title: Synthesis of a new [6]-gingerol analogue and its protective effect with respect to the development of metabolic syndrome in mice fed a high-fat diet.
abstract: To determine the effects of a [6]-gingerol analogue (6G), a major chemical component of the ginger rhizome, and its stable analogue after digestion in simulated gastric fluid, aza-[6]-gingerol (A6G), on diet-induced body fat accumulation, we synthesized 6G and A6G. Mice were fed either a control regular rodent chow, a high-fat diet (HFD), or a HFD supplemented with 6G and A6G. Magnetic resonance imaging adiposity parameters of the 6G- and A6G-treated mice were compared with those of control mice. Supplementation with 6G and A6G significantly reduced body weight gain, fat accumulation, and circulating levels of insulin and leptin. The mRNA levels of sterol regulatory element-binding protein 1c (SREBP-1c) and acetyl-CoA carboxylase 1 in the liver were significantly lower in mice fed A6G than in HFD control mice. Our findings indicate that A6G, rather than 6G, enhances energy metabolism and reduces the extent of lipogenesis by downregulating SREBP-1c and its related molecules, which leads to the suppression of body fat accumulation.
authors.affiliation: Department of Applied Chemistry, School of Advanced Science and Engineering, Waseda University, Shinjuku-ku, Tokyo, Japan. okamoto@aoni.waseda.jp
authors.forename: Mayumi
authors.initials: M
authors.lastname: Okamoto
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Irii
authors.forename: Yu
authors.initials: Y
authors.lastname: Tahara
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Ishii
authors.forename: Akiko
authors.initials: A
authors.lastname: Hirao
authors.forename: Haruhide
authors.initials: H
authors.lastname: Udagawa
authors.forename: Masaki
authors.initials: M
authors.lastname: Hiramoto
authors.forename: Kazuki
authors.initials: K
authors.lastname: Yasuda
authors.forename: Atsuo
authors.initials: A
authors.lastname: Takanishi
authors.forename: Shigenobu
authors.initials: S
authors.lastname: Shibata
authors.forename: Isao
authors.initials: I
authors.lastname: Shimizu
mesh_terms: D000103:Acetyl-CoA Carboxylase / Q000235:genetics / Q000378:metabolism; D052242:Adiponectin / Q000235:genetics / Q000378:metabolism; D000273:Adipose Tissue / Q000187:drug effects / Q000378:metabolism / Q000473:pathology; D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000818:Animals; D019440:Anti-Obesity Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001786:Blood Glucose / Q000032:analysis; D001835:Body Weight / Q000187:drug effects; D002396:Catechols / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004041:Dietary Fats / Q000008:administration & dosage*; D004734:Energy Metabolism / Q000187:drug effects; D005233:Fatty Alcohols / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D005951:Glucose Tolerance Test; D006139:Guaiacol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D007328:Insulin / Q000378:metabolism; D020738:Leptin / Q000235:genetics / Q000378:metabolism; D050155:Lipogenesis / Q000187:drug effects; D008099:Liver / Q000187:drug effects / Q000378:metabolism; D008297:Male; D024821:Metabolic Syndrome / Q000209:etiology / Q000378:metabolism / Q000517:prevention & control*; D051379:Mice; D008813:Mice, Inbred ICR; D012333:RNA, Messenger / Q000378:metabolism; D051780:Sterol Regulatory Element Binding Protein 1 / Q000235:genetics / Q000378:metabolism
chemical_list: D052242:Adiponectin; D000577:Amides; D019440:Anti-Obesity Agents; D001786:Blood Glucose; D002396:Catechols; D004041:Dietary Fats; D005233:Fatty Alcohols; D007328:Insulin; D020738:Leptin; D012333:RNA, Messenger; C497388:Srebf1 protein, mouse; D051780:Sterol Regulatory Element Binding Protein 1; C562236:aza-(6)-gingerol; D006139:Guaiacol; C007845:gingerol; D000103:Acetyl-CoA Carboxylase