title: Cholesterol and its derivatives, are the principal steroids isolated from the leech species Hirudo medicinalis.
abstract: Steroids were isolated from the blood-sucking leech species Hirudo medicinalis and their structure was studied with one- and two-dimensional NMR spectroscopy (DQF-COSY and HMQC), GC-MS and ESI-MS spectrometry. Fractionating leech lipid using silicic acid chromatography led to the isolation of cholesterol in an early chloroform-eluted peak. Only minor traces of cholest-4-en-3-one, 4 beta-methylcholesterol, and sitosterol were present. The subsequent acetone-eluted fraction contained steroidtriols that were further purified by preparative TLC; these included cholest-7-ene-3,5,6 triol, cholest-4,7-diene-3,6,15 triol and to a lesser amount, cholestane-3,5,6 triol. A developmental study on cholesterol content in the leech showed that it is also the principal steroid in embryonic and freshly hatched leeches prior to feeding. The abundance of cholesterol, comprising approximately 5% of the total leech lipid, suggests that H. medicinalis, a blood sucking leech, has adapted itself fully to its mammalian host in terms of its steroid content. It remains to be seen whether lipids are directly transferred from the host to the parasite or whether leeches have evolved mechanisms to synthesize their own steroids.
authors.affiliation: Department of Physiology, Michigan State University, East Lansing 48824, USA. Zipser@PSL.MSU.edu
authors.forename: B
authors.initials: B
authors.lastname: Zipser
authors.forename: J J
authors.initials: JJ
authors.lastname: Bradford
authors.forename: R I
authors.initials: RI
authors.lastname: Hollingsworth
mesh_terms: D000818:Animals; D002777:Cholestanols / Q000302:isolation & purification; D002783:Cholestenones / Q000302:isolation & purification; D002784:Cholesterol / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification; D002855:Chromatography, Thin Layer; D008401:Gas Chromatography-Mass Spectrometry; D006888:Hydroxycholesterols / Q000737:chemistry / Q000302:isolation & purification; D007865:Leeches / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D012855:Sitosterols / Q000302:isolation & purification
chemical_list: D002777:Cholestanols; D002783:Cholestenones; D006888:Hydroxycholesterols; D012855:Sitosterols; C115804:cholest-4,7-diene-3,5,15 triol; C115803:cholest-7-ene-3,5,6 triol; C000474:cholestane-3,5,6-triol; C025473:gamma-sitosterol; C000475:cholest-4-en-3-one; D002784:Cholesterol