1.Mandibular Gland Volatiles and Their Ontogenetic Patterns in Queen Honey Bees, Apis mellifera carnica.
FRANCKE W1, LUBKE G, TAGHIZADEH T, ADLER A, ROSENKRANZ P, ENGELS W. J Insect Physiol. 1997 Apr;43(4):307-313.
Extracts of mandibular glands taken from adult queens of the honey bee, Apis mellifera carnica, were analysed by gas chromatography-mass spectroscopy. More than 100 compounds could be identified among which oxygenated fatty acids with six, eight, 10 and 12 carbon atoms are particularly interesting since they show structural relationships to the queen substance, (E)-9-oxo-2-decenoic acid. Changes in the patterns of volatiles were followed up from emergence until the full dominant status of an egg-laying queen in a strong colony. Generally, the amount of volatiles per gland was found to increase with age. The final level of queen substance (9-ODA) content is reached at the postmating stage about 10 days after emergence. Ontogenetic patterns of concentrations were determined for those components regarded to predominantly contribute to the royal pheromone. Characteristic compositions of signals, possibly involved in the premating, mating and postmating dominance status of a honey bee queen are discussed.
2.Effect of ovariectomy on the in vitro and in vivo activation of carcinogenic N-2-fluorenylhydroxamic acids by rat mammary gland and liver.
Ritter CL1, Bennett KK, Fullerton NF, Beland FA, Malejka-Giganti D. Carcinogenesis. 1996 Nov;17(11):2411-8.
N-Hydroxy-N-2-fluorenylacetamide (N-OH-2-FAA) and its benzamide analogue N-OH-2-FBA are mammary gland carcinogens in the female Sprague-Dawley rat. Ovariectomy inhibits tumorigenicity of topically applied N-OH-2-FAA suggesting modulation of carcinogen-activating enzymes in the gland. This study concerned the activation of N-OH-2-FAA and N-OH-2-FBA by the mammary gland and liver, a chief site of metabolism, from 50-day-old female rats and effects on the activation of ovariectomy performed at 22 days of age. The levels of N-debenzolyation of N-OH-2-FBA to N-hydroxy-N-2-fluorenamine (N-OH-2-FA), catalyzed by microsomal carboxylesterases in mammary gland and liver were similar and increased 1.5- and 1.7-fold, respectively, by ovariectomy. N-Debenzoylating activity in cytosols of both tissues appeared to be partially of microsomal origin. Mammary gland cytosol contained N-, O- and N,O-acyltransferase activities at levels 40-50% those of liver.
3.A honey bee odorant receptor for the queen substance 9-oxo-2-decenoic acid.
Wanner KW1, Nichols AS, Walden KK, Brockmann A, Luetje CW, Robertson HM. Proc Natl Acad Sci U S A. 2007 Sep 4;104(36):14383-8. Epub 2007 Aug 30.
By using a functional genomics approach, we have identified a honey bee [Apis mellifera (Am)] odorant receptor (Or) for the queen substance 9-oxo-2-decenoic acid (9-ODA). Honey bees live in large eusocial colonies in which a single queen is responsible for reproduction, several thousand sterile female worker bees complete a myriad of tasks to maintain the colony, and several hundred male drones exist only to mate. The "queen substance" [also termed the queen retinue pheromone (QRP)] is an eight-component pheromone that maintains the queen's dominance in the colony. The main component, 9-ODA, acts as a releaser pheromone by attracting workers to the queen and as a primer pheromone by physiologically inhibiting worker ovary development; it also acts as a sex pheromone, attracting drones during mating flights. However, the extent to which social and sexual chemical messages are shared remains unresolved. By using a custom chemosensory-specific microarray and qPCR, we identified four candidate sex pheromone Ors (AmOr10, -11, -18, and -170) from the honey bee genome based on their biased expression in drone antennae.
4.Diazabicyclononanones, a potent class of kappa opioid analgesics.
Holzgrabe U1, Cambareri A, Kuhl U, Siener T, Brandt W, Strassburger W, Friderichs E, Englberger W, Kögel B, Haurand M. Farmaco. 2002 Jul;57(7):531-4.
The 1,5-dimethyl 3,7-diaza-3,7-dimethyl-9-oxo-2,4-di-2-pyridine-bicyclo[3.3.1]nonane-1,5-dicarboxylate, HZ2, has a high and selective affinity for the kappa opioid receptor and an antinociceptive activity comparable to morphine. In addition, it is characterized by a long duration of action and a high oral bioavailability. QSAR studies within series of kappa agonists revealed a chair-boat conformation of a double protonated HZ2 characterized by an almost parallel orientation of the C9 carbonyl group and the N7-H group and at least one aromatic ring to be the pharmacophoric arrangement. Structural variations showed that the pyridine rings in 2 and 4 position can be replaced with p-methoxy-, m-hydroxy- and m-fluoro-substituted phenyl rings. However, all other substituents have to be kept the same for a high affinity to the kappa receptor.