Dieldrin: extraction of accumulations by root uptake.

Certain forage crops can absorb and translocate the chlorinated hydrocarbon insecticide dieldrin from soil or sand. An extraction technique routinely used for analyses of residues does not quantitatively remove this internal chemical, but a method employing chloroform-methanol extraction leads to essentially quantitative recovery.

Sex pheromone of the oak leaf roller: a complex chemical messenger system identified by mass fragmentography.

The sex pheromone of the oak leaf roller, Archips semiferanus Walker, is composed of a complex mixture of chemical signals. The attractant component of the pheromone contains a series of tetradecenyl acetates having double bonds in positions 2 to 12. Mass fragmentography of the ozonolysis products of the attractant component was used to locate the double bonds in the various isomer.

Evidence for origin of insect sex pheromones: presence in food plants.

Compounds identified as sex attractant pheromones in a number of phytophagous insects were found in a variety of host plants. These agents vary in chemical composition in different plant species, which suggests that dietary factors may provide an evolutionary mechanism for diversification of certain insect species. A theoretical framework to explain this phenomenon is postulated on the basis of experiments with the oak leaf roller moth.

In vitro activation assays with hepatic S9 preparation from wild and laboratory reared woodchucks in the Salmonella mutagenicity test.

The Salmonella mutagenicity assay was utilized to compare hepatic S9 fractions derived from wild and laboratory reared woodchucks (Marmota monax). Two promutagens, 7,12-dimethylbenz[a]anthracence (DMBA) and 2-amino-fluorene (AF) were tested at 5 concentrations with the tester strains TA98 and TA100, against 2 levels of S9 fraction. AF produced similar number of revertants with the S9 fraction from wild and laboratory-reared animals. DMBA produced 2-4 times more revertant colonies at 50 microliter S9/plate with wild woodchuck S9 than with S9 from the laboratory-reared animals with both tester strains. It was concluded that natural inducers in the wild woodchuck diet may have contributed to the increased reversion frequency over laboratory reared woodchucks. Dose-response parameters for the activation of DMBA by S9 fraction from woodchucks and rats were compared with TA100. Woodchuck S9 had 3-40 more revertants/nmol and a 100-fold lower threshold of response than S9 from Aroclor 1254-induced rats.

Comparative mutagenicity tests in the Salmonella/microsome assay with rat and woodchuck S9 preparations.

The Salmonella mutagenicity assay was utilized to compare the hepatic S9 fractions from untreated and 3-methylcholanthrene (MC) induced woodchucks with Aroclor 1254 induced rats. Three known promutagens, benzo[a]pyrene (BP), 7,12-dimethylbenz[a]anthracene (DMBA), and 2-aminofluorene (AF) were tested at 5 concentrations with the strain TA100 against 3 levels of S9 fraction. Both woodchuck S9 fractions were as effective as the rat S9 in activating BP and both were more effective than the rat S9 in activating DMBA. Untreated woodchuck S9 was also as effective as rat S9 in activating AF. The protein content of the S9 fraction did not differ significantly between rats and woodchucks, but the P-450 content of the rat S9 was approximately 3.5 times that of woodchuck.

Structure-mutagenicity relationships of chalcones and their oxides in the Salmonella assay.

31 p-monosubstituted chalcones (E-1, 3-diphenylpropene-1-one) and the corresponding oxides (E-1-benzoyl-2-phenyloxirane) were tested for mutagenic activity on two strains of Salmonella typhimurium (TA98 and TA100) with and without rat liver microsomal and cytosolic enzymes. Highest mutagenicity (3.0 revertants/nmole in either strain) was seen with the 4-nitrochalcone, especially after S9 activation. Epoxidation, in general, increased the mutagenic activity of the respective chalcone. Benzoyl (4') substituted chalcones and their oxides with an electron-withdrawing substituent (e.g., nitro, fluoro) usually had higher activity than their phenyl (4) substituted counterparts, whereas the converse was the case with electron-donating substituents (e.g., acetamido, methoxy). Further multiple factorial analysis revealed that increasing hydrophilicity as indicated by the Hansch pi parameter, and resonance electronic contributions were more important than other factors including steric terms in explaining the mutagenicity of these compounds. Mutagenic effects of some chalcone oxides, particularly the 4-methoxy derivative, were markedly decreased by S9 treatment. The consequence of the weak-to-moderate mutagenicity of these compounds to dietary intake of hydroxylated and methoxylated chalcones is discussed.

Mutagenic potency of some conjugated nitroaromatic compounds and its relationship to structure.

