|Maurice Wilkins Centre for Molecular Biodiscovery, The University of Auckland , 3 Symonds Street, Auckland 1010, New Zealand.
authors.forename: Daniel P
authors.initials: DP
authors.lastname: Furkert
authors.affiliation: School of Chemical Sciences, The University of Auckland , 23 Symonds Street, Auckland 1010, New Zealand.|Maurice Wilkins Centre for Molecular Biodiscovery, The University of Auckland , 3 Symonds Street, Auckland 1010, New Zealand.
authors.forename: Margaret A
authors.initials: MA
authors.lastname: Brimble
mesh_terms: D015415:Biomarkers / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D006722:Honey / Q000032:analysis*; D031649:Leptospermum / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D057048:Plant Nectar / Q000737:chemistry; D011621:Pteridines / Q000737:chemistry* / Q000302:isolation & purification
chemical_list: C000617211:3,6,7-trimethyllumazine; D015415:Biomarkers; D057048:Plant Nectar; D011621:Pteridines
keywords: Leptospermum; biomarker; lepteridine; lumazine; ma̅nuka honey