title: [10]-Gingerdiols as the major metabolites of [10]-gingerol in zebrafish embryos and in humans and their hematopoietic effects in zebrafish embryos.
abstract: Gingerols are a series of major constituents in fresh ginger with the most abundant being [6]-, [8]-, and [10]-gingerols (6G, 8G, and 10G). We previously found that ginger extract and its purified components, especially 10G, potentially stimulate both the primitive and definitive waves of hematopoiesis (blood cell formation) in zebrafish embryos. However, it is still unclear if the metabolites of 10G retain the efficacy of the parent compound toward pathological anemia treatment. In the present study, we first investigated the metabolism of 10G in zebrafish embryos and then explored the biotransformation of 10G in humans. Our results show that 10G was extensively metabolized in both zebrafish embryos and humans, in which two major metabolites, (3S,5S)-[10]-gingerdiol and (3R,5S)-[10]-gingerdiol, were identified by analysis of the MS(n) spectra and comparison to authentic standards that we synthesized. After 24 h of treatment of zebrafish embryos, 10G was mostly converted to its metabolites. Our results clearly indicate that the reductive pathway is a major metabolic route for 10G in both zebrafish embryos and humans. Furthermore, we investigated the hematopoietic effect of 10G and its two metabolites, which show similar hematopoietic effects as 10G in zebrafish embryos.
authors.affiliation: Center for Excellence in Post-Harvest Technologies, North Carolina Agricultural and Technical State University, North Carolina Research Campus, 500 Laureate Way, Kannapolis, North Carolina 28081, United States.
authors.forename: Huadong
authors.initials: H
authors.lastname: Chen
authors.forename: Dominique N
authors.initials: DN
authors.lastname: Soroka
authors.forename: Jamil
authors.initials: J
authors.lastname: Haider
authors.forename: Karine F
authors.initials: KF
authors.lastname: Ferri-Lagneau
authors.forename: TinChung
authors.initials: T
authors.lastname: Leung
authors.forename: Shengmin
authors.initials: S
authors.lastname: Sang
mesh_terms: D000328:Adult; D000818:Animals; D001628:Beverages / Q000032:analysis; D001711:Biotransformation; D002396:Catechols / Q000378:metabolism* / Q000652:urine; D019587:Dietary Supplements; D004625:Embryo, Nonmammalian / Q000378:metabolism*; D005233:Fatty Alcohols / Q000737:chemistry / Q000378:metabolism* / Q000652:urine; D019648:Foods, Specialized / Q000032:analysis; D020939:Zingiber officinale / Q000737:chemistry; D006139:Guaiacol / Q000031:analogs & derivatives / Q000737:chemistry / Q000378:metabolism / Q000652:urine; D006397:Hematinics / Q000378:metabolism* / Q000652:urine; D006410:Hematopoiesis; D006801:Humans; D006900:Hydroxylation; D008297:Male; D015394:Molecular Structure; D009657:North Carolina; D010084:Oxidation-Reduction; D027343:Rhizome / Q000737:chemistry; D013237:Stereoisomerism; D015027:Zebrafish
chemical_list: C000589423:(10)-gingerdiol; D002396:Catechols; D005233:Fatty Alcohols; D006397:Hematinics; D006139:Guaiacol; C007845:gingerol