Aflatoxin B2
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Aflatoxin B2
structure -
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CAS No:
7220-81-7
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Formula:
C17H14O6
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Chemical Name:
Aflatoxin B2
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Synonyms:
Cyclopenta[c]furo[3′,2′:4,5]furo[2,3-h][1]benzopyran-1,11-dione,2,3,6a,8,9,9a-hexahydro-4-methoxy-,(6aR,9aS)-;Aflatoxin B2;Cyclopenta[c]furo[3′,2′:4,5]furo[2,3-h][1]benzopyran-1,11-dione,2,3,6aα,8,9,9aα-hexahydro-4-methoxy-;Cyclopenta[c]furo[3′,2′:4,5]furo[2,3-h][1]benzopyran-1,11-dione,2,3,6a,8,9,9a-hexahydro-4-methoxy-,(6aR-cis)-;(6aR,9aS)-2,3,6a,8,9,9a-Hexahydro-4-methoxycyclopenta[c]furo[3′,2′:4,5]furo[2,3-h][1]benzopyran-1,11-dione;Dihydroaflatoxin B1;Dihydroaflatoxine B1
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CAS No:
Description
Aflatoxin B2 is a major naturally produced aflatoxin. Aflatoxin B2 is a mycotoxin produced by the fungi Aspergillus flavus and Aspergillus parasiticus.The level of toxicity associated with Aflatoxin is Aflatoxin B1>Aflatoxin M1>Aflatoxin G1>Aflatoxin B2>Aflatoxin M2>Aflatoxin G2[1].
Aflatoxin B2 is an aflatoxin having a hexahydrocyclopenta[c]furo[3',2':4,5]furo[2,3-h]chromene skeleton with oxygen functionality at positions 1, 4 and 11.
Aflatoxin B2 Basic Attributes
314.29
314.29
230-618-8
7SKR7S646P
DTXSID70222535
Crystals|Colorless to pale yellow crystals|Crystals from chloroform and pentane|Yellow crystals with blue fluorescence
29322090
Characteristics
71.1
1.45 (est)
1.52±0.1 g/cm3
286-289 °C
521.0±50.0 °C at 760 mmHg
11 °C
1.660
H2O: Practically insoluble (0.012 g/L) (25 ºC)
2-8°C
1.65X10-10 mm Hg at 25 deg C (est)
Oral-Duck LD50: 1.70 mg/kg
Flammable; burning releases irritating fumes
D -492° (c = 0.1 in CHCl3)
Henry's Law constant = 2.99X10-15 atm-cu m/mol at 25 °C (est)
162 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine]|176.8 Ų [M+Na]+ [CCS Type: TW, Method: calibrated with polyalanine]|181.4 Ų [M+K]+ [CCS Type: TW, Method: calibrated with polyalanine]|174.42 Ų [M-H]-
Exhibits blue fluorescence|Aflatoxins are densely fluorescent; the B refers to blue, while the G signifies green fluorescence. /Aflatoxins/
Safety Information
I
6.1(a)
UN 3462 6.1/PG 1
3
45-26/27/28-39/23/24/25-23/24/25-11-65-48/23/24/25-36/38-46-36-20/21/22
53-36-45-36/37-26-62-28-16
GY1722000
T+,T,F,Xn
Treasury is ventilated, low temperature and dry; stored separately from food materials
AFLATOXINS B1, B2, G1, & G2 IN WATER OR CHLOROFORM SOLUTIONS OR IN SOLID FILMS WERE DECOMPOSED BY UV IRRIDIATION.
