Total synthesis and dual PPARα/γ agonist effects of Amorphastilbol and its synthetic derivatives

Kim, Taejung; Lee, Woojung; Jeong, Kyu Hyuk; Song, Jung Ho; Park, Soon-Hye; Choi, Pilsoon; Kim, Su‐Nam; Lee, Seokjoon; Ham, Jungyeob

doi:10.1016/j.bmcl.2012.04.062

Cited by 20 publications

(5 citation statements)

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“…ACgeranylated resveratrol, the amorphastilbol (Figure 1), is the most active compound extractedf rom the Robinia pseudoacacia var.umbraculifer (RPU). [36] Notably,t he natural( Z)-stilbene combretastatin A-4 (CA-4, Figure 1), isolated from the bark of the African willow tree Combretum caffrum in 1982, shows biological activities. [37,38] CA-4 belongs to ac omplex family of potent Z-stilbenoid depolymerizing agentsa nd it is as trong inhibitor of tubulin polymerization and promotes cancerc ell death.…”

Section: Natural Anticancer Stilbenesmentioning

confidence: 99%

“…Both E and Z isomers showed nanomolarg rowth inhibitioni naNCl-60-celll ine screen. [103] As an extension of this study,aseries of (Z)-quinolyl cyanostilbene analogues that incorporate 3,4,5-trimethoxyphenyl or 3,5-dimethoxyphenyl, were also synthesizeda nd testeda sa nticancer agentsa gainst an extensive panel of humanc ancer cell lines (compound 36,Figure9). These compounds exhibitedt he most potent growth inhibition in the micromolar range,a gainst most of the human cancer cell lines in the panel.…”

Section: Heteroaromatic Stilbenesmentioning

confidence: 99%

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Anticancer Activity of Stilbene‐Based Derivatives

et al. 2017

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Stilbene is an abundant structural scaffold in nature, and stilbene-based compounds have been widely reported for their biological activity. Notably, (E)-resveratrol and its natural stilbene-containing derivatives have been extensively investigated as cardioprotective, potent antioxidant, anti-inflammatory, and anticancer agents. Starting from its potent chemotherapeutic activity against a wide variety of cancers, the stilbene scaffold has been subject to synthetic manipulations with the aim of obtaining new analogues with improved anticancer activity and better bioavailability. Within the last decade, the majority of new synthetic stilbene derivatives have demonstrated significant anticancer activity against a large number of cancer cell lines, depending on the type and position of substituents on the stilbene skeleton. This review focuses on the structure-activity relationship of the key compounds containing a stilbene scaffold and describes how the structural modifications affect their anticancer activity.

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Section: Natural Anticancer Stilbenesmentioning

confidence: 99%

Section: Heteroaromatic Stilbenesmentioning

confidence: 99%

Anticancer Activity of Stilbene‐Based Derivatives

et al. 2017

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“…Recently, there has been a growing interest in the therapeutic use of natural compounds to treat metabolic syndrome as natural compounds may exert their diverse pharmacological properties by interacting with multiple cellular targets. Recently, we reported that amorphastilbol (APH) from Amorpha fruticosa (AF) stimulates transcriptional activities of PPARα/γ (21), and improves glucose and lipid metabolisms in the diabetic db/db mouse model (22). To support the anti-diabetic effects of APH and AF, the present study evaluated their pharmacological properties in a high-fat-diet (HFD) mouse model and their effects on insulin sensitivity.…”

Section: Introductionmentioning

confidence: 99%

Amorphastilbol exerts beneficial effects on glucose and lipid metabolism in mice consuming a high-fat-diet

Lee¹,

Ham²,

Kwon³

et al. 2015

International Journal of Molecular Medicine

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In the present study, the anti-diabetic effects of amorphastilbol (APH) from Amorpha fruticosa (AF) were evaluated in high-fat-diet (HFD) mice. HFD-induced blood glucose and insulin levels are significantly reduced in AF extract or APH treatment groups. HFD-induced weight gain was reduced by AF treatment, which is accompanied by reduction of fat mass and adipocyte size and number in white adipose tissues. Furthermore, total cholesterol and low-density lipoprotein-cholesterol levels are decreased in AF- or APH-treated mice. In addition, AF and APH are able to improve insulin sensitivity through inhibition of protein tyrosine phosphatase 1B, a negative regulator of the insulin-signaling pathway. Taken together, the data suggest that AF has beneficial effects on glucose and lipid metabolism and its pharmacological effects are driven, in part, by its active component, APH. Therefore, AF and APH can be used as potential therapeutic agents against type 2 diabetes and associated metabolic disorders, including obesity, by enhancing glucose and lipid metabolism.

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“…It is characterized by the imperfection of insulin secretion in the pancreas and/or insulin action. [1][2][3] The prevalence of diabetes is rapidly increasing and considered to be one of the major and growing public health problems worldwide. According to the International Diabetic Federation, approximately 246 million people are affected by diabetes and with an anticipated 380 million in 2025.…”

Section: Introductionmentioning

confidence: 99%