9-Methoxytariacuripyrone, a naturally occurring nitro-aromatic compound with strong mutagenicity in <i>Salmonella typhimurium</i>

Schimmer, Oskar; Drewello, Ursula

doi:10.1093/mutage/9.6.547

Cited by 8 publications

(6 citation statements)

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“…The experiments were performed with Salmonella typhimurium strains TA 98 (his D3052, pkM101 as indicator for frameshift mutations) and TA100 [hisG46, pkM101 as indicator for base-pair mutations (AT c CG)] without exogenous metabolic system for the mutagens EMS, 2-NF and 1-NP and with S9-mix for tests using IQ and MelQ. Mutagens were used in fixed doses and the resulting number of induced revertants [1-NP: about 550 ; 10 % at 0.1 mg/plate (TA 98); 2-NF: about 700 ; 11 % at 2 mg/plate (TA 98); EMS: about 640 ; 11 % at 5 ml/plate (TA 100); IQ: 1200 ; 4 % at 8 ng/plate, MelQ: 1400 ; 10 at 40 ng/plate] were in agreement with the data from literature (5,8,9,13,18).…”

Section: Ames Assaysupporting

confidence: 88%

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Pectins and Xyloglucans Exhibit Antimutagenic Activities against Nitroaromatic Compounds

Hensel

Meier²

1999

Planta med

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Because a high daily consumption of polysaccharides-containing food is assessed to decrease the risk of cancer of the gastrointestinal system, different types of carbohydrates were investigated for their antimutagenic activity against different standard mutagens. Within the screening pronounced antimutagenic effects were found for xyloglucan and different pectins and pectin-like rhamnogalacturonans against 1-nitropyrene induced mutagenicity. Inhibition rates were dose-dependent and varied between 20 and 50%. Concerning the mode of action a direct interaction of the polymers with the cells is claimed, protecting the organisms from the mutagenic attack.

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Section: Ames Assaysupporting

confidence: 88%

“…The S9 mix contained per ml: S9 fraction 0.1 ml, 70 mmol/l MgSO 4 , 0.1 ml, 40 mmol/l NADP, 0.1 ml, 200 mmol/l D,L-isocitrate, 0.1 ml, 100 mmol/l phosphate buffer (pH 7.4) 0.6 ml. For additional information see (18).…”

Section: Methodsmentioning

confidence: 99%

Pectins and Xyloglucans Exhibit Antimutagenic Activities against Nitroaromatic Compounds

Hensel

Meier²

1999

Planta med

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“…The intermediates are covalently bound at the exocyclic amino groups of the purines (Pfau et al, 1990a). AA II can also be activated by the cytosolic fraction of liver homogenates from Wistar rats (Schimmer and Drewello, 1994). In S. typhimurium, the microsomal fraction was capable of detoxification and reduced the mutagenic effect.…”

Section: Significant Endogenous Mutagens/carcinogensmentioning

confidence: 99%

“…This may be discussed as a particular evolutionary aspect of these secondary plant products. 9-Methoxytariacuripyrone, another naturally occurring and closely related nitro aromatic compound showed much stronger mutagenicity than AA II in the Ames assay (Schimmer and Drewello, 1994).…”

Section: Significant Endogenous Mutagens/carcinogensmentioning

confidence: 99%

Molecular Modes of Action of Defensive Secondary Metabolites

Wink

Schimmer

2010

Functions and Biotechnology of Plant Secondary Metabolites

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Secondary metabolites (SM) have been shaped by evolution for more than 500 million years. As a result, many of them have distinctive biochemical and pharmacological properties. The molecular modes of action of the main groups of SM are reviewed in this chapter. Details are given on interactions of SM with proteins that can induce conformational changes and thus a modification of their bioactivity. The fluidity and permeability of biomembranes constitute another important target, which is influenced by many lipophilic and amphiphilic SM. A number of SM can either alkylate or intercalate DNA, which can cause mutations and in consequence cancer or malformations. Many SM are cytotoxic because they interfere with biomembranes, proteins of the cytoskeleton or DNA; they often induce programmed cell death (apoptosis). A large number of SM, especially alkaloids modulate neuronal signal transduction by interfering with ion channels, ion pumps, neuroreceptors, choline esterase, monoamine oxidase and other enzymes related to signal transduction pathways. A typical feature of SM is their ability to modulate more than one molecular target; thus, additive and even synergistic activities can be expected.

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“…Other alkaloids of this type also have been isolated in Aristolochia constricita , and these demonstrated a significant decrease in the electrically induced contraction, with acetylcholine and guinea pig ileum-isolated histamine [ 14 ], while compounds 3 and 4 are 5-nitro-2 H -benzo[h]chromenones (presumably derived from aristolochic acid) [ 15 ], popularly known as “tariacuripironas”. To our knowledge, there are no reports in the literature on biological evaluations of this type of compounds; we only found the description of strong mutagenic activity for 9-methoxy-tariacuripyrone ( 4 ) against TA98, TA100, and YG of Salmonella typhimurium strains [ 16 ]. With regard to the antituberculous activity of these compounds, i.e.…”

Section: Resultsmentioning

confidence: 99%

Antibacterial Activity of Aristolochia brevipes against Multidrug-Resistant Mycobacterium tuberculosis

Navarro-García¹,

Luna-Herrera²,

Rojas-Bribiesca³

et al. 2011

Molecules

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The increased incidence of Multidrug-Resistant Mycobacterium tuberculosis (MDR-MT) requires the search for alternative antimycobacterial drugs. The main aim of this study was to evaluate the dichloromethane extract from Aristolochia brevipes (Rhizoma) and the compounds isolated from this extract against several mycobacterial strains, sensitive, resistant (monoresistant), and clinical isolates (multidrug-resistant), using the alamarBlue™ microassay. The extract was fractionated by column chromatography, yielding the following eight major compounds: (1) 6α-7-dehydro-N-formylnornantenine; (2) E/Z-N-formylnornantenine; (3) 7,9-dimethoxytariacuripyrone; (4) 9-methoxy-tariacuripyrone; (5) aristololactam I; (6) β-sitosterol; (7) stigmasterol; and (8) 3-hydroxy-α-terpineol. The structures of these compounds were elucidated by 1H- and 13C- (1D and 2D) Nuclear Magnetic Resonance (NMR) spectroscopy. This study demonstrates that the dichloromethane extract (rhizome) of A. brevipes possesses strong in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv (Minimum Inhibitory Concentration value [MIC], 12.5 µg/mL). The most active compound against all mycobacterial strains tested was the compound aristolactam I (5), with MIC values ranging between 12.5 and 25 µg/mL. To our knowledge, this the first report of antimycobacterial activity in this plant.

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9-Methoxytariacuripyrone, a naturally occurring nitro-aromatic compound with strong mutagenicity in Salmonella typhimurium

Cited by 8 publications

References 0 publications

Pectins and Xyloglucans Exhibit Antimutagenic Activities against Nitroaromatic Compounds

Pectins and Xyloglucans Exhibit Antimutagenic Activities against Nitroaromatic Compounds

Molecular Modes of Action of Defensive Secondary Metabolites

Antibacterial Activity of Aristolochia brevipes against Multidrug-Resistant Mycobacterium tuberculosis

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