P201-P260-P264-P280-P284-P301 + P310
H300 + H310 + H330-H350
SRP: Criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.|Chemical treatment: Any chemical detoxification must reduce the mycotoxin level to within limits set by proper regulatory agencies, must have no toxic residues, and should not decrease the nutritive value of the treated commodity. These restrictions as well as simple economic considerations have narrowed the types of chemical agents likely to achieve significance in a commercially scaled detoxification process. Chemicals having good promise in this regard can be classified simply as oxidizing agents, acid, and bases. Of oxidizing systems that destroy all the aflatoxin only hydrogen peroxide has shown promise to detoxify foods and feeds. ... Aqueous suspensions of peanut meals containing 90 ppm aflatoxin /were treated/ with 6% soln of hydrogen peroxide at pH 9.5 for 30 min at 80 °C. The treatment destroyed 97% of the toxin ... . The use of acids as detoxifying agents has a definite potential in the recovery process of free fatty acids from commercial soapstock prepn. The use of inorganic and organic bases affords an efficient and relatively inexpensive means to achieve aflatoxin destruction or removal from large quantities of contaminated agricultural commodities. The refinement of edible oils is a classic example of the use of bases under conditions that would destroy or remove aflatoxins.|PRECAUTIONS FOR "CARCINOGENS": There is no universal method of disposal that has been proved satisfactory for all carcinogenic compounds & specific methods of chem destruction ... published have not been tested on all kinds of carcinogen-containing waste. ... summary of avail methods & recommendations ... /given/ must be treated as guide only. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": ... Incineration may be only feasible method for disposal of contaminated laboratory waste from biological expt. However, not all incinerators are suitable for this purpose. The most efficient type ... is probably the gas-fired type, in which a first-stage combustion with a less than stoichiometric air:fuel ratio is followed by a second stage with excess air. Some ... are designed to accept ... aqueous & organic-solvent solutions, otherwise it is necessary ... to absorb soln onto suitable combustible material, such as sawdust. Alternatively, chem destruction may be used, esp when small quantities ... are to be destroyed in laboratory. /Chemical Carcinogens/|For more Disposal Methods (Complete) data for AFLATOXIN B2 (7 total), please visit the HSDB record page.
U.S. Department of Health & Human Services/National Toxicology Program; Twelfth Report on Carcinogens (2011). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. Aflatoxins (1402-68-2) are known to be human carcinogens. First listed in the First Annual Report on Carcinogens (1980). /Aflatoxins/[Available from, as of July 25, 2013: http://ntp.niehs.nih.gov/]|WHO; Environmental Health Criteria 11: Mycotoxins (1979)
|Danger|H300+H310+H330 (25%): Fatal if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]|P201, P202, P260, P262, P264, P270, P271, P280, P281, P284, P301+P310, P302+P350, P304+P340, P308+P313, P310, P320, P321, P322, P330, P361, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 4 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
PRECAUTIONS FOR "CARCINOGENS": ... Dispensers of liq detergent /should be available./ ... Safety pipettes should be used for all pipetting. ... In animal laboratory, personnel should ... wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. ... Gowns ... /should be/ of distinctive color, this is a reminder that they are not to be worn outside the laboratory. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labelled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": Smoking, drinking, eating, storage of food or of food & beverage containers or utensils, & the application of cosmetics should be prohibited in any laboratory. All personnel should remove gloves, if worn, after completion of procedures in which carcinogens have been used. They should ... wash ... hands, preferably using dispensers of liq detergent, & rinse ... thoroughly. Consideration should be given to appropriate methods for cleaning the skin, depending on nature of the contaminant. No standard procedure can be recommended, but the use of organic solvents should be avoided. Safety pipettes should be used for all pipetting. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": In animal laboratory, personnel should remove their outdoor clothes & wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... Clothing should be changed daily but ... discarded immediately if obvious contamination occurs ... /also,/ workers should shower immediately. In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. If gowns are of distinctive color, this is a reminder that they should not be worn outside of lab. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": ... Operations connected with synth & purification ... should be carried out under well-ventilated hood. Analytical procedures ... should be carried out with care & vapors evolved during ... procedures should be removed. ... Expert advice should be obtained before existing fume cupboards are used ... & when new fume cupboards are installed. It is desirable that there be means for decreasing the rate of air extraction, so that carcinogenic powders can be handled without ... powder being blown around the hood. Glove boxes should be kept under negative air pressure. Air changes should be adequate, so that concn of vapors of volatile carcinogens will not occur. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": Vertical laminar-flow biological safety cabinets may be used for containment of in vitro procedures ... provided that the exhaust air flow is sufficient to provide an inward air flow at the face opening of the cabinet, & contaminated air plenums that are under positive pressure are leak-tight. Horizontal laminar-flow hoods or safety cabinets, where filtered air is blown across the working area towards the operator, should never be used ... Each cabinet or fume cupboard to be used ... should be tested before work is begun (eg, with fume bomb) & label fixed to it, giving date of test & avg air-flow measured. This test should be repeated periodically & after any structural changes. /Chemical Carcinogens/|For more Preventive Measures (Complete) data for AFLATOXIN B2 (9 total), please visit the HSDB record page.
