Quinolone alkaloids with antibacterial and cytotoxic activities from the fruits of Evodia rutaecarpa

Wang, Xiaoxia; Zan, Ke; Shi, She‐Po; Zeng, Ke-Wu; Jiang, Yong; Gao, Yan; Xiao, Chunling; Gao, Huiyuan; Wu, Lijun; Tu, Pengfei

doi:10.1016/j.fitote.2013.04.007

Cited by 52 publications

(41 citation statements)

References 19 publications

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Section: Introductionmentioning

confidence: 99%

“…T.G.Hartley; Rutaceae) has long been appreciated for its bioactive components, serving as a rich source of quinolinone and indoloquinazole alkaloids, with evodiamine (1), rutaecarpine (2) and cis-evocarpine (9) being the most important ones (Huang et al, 2012). Moreover these compounds exhibited promising antimicrobial effects (Pan et al, 2014;Wang et al, 2013). The aim of the study was to test the biofilm formation of C. jejuni NCTC 11168 wild-type, cmeB and luxS mutants on stainless steel (SS) surface (AISI type 304), and to evaluate the antimicrobial, antibiofilm and antiquorum potential of E. ruticarpa fruit ethanol solution extract (EREE), evodiamine (1), rutaecarpine (2) and a quinolinone fraction (fraction Q).…”

Section: Introductionmentioning

confidence: 99%

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Attenuation of Adhesion, Biofilm Formation and Quorum Sensing ofCampylobacter jejunibyEuodia ruticarpa

et al. 2016

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Thermophilic campylobacters are a major cause of bacterial food-borne diarrhoeal disease. Adherence and biofilm formation are key elements of Campylobacter jejuni persistence in unfavourable environmental conditions. The phytochemical analysis of Euodia ruticarpa fruit ethanol solution extract (EREE) indicated that the major compounds were evodiamine (1), rutaecarpine (2) and evocarpine (9). E. ruticarpa fruit ethanol solution extract, compounds 1 and 2 as well as a mixture of quinolinone alkaloids with 41.7% of 9 were tested for antibacterial, antibiofilm and antiquorum sensing activities against C. jejuni. Minimal inhibitory concentrations varied from 64 to 1024 µg/mL. A mutant strain that lacks the functional gene coding for the CmeB efflux pump protein was the most susceptible. Interestingly, in addition to the wild-type (NCTC 11168) and cmeB mutant, also a mutant that lacks autoinducer-2 production (luxS) was able to adhere (1 h) and to produce a biofilm (24, 48 and 72 h). The subinhibitory concentrations of all preparations at least partly inhibited C. jejuni adhesion and biofilm formation with the most visible effect of the quinolinone alkaloid fraction. Using a Vibrio harveyi luminescence assay, the inhibition of autoinducer-2 production was observed in the wild-type and cmeB mutant after 48 h with the most visible effect of EREE and its fraction Q. Copyright © 2016 John Wiley & Sons, Ltd.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Attenuation of Adhesion, Biofilm Formation and Quorum Sensing ofCampylobacter jejunibyEuodia ruticarpa

et al. 2016

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“…As an example of alkaloids with anti-biofilm activities against C. jejuni, interesting data have been reported for an extract of Euodia rutaecarpa fruit (also known as Tetradium ruticarpum), a quinolone-rich fraction from this extract, and its isolated rutaecarpine, an indoloquinazoline alkaloid (Bezek et al 2016). These compounds have shown promising antimicrobial effects (Pan et al 2014;Wang et al 2013). The greatest inhibition of biofilm formation seen here for stainless steel coupons was obtained for a complex mixture of structurally closely related 2-alkyl-4quinolones, which included evocarpine as its major component (42%).…”

