Toxicity of theAlternaria spp metabolites, tenuazonic acid, alternariol, altertoxin-i, and alternariol monomethyl ether to brine shrimp (Artemia salina L) larvae

1994 ◽  
Vol 66 (4) ◽  
pp. 493-496 ◽  
Author(s):  
Shantanu Panigrahi ◽  
Stephen Dallin
Keyword(s):  
Brine Shrimp ◽  
Monomethyl Ether ◽  
Artemia Salina ◽  
Tenuazonic Acid ◽  
Alternariol Monomethyl Ether

scholarly journals Cytotoxic Metabolites Produced by Alternaria No.28, an Endophytic Fungus Isolated from Ginkgo biloba

2009 ◽  
Vol 4 (11) ◽  
pp. 1934578X0900401 ◽  
Author(s):  
Jian-Chun Qin ◽  
Ya-Mei Zhang ◽  
Ling Hu ◽  
Ya-Tuan Ma ◽  
Jin-Ming Gao
Keyword(s):  
Ginkgo Biloba ◽  
Endophytic Fungus ◽  
Brine Shrimp ◽  
Culture Media ◽  
Monomethyl Ether ◽  
Artemia Salina ◽  
Fungal Endophyte ◽  
Alternariol Monomethyl Ether ◽  
Cytotoxic Effects

From the medicinal plant Ginkgo biloba the fungal endophyte Alternaria no.28 was isolated. Extract of the fungus grown in liquid culture media exhibited marked cytotoxic activity when tested in vitro against brine shrimp (Artemia salina). Eight compounds were isolated from the extract of cultures of this endophytic fungus and were elucidated as alterperylenol (1), altertoxin I (2), alternariol (3), alternariol monomethyl ether (4), tenuazonic acid (5) and its derivative (6), together with ergosterol and ergosta-4, 6, 8, 22-tetraen-3-one by means of spectroscopic analysis. Among them, both 5 and 6 showed significant cytotoxic effects in the brine shrimp bioassy, with mortality rates of 73.6% and 68.9%, respectively, at a concentration of 10 μg.mL−1, and they were first isolated from endophytic fungi.

Alternaria mycotoxins: an overview of chemical characterization, producers, toxicity, analysis and occurrence in foodstuffs

2008 ◽  
Vol 1 (2) ◽  
pp. 175-188 ◽  
Author(s):  
V. Ostry
Keyword(s):  
Topoisomerase I ◽  
Edible Oils ◽  
Solid Phase ◽  
Chemical Characterization ◽  
Monomethyl Ether ◽  
Dna Integrity ◽  
Natural Occurrence ◽  
Tenuazonic Acid ◽  
Alternariol Monomethyl Ether ◽  
Alternaria Mycotoxins

Microfungi of the genus Alternaria are ubiquitous pathogens and saprophytes. Many species of the genus Alternaria commonly cause spoilage of various food crops in the field or post-harvest decay. Due to their growth even at low temperatures, they are also responsible for spoilage of these commodities during refrigerated transport and storage. Several Alternaria species are known producers of toxic secondary metabolites - Alternaria mycotoxins. A. alternata produces a number of mycotoxins, including alternariol, alternariol monomethyl ether, altenuene, altertoxins I, II, III, tenuazonic acid and other less toxic metabolites. Tenuazonic acid is toxic to several animal species, e.g. mice, chicken, dogs. Alternariol, alternariol monomethyl ether, altenuene and altertoxin I are not very acutely toxic. There are several reports on the mutagenicity and genotoxicity of alternariol, and alternariol monomethyl ether. Alternariol has been identified as a topoisomerase I and II poison which might contribute to the impairment of DNA integrity in human colon carcinoma cells. Analytical methods to determine Alternaria toxins are largely based on procedures, involving cleanup by solvent partitioning or solid phase extraction, followed by chromatographic separation techniques, in combination with ultraviolet, fluorescence, electrochemical and mass spectroscopic detection. A large number of Alternaria metabolites has been reported to occur naturally in food commodities (e.g. fruit, vegetables, cereals and oil plants). Alternariol, alternariol monomethyl ether and tenuazonic acid were frequently detected in apples, apple products, mandarins, olives, pepper, red pepper, tomatoes, tomato products, oilseed rape meal, sunflower seeds, sorghum, wheat and edible oils. Alternariol and alternariol monomethyl ether were detected in citrus fruit, Japanese pears, prune nectar, raspberries, red currant, carrots, barley and oats. Alternariol monomethyl ether and tenuazonic acid were detected in melon. Natural occurrence of alternariol has been reported in apple juice, cranberry juice, grape juice, prune nectar, raspberry juice, red wine and lentils.

