Synthesis and Biological Properties of Benzo-Annulated Rutaecarpines

Hong, Young Hwan; Lee, Woojin; Lee, Seung Ho; Son, Jong Keun; Kim, Hye Lin; Nam, Jung Min; Kwon, Young Joo; Jahng, Yurngdong

doi:10.1248/bpb.33.1704

Cited by 16 publications

(7 citation statements)

References 31 publications

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“…Due to the fact that the DNA gyrase is also involved in gene transcription, this indicates a competition with each other for the RNA synthesis, as the point of application (Tomioka et al 2002). However, the tested compounds in the present study do not inhibit DNA gyrase (Xu et al 2006;Hong et al 2010). No antagonism or synergism could be observed for combinations of 1, 2 or 3 with first-line anti-TB drugs isoniazid and rifampicin.…”

Section: Discussioncontrasting

confidence: 56%

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Antagonistic effects of indoloquinazoline alkaloids on antimycobacterial activity of evocarpine

et al. 2015

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Section: Discussioncontrasting

confidence: 56%

“…; Hong et al . ). No antagonism or synergism could be observed for combinations of 1 , 2 or 3 with first‐line anti‐TB drugs isoniazid and rifampicin.…”

Section: Discussionmentioning

confidence: 97%

Antagonistic effects of indoloquinazoline alkaloids on antimycobacterial activity of evocarpine

et al. 2015

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“…Structural modifications of RUT were designed to enhance its biological activities. However, increased cytotoxicity hampers their application in vascular disorders [ 23 , 26 , 30 ]. F-RUT, a novel analog synthesized in this study with very low cytotoxicity showed anti-inflammatory activity and migration/invasion-suppressive activities that are beneficial in reducing side effects when used for pharmaceutics.…”

Section: Discussionmentioning

confidence: 99%

Synthetic Fluororutaecarpine Inhibits Inflammatory Stimuli and Activates Endothelial Transient Receptor Potential Vanilloid-Type 1

Lee

Rau

et al. 2017

Molecules

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The natural product, rutaecarpine (RUT), is the main effective component of Evodia rutaecarpa which is a widely used traditional Chinese medicine. It has vasodilation, anticoagulation, and anti-inflammatory activities. However, further therapeutic applications are limited by its cytotoxicity. Thus, a derivative of RUT, 10-fluoro-2-methoxyrutaecarpine (F-RUT), was designed and synthesized that showed no cytotoxicity toward RAW264.7 macrophages at 20 μM. In an anti-inflammation experiment, it inhibited the production of nitric oxide (NO) and tumor necrosis factor (TNF)-α in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages; cyclooxygenase (COX)-2 and inducible NO synthase (iNOS) induced by LPS were also downregulated. After 24 h of treatment, F-RUT significantly inhibited cell migration and invasion of ovarian A2780 cells. Furthermore, F-RUT promoted expressions of transient receptor potential vanilloid type 1 (TRPV1) and endothelial (e)NOS in human aortic endothelial cells, and predominantly reduced the inflammation in ovalbumin/alum-challenged mice. These results suggest that the novel synthetic F-RUT exerts activities against inflammation and vasodilation, while displaying less toxicity than its lead compound.

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“…Structural modifications of RUT and EVO were designed to enhance their biological activities. However, increased cytotoxicity hampers their application to vascular disorders [20, 33]. Br-RUT, a novel analogue synthesized in this study, had very low cytotoxicity and showed anti-inflammatory and migration/invasion-suppression activities that were beneficial with reduced side effects, so it has the potential to be developed for pharmaceutical applications.…”

Section: Discussionmentioning

confidence: 99%

Low-Cytotoxic Synthetic Bromorutaecarpine Exhibits Anti-Inflammation and Activation of Transient Receptor Potential Vanilloid Type 1 Activities

Lee

Rau

et al. 2013

BioMed Research International

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Rutaecarpine (RUT), the major bioactive ingredient isolated from the Chinese herb Evodia rutaecarpa, possesses a wide spectrum of biological activities, including anti-inflammation and preventing cardiovascular diseases. However, its high cytotoxicity hampers pharmaceutical development. We designed and synthesized a derivative of RUT, bromo-dimethoxyrutaecarpine (Br-RUT), which showed no cytotoxicity at 20 μM. Br-RUT suppressed nitric oxide (NO) production and tumor necrosis factor-α release in concentration-dependent (0~20 μM) manners in lipopolysaccharide (LPS)-treated RAW 264.7 macrophages; protein levels of inducible NO synthase (iNOS) and cyclooxygenase-2 induced by LPS were downregulated. Br-RUT inhibited cell migration and invasion of ovarian carcinoma A2780 cells with 0~48 h of treatment. Furthermore, Br-RUT enhanced the expression of transient receptor potential vanilloid type 1 and activated endothelial NOS in human aortic endothelial cells. These results suggest that the synthetic Br-RUT possesses very low cytotoxicity but retains its activities against inflammation and vasodilation that could be beneficial for cardiovascular disease therapeutics.

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Synthesis and Biological Properties of Benzo-Annulated Rutaecarpines

Cited by 16 publications

References 31 publications

Antagonistic effects of indoloquinazoline alkaloids on antimycobacterial activity of evocarpine

Antagonistic effects of indoloquinazoline alkaloids on antimycobacterial activity of evocarpine

Synthetic Fluororutaecarpine Inhibits Inflammatory Stimuli and Activates Endothelial Transient Receptor Potential Vanilloid-Type 1

Low-Cytotoxic Synthetic Bromorutaecarpine Exhibits Anti-Inflammation and Activation of Transient Receptor Potential Vanilloid Type 1 Activities

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