B. K. Bailey

Coumarins and alkaloids from cell cultures of Ruta graveolens

Abstract Cells of Ruta graveolens L., grown in continuous light in liquid medium produced the coumarins umbelliferone, scopoletin, psoralen, xanthotoxin, isopimpinellin, rutamarin and rutacultin (6,7-dimethoxy- 3-(1,1-dimethylallyl)coumarin), a new natural product. Four alkaloids were also identified: skimmianine, kokusaginine, 6-methoxydictamnine and edulinine (1-methyl-4-methoxy-3-[2,3-dihydroxy-3-methylbutyl]-2-quinolone).

Triunsaturated hydrocarbons, sex pheromone components ofCaenurgina erechtea.

Abstract(Z,Z,Z)-3,6,9-Eicosatriene and (Z,Z,Z)-3,6,9-heneicosatriene have been identified as components of the sex pheromone of the noctuid,Caenurgina erechtea (Cramer), the forage looper. Structural assignments were made on the basis of spectroscopic and chromatographic data and were confirmed by comparison with synthetic material. Flight tunnel behavioral studies demonstrated that either component, when tested individually, would elicit wing fanning responses in males; however, mixtures of the two components increased this response and were essential for initiation of upwind flight and landing. In field experiments, traps baited with either component alone captured few or no adult forage looper males while those baited with both components captured several target males.

Formation of edulinine and furoquinoline alkaloids from quinoline derivatives by cell suspension cultures of Ruta graveolens

Abstract The formation of furoquinoline alkaloids and of edulinine, elaborated by cell suspension cultures of Ruta graveolens , was found to occur by way of 4-hydroxy-2-quinolone. Other substrates transformed to furoquinolines included 4-hydroxy- and 4-methoxy-3-(3-methyl-2-butenyl)-2-quinolone, known earlier as natural precursors in studies with whole plants. Involvement of dictamnine as a natural precursor of 8-methoxydictamnine (γ-fagarine) and skimmianine was proved using 14 C-labelled compounds. Edulinine in the cell suspensions was formed from such substrates as 4-hydroxy- N -methyl-2-quinolone, 4-hydroxy-3-(3-methyl-2-butenyl)- N -methyl-2-quinolone and its 4- methyl ether; this is probably the natural biosynthetic sequence. Changes in alkaloid yields were noted upon prolonged subculturing.

Synthesis of sex pheromone components of the forest tent caterpillar, Malacosoma disstria (Hubner) and of the western tent caterpillar, Malacosoma californicum (Packard).

All four geometrical isomers of 5,7-dodecadien-1-ol have been stereoselectively synthesized by using Wittig condensation reactions. (5 Z,7E)-5,7-Dodecadien-1-ol and its corresponding aldehyde are components of the sex pheromone of the forest tent caterpillar. (5 E,7 Z)-5,7-Dodecadienal is a component of the pheromone of the western tent caterpillar. These compounds have been successfully tested in the field.

Trace co-attractants in synthetic sex lures for 22 noctuid moths

Trace components contributed significantly to the potency of synthetic sex attractant lures for males of many species of Noctuidae. Improved synthetic blends for 12 moths includingEuxoa ochrogaster andTrichoplusia ni, and new lure blends for 10 moths are described. In every case the trace constituents were structural analogs of the main lure components.

A 4-component sex attractant for male moths of the armyworm, Pseudaletia unipuncta.

The principal sex pheromone component of the Armyworm, Pseudaletia unipuncta (Haworth) is (Z)-ll-hexadecenyl acetate ( Z l l 1 6 : A c ) (Hill & Roelofs, 1980; McDonough et al., 1980; Farine et al., 1981). The corresponding alcohol has been reported as a minor component (McDonough et al., 1980; Farine et al., 1981), the optimum acetate: alcohol ratio in field lures being about 5 0 0 : 1 (Steck et al., 1980). Although this mixture is a useful and specific lure for monitoring populations, trap captures were often lower than those obtained by light-trapping. We therefore set out to find chemical synergists for the lure. Previously, workers had detected several other compounds in extracts from 9 sex pheromone glands: (Z)-9-hexadecenyl acetate (Z9--16: Ac) and hexadecyl acetate (McDonough et al., 1980). However, our preliminary field tests indicated that none of these compounds had measureable effect on the lure. We concluded that if pheromone components other than Z l I 1 6 : Ac and Z l I 1 6 : OH are produced by 9 9, their amounts must be so small as to escape detection by instrumental analysis using normal procedures. If this were not true, they should have been encountered by the earlier authors during their analyses. The existence of trace co-attractants in some pheromone systems has been established recently (Klun et al., 1980a, b).

(Z)-5-Tetradecenyl acetate, a trapping synergist for the major sex pheromone of the spotted cutworm, Amathes c-nigrum

other tissues in T. ni during development to determine whether this increase in esterase activity is unique to the antennae. Materials and methods. The pheromone, (Z)-7-dodecen-l-ol acetate (99+% pure; tritium-labeled in the acetate moiety, 200 mCi/ mmole), was prepared from (Z)-7-dodecen-1oi and labeled acetic anhydride (400 mCi/ mmole, New England Nuclear). The assay for measuring pheromone hydrolysis and the preparation of antennal and other tissue homogenates for that assay were as previously described, except that the homogenates were sonicated in a probetype sonicator for 30 min at minimum intensity (Biosonik III, Brownwill Scientific Inc.) prior to centrifugation at 20,000 g for 30 min at 4 ° (Ferkovich et al., 1980). The supernatants were assayed for protein concentration, with Bio-Rad (Bio-Rad Laboratories, Richmond, CA) bovine gamma-globulin as standard (Anonymous, 19791. Results and discussion. Pheromone catabolism by antennal esterases of both the male and female cabbage looper was minimal at 6 and 12 hr after eclosion, but increased dramatically by 24 hr (I day) after emergence (Fig. 1). The antennai supernatant of the female, however, was less active than that of the male in hydrolyzing the pheromone. These results are consistent with an earlier report by Taylor et al. (1981) that pheromone hydrolysis in T. ni increased on day-1 after eclosion. The authors indicated the possible relevance of this finding to oifaction by pointing out a coincidental increase in electroantennogram and behavioral responses in moths of the same age. Of the tissues examined in our study, only antennal tissues showed the sharp increase in esterolytic activity. It is tempting to suggest from these findings that the observed enzymatic activity in the antennae is tied in with the olfactory process. However, evidence that such is the case in the cabbage looper cannot be determined from the present experiments.