Antitumor and immunomodulatory effects of the naphthoquinone 5-methoxy-3,4-dehydroxanthomegnin

Kitagawa, Rodrigo Rezende; Vilegas, Wagner; Carlos, Iracilda Zeppone; Raddi, Maria Stella Gonçalves

doi:10.1590/s0102-695x2011005000136

Cited by 12 publications

(10 citation statements)

References 22 publications

(28 reference statements)

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“…Previous studies have shown that this compound has antitumor and immunomodulatory effects (Kitagawa et al, 2011), as well as anti-Helicobacter pylori and antioxidant properties http (Kitagawa et al, 2012). The antitumor effect of 5-methoxy-3,4-dehydroxanthomegnin may be enhanced by association with ascorbic acid as demonstrated by a significant cytotoxic index (CI) for McCoy cells.…”

Section: Introductionmentioning

confidence: 99%

Evaluation of mutagenicity and metabolism-mediated cytotoxicity of the naphthoquinone 5-methoxy-3,4-dehydroxanthomegnin from Paepalanthus latipes

Kitagawa

Vilegas

Varanda

et al. 2015

Revista Brasileira de Farmacognosia

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Please cite this article in press as: Kitagawa, R.R., et al. Evaluation of mutagenicity and metabolism-mediated cytotoxicity of the naphthoquinone 5-methoxy-3,4-dehydroxanthomegnin from Paepalanthus latipes. Revista Brasileira de Farmacognosia (2015), http://dx.BJP 83 1-6 Revista Brasileira de Farmacognosia xxx (2015) xxx-xxx w w w . s b f g n o s i a . o r g . b r / r e v i s t aOriginal Article a b s t r a c t A large number of quinones have been associated with antitumor, antibacterial, antimalarial, and antifungal activities. Results of previous studies of 5-methoxy-3,4-dehydroxanthomegnin, a naphthoquinone isolated from Paepalanthus latipes Silveira, Eriocaulaceae, revealed antitumor, antibacterial, immunomodulatory, and antioxidant activities. In this study, we assessed the mutagenicity and metabolism-mediated cytotoxicity of 5-methoxy-3,4-dehydroxanthomegnin by using the Ames test and a microculture neutral red assay incorporating an S9 fraction (hepatic microsomal fraction and cofactors), respectively. We also evaluated the mutagenic activity in Salmonella typhimurium strains TA100, TA98, TA102, and TA97a, as well as the cytotoxic effect on McCoy cells with and without metabolic activation in both tests. Results indicated that naphthoquinone does not cause mutations by substitution or by addition and deletion of bases in the deoxyribonucleic acid sequence with and without metabolic activation. As previously demonstrated, the in vitro cytotoxicity of 5-methoxy-3,4-dehydroxanthomegnin to McCoy cells showed a significant cytotoxic index (CI 50 ) of 11.9 g/mL. This index was not altered by addition of the S9 fraction, indicating that the S9 mixture failed to metabolically modify the compound. Our results, allied with more specific biological assays in the future, would contribute to the safe use of 5-methoxy-3,4-dehydroxanthomegnin, compound that has showed in previous studies beneficial properties as a potential anticancer drug.

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Section: Introductionmentioning

confidence: 99%

Evaluation of mutagenicity and metabolism-mediated cytotoxicity of the naphthoquinone 5-methoxy-3,4-dehydroxanthomegnin from Paepalanthus latipes

Kitagawa

Vilegas

Varanda

et al. 2015

Revista Brasileira de Farmacognosia

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“…The antitumor activity of naturally occurring quinones is exhibited predominantly by three main groups, namely, benzoquinone, naphthoquinone, and anthraquinone [43]. Cancer cells are particularly vulnerable to treatments impairing redox homeostasis [44].…”

Section: Discussionmentioning

confidence: 99%

“…In light of this, significant progress has been made in the screening of the quinone moiety for antitumor activity [ 24 ]. The redox cycling of the quinone moiety is implicated in the antitumor activity of anticancer compounds containing a quinone moiety [ 25 ].…”

Section: Introductionmentioning

confidence: 99%

Antiproliferative Activity of the Isofuranonaphthoquinone Isolated fromBulbine frutescensagainst Jurkat T Cells