PRECAUTIONS FOR "CARCINOGENS": Procurement ... of unduly large amt ... should be avoided. To avoid spilling, carcinogens should be transported in securely sealed glass bottles or ampoules, which should themselves be placed inside strong screw-cap or snap-top container that will not open when dropped & will resist attack from the carcinogen. Both bottle & the outside container should be appropriately labelled. ... National post offices, railway companies, road haulage companies & airlines have regulations governing transport of hazardous materials. These authorities should be consulted before ... material is shipped. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": When no regulations exist, the following procedure must be adopted. The carcinogen should be enclosed in a securely sealed, watertight container (primary container), which should be enclosed in a second, unbreakable, leakproof container that will withstand chem attack from the carcinogen (secondary container). The space between primary & secondary container should be filled with absorbent material, which would withstand chem attack from the carcinogen & is sufficient to absorb the entire contents of the primary container in the event of breakage or leakage. Each secondary container should then be enclosed in a strong outer box. The space between the secondary container & the outer box should be filled with an appropriate quantity of shock-absorbent material. Sender should use fastest & most secure form of transport & notify recipient of its departure. If parcel is not received when expected, carrier should be informed so that immediate effort can be made to find it. Traffic schedules should be consulted to avoid ... arrival on weekend or holiday ... /Chemical Carcinogens/
Toxicity
most toxic
LD50 Duck oral 1700 ug/kg
/BIRDS AND MAMMALS/ The toxic properties of aflatoxin B2 were similar to those for aflatoxin B1; however, potency was markedly reduced compared to aflatoxin B1. A dosage in ducklings of 50 ug of aflatoxin B2 was required to produce the same degree of bile duct proliferation produced by 3.9 ug of aflatoxin B1.
Aflatoxin B2 is a toxic metabolite of the fungi Aspergillus flavus and A. parasiticus(1).
TERRESTRIAL FATE: Based on a classification scheme(1), a Koc range of 682 to 2.3X10+4 for analogous aflatoxin B1(2), indicates that aflatoxin B2 is expected to have low to no mobility in soil(SRC). Volatilization of aflatoxin B2 from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.0X10-15 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Aflatoxin B2 is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.7X10-10 mm Hg at 25 °C(SRC), determined from a fragment constant method(4).|AQUATIC FATE: Based on a classification scheme(1), a Koc range of 682 to 2.3X10+4 for analogous aflatoxin B1(2), indicates that aflatoxin B2 is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 3.0X10-15 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 4(SRC), from an estimated log Kow of 1.45(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), aflatoxin B2, which has an estimated vapor pressure of 1.7X10-10 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase aflatoxin B2 may be removed from the air by wet and dry deposition(SRC). Aflatoxin B2 absorbs UV light at wavelengths of 265 and 363 nm(3) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).
The aflatoxins may undergo hydrolysis in the environment as they contain a cyclic ester functionality(1). Rates may be similar to non-cyclic esters, which are in the range of months to years time frame; however, steric hindrance and ring strain effects may be important(2). Aflatoxin B2 absorbs UV light at wavelengths of 265 and 363 nm(3) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).