scholarly journals Contamination of grain in West Siberia by Alternaria fungi and their mycotoxins

2021 ◽  
Vol 104 (3) ◽  
pp. 153-162
Author(s):  
Alexandra Stanislavovna Orina* ◽  
Olga Pavlovna Gavrilova ◽  
Tatyana Yuryevna Gagkaeva ◽  
Nadezhda Nikolayevna Gogina
Keyword(s):  
Real Time Pcr ◽  
West Siberia ◽  
Monomethyl Ether ◽  
Barley Grain ◽  
Tenuazonic Acid ◽  
Alternariol Monomethyl Ether ◽  
Dna Amount ◽  
Alternaria Mycotoxins ◽  
Positive Significant Correlation

The ubiquitous occurrence of Alternaria fungi belonging to sections Alternaria and Infectoriae was confirmed using real-time PCR in wheat, barley and oat grain grown in West Siberia in 2018‒2019. The DNA amount of Alternaria section Alternaria fungi varied from 53×10-4 to 21731×10-4 pg/ng and on average exceeded the DNA amount of Alternaria section Infectoriae fungi by 4.5‒14.6 times, depending on the crop and harvest year.The average DNA amount of Alternaria fungi belonging to both sections in the oat grain was lower than in wheat and barley grain. The grain samples from Altay region were the most infected with Alternaria fungi. The alternariol (AOH), alternariol monomethyl ether (AME), tentoxin (TEN), and tenuazonic acid (TeA) mycotoxins produced by Alternaria fungi were detected by HPLC-MS/MS in 23 %, 6 %, 85 %, and 83 % of analyzed grain samples, respectively. The majority (61 %) of the samples contained two Alternaria mycotoxins in the grain (mainly TEN and TeA), 19 % of the samples three mycotoxins, and only one sample all four together. In the most of samples the content of Alternaria mycotoxins did not exceed 100 μg/kg, and only TeA content was higher (from 113 to 14963 μg/kg) than others. The significant differences in grain crops by the Alternaria mycotoxins content were revealed: more amounts of AOH, AME, and less amount of TEN were found in oat grain then in barley grain. A high positive significant correlation between the DNA amount of Alternaria section Alternaria fungi and TeA was established that indicates the role of these fungi as the main producers of TeA in the grain.

Alternaria Toxins in Wheat during the 2004 to 2005 Argentinean Harvest

2008 ◽  
Vol 71 (6) ◽  
pp. 1262-1265 ◽  
Author(s):  
M. P. AZCARATE ◽  
A. PATRIARCA ◽  
L. TERMINIELLO ◽  
V. FERNÁNDEZ PINTO
Keyword(s):  
Monomethyl Ether ◽  
Fungal Species ◽  
The Other ◽  
Natural Occurrence ◽  
Tenuazonic Acid ◽  
Alternariol Monomethyl Ether ◽  
Wide Range ◽  
Alternaria Mycotoxins ◽  
Alternaria Species ◽  
Main Component

