Antiviral Activity of Tenuazonic Acid

Miller, F. A.; Rightsel, Wilton A.; Sloan, Bernard J.; Ehrlich, John; French, James C.; Bartz, Quentin R.; Dixon, Glen J.

doi:10.1038/2001338a0

Cited by 77 publications

(56 citation statements)

References 3 publications

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“…Previously, experiments to determine the susceptibility of VV (7,10,15) and of herpesvirus (7,8,10,15) to Ara-A have not taken into account deamination of the nucleoside to AraHx by ADA produced by indicator cells and present in bovine serum. Therefore, those reports probably found inhibitory levels of Ara-A at concentrations higher than actual susceptibility or reflect susceptibility to Ara-Hx, not Ara-A.…”

Section: Resultsmentioning

confidence: 99%

“…Our itfteregt in pharmacology of Ara-A led to develcpment of a method which measures plaque fdudtion activity at concentrations much lower than previously reported. This has been acebnAlished by inhibiting completely the activity of adenosine deaminase (ADA) (13) generated by dniyral cells of the Dlaque indicator system, thus preventing deamination of Ara-A to the metatolite, 9-fl-D-arabinofuranosylhypoxanthine (hyp6kanthine arabinoside, Ara-Hx), reported (15) to have less antiviral activity. The effect of ADA upon the antiviral activity in vitro of Ara-A for vaccinia virus (VV) is reported herein.…”

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confidence: 99%

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Effect of Adenosine Deaminase upon the Antiviral Activity In Vitro of Adenine Arabinoside for Vaccinia Virus

Connor

Sweetman

Carey

et al. 1974

Antimicrob Agents Chemother

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This study determined that the effect of 9-fl-D-arabinofuranosyl-adenine (adenine arabinoside, Ara-A) upon vaccinia virus plaque developmeAt in the stable monkey kidney line, LLC-MK2, was increased approximately 40-fold when an inhibitor of adenosine deaminase (ADA) was added to the tissue culture media along with infective inocula. The concentration of Ara-A required to completely suppress plaqtet development (total plaque inhibitory concentra. tion,0 ; TPIC OO) was greater than 10 ,g/ml, However, when ADA activity was inhibited, the TPIC,O0 was 0.5 gg/ml or less. Chromatographic assay of arabinosylpurines in the media provided evidence that adenine arabinoside was rapidly deaminated to 9-#-D-arabihefuranosy!hypoxanthine by the cellular monolayers, in the absence of animal serum, and that the rate of deamination, at 5 #g/ml, by the cells was equal to the rate of diffusion of Ara-A across the cellular iiiembrane. The half-life of Ara-A in the media, startnhg with 5 ,ug/ml, was 2 to 3 h and shorter at lower concentrations. The study demonstrates the profound effect that an indicator system, acting as an intact biological unit, can have upon a potential antiviral compound.-

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Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 99%

Effect of Adenosine Deaminase upon the Antiviral Activity In Vitro of Adenine Arabinoside for Vaccinia Virus

Connor

Sweetman

Carey

et al. 1974

Antimicrob Agents Chemother

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“…From the toxicological standpoint, TEN-AC is known to be toxic in chick embryo and some animal species by inducing hemorrhages in vital organs principally through the inhibition of protein synthesis [41,42]. Therefore, the concentration levels in the commodities that are far lower (100-fold less) than the LD 50 value from literature (between 182 and 225 mg/kg) for acute toxicosis by TEN-AC [41,43] may still pose a threat to consumers. Although chronic exposure of TEN-AC has not yet been investigated, toxic situations may be more complicated in this case and possibly due to synergism by the many metabolite combinations.…”

Section: Other Metabolites Without Any Regulationmentioning

confidence: 99%

Multi-microbial metabolites in fonio millet (acha) and sesame seeds in Plateau State, Nigeria

Ezekiel

Sulyok

Warth

et al. 2012

Eur Food Res Technol

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We investigated 16 fonio millet and 17 sesame samples by LC/ESI-MS/MS for the spectrum of microbial metabolites contaminating these seeds. Forty-eight fungal and four bacterial metabolites were detected in fonio, while 28 fungal and two bacterial metabolites were found in sesame. Altogether, 55 metabolites were identified in both grains, 18 of which are reported for the first time to naturally occur in cereals and oil seeds. The metabolite concentrations reached 7,280 lg/kg in fonio for aurofusarin and 64,600 lg/kg in sesame for kojic acid. Aflatoxin contaminated 81 % of fonio samples at concentrations less than the 4 lg/kg maximum allowable limit (MAL) set by European Union (EU). In contrast, aflatoxin was not detected in sesame. Zearalenone levels exceeded the EU MAL (75 lg/kg) in one sample of fonio (987 lg/kg). About 62.5 % (30 out of 48) of the metabolites without regulations occurred in more than 50 % of samples of one or both seeds, while 3-nitropropionic acid, beauvericin, brevianamid F, curvularin, emodin, equisetin, macrosporin A, monocerin and tenuazonic acid were the most prevalent, occurring in all samples of either fonio, sesame or both. This is the first study reporting mycotoxin contamination in sesame in Nigeria and the broad range of microbial metabolites in millet and sesame.

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“…Tenuazonic acid (TA) is a mycotoxin predominantly produced by molds of the genus Alternaria (Bottalico and Logrieco 1998), although fungi like Piricularia orycae (Umetsu et al 1972;Umetsu et al 1974), Phoma sorghina (Steyn and Rabiet 1976) and even Aspergillus (Miller et al 1963) have also been reported to produce this substance. After its first isolation from culture extracts of Alternaria tenuis in 1957 (Rosett et al 1957), its structure thereafter was assigned as 3-acetyl-5-sec-butyl-tetramic acid (Stickings 1959) (Fig.…”

Section: Introductionmentioning

confidence: 99%

Content of the Alternaria mycotoxin tenuazonic acid in food commodities determined by a stable isotope dilution assay

et al. 2011

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The Alternaria mycotoxin tenuazonic acid (TA) was quantified in fruit juices (n = 50), cereals (n = 12) and spices (n = 38) using a recently developed stable isotope dilution assay (SIDA). [(13) C6,(15) N]-TA was used as the internal standard. Method validation revealed low limits of detection (LODs) of 0.15 μg/kg (fruit juices), 1.0 μg/kg (cereals) and 17 μg/kg (spices). The respective limits of quantitation were about three times higher. Recovery was about 100% for all matrices. The precision (relative standard deviation of replicate analyses of naturally contaminated samples) was 4.2% (grape juice; 1.7 μg/kg), 3.5% (whole wheat flour; 36 μg/kg) and 0.9% (curry powder; 215 μg/kg). The median content of TA in the analyzed samples was 1.8 μg/kg (fruit juices), 16 μg/kg (cereals) and 500 μg/kg (spices). Positive samples amounted to 86% (fruit juices), 92% (cereals) and 87% (spices).

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Antiviral Activity of Tenuazonic Acid

Cited by 77 publications

References 3 publications

Effect of Adenosine Deaminase upon the Antiviral Activity In Vitro of Adenine Arabinoside for Vaccinia Virus

Effect of Adenosine Deaminase upon the Antiviral Activity In Vitro of Adenine Arabinoside for Vaccinia Virus

Multi-microbial metabolites in fonio millet (acha) and sesame seeds in Plateau State, Nigeria

Content of the Alternaria mycotoxin tenuazonic acid in food commodities determined by a stable isotope dilution assay

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