An estimated BCF of 4 was calculated in fish for aflatoxin B2(SRC), using an estimated log Kow of 1.45(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low.
Koc values of 23170, 1570 and 682 were calculated(SRC) from Freundlich's adsorption coefficients of 238.49, 76.19 and 17.40 mg/kg soil, respectively, for analogous aflatoxin B1 in a silty clay loam (pH 7.3, 0.597% organic matter, CEC of 18.0 cmol/kg), a silt loam (pH 5.8, 2.818% organic matter, CEC of 11.7 cmol/kg) and a sandy loam (pH 6.0, 1.478% organic matter, CEC of 5.4 cmol/kg), respectively(1). According to a classification scheme(2), these Koc values suggest that the aflatoxins may range in mobility from low to immobile depending on the soil. Cation exchange capacity was positively correlated with the adsorption coefficient value(1). In addition, the type of clay (2:1 expanding clays were found in the silty clay loam) appears to influence the amount of adsorption to soil(1).
The Henry's Law constant for aflatoxin B2 is estimated as 3.0X10-15 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that aflatoxin B2 is expected to be essentially nonvolatile from water and moist soil surfaces(2). Aflatoxin B2 is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.7X10-10 mm Hg(SRC), determined from a fragment constant method(3).
Commercially available market basket samples were collected in Tokyo, Japan during 1986 to 1990; aflatoxin concentrations were determined in 3054 samples (803 samples of cereals, 540 samples of nuts, 540 samples of beans, 564 samples of spices, and 607 samples of other foods). Aflatoxin B2 was detected as follows (range, average ppb): rice, 0-trace, <0.1; sugar, 0.1-0.2, 0.1; peanut, 0.1-5.3, 0.9; pistachio nut, 0.5-260, 58.0; brazil nut, 0.8; sesame 0.2-0.5, 0.4; beans for bean jam, 0.4-1.5, 0.7; white pepper, 0-0.3, <0.1; red pepper, 0-0.4, 0.2; nutmeg, 0-2.5, 0.5; mixed spice 0-0.4, <0.1(1).|Aflatoxin B2 concentrations of
Occupational exposure to aflatoxin B2 may occur through inhalation and dermal contact with this compound at workplaces where commodities such as peanuts are processed. Monitoring data indicate that the general population may be exposed to aflatoxin B2 via ingestion of contaminated food. (SRC)
Drug Information
Administration of (3)H-aflatoxin b2 to male rats gave levels of hepatic DNA & ribosomal (r)RNA aflatoxin adducts that were about 1% of those for rats given (3)H-aflatoxin b1. Levels of hepatic protein aflatoxin adducts were 35-70% as great for aflatoxin b2-treated rats as for aflatoxin b1-treated rats.|A study was conducted to determine aflatoxin levels in the tissues of broiler chickens that had been fed a diet containing 2057 micrograms aflatoxin B1 and 1323 micrograms aflatoxin B2/kg for 35 days. Results showed that aflatoxins were deposited in all tissues. The highest levels of aflatoxins were present in the gizzards, livers and kidneys. There was evidence that the high levels of aflatoxins B1 and B2 in the gizzards might have been caused by contamination by the gizzard contents during the slaughtering process. After feeding the aflatoxin-contaminated diet for 35 days, mean values for the combined aflatoxins were less than 3 micrograms/kg of tissue. Four days after withdrawal of the aflatoxin-contaminated ration, there were no detectable amounts of aflatoxins in any of the tissues. The results indicate that broiler chickens rapidly clear aflatoxins from their tissues once they are transferred to an aflatoxin-free diet.|To evaluate the rate at which the four main aflatoxins (aflatoxins B1, B2, G1 and G2) are able to cross the luminal membrane of the rat small intestine, a study about intestinal absorption kinetics of these mycotoxins has been made. In situ results obtained showed that the absorption of aflatoxins in rat small intestine is a very fast process that follows first-order kinetics, with an absorption rate constant (ka) of 5.84 +/- 0.05 (aflatoxin B1), 4.06 +/- 0.09 (aflatoxin B2), 2.09 +/- 0.03 (aflatoxin G1) and 1.58 +/- 0.04 (aflatoxin G2) h-1, respectively.