The mutagenicities of 12 conjugated non-fused nitroaromatic compounds and 1 amino analogue were determined in strains TA100 and TA98 of Salmonella typhimurium. Reversions by p-nitroaromatics increased in the order of the acetophenone, benzaldehyde, styrene, chalcone, cinnamic acid and stilbene indicating the importance for mutagenic potency of extended conjugation to the p-nitrophenyl substituent. Highest mutagenicity was found with alpha-substituted 4-nitrostyryl derivatives of which the phenyl derivative (31 revertants per nmole in TA100) was the most active. Generally, the TA100 strain was more sensitive than TA98 to these mutagens and S9 treatment was unnecessary for activity, although 4-nitrochalcone required S9 activation. Para-nitro isomers of the cinnamic acids and chalcones were much more active than the corresponding ortho and meta isomers. The 4-aminocinnamic acid analogue was inactive suggesting that complete reduction in Salmonella of 4-nitrocinnamic acid to an active amino derivative is not response for the high mutagenicity of the former. Mutagenicity of these p-nitrostyryl compounds may be explained by the covalent interaction of the electrophilic benzylic carbon with Salmonella DNA.

Testing of 2,4,5-T-amino acid conjugates for mutagenic activity in Salmonella typhimurium strains.

Since amino acid conjugates are plant metabolites of the herbicide 2,4,5-trichlorophenoxyacetic acid (2,4,5-T), 5 amino acid conjugates (aspartic acid, glutamic acid, leucine, methionine and tryptophan) of 2,4,5-T were tested for possible mutagenic activity utilizing 5 strains of Salmonella typhimurium (TA97, TA98, TA100, TA1535 and TA1538) with and without rat-liver microsomal and cytosolic enzymes. These compounds did not cause any significant increase in reversions when compared with controls in the presence or absence of the activating system. Further, linear regression analysis showed no significant (p less than 0.05) dose-response relationships. Thus, it was concluded that the tested amino acid conjugates of 2,4,5-T are not mutagens or promutagens in these assays.

Preparation of sulfate esters.

This communication reports a new method for the synthesis of sulfate esters, in good yield, under mild conditions. Sulfuric acid reacts with an alcohol and dicyclohexylcarbodiimide in a polar solvent to produce sulfate esters.

Thermophilic fungi: II. Fatty acid composition of polar and neutral lipids of thermophilic and mesophilic fungi.

The relative per cents of polar and neutral lipids and the fatty acid profile of the polar and neutral lipids of nine thermophilic and nine mesophilic fungi were examined and compared. The polar lipids of the thermophiles contained an average of 0.89 double bonds per mole fatty acid (unsaturation index, USI) and were considerably more saturated than the corresponding lipids of the mesophiles (average 1.32 USI). Within the thermophilic species the polar lipids were generally more saturated than the neutral lipids (average 0.95 USI) and in the mesophilic species the polar lipids were usually more saturated than the neutral lipids (average 1.14 USI). The mesophiles produced higher levels of 16∶1, 18∶2 and 18∶3 fatty acids than the thermophiles and preferentially incorporated 16∶1 and 16∶2 into their polar lipids. The thermophiles produce higher levels of saturated fatty acids and 18∶1 than the mesophiles and preferentially incorporated the saturated fatty acids into their polar lipids.

Thermophilic fungi: III. The lipids ofHumicola grisea var.thermoidea.

The lipids of the thermophilic fungusHumicola grisea var.thermoidea were qualitatively and quantitatively determined. The polar lipids consisted of 38.4-42.3% of the total lipids. The relative per cent phospholipids based upon the total phospholipids were as follows: phosphatidyl choline, 32.3-33.7%; phosphatidic acid, 24.5-31.7%; phosphatidyl ethanolamine, 15.8-20.9%; phosphatidyl inositol, 12.5-13.0%; phosphatidyl serine, 2.3-5.4%; and diphosphatidyl glycerol, 3.9-4.0%. The relatively high concentration of phosphatidic acid may be characteristic of fungi grown at elevated temperatures. Several sterol glycosides (3.1-6.0%) were present in the polar lipids. The neutral lipids consist of triglycerides, 28.6-36.0%; free fatty acids, 5.3-13.5%; sterols, 11.4-13.9%; sterol esters, 1.8-3.0%; and diglycerides, 2.2-3.4%. The sterols and derivatives comprise an unusually large fraction of the total lipids (16.3-22.9%) suggesting a role in thermostability.

Toxic and protective constituents in pet foods.

An analytical survey of mutagens, nitrosamines, polychlorinated biphenyls, toxic elements, and gamma-emission, as well as the toxicologically protective constituents zinc, selenium, and vitamin C, in 48 pet foods was conducted. Aside from high concentrations of fluoride and iodide in some samples and the expectedly higher concentrations of mercury and selenium in certain cat foods containing fish, the samples were notably free of the other toxic constituents. Direct-acting and promutagens and nitrosamines were not detectable in any of the samples. gamma-Emission was very low in all of the foods. Polychlorinated biphenyls were only detected in one cat food.