1. Comvita Innovation Academic studyDrug discovery/biochemistry Medicinal Chemistry

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3. Unique fluorescent signatures in manuka honey 3 New molecule (Lepteridine) Jessie Bin Ben Gordana Jonathan

4. Manuka honey fluoresce strongly at 270-365 nm excitation-emission (MM1) Leptosperin is a distinct and detectable fluorophore in Leptospermum honeys (Bong et al. Food Chemistry (in press) Source: Kato et al. (2012) PhD supervisors: Dr. Kerry Loomes & Dr. Jonathan Stephens

5. Stable at 37 °C over prolonged storage Leptosperin is a distinct and detectable fluorophore in Leptospermum honeys (Bong et al. Food Chemistry (in press) Leptosperin is nectar-derived PhD supervisors: Dr. Kerry Loomes & Dr. Jonathan Stephens

6. HPLC signal from an unknown compound observed in mānuka honey and nectar Novel compound was isolated via honey sample fractionation and chromatography Chemical identification required to correlate structure, properties and occurrence Lepteridine Unique, quantifiable biomarker for Mānuka honey 6 Ben Daniels. PhD Supervisor: Distinguished Professor Margaret Brimble. Co-supervisors: Daniel Furkert, Kerry Loomes, Jonathan Stephens, Ralf Schlothauer Daniels et al. (2016). Journal of agricultural and food chemistry. DOI: 10.1021/acs.jafc.6b01596, PMID: 27210444

7. Spectroscopic analysis (NMR, MS) enabled tentative structure identification A chemical synthesis was developed, for unambiguous characterisation Pure synthetic material is now available for analysis and assay development Using this method a novel probe was prepared, for reliable Lepteridine quantitation by MS 7 Lepteridine Unique, quantifiable biomarker for Mānuka honey Ben Daniels. PhD Supervisor: Distinguished Professor Margaret Brimble. Co-supervisors: Daniel Furkert, Kerry Loomes, Jonathan Stephens, Ralf Schlothauer

8. Lepteridine is responsible fo the MM2 fluorescent marker in manuka honey Responsible for MM2 fluorescence Concentration: 5-52mg/kg Originates from Leptospermum nectar Present in Australian Leptospermum honeys Stable during prolonged storage at 37 °C

9. Endogenous lepteridine Isotopic lepteridine Absolute quantification of lepteridine using high-performance liquid chromatography–tandem mass spectrometry (LC- MS/MS)

10. 10 Potential to interrogate Manuka authenticity using the MM1 and MM2 fluorescence markers. Absolute quantitation of lepteridine. Could be added to existing MS testing platforms. Applications