Yields Alfatoxin m2 in rat. From table/|Metabolism of aflatoxin b2 by postmitochondrial supernatant fractions of duck, rat, mouse & human livers was studied in an in vitro system. Postmitochondrial supernatant from duck equivalent to 0.2 g whole liver metabolized 40-80% of the initial substrate in 30 min, compared to less than 6% for other species. Among several metabolites formed by duck liver, aflatoxin b1 was produced in amt equivalent to 2-8% of the initial substrate, & metabolites having chromatographic properties postulated for aflatoxicols 1 & 2 & aflatoxins m1 & m2 were also formed in small amounts. The greater susceptibility of duck liver to the toxicity of aflatoxin b2 may be attributable to its ability to form aflatoxin b1, which could be activated through further metabolism.|Aflatoxin b2 admin iv to rats was rapidly metabolized to 7 groups of metabolites, 6 of which were excreted in the bile. Aflatoxin b2 was hydroxylated at the 2- & 4-positions. Bile from rats given aflatoxin b2 contained 2 glucuronides.
With the 4 principal aflatoxins tested, the order of inhibitory effect on RNA polymerase ii was: b1 greater than g1 greater than b1, g2.|Ability of aflatoxin b1, aflatoxin b2, & aflatoxin g1 to inhibit RNA polymerase activity & decr RNA content in rat hepatocyte nuclei was qualitatively similar to the carcinogenic & acute & subacute toxic actions of these compounds.|The interaction of aflatoxin B2 (AFB2) in vivo with rat liver nuclear macromolecules was examined in an attempt to correlate this binding with biological potency. The incorporation of [(3)H]AFB2 residues into rat liver histones and DNA was determined 2, 24 and 48 hr following administration of a single ip dose of 1 mg [(3)H]AFB2/kg bw. At each time point, histone H1 and the total histone fraction contained 5--30-fold more [(3)H]AFB2 moieties than did DNA on a weight basis. Analytical reversed-phase HPLC of the acid hydrolysis products resulting from AFB2 binding to DNA revealed that 85% of the radioactivity co-chromatographed with the major aflatoxin B1-DNA adduct, 2,3-dihydro-2-(N7-guanyl)-3-hydroxyaflatoxin B1. These studies revealed an apparent correlation between AFB2 derived binding to DNA in vivo in rats and its potency as a toxin and carcinogen in this species.|Aflatoxins produce singlet oxygen upon their exposure to UV (365-nm) light. Singlet oxygen in turn activates them to mutagens and DNA binding species. DNA binding and mutagenesis by aflatoxins were enhanced in D2O as compared to reactions in H2O, and a singlet oxygen scavenger inhibited mutagenesis. DNA photobinding of 3H-aflatoxin B1 increased in the presence of unlabeled aflatoxin B2, and the addition of aflatoxin B2 enhanced mutagenesis by aflatoxin B1 in a synergistic manner. These results are compatible with the notion that singlet oxygen, formed by one aflatoxin molecule, can readily activate another aflatoxin molecule. This may bear an environmental implication in that the weakly carcinogenic aflatoxin B2, which is often produced in nature together with aflatoxin B1, may be important in enhancing the activation of aflatoxin B1 by sunlight.
