Ronald G. Binder

Eight 1,4-naphthoquinones from Juglans

Abstract Eight volatile 1,4-naphthoquinones from acetone extracts of unripe black walnut (Juglans nigra) and English walnut (Juglans regia) fruit were identified by gas chromatography-mass spectrometry assisted by 1H NMR. Compounds not previously reported in walnut are 2-methyl-1,4-naphthoquinone, 2,3-dihydro-5-hydroxy-2-methyl-1,4-naphthalenedione (β-hydroplumbagin), 5-hydroxy-2-methyl-1,4-naphthoquinone (plumbagin), 5-hydroxy-3-methyl-1,4-naphthoquinone and 2,3-dimethyl-5-hydroxy-1,4-naphthoquinone. The latter two compounds are here first reported as natural products.

Alfalfa cyclitols in the honeydew of an aphid

Abstract The free cyclitols pinitol, ononitol and myo-inositol occur in the honeydew (excreta) of pea aphids (Acyrthosiphon pisum) which feed on pea aphid-susceptible alfalfa (Medicago sativa cv Caliverde). These cyclitols also occur in the leaves and stems of alfalfa. Aphids were incapable of de novo synthesis of these cyclitols. Honeydew production by the pea aphid results from ingesting phloem-sap, so the occurrence of cyclitols in honeydew results from their translocation in the phloem. The relatively high content of myo-inositol in honeydew indicates that it is selectively translocated. The most abundant alfalfa cyclitol, pinitol, had no effect on aphid feeding behavior at concentrations up to 1% (w/v; artificial diet).

Analysis of O-methylinositols by gas-liquid chromatography-mass spectrometry☆

Abstract A procedure for identifying natural O -methylinositols by g.l.c.-m.s. analysis is described. Chromatographic retention-index values for these compounds and commonly co-occurring compounds are given. The procedure is illustrated by analyses of clover and peanut cyclitols.

EFFECTS OF CYCLOPROPANOID AND CYCLOPROPENOID FATTY ACIDS ON GROWTH OF PINK BOLLWORM, BOLLWORM AND TOBACCO BUDWORM

The effects of dietary methyl esters of cyclopropanoid and cyclopropenoid fatty acids on the growth of larvae of the pink bollworm, Pectinophora gossypiella, the bollworm, Heliothis zea and the tobacco budworm, Heliothis virescens, was investigated. The major cotton cyclopropenoid, malvalate, had an ED50 of 0.28% for larvae of P. gossypiella, 0.64% for larvae of H. zea and 0.66% for larvae of H. virescens.

2-Morpholinoethylisocyanide as a coupling agent for hapten-protein conjugates

Abstract Conjugation of haptens to proteins and enzymes is essential for the production of antibodies and development of ELISAs for these low molecular weight compounds. In this study, protein conjugates of several carboxylic haptens were prepared using the peptide synthesis reagent, 2-morpholinoethylisocyanide. The haptens included derivatives of benzimidazole and pyridoxine. The main advantage of this conjugation procedure is its simplicity involving only small volumes of water-miscible organic reagents. The resulting conjugates were purified by dialysis and could be used to elicit antibodies and establish immunoassays.

Halogenated 2,5-pyrrolidinediones: synthesis, bacterial mutagenicity in Ames tester strain TA-100 and semi-empirical molecular orbital calculations

The chloroimide 3,3-dichloro-4-(dichloromethylene)-2,5-pyrrolidinedione, a tetrachloroitaconimide, is the principal mutagen produced by chlorination of simulated poultry chiller water. It is the second most potent mutagenic disinfection by-product of chlorination ever reported. Six of seven new synthetic analogs of this compound are direct-acting mutagens in Ames tester strain TA-100. Computed energies of the lowest unoccupied molecular orbital (E(LUMO)) and of the radical anion stability (DeltaH(f)(rad)-DeltaH(f)) from MNDO-PM3 for the chloroimides show a quantitative correlation with the Ames TA-100 bacterial mutagenicity values. The molar mutagenicities of these direct acting mutagenic imides having an exocyclic double bond fit the same linear correlation (lnM(m) vs. E(LUMO); lnM(m) vs. DeltaH(f)(rad)--DeltaH(f)) as the chlorinated 2(5H)-furanones, including the potent mutagen MX, 3-chloro-4-(dichloro-methyl)-5-hydroxy-2(5H)-furanone, a by-product of water chlorination and paper bleaching with chlorine. Mutagenicity data for related haloimides having endocyclic double bonds are also given. For the same number of chlorine atoms, the imides with endocyclic double bonds have significantly higher Ames mutagenicity compared to their structural analogs with exocyclic double bonds, but do not follow the same E(LUMO) or DeltaH(f)(rad)-DeltaH(f) correlation as the exocyclic chloroimides and the chlorinated 2(5H)-furanones.

Growth and hemolymph trehalose levels of Heliothis zea larvae fed diets containing various sugars

Abstract 1. 1. The amount of sugar required for growth of Heliothis zea larvae on a chemically defined diet was determined. 2. 2. Larvae grew well on fructose, galactose, sucrose, trehalose and raffinose diets but not on diets containing more than 0.5% glucose. 3. 3. A starch diet did not promote rapid larval growth. 4. 4. Hemolymph trehalose levels in 12-day-old larvae ranged from none to 45μmoles/ml. 5. 5. A method for analysis of hemolymph trehalose by gas chromatography is described.