Cytotoxic and antioxidant activities of alkylated benzoquinones from <i>Maesa lanceolata</i>

Muhammad, Ilias; Takamatsu, Satoshi; Walker, Larry; Mossa, Jaber S.; Fong, Harry H. S.; El‐Feraly, Farouk S.

doi:10.1002/ptr.1237

Cited by 21 publications

(20 citation statements)

References 21 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Quinones are important biological molecules that are active against a variety of cancer cells [2,25], viruses [12], and fungi [17]. Some semisynthetic analogs of substituted 1,4-benzoquinones have in vitro cytotoxic and antioxidant activities [19]. Quinones also play a critical role in energy metabolism and even in chemotherapy where redox cycling drugs are utilized.…”

Section: Time-kill Curves Of Selected 14-benzoquinonesmentioning

confidence: 99%

Antimicrobial Activities of 1,4-Benzoquinones and Wheat Germ Extract

Kim

Jo²,

Ha³

et al. 2010

J. Microbiol. Biotechnol.

View full text Add to dashboard Cite

We evaluated the antibacterial activities of selected edible Korean plant seeds against the food-borne pathogens Staphylococcus aureus KCTC1927, Escherichia coli KCTC2593, Salmonella typhimurium KCTC2054, and Bacillus cereus KCTC1014. While screening for antibacterial agents, we discovered that wheat germ extract contains 2,6-dimethoxy-1,4-benzoquinone (DMBQ) and is highly inhibitory to S. aureus and B. cereus. This is the first report of the antibacterial activity of wheat germ extract. We also investigated the antibacterial activities of the 1,4benzoquinone standards 1,4-benzoquinone (BQ), hydroquinone (HQ), methoxybenzoquinone (MBQ), and 2,6-dimethoxy-1,4-benzoquinone (DMBQ). DMBQ and BQ were the most highly inhibitory to S. aureus and S. typhimurium, followed by MBQ and HQ. MICs for DMBQ and BQ ranged between 8 and 64 µg/ml against the four foodborne pathogens tested. DMBQ and BQ showed significant antibacterial activity; the most sensitive organism was S. aureus with an MIC of 8 µg/ml. BQ exhibited good activity against S. typhimurium (32 µg/ml) and B. cereus (32 µg/ml). The results suggest that wheat germ extract has potential for the development of natural antimicrobials and food preservatives for controlling foodborne pathogens.

show abstract

Section: Time-kill Curves Of Selected 14-benzoquinonesmentioning

confidence: 99%

Antimicrobial Activities of 1,4-Benzoquinones and Wheat Germ Extract

Kim

Jo²,

Ha³

et al. 2010

J. Microbiol. Biotechnol.

View full text Add to dashboard Cite

show abstract

“…The level of toxicity of each compound was determined by measuring the effect on a fibroblast cell line from African monkey kidney (VERO) [16,23]. For primary evaluation, fractions and isolated compounds were screened at three concentrations (4.76, 1.58 and 0.52 µg/mL), using a culture-treated 96 well micro plate for secondary assay.…”

Section: Cytotoxicity On Vero Cellsmentioning

confidence: 99%

“…All the isolated compounds were tested for their antimalarial activity [21]; among them isoimperatorin (5), bergapten (2), dihydrochelerythrin (12), chelerythrine acetonate (13), dihydrorutaecarpine (14) and sesamin (15) displayed mild activities ( Cytotoxicity was measured using the XTT assay [23].…”

mentioning

confidence: 99%

Constituents of Zanthoxylum Flavum and their Antioxidant and Antimalarial Activities

Ross

Krishnaven

Radwan

et al. 2008

Natural Product Communications

Self Cite

View full text Add to dashboard Cite

Biologically guided fractionation of the methanolic extract of the roots of Zanthoxylum flavum Vahi. has led to the isolation of 18 constituents: seven coumarins, seven alkaloids, one lignan, two sterols and one triterpene. The isolated compounds have been identified by comparison of their spectral data with those reported. Among the isolates, 14 compounds have been isolated for the first time from Z. flavum. The coumarin oxypeucedanin (6) displayed significant antioxidant activity with an IC 50 value of 8.3 μg/mL in the cell-based DCFH-DA assay. The isolated compounds were also evaluated for their antimalarial and cytotoxic activities.