/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/
/HUMAN EXPOSURE STUDIES/ There are four generally recognized aflatoxins, b1, b2, g1, & g2. Although they are generally associated with Aspergillus flavus, many other aspergillus species & also members of the penicillium & rhizopus genera can also produce the carcinogens. This means that a range of both animal & human foodstuffs & not just the major source, peanuts, can become contaminated with aflatoxin. There is clearly therefore the possibility of a real hazard to man since the first criterion, the presence of the carcinogen in the diet, has been established.|/IMMUNOTOXICITY/ /Investigators/ aimed to examine the effect of mixed AFs on immunologically relevant molecules and on viability in human peripheral blood mononuclear cells (PBMCs), in conditions similar to those occurring naturally, i.e. using a mixture of environmentally relevant levels of AFB1, AFB2, AFG1 and AFG2. /Investigators/ evaluated the mRNA expression of MyD88, toll-like receptor (TLR)-2, TLR4 and CD14, in human PBMCs treated with a mixture of AFB1, AFB2, AFG1 and AFG2 at different doses for 2, 12 and 24 hr. /qRT-PCR was used/ to assess changes in transcripts of MyD88, TLR2, TLR4 and CD14 in PBMCs. The viability of PBMCs exposed to AFs /was also evaluated/. Biologically relevant levels of mixed AFs elicited early immune modulation in human PBMCs. qRT-PCR results showed several folds increase of MyD88, TLR2, TLR4 and CD14 transcripts in PBMCs as early as 2hr post-exposure to mixed AFs. Kinetics and dose-response of the up-regulation differed for mentioned gene transcripts. Further, prolonged exposure to mixed AFs decreased PBMCs viability. Immunotoxicity of AFs on PBMCs may be mediated by up-regulation of key immune-surveillance molecule transcripts. The description of these effects induced by AFs on PBMCs are novel and should be taken into account when considering AF-related infectious and noninfectious diseases in areas highly exposed to AFs.|/OTHER TOXICITY INFORMATION/ Studies of the effects of the various aflatoxins on human embryo & adult liver cells in vitro have demonstrated that the order of toxicity is b1 >g1 >g2 >b2.|/OTHER TOXICITY INFORMATION/ Ten compounds /including Aflatoxin B2/ ...were evaluated for their cytotoxicity and transforming ability to human skin fibroblasts in vitro. ...Aflatoxin B2 (AFB2)... exhibited <40% inhibition of colony formation even at ...50 ug/mL... . Anchorage-independent growth of exposed cells in soft agar was used as a biological endpoint for the expression of chemical transformation. ...AFB2 was a weak transforming agent. ...
aflatoxin B2
Aflatoxin B2 Use and Manufacturing
... Aflatoxins are produced only in small quantities for research purposes, by fermentation of Aspergillus flavus or Aspergillus parasiticus on solid substrates or media in the laboratory. Aflatoxins are extracted by solvents and purified by chromatography. /Aflatoxins/
Aflatoxins are naturally occuring mycotoxins produced by various species of the mold Aspergillus, which can be found in legumes, corn, soybeans, rice, milk, and cheese. They are highly carcinogenic substances that are metabolized by the liver to a reactive epoxide intermediate, which produces adducts that modify DNA. Aflatoxin B1 induces transversion of G to T at codon 249 of the p53 tumor suppressor gene. This transversion is common in hepatocellular carcinoma patients living in regions with high levels of aflatoxin contamination. Aflatoxin B2 is the dihydro derivative of aflatoxin B1, a naturally occuring mycotoxin and food contaminant that is a likely pathogen that causes hepatocellular carcinoma.[Cayman Chemical]
Aflatoxins are produced primarily by the common fungus Aspergillus flavus and the closely related species A. parasiticus. These are well defined species: A. flavus produces only B aflatoxins and sometimes the mycotoxin cyclopiazonic acid (CPA), while A. parasiticus produces both B and G aflatoxins, but not CPA. Aflatoxin M1 is a metabolite of aflatoxin B1 that can occur in milk and milk products from animals consuming feed contaminated with B aflatoxins.|A mutant of Aspergillus flavus having a high and relatively stable aflatoxin B2/B1 ratio was recovered after treatment with nitrosoguanidine|A strain of Aspergillus flavus isolated from ground black pepper produced only aflatoxin B2 on several natural substrates.|The 8,9-dihydro derivative of aflatoxin B1.|Of the four major aflatoxins (B1, G1, B2, G2), B1 is the most potent and most common. Whenever they occur as food contaminants, aflatoxin B1 always is present. The other major aflatoxins have not been reported in the absence of B1. Aflatoxins are densely fluorescent; the B refers to blue, while the G signifies green fluorescence.
