- Ajoene, A stable garlic by-product, inhibits high fat diet-induced hepatic steatosis and oxidative injury through LKB1-dependent AMPK activation
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Hepatic steatosis, a hepatic component of metabolic syndrome, is common and may progress to steatohepatitis and cirrhosis. The liver X receptor-α (LXRα)-sterol regulatory element binding protein-1c (SREBP-1c) pathway plays a key role in hepatic steatosis. This study investigated the potential of ajoene, a stable garlic by-product, to inhibit high fat diet (HFD)-induced hepatic steatosis and the underlying mechanism. Ajoene treatment attenuated fat accumulation and induction of lipogenic genes in the liver of HFD-fed mice. Blood biochemical analyses and histopathologic examinations showed that ajoene prevented liver injury with the inhibition of oxidative stress, as evidenced by thiobarbituric acid reactive substances formation and nitrotyrosinylation. Moreover, ajoene treatment inhibited LXRα agonist (T0901317)-mediated SREBP-1c activation, and transactivation of the lipogenic target genes in hepatocytes. Ajoene was found to activate AMP-activated protein kinase (AMPK) via LKB1, responsible for the inhibition of p70 ribosomal S6 kinase-1 (S6K1). The ability of ajoene to repress T0901317-induced SREBP-1c expression was antagonized by inhibition of AMPK or activation of S6K1, supporting the role of these kinases in the antisteatotic effect. Our results demonstrate that ajoene has an effect of activating AMPK through LKB1 and inhibit S6K1 activity, contributing to the prevention of SREBP-1c-mediated hepatic lipogenesis via the inhibition of LXRα activity.
- Han, Chang Yeob,Ki, Sung Hwan,Kim, Young Woo,Noh, Kyoung,Lee, Da Yeon,Kang, Bomi,Ryu, Jae-Ha,Jeon, Raok,Kim, Eun Hyun,Hwang, Se Jin,Kim, Sang Geon
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Read Online
- Short Total Synthesis of Ajoene
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We describe a short total synthesis of ajoene, a major biologically active constituent of garlic. The instability of allicin as the only other known alternative starting material has led to the development of a reliable procedure for the synthesis of ajoene from simple building blocks that is also suitable for upscale operations.
- Silva, Filipa,Khokhar, Shaista S.,Williams, Danielle M.,Saunders, Robert,Evans, Gareth J. S.,Graz, Michael,Wirth, Thomas
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supporting information
p. 12290 - 12293
(2018/09/18)
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- Novel Ajoene derivatives, preparation method thereof, and pharmaceutical composition for use in preventing or treating cancer containing the same as an active ingredient
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The present invention relates to novel ajoene derivatives, to a preparation method thereof, and to a pharmaceutical composition for preventing or treating cancer containing the same as active ingredients, wherein the novel ajoene derivatives according to the present invention were confirmed to inhibit proliferation of human renal cancer cell line (ACHN), breast cancer cell line (MDA-MB-231), colorectal cancer cell line (HCT-15), prostate cancer cell line (PC-3), stomach cancer cell line (NUGC-3) and lung cancer cell line (NCI-H23) to be usefully used as a pharmaceutical composition for preventing or treating cancer containing the same as the active ingredients.COPYRIGHT KIPO 2018
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Paragraph 0204-0205; 0211-0214; 0330-0333; 0335-0338
(2018/03/01)
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- PROCESS FOR THE MANUFACTURE OF AJOENE DERIVATIVES
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The present invention relates to the compound (E,Z)-ajoene of formula (1) for use in treatment of bacterial infections. Another aspect of the present invention is a composition comprising (E,Z)-ajoene of formula (1) and at least one antibiotic. Yet another aspect of the invention relates to a method for manufacturing (E,Z) ajoene of formula (1) wherein the conformation of the internal C=C- bond can be either E or Z or a mixture thereof, said method comprising reacting allicin of formula (3) with an acid in the presence of a solvent to provide (E,Z ajoene) of formula (1) as defined above. Yet another aspect of the invention is (E,Z)-ajoene of formula 1 obtainable by the method described above.
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Page/Page column 19-20
(2012/06/30)
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- PROCESS FOR THE PREPARATION OF AJOENE
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The present invention is directed to a process for the preparation of ajoene, and to ajoene having a relatively high purity which may be obtained by the process. The invention also relates to processes for the preparation of allicin, to a process for freeze concentrating allicin.
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Page/Page column 23-24
(2010/09/18)
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- Substituted ajoenes as novel anti-cancer agents
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A new synthesis of the ajoene pharmacophore core is presented involving the regioselective radical addition of a thiyl radical to a terminal alkyne as the key step. The synthesis allows structural variation of the two end groups on sulfur, and a range of novel derivatives varying the R1 group (sulfoxide end) has been prepared and tested against CT-1 transformed fibroblast cells for anti-cancer activity. The results indicate comparable or even improved activity compared to the parent natural product ajoene isomers. This opens up the way to systematically studying the biology of the ajoene core.
- Hunter, Roger,Kaschula, Catherine H.,Parker, Iqbal M.,Caira, Mino R.,Richards, Philip,Travis, Susan,Taute, Francois,Qwebani, Thozama
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supporting information; experimental part
p. 5277 - 5279
(2009/05/07)
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- (E,Z)-Ajoene: A potent antithrombotic agent from garlic
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A report is presented of the structural characterization and simple synthesis of (E,Z)-ajoene.
- Block,Ahmad,Jain,et al.
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p. 8295 - 8296
(2007/10/02)
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