Tambama

Abegaz

Mukanganyama

2014

BioMed Research International

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Cancer is a major public health burden in both developed and developing countries. The quinone moiety has been shown to possess antitumor activity and several cancer drugs in clinical use contain this entity. The effect of isofuranonaphthoquinone isolated from Bulbine frutescens on Jurkat T cells was determined. Cells were exposed to the isofuranonaphthoquinone (IFNQ) at different concentrations. Significant antiproliferative effects were observed which were comparable to that of the anticancer drug 1,3-bis(2-chloroethyl)-1-nitrosourea (BCNU). A combination of IFNQ with BCNU produced synergistic effects which were observed after 72 hrs. It was also observed that combining IFNQ with reduced glutathione abolished the anticancer activity of the compound. It is, therefore, proposed that the isofuranonaphthoquinone may exert part of its effect by producing reactive oxygen species resulting in death of the cells as the effects of this compound were antagonized by reduced glutathione. An investigation on the effects of isofuranonaphthoquinone on glutathione transferase (GST) activity and drug efflux pumps showed that this compound exhibited inhibitory effects on both the GST and the drug efflux pumping activities. Thus, the isofuranonaphthoquinone showed cytotoxicity, works through inhibition of some cellular mechanisms, and could present a potential source of lead compounds for anticancer drug development.

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“…This class of isocoumarin‐containing compounds shows a wide range of biological activities. For example, 5‐methoxy‐3,4‐dehydrosemixanthomegnin 2 shows cytotoxicity against murine mammary tumor cells (LM2, CI 50 74.6 µ m ) and lung adenocarcinoma cells (LPO7, CI 50 6.2 µ m ) while paepalantine 3 shows antimicrobial activity against bacteria including Bacillus cereus (MIC 7.5 µg mL –1 ), Staphylococcus aureus (MIC 7.5 µg mL –1 ) and Staphylococcus epidermidis (MIC 15 mg mL –1 ) . In addition, both of these isocoumarins show promising activity against the Helicobacter pylori bacterium, which is one of the main causes of chronic gastritis, peptic ulcers and possibly gastric cancer , .…”

Section: Introductionmentioning

confidence: 99%

The synthesis of 9‐O‐Methylpaepalantine and Dehydroxanthomegnin: Related Isocoumarin‐Containing Natural Products

et al. 2019

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The first synthesis of two related isocoumarin‐containing natural products, 9‐O‐methylpaepalantine and dehydroxanthomegnin is described. Commencing with 2,4‐dimethoxybenzaldehyde and utilizing the Stobbe reaction as a key step resulted in the formation of the required naphthalene containing compound, ethyl 4‐acetoxy‐3‐allyl‐6,8‐dimethoxynaphthalene‐2‐carboxylate. O‐Allylation of 4‐hydroxy‐6,8‐dimethoxynaphthalene‐2‐carboxylate followed by a Claisen rearrangement afforded the naphthol, ethyl 3‐allyl‐4‐hydroxy‐6,8‐dimethoxynaphthalene‐2‐carboxylate. Introduction of a methoxy substituent onto the 1‐position of the naphthalene nucleus utilizing a PIFA‐mediated method afforded, after O‐methylation, ethyl 3‐allyl‐1,4,6,8‐tetramethoxynaphthalene‐2‐carboxylate. Reduction of the ester was followed by oxidation to the aromatic acid, utilizing firstly a PCC oxidation and then a Pinnick oxidation to afford 3‐allyl‐1,4,6,8‐tetramethoxynaphthalene‐2‐carboxylic acid. Wacker oxidation of the aromatic acid resulted in the formation of 5,7,9,10‐tetramethoxy‐3‐methyl‐1H‐benzo[g]isochromen‐1‐one, which was then converted into 9‐O‐methylpaepalantine by treatment with boron trichloride. Utilizing similar synthetic methodology dehydroxanthomegnin was synthesized in thirteen steps commencing from 2,4,5‐trimethoxybenzaldehyde in an overall yield of 1.3 %.

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Antitumor and immunomodulatory effects of the naphthoquinone 5-methoxy-3,4-dehydroxanthomegnin

Cited by 12 publications

References 22 publications

Evaluation of mutagenicity and metabolism-mediated cytotoxicity of the naphthoquinone 5-methoxy-3,4-dehydroxanthomegnin from Paepalanthus latipes

Evaluation of mutagenicity and metabolism-mediated cytotoxicity of the naphthoquinone 5-methoxy-3,4-dehydroxanthomegnin from Paepalanthus latipes

Antiproliferative Activity of the Isofuranonaphthoquinone Isolated fromBulbine frutescensagainst Jurkat T Cells

The synthesis of 9‐O‐Methylpaepalantine and Dehydroxanthomegnin: Related Isocoumarin‐Containing Natural Products

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