A confirmatory test for aflatoxins B1 & B2 involves treatment of aflatoxins with excess sodium borohydride for 10 min at room temp to yield a fluorescent trihydroxy deriv of each aflatoxin.|A device is described for detecting aflatoxin corn contamination utilizing UV light.|Efficient detection of aflatoxins B1, B2, G1, and G2 has been performed by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry using a UV-absorbing ionic liquid matrix to obtain "matrix-free" mass spectra and addition of NaCl to enhance sensitivity via Na+ cationization. Using ionic alpha-cyano-4-hydroxycinnamic acid (Et3N-alpha-CHCA) as the matrix, matrix-free mass spectra in the m/z range of interest are acquired, and the B1, B2, G1, and G2 aflatoxins are readily detected with an LOD as low as 50 fmol. The technique is fast, requires little sample preparation and no derivatization or chromatographic separation, and seems therefore to be suitable for high-throughput aflatoxin screening. It should be easily extended to other micotoxins and provide an attractive technique to control the quality of major crops subjected to huge world commercial trades such as peanuts, corn, and rice as well as to monitor bioterrorism threats by micotoxin poisoning.|A high-performance liquid chromatographic method with on-line post-column photochemical derivatization and fluorimetric detection for the simultaneous separation and quantitative determination of aflatoxin (AF) B(1), B(2), G(1), and G(2) in foodstuffs and feed materials is reported. The chromatographic separation is accomplished by using a C(18) column eluted with an isocratic mobile phase consisting of water, methanol, and acetonitrile. The sample preparation requires a simple extraction of aflatoxins with a mixture of water and methanol, and a purification step by immunoaffinity column clean-up. The total analysis time, including sample preparation and chromatographic separation, does not exceed 40 min with a run time of 10 min. The procedure for the determination of aflatoxins in food samples and cereals for animal consumption has been extensively validated, in agreement with Regulation (EC) No. 882/2004, demonstrating the conformity of the method with provisions of Regulation (EC) No. 401/2006 in terms of sensitivity, linearity, selectivity, and precision.|For more Analytic Laboratory Methods (Complete) data for AFLATOXIN B2 (21 total), please visit the HSDB record page.
Aflatoxin B2 recoveries from spiked human serum samples following hexane-chloroform extraction, chloroform extraction with pentane cleanup, or acetone-ferric gel-chloroform extraction ranged from 80-95%, 59-82% & 33-67%, respectively. Quantitation was by high pressure liquid chromatography with fluorescence detector.|Human urine and methanol extracted tissues and sputum were examined. Trichothecenes were tested using competitive ELISA techniques. Aflatoxins B1, B2, G1, and G2, and ochratoxin A were tested by using immunoaffinity columns and fluorometry. Test sensitivity and specificity were determined. Levels of detection for the various mycotoxins varied from 0.2 ppb for trichothecenes, 1.0 ppb for aflatoxins, and 2.0 ppb for ochratoxins. Trichothecene levels varied in urine, sputum, and tissue biopsies (lung, liver, brain) from undetectable (<0.2 ppb) to levels up to 18 ppb. Aflatoxin levels from the same types of tissues varied from 1.0 to 5.0 ppb. Ochratoxins isolated in the same type of tissues varied from 2.0 ppb to > 10.0 ppb. Negative control patients had no detectable mycotoxins in their tissues or fluids. These data show that mycotoxins can be detected in body fluids and human tissue from patients exposed to mycotoxin producing molds in the environment, and demonstrate which human tissues or fluids are the most likely to yield positive results.
Computed Properties
Molecular Weight:314.29
XLogP3:1.3
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:1
Exact Mass:314.07903816
Monoisotopic Mass:314.07903816
Topological Polar Surface Area:71.1
Heavy Atom Count:23
Complexity:610
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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