The natural occurrence of Alternaria mycotoxins in Argentinean wheat from the zone 5 South during the 2004 to 2005 harvest was investigated in 64 wheat samples. All samples were highly contaminated with a wide range of fungal species. Alternaria was found as the main component of the mycota, with an infection percentage of 100%. Three mycotoxins produced by species of Alternaria were determined in wheat: alternariol, alternariol monomethyl ether, and tenuazonic acid. Alternariol was detected in 4 (6%) of 64 samples, with a range of 645 to 1,388 μg/kg (mean of 1,054 μg/kg); alternariol monomethyl ether, with a range of 566 to 7,451 μg/kg (mean of 2,118 μg/kg) in 15 (23%) of 64 samples; and tenuazonic acid in 12 (19%) of 64 samples, with a range of 1,001 to 8,814 μg/kg (mean, 2,313 μg/kg). Alternariol monomethyl ether was the predominant toxin, but tenuazonic acid was detected in higher concentrations. Alternariol was present in fewer samples and in lower levels than were the other toxins. Tenuazonic acid and alternariol monomethyl ether occurred together in four samples, while tenuazonic acid and alternariol co-occurred in one sample. This the first report of the natural occurrence of Alternaria mycotoxins in Argentinean wheat. Toxin levels were high, probably due to the heavy infection with Alternaria species found in the samples.

Incidence of Mycotoxigenic Alternaria alternata and Aspergillus flavus in Barley

1993 ◽  
Vol 56 (3) ◽  
pp. 246-248 ◽  
Author(s):  
V. SANCHIS ◽  
A. SANCLEMENTE ◽  
J. USALL ◽  
I. VIÑAS
Keyword(s):  
Aspergillus Flavus ◽  
Alternaria Alternata ◽  
Monomethyl Ether ◽  
Fungal Species ◽  
Tenuazonic Acid ◽  
Alternariol Monomethyl Ether ◽  
Penicillium Spp

The predominant fungal species present in 60 samples of barley collected in Spain were Alternaria alternata, Penicillium spp. and Aspergillus flavus. Of the 176 Alternaria isolates examined, 88.6% produced tenuazonic acid, 15.3% produced alternariol, and 9% produced alternariol monomethyl ether. Only 6% of the 190 isolates of A. flavus produced aflatoxin.

Alternaria toxins in weather-damaged wheat and sorghum in the 1995-1996 Australian harvest

1997 ◽  
Vol 48 (8) ◽  
pp. 1249 ◽  
Author(s):  
D. J. Webley ◽  
K. L. Jackson ◽  
J. D. Mullins ◽  
A. D. Hocking ◽  
J. I. Pitt
Keyword(s):  
Alternaria Alternata ◽  
Primary Infection ◽  
New South ◽  
Geographical Location ◽  
Monomethyl Ether ◽  
The Other ◽  
Tenuazonic Acid ◽  
Alternariol Monomethyl Ether ◽  
South Wales ◽  
Low Levels

Weather-damaged wheat from northern New South Wales in 1995-96 was heavily infected with the fungus Alternaria alternata. The mycotoxins tenuazonic acid, alternariol, and alternariol monomethyl ether were detected at low levels which corresponded with the degree of A. alternata infection and the geographical location. Sorghum and undamaged wheat from the same region also showed moderate levels of A. alternata infection and low levels of tenuazonic acid but none of the other toxins. These mycotoxins were not found in weather-damaged wheat from other areas of Australia where the primary infection was by A. infectoria rather than A. alternata.

Occurrence of alternariol, alternariol monomethyl ether and tenuazonic acid in Argentinean tomato puree

2006 ◽  
Vol 22 (4) ◽  
pp. 236-240 ◽  
Author(s):  
L. Terminiello ◽  
A. Patriarca ◽  
G. Pose ◽  
V. Fernandez Pinto
Keyword(s):  
Monomethyl Ether ◽  
Tenuazonic Acid ◽  
Alternariol Monomethyl Ether ◽  
Tomato Puree

Phytotoxicity of AAL-toxin and other compounds produced by Alternaria alternata to jimsonweed (Datura stramonium)

1993 ◽  
Vol 71 (1) ◽  
pp. 155-160 ◽  
Author(s):  
Hamed K. Abbas ◽  
R. F. Vesonder ◽  
C. D. Boyette ◽  
S. W. Peterson
Keyword(s):  
Alternaria Alternata ◽  
Soft Rot ◽  
Datura Stramonium ◽  
Monomethyl Ether ◽  
Control Agent ◽  
Corn Meal ◽  
Corn Meal Agar ◽  
Tenuazonic Acid ◽  
Alternariol Monomethyl Ether ◽  
Aal Toxin

