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

Mayumi Okamoto, Hiroyuki Irii, Yu Tahara, Hiroyuki Ishii, Akiko Hirao, Haruhide Udagawa, Masaki Hiramoto, Kazuki Yasuda, Atsuo Takanishi, Shigenobu Shibata, Isao Shimizu

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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.

Original languageEnglish
Pages (from-to)6295-6304
Number of pages10
JournalJournal of Medicinal Chemistry
Volume54
Issue number18
DOIs
Publication statusPublished - 2011 Sep 22

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High Fat Diet
Sterol Regulatory Element Binding Protein 1
Adipose Tissue
Rodent Control
Ginger
Acetyl-CoA Carboxylase
Lipogenesis
Rhizome
Adiposity
Leptin
Energy Metabolism
Weight Gain
gingerol
Digestion
Stomach
Down-Regulation
Fats
Body Weight
Magnetic Resonance Imaging
Insulin

ASJC Scopus subject areas

  • Molecular Medicine
  • Drug Discovery

Cite this

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. / Okamoto, Mayumi; Irii, Hiroyuki; Tahara, Yu; Ishii, Hiroyuki; Hirao, Akiko; Udagawa, Haruhide; Hiramoto, Masaki; Yasuda, Kazuki; Takanishi, Atsuo; Shibata, Shigenobu; Shimizu, Isao.

In: Journal of Medicinal Chemistry, Vol. 54, No. 18, 22.09.2011, p. 6295-6304.

Research output: Contribution to journalArticle

Okamoto, Mayumi ; Irii, Hiroyuki ; Tahara, Yu ; Ishii, Hiroyuki ; Hirao, Akiko ; Udagawa, Haruhide ; Hiramoto, Masaki ; Yasuda, Kazuki ; Takanishi, Atsuo ; Shibata, Shigenobu ; Shimizu, Isao. / 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. In: Journal of Medicinal Chemistry. 2011 ; Vol. 54, No. 18. pp. 6295-6304.
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