The queen recognition pheromone of , preparation of (-6-(1-pentenyl)-2H-pyran-2-one.

Rocca, James R.; Tumlinson, James H.; Glancey, B. M.; Lofgren, C. S.

doi:10.1016/s0040-4039(00)81798-0

Cited by 70 publications

(45 citation statements)

References 9 publications

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“…The only other known a-pyrone is the queen recognition pheromone of the red imported fire ant (28); this same 6-alkyl-substituted compound was reported as a volatile metabolite from a soil fungus, Trichoderma viride (29). A few other types of pyrones do occur in insects.…”

Section: Discussionmentioning

confidence: 92%

Sex pheromone for the brownbanded cockroach is an unusual dialkyl-substituted alpha-pyrone.

Charlton

Webster

Zhang

et al. 1993

Proc. Natl. Acad. Sci. U.S.A.

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Female brownbanded cockroaches, SupeUa longipalpa, emit a sex pheromone that attracts males from a distance. This pheromone was isolated and identified as 5-(2,4-dimethylheptanyl)-3-methyl-2H-pyran-2-one (which we refer to as supeUlapyrone), and its structure was confirmed by synthesis. A racemic blend of the synthetic compound elicited behavioral and electrophysiological responses comparable to the natural pheromone across a range of doses. This compound is not only a very different type of cockroach pheromone but also makes up an additional class ofnatural products-namely, 3,5-dialkyl-substituted a-pyrones.

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Section: Discussionmentioning

confidence: 92%

Sex pheromone for the brownbanded cockroach is an unusual dialkyl-substituted alpha-pyrone.

Charlton

Webster

Zhang

et al. 1993

Proc. Natl. Acad. Sci. U.S.A.

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“…Then it was discovered in bodies of queens of the red ant Solenopsis invicta, in which it is one of pheromones that enforce obedience to the queen's attendants (Rocca et al 1983). In brown algae Sargassum crassifolium living in the seas stereoisomer epiloliolide (2) ( Fig.…”

Section: Occurence Of Loliolide and Its Derivativesmentioning

confidence: 99%

Loliolide - the most ubiquitous lactone

et al. 2015

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The searching for biologically active compounds produced by living organisms led to the discovery of a number of compounds with more or less complicated structure. One of the simplest molecules are monoterpenoid lactones and loliolide is the most common among them. Loliolide was found in animals (insects) and plants (flowers, shrubs, trees) both terrestrial and marine, such as algae and corals. Many years of research on plants used in traditional folk medicine of different countries have led to the conclusion that this compound has a variety of biological properties such as anti-cancer, antibacterial, antifungal and antioxidant ones. Moreover, plants containing loliolide are used in alternative medicine in treatment of diabetes and depression. It is extremely interesting that this lactone also affects the behavior of ants as well as the development of certain plants (allelopathic activity). However, sometimes there are side effects as in the case of structural analogues of loliolide contributing to extinction of tropical coral.

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“…The venom sac also has been shown to be the source of large amounts of venom alkaloids (Brand et al, 1972, 1973) and of pyranones. The latter are attractive to workers (Rocca et al, 1983a,b) but do not inhibit the reproductive development of winged queens (Glancey et al, 1984). In workers, the most abundant components of the alkaloids are trans -2-methyl-6-( cis -4′- n -tridecenyl) piperidine ( trans -C 13:1 ), trans -2-methyl-6- n -tridecylpiperidine ( trans -C 13 ), trans -2-methyl-6-( cis -6′- n -pentadecenyl) piperidine ( trans -C 15:1 ), and trans -2-methyl-6- n -pentadecylpiperidine (C 15 ).…”

Section: Introductionmentioning

confidence: 99%

Venom Alkaloid and Cuticular Hydrocarbon Profiles Are Associated with Social Organization, Queen Fertility Status, and Queen Genotype in the Fire Ant Solenopsis invicta

et al. 2011

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Queens in social insect colonies advertise their presence in the colony to: a) attract workers’ attention and care; b) gain acceptance by workers as replacement or supplemental reproductives; c) prevent reproductive development in nestmates. We analyzed the chemical content of whole body surface extracts of adult queens of different developmental and reproductive stages, and of adult workers from monogyne (single colony queen) and polygyne (multiple colony queens) forms of the fire ant Solenopsis invicta. We found that the composition of the most abundant components, venom alkaloids, differed between queens and workers, as well as between reproductive and non-reproductive queens. Additionally, workers of the two forms could be distinguished by alkaloid composition. Finally, sexually mature, non-reproductive queens from polygyne colonies differed in their proportions of cis-piperidine alkaloids, depending on their Gp-9 genotype, although the difference disappeared once they became functional reproductives. Among the unsaturated cuticular hydrocarbons characteristic of queens, there were differences in amounts of alkenes/alkadienes between non-reproductive polygyne queens of different Gp-9 genotypes, between non-reproductive and reproductive queens, and between polygyne and monogyne reproductive queens, with the amounts increasing at a relatively higher rate through reproductive ontogeny in queens bearing the Gp-9 b allele. Given that the genotype-specific piperidine differences reflect differences in rates of reproductive maturation between queens, we speculate that these abundant and unique compounds have been co-opted to serve in fertility signaling, while the cuticular hydrocarbons now play a complementary role in regulation of social organization by signaling queen Gp-9 genotype.

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The queen recognition pheromone of , preparation of (-6-(1-pentenyl)-2H-pyran-2-one.

Cited by 70 publications

References 9 publications

Sex pheromone for the brownbanded cockroach is an unusual dialkyl-substituted alpha-pyrone.

Sex pheromone for the brownbanded cockroach is an unusual dialkyl-substituted alpha-pyrone.

Loliolide - the most ubiquitous lactone

Venom Alkaloid and Cuticular Hydrocarbon Profiles Are Associated with Social Organization, Queen Fertility Status, and Queen Genotype in the Fire Ant Solenopsis invicta

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