Nine isolates of Alternaria alternata were obtained from infected tomato (cv. Beefsteak) plants. Each isolate was grown on autoclaved rice medium and corn meal agar medium and evaluated for pathogenesis and phytotoxicity to jimsonweed plants. Only A. alternata SWSL 1 (NRRL 18822) caused lodging on 1-week-old jimsonweed plants when sprayed at a rate of 20 g of fungus-infested rice per 100 mL distilled water. The symptoms began within 24 to 48 h following inoculation, and all plants were dead after 96 h. Treatment of 2-week-old jimsonweed plants in the same manner affected growth only. No symptoms occurred when SWSL 1 spores from corn meal agar were applied to jimsonweed at a rate of 2 × 107 spores/mL, with or without dew. The filtrates of fungus-infested rice of the SWSL 1 isolate were found to contain the following phytotoxins: AAL-toxin (100 μg/g), tenuazonic acid (10 μg/g), and alternariol monomethyl ether (580 μg/g). Crude and cell-free filtrates and AAL-toxin (concentration 200 μg/mL) caused similar damage on excised leaves, characterized by soft rot diffusing from the point of inoculation along the veins, adaxially or abaxially to leaves. Alternariol monomethyl ether (concentration 800 μg/mL) and tenuazonic acid (concentration 420 μg/mL) applied to excised jimsonweed leaves caused no visible damage. In intact plants, symptoms resulting from the crude filtrate, cell-free filtrate, and the AAL-toxin were identical. A dose–response study of AAL-toxin on excised jimsonweed and black nightshade (Solanum nigrum L.) leaves showed effects at concentrations of 1.56 μg/mL and 0.01 μg/mL, respectively. This is the first report of phytotoxicity of AAL-toxin to these two weeds and it may have potential as a weed control agent. Key words: weed, natural products, solid media, fungi.

scholarly journals Development and Application of a QuEChERS-Based Liquid Chromatography Tandem Mass Spectrometry Method to Quantitate Multi-Component Alternaria Toxins in Jujube

Toxins ◽  
2018 ◽  
Vol 10 (10) ◽  
pp. 382 ◽  
Author(s):  
Cheng Wang ◽  
Yingying Fan ◽  
Weizhong He ◽  
Dongqiang Hu ◽  
Aibo Wu ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Liquid Chromatography ◽  
Tandem Mass Spectrometry ◽  
Extraction Procedure ◽  
Monomethyl Ether ◽  
Tandem Mass ◽  
Tenuazonic Acid ◽  
Alternariol Monomethyl Ether ◽  
Infection Level ◽  
Alternaria Toxins

A simple, rapid and efficient methodology was developed and validated for the analysis of four Alternaria toxins in jujube: Tenuazonic acid, alternariol, alternariol monomethyl ether, and tentoxin. Under the optimized extraction procedure, chromatographic conditions, and instrumental parameters, the four toxins were effectively extracted via a quick, easy, cheap, effective, rugged, and safe (QuEChERS) method, and quantified by ultra-performance liquid chromatography coupled to tandem mass spectrometry (UPLC-MS/MS). Matrix-matched calibrations ranging from 0.01 to 0.5 μg mL−1 were conducted for the quantification due to the matrix effect. A blank jujube sample was spiked at 40, 80 and 160 μg kg−1, obtaining recoveries in the range of 83.5–109.6%. Limits of detection and limits of quantification were in the range of 0.14–0.26 and 0.47–0.87 μg kg−1, respectively. Finally, the developed method was applied for the quantification of the four toxins in 14 jujube samples, including black spot-infected and uninfected samples. Results showed that the predominant toxin detected in all the samples was tenuazonic acid, the content of which was associated with the infection level; alternariol, alternariol monomethyl ether, and tentoxin were detected in all the infected samples and some of the uninfected samples with rather low contents.

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