show abstract

“…Furthermore Kaul and co-workers isolated a known cytotoxic quinine Irisoquin which demonstrated cytotoxic properties [3]. In previous reports Muhammad et al [4] evaluated cytotoxic and antioxidant activities of alkylated benzoquinones from the leaves of Maesa Lanceolata . Moreover, another important 2,5-dihydroxy-3-alkyl-1,4-benzoquinone is Embelin known for a very long time in Indian and Chinese pharmacopoeias.…”

Section: Introductionmentioning

confidence: 99%

Cyclohexa-2,5-diene-1,4-dione-based antiproliferative agents: design, synthesis, and cytotoxic evaluation

Petronzi

Festa

Peduto

et al. 2013

J Exp Clin Cancer Res

View full text Add to dashboard Cite

BackgroundTumors are diseases characterized by uncontrolled cell growth and, in spite of the progress of medicine over the years, continue to represent a major threat to the health, requiring new therapies. Several synthetic compounds, such as those derived from natural sources, have been identified as anticancer drugs; among these compounds quinone represent the second largest class of anticancer agents in use. Several studies have shown that these act on tumor cells through several mechanisms. An important objective of this work is to develop quinoidscompounds showing antitumor activity, but with fewer side effects. The parachinone cannabinol HU-331, is a small molecule that with its core 4-hydroxy-1,4-benzoquinone, exhibits a potent and selective cytotoxic activity on different tumor cell lines. A series of derivatives 3-hydroxy-1,4-benzochinoni were thus developed through HU-331 chemical modifications. The purpose of the work is to test the ability of the compounds to induce proliferative inhibition and study the mechanisms of cell death.MethodsThe antitumor activities were evaluated in vitro by examining their cytotoxic effects against different human cancer cell lines. All cell lines tested were plated in 96-multiwell and treated with HU-100-V at different concentrations and cell viability was evaluated byMTT assay. Subsequently via flow cytometry (FACS) it was possible to assess apoptosis by the system of double labeling with PI and Annexin-V, and the effect of the compounds on ROS formation by measuring the dichlorofluorescein fluorescence.ResultsThe substitution by n-hexyl chain considerably enhanced the bioactivity of the compounds. In details, 2-hexyl-5-hydroxycyclohexa-2,5-diene-1,4-dione (V), 2,5-Dimethoxy-3-hexyl-2,5-cyclohexadiene-1,4-dione (XII) and 2-hydroxy-5-methoxy-3-hexyl-cyclohexa-2,5-diene-1,4-dione (XIII) showed most prominent cytotoxicity against almost human tumour cell lines. Compound V was further subjected to downstream apoptotic analysis, demostrating a time-dependent pro-apoptotic activity on human melanoma M14 cell line mediated by caspases activation and poly-(ADP-ribose)-polymerase (PARP) protein cleavage.ConclusionsThese findings indicate that 2-hexyl-5-idrossicicloesa-2,5-diene-1,4-dione can be a promising compound for the design of a new class of antineoplastic derivatives.Carmen Petronzi, Michela Festa, Antonella Peduto and Maria Castellano: equally contributed equally to this work.

show abstract

Cytotoxic and antioxidant activities of alkylated benzoquinones from Maesa lanceolata

Cited by 21 publications

References 21 publications

Antimicrobial Activities of 1,4-Benzoquinones and Wheat Germ Extract

Antimicrobial Activities of 1,4-Benzoquinones and Wheat Germ Extract

Constituents of Zanthoxylum Flavum and their Antioxidant and Antimalarial Activities

Cyclohexa-2,5-diene-1,4-dione-based antiproliferative agents: design, synthesis, and cytotoxic evaluation

Contact Info

Product

Resources

About