Progress in Studies on Rutaecarpine. II.—Synthesis and Structure-Biological Activity Relationships

Son, Jong‐Keun; Chang, Hyeun Wook; Jahng, Yurngdong

doi:10.3390/molecules200610800

Cited by 57 publications

(34 citation statements)

References 71 publications

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“…They are present in several plant families as secondary metabolites, including the Strychnaceae, Apocynaceae, Rutaceae, and Rubiaceae [10]. Rutaecarpine is an indolopyridoquinazolinone alkaloid with diverse biological activities which is one of the main components isolated from the unripe fruits of the traditional Chinese medicine Tetradium ruticarpum (A. Jussieu) T. G. Hartley (synonym: Euodia ruticarpa) ( Figure 1) [12][13][14][15]. The beneficial properties of rutaecarpine have led to a high demand for extracts containing rutaecarpine in the pharmaceutical industry.…”

Section: Introductionmentioning

confidence: 99%

Novel Deep Eutectic Solvent Based on Levulinic Acid and 1,4-Butanediol as an Extraction Media for Bioactive Alkaloid Rutaecarpine

Sun

Liu

et al. 2019

Processes

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Deep eutectic solvents (DESs) are increasingly receiving interest as a new type of green and sustainable alternative to hazardous organic solvents. In this work, a novel DES based on levulinic acid (La) and 1,4-butanediol (Buta) as an extraction media was developed for extracting the bioactive alkaloid rutaecarpine from the unripe fruits of Tetradium ruticarpum. 24 different DESs consisting of choline chloride, betaine, sugar alcohols, organic acids, amides, and sugars were prepared and tailored to test their extraction efficiency. After initial screening, a hydrophilic DES composed of La and Buta with 1:0.5 molar ratio containing 25% water was tailored for the highest extraction efficiency, followed by the optimizations of molar ratio and water content. The interaction between the molecules of La-Buta DES was investigated by nuclear magnetic resonance spectroscopy in order to confirm its deep eutectic supermolecular structure feature. The extraction conditions were optimized by single-factor experiments, including extraction temperature, extraction time, and solid-liquid ratio. The developed La-Buta DES extraction procedure was successfully applied for the analysis of rutaecarpine in Chinese patent medicines containing the unripe fruits of T. ruticarpum. The excellent property of La-Buta DES indicated its potential as a promising green solvent instead of conventional organic solvent for the extraction of rutaecarpine from the unripe fruits of T. ruticarpum, and that it can used as a sustainable and safe extraction media for other applications.

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Section: Introductionmentioning

confidence: 99%

Novel Deep Eutectic Solvent Based on Levulinic Acid and 1,4-Butanediol as an Extraction Media for Bioactive Alkaloid Rutaecarpine

Sun

Liu

et al. 2019

Processes

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“…Previous studies showed that Ru has many biological activities, such as anti-inflammatory, anti-obesity, anti-hypertensive, and it is used for the treatment of cardiovascular diseases [ 24 , 25 , 26 , 27 , 28 ]. The anti-tumor activity of Ru is weak, and its underlying mechanism is unclear [ 29 ]. However, the anti-angiogenic effects of Ru have not been reported.…”

Section: Discussionmentioning

confidence: 99%

Rutacecarpine Inhibits Angiogenesis by Targeting the VEGFR2 and VEGFR2-Mediated Akt/mTOR/p70s6k Signaling Pathway

Zeng

2018

Molecules

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This study aimed to investigate the effect of Ru (Rut) on angiogenesis, and the underlying regulation mechanism of signal transduction. 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) assay, adhesion inhibition experiment, migration inhibition experiment, and chick embryo chorioallantoic membrane (CAM) assays were performed on models of angiogenesis. The potential targets of rutaecarpine (Ru) were reverse screened with Discovery Studio 2017. The interaction between the compound and target were detected by surface plasmon resonance (SPR), enzyme-activity experiment, and Western blot assay. The obtained results confirmed that Ru exhibited modest inhibitory activity against human umbilical vein endothelial cells (HUVECs) (IC50 =16.54 ± 2.4 μM) and remarkable inhibitive effect against the migration and adhesion of HUVECs, as well as significant anti-angiogenesis activities in the CAM assay. The possible targets of vascular endothelial growth factor receptor 2 (VEGFR2) were identified by computer-aided simulation. Results showed a good binding relationship between the ligand and target through molecular docking, and this relationship was confirmed by SPR analysis. Furthermore, enzyme-activity experiment and western blot assay showed that Ru remarkably inhibited the activity of VEGFR2 and blocked the VEGFR2-mediated Akt/ (mTOR)/p70s6k signaling pathway in vitro. Ru can be a potential drug candidate for cancer prevention and cancer therapy.

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“…Rutaevin, evodiamine, and rutaecarpine were determined quantitatively in the EEER used in this study ( Figure 1 and Figure 2 ). Rutaecarpine exhibits pharmacological properties, including a cardiovascular effect, antiplatelet activity, and anti-inflammatory activity [ 34 ]. Evodiamine has a robust anticancer bioactivity via the inhibition of cell proliferation or the induction of apoptosis [ 35 , 36 ].…”

Section: Discussionmentioning

confidence: 99%

Ethanol Extract of Evodia rutaecarpa Attenuates Cell Growth through Caspase-Dependent Apoptosis in Benign Prostatic Hyperplasia-1 Cells

et al. 2018

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The dried fruits of Evodia rutaecarpa Bentham have been used widely as a herbal medicine for the treatment of inflammatory disorders and abdominal pain. Benign prostatic hyperplasia (BPH) is a nonmalignant disease characterized by overgrowth of prostates. Despite the pharmacological efficacy of the fruits of E. rutaecarpa against various diseases, their effects against BPH have not been reported. Here, we investigated the inhibitory activity of a 70% ethanol extract of E. rutaecarpa (EEER) against BPH, and its underlying mechanisms regarding cell growth of BPH using BPH-1 cells. An in vitro 5α-reductase activity assay showed that EEER exhibited inhibitory activity against 5α-reductase. In BPH-1 cells, EEER treatment inhibited cell viability and reduced the expression of the proliferating cell nuclear antigen proliferating cell nuclear antigen (PCNA), cyclin D1, and phosphor-ERK1/2 proteins. Moreover, EEER also induced apoptosis, with chromatin condensation, apoptotic bodies, and internucleosomal DNA fragmentation. Regarding its underlying mechanisms, EEER exacerbated the activation of caspase-8 and caspase-3 in a concentration-dependent manner and eventually caused the cleavage of PARP. Taken together, these data demonstrated that EEER had a potent 5α-reductase inhibitory activity and that EEER treatment in BPH-1 cells inhibited cell viability via caspase-8- and caspase-3-dependent apoptosis. Therefore, EEER may be a potential phytotherapeutic agent for the treatment of BPH.

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Progress in Studies on Rutaecarpine. II.—Synthesis and Structure-Biological Activity Relationships

Cited by 57 publications

References 71 publications

Novel Deep Eutectic Solvent Based on Levulinic Acid and 1,4-Butanediol as an Extraction Media for Bioactive Alkaloid Rutaecarpine

Novel Deep Eutectic Solvent Based on Levulinic Acid and 1,4-Butanediol as an Extraction Media for Bioactive Alkaloid Rutaecarpine

Rutacecarpine Inhibits Angiogenesis by Targeting the VEGFR2 and VEGFR2-Mediated Akt/mTOR/p70s6k Signaling Pathway

Ethanol Extract of Evodia rutaecarpa Attenuates Cell Growth through Caspase-Dependent Apoptosis in Benign Prostatic Hyperplasia-1 Cells

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