Leptosperin

Leptosperin
Names
	IUPAC name Methyl 3,5-dimethoxy-4-[3,4,5-trihydroxy-6-[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxybenzoate
Identifiers
3D model (JSmol)	Interactive image; Interactive image;
ChemSpider	30900649;
PubChem CID	90442030;
	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 Key: YSIIUTBDRZJOBX-UHFFFAOYSA-N; 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 O1C(CO)C(O)C(O)C(O)C1OCC(O2)C(O)C(O)C(O)C2Oc3c(OC)cc(C(=O)OC)cc3OC; 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;
	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 Manuka honey. 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 Manuka honey[2] or other Leptospermum species derived honey.[3]

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.
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.
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.

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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.

[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.

[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.