Leptosperin

Leptosperin
Names
	IUPAC name Methyl 3,5-dimethoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxybenzoate
	Other names Methyl 4-{[6-O-(β-D-glucopyranosyl)-β-D-glucopyranosyl]oxy}-3,5-dimethoxybenzoate
Identifiers
CAS Number	486-23-7;
3D model (JSmol)	Interactive image;
ChemSpider	30900649 ;
PubChem CID	102200470;
	InChI InChI=1S/C22H32O15/c1-31-9-4-8(20(30)33-3)5-10(32-2)19(9)37-22-18(29)16(27)14(25)12(36-22)7-34-21-17(28)15(26)13(24)11(6-23)35-21/h4-5,11-18,21-29H,6-7H2,1-3H3/t11-,12-,13-,14-,15+,16+,17-,18-,21-,22+/m1/s1 Key: YSIIUTBDRZJOBX-GISOMYDASA-N ;
	SMILES COc1cc(cc(c1O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O)O)OC)C(=O)OC;
Properties
Chemical formula	C22H32O15
Molar mass	536.483 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Leptosperin (originally but no longer "leptosin") is a bioactive component of Mānuka honey. It is the gentiobiose glycoside of syringic acid methyl ester. It is named for the genus Leptospermum, the shrubs from which bees harvest nectar to make this type of honey.^[1] This bioactive component is the source of antibacterial property of Mānuka honey^[2] or other Leptospermum species derived honey.^[3]

Due to leptosperin being present in Mānuka honey but not other honeys, its presence can be used as a marker to confirm the authenticity of claimed Mānuka products.^[4]

References

^ Kato, Yoji; Umeda, Natsuki; Maeda, Asuna; Matsumoto, Daiki; Kitamoto, Noritoshi; Kikuzaki, Hiroe (4 April 2012). "Identification of a Novel Glycoside, Leptosin, as a Chemical Marker of Manuka Honey". Journal of Agricultural and Food Chemistry. 60 (13): 3418–3423. doi:10.1021/jf300068w. PMID 22409307.
^ Kato, Yoji; Kawai, Masaki; Kawai, Shota; Okano, Yayako; Rokkaku, Natsumi; Ishisaka, Akari; Murota, Kaeko; Nakamura, Toshiyuki; Nakamura, Yoshimasa; Ikushiro, Shinichi (2 October 2019). "Dynamics of the Cellular Metabolism of Leptosperin Found in Manuka Honey". Journal of Agricultural and Food Chemistry. 67 (39): 10853–10862. doi:10.1021/acs.jafc.9b03894. PMID 31496237.
^ Bong, Jessie; Prijic, Gordana; Braggins, Terry J.; Schlothauer, Ralf C.; Stephens, Jonathan M.; Loomes, Kerry M. (1 January 2017). "Leptosperin is a distinct and detectable fluorophore in Leptospermum honeys". Food Chemistry. 214: 102–109. doi:10.1016/j.foodchem.2016.07.018. ISSN 1873-7072. PMID 27507454.
^ Hegazi, Nesrine M.; Elghani, Ghada E. Abd; Farag, Mohamed A. (2022). "The super-food Manuka honey, a comprehensive review of its analysis and authenticity approaches". Journal of Food Science and Technology. 59 (7): 2527–2534. doi:10.1007/s13197-021-05181-7. PMC 9206949. PMID 35734106.

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[1] Kato, Yoji; Umeda, Natsuki; Maeda, Asuna; Matsumoto, Daiki; Kitamoto, Noritoshi; Kikuzaki, Hiroe (4 April 2012). "Identification of a Novel Glycoside, Leptosin, as a Chemical Marker of Manuka Honey". Journal of Agricultural and Food Chemistry. 60 (13): 3418–3423. doi:10.1021/jf300068w. PMID 22409307.

[2] Kato, Yoji; Kawai, Masaki; Kawai, Shota; Okano, Yayako; Rokkaku, Natsumi; Ishisaka, Akari; Murota, Kaeko; Nakamura, Toshiyuki; Nakamura, Yoshimasa; Ikushiro, Shinichi (2 October 2019). "Dynamics of the Cellular Metabolism of Leptosperin Found in Manuka Honey". Journal of Agricultural and Food Chemistry. 67 (39): 10853–10862. doi:10.1021/acs.jafc.9b03894. PMID 31496237.

[3] Bong, Jessie; Prijic, Gordana; Braggins, Terry J.; Schlothauer, Ralf C.; Stephens, Jonathan M.; Loomes, Kerry M. (1 January 2017). "Leptosperin is a distinct and detectable fluorophore in Leptospermum honeys". Food Chemistry. 214: 102–109. doi:10.1016/j.foodchem.2016.07.018. ISSN 1873-7072. PMID 27507454.

[4] Hegazi, Nesrine M.; Elghani, Ghada E. Abd; Farag, Mohamed A. (2022). "The super-food Manuka honey, a comprehensive review of its analysis and authenticity approaches". Journal of Food Science and Technology. 59 (7): 2527–2534. doi:10.1007/s13197-021-05181-7. PMC 9206949. PMID 35734106.

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