Section: Anti-adhesion and Anti-biofilm Compounds Of Natural Originmentioning

confidence: 99%

Anti-adhesion activity of phytochemicals to prevent Campylobacter jejuni biofilm formation on abiotic surfaces

et al. 2020

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Biofilms provide a protective environment for pathogens such as Campylobacter jejuni, the most prevalent foodborne pathogen, and biofilm formation can enhance bacterial survival in hostile environments. Adhesion of bacteria to the different materials of industrial surfaces is the first step in biofilm formation. Modulation of bacterial adhesion and biofilm formation thus represent important targets in alternative control strategies for reduction of pathogens in food-processing environments. With the high prevalence of C. jejuni and the lack of effective control measures, new control strategies are needed to block adhesion and biofilm formation on food contact surfaces in the food industry, with a focus here on natural antimicrobial phytochemicals. Plants remain a poorly recognized yet vast source of such antimicrobials. Valuable phytochemicals can be obtained directly from plant materials but also from agro-food by-products and waste materials. These materials represent a source of important plant bioactive phytochemicals that are effective for prevention of bacterial adhesion. In this review, we will focus on the anti-adhesion activities of phytochemicals targeted against C. jejuni, on the appropriate methodologies to determine anti-adhesion effects of phytochemicals, on the mechanisms of C. jejuni adhesion, and thus possible targets for reduction and control of this foodborne pathogen in food processing environments.

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“…and related varieties, is officially listed in the 2010 Chinese Pharmacopoeia for the treatment of headache, abdominal pain, dermatophytosis, amenorrhea and dysentery. Modern pharmacology and clinical researches have indicated promising values of E. rutaecarpa for abirritation (Matsuda et al ., ), antioxidant (Tan et al ., ), antibacterial (Wang et al ., ), anti‐cancer (Chien et al ., ) and cytotoxic activities (Huang et al ., ). So far, a number of chemical constituents have been isolated from E. rutaecarpa , including alkaloids, limonoids, essential oils and flavonoids (Sugimoto et al ., ; Tang et al ., ; Chuang et al ., ; Cai et al ., ).…”

Section: Introductionmentioning

confidence: 99%

Screening and identification of hepatotoxic component in Evodia rutaecarpa based on spectrum–effect relationship and UPLC‐Q‐TOFMS

Sun

Liu

et al. 2016

Biomedical Chromatography

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Evodia rutaecarpa (E. rutaecarpa) has been used to treat aches, vomiting and dysentery in traditional Chinese medicine. However, as a mildly toxic herb its toxic components have not been elucidated. An attempt was made to illuminate the hepatotoxic constituents of E. rutaecarpa. The 50% ethanol extracts of E. rutaecarpa from 19 different sources were used to establish UPLC fingerprints and administered to mice at a dose of 35 g/kg (crude medicine weight/mouse weight) once daily for 14 days. Serum levels of alanine transaminase, aspartate aminotransferase and liver coefficient were used as indices of liver injury. Additionally, the characteristic peaks of 19 fingerprints were identified. Spectrum-effect relationships between fingerprints and hepatotoxic indicators were analyzed using bivariate correlation analysis (BCA). The UPLC fingerprints were established and a total of 28 main compounds were identified. Because of the inherent variations in chemical compositions, the liver injury levels were different among the E. rutaecarpa samples from 19 sites of production. BCA results indicated that compounds dihydrorutaecarpine, 6-acetoxy-5-epilimonin, goshuyuamide I, 1-methyl-2-[(Z)-5-undecenyl]-4(1H)-quinolone, 1-methyl-2-[(4Z,7Z)-4,7-tridecadienyl]-4(1H)-quinolone, evocarpine and 1-methyl-2-[(6Z,9Z)-6,9-pentadecadienyl]-4(1H)-quinolone were tentatively determined as the primary hepatotoxic components. The present study provides a valuable method for the discovery of hepatotoxic constituents by combination of fingerprints and hepatotoxicity index.

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Quinolone alkaloids with antibacterial and cytotoxic activities from the fruits of Evodia rutaecarpa

Cited by 52 publications

References 19 publications

Attenuation of Adhesion, Biofilm Formation and Quorum Sensing ofCampylobacter jejunibyEuodia ruticarpa

Attenuation of Adhesion, Biofilm Formation and Quorum Sensing ofCampylobacter jejunibyEuodia ruticarpa

Anti-adhesion activity of phytochemicals to prevent Campylobacter jejuni biofilm formation on abiotic surfaces

Screening and identification of hepatotoxic component in Evodia rutaecarpa based on spectrum–effect relationship and UPLC‐Q‐TOFMS

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