β-Springene in the paracloacal gland secretions of the smooth-fronted caiman (Paleosuchus trigonatus)

Avery, James; Shafagati, A.; Turner, A.; Wheeler, J. W.; Weldon, Paul J.

doi:10.1016/0305-1978(93)90112-5

Cited by 13 publications

(17 citation statements)

References 6 publications

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“…The volatile contents of the Dufour gland of H. hebetor were found to consist of a diterpene, bspringene, previously characterized from several mammals and a reptile (Burger et al, 1978(Burger et al, , 1981Avery et al, 1993;Waterhouse et al, 1996Waterhouse et al, , 2001Ibrahim et al, 1998). In addition, a homoditerpene that appears to be closely related to the bspringene, a tertiary alcohol that appears to be a homo-geranyllinalool, and 41 non-terpenoid hydrocarbons were also present ( Fig.…”

Section: Resultsmentioning

confidence: 87%

Novel diterpenoids and hydrocarbons in the Dufour gland of the ectoparasitoid Habrobracon hebetor (Say) (Hymenoptera: Braconidae)

Howard¹,

Baker²,

Morgan

2003

Arch Insect Biochem Physiol

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Chemical constituents contained in the Dufour gland of the ectoparasitoid Habrobracon hebetor (Say) (Hymenoptera: Braconidae) were characterized. Three terpenes, beta-springene, a homo-beta-springene, and a homo-geranyllinalool constitute approximately 37% of the gland components, with the remaining 63% all being hydrocarbons. The hydrocarbons consist of a homologous series of n-alkanes (n-C21 to n-C31), a trace amount of 3-methyl C23, a homologous series of internally methyl-branched alkanes (11-methyl C23 to 13-methyl C35), one dimethylalkane (13,17-dimethyl C33), a homologous series of monoenes (C(25:1) to C(37:1)) with the double bonds located at Delta9, Delta13 and Delta15 for alkenes of carbon number 25 to 31 and at Delta13 and Delta15 for carbon numbers 33 to 37 and three homologous dienes in very low amounts with carbon numbers of 31, 32, and 33. The terpenoid and hydrocarbon composition of the Dufour gland was similar in virgin and mated females. However, in contrast to the hydrocarbons, the amount of beta-springene and homo-geranyllinalool increased significantly with time after adult emergence from the cocoon. Although many hydrocarbons in the Dufour gland are the same as those on the cuticle of this species [Howard and Baker, Arch. Insect Biochem. Physiol. 53:1-18 (2003)], substantial differences also occur. Of particular note is the chain length of alkenes and location of the double bonds: cuticular alkenes have a chain length of C23 to C29 and double bond locations at Delta5, Delta7, and Delta9, whereas the Dufour gland alkenes contains a greater range of carbon numbers and have no Delta5 or Delta7 alkenes. The Dufour gland contains only one of the long-chain dimethylalkanes found on the cuticle. Also, no terpenoids are found on the cuticle, and the Dufour gland contains none of the secondary wax esters that are major components on the cuticle. GC-MS analysis of lipids carried in the hemolymph of H. hebetor indicated that all hydrocarbons found on both the cuticle and in the Dufour gland are present, as are some of the wax esters. However, none of the terpenoids were detected in the hemolymph. This suggests that the hydrocarbons are synthesized in other tissues or cells, probably by oenocytes, and differentially partitioned between the cuticle and the Dufour gland. The terpenoids are most likely synthesized within the Dufour gland. Analysis of surface lipids from eggs laid within 18 h indicated that no diterpenoids were present. Rather, the lipids present on the eggs were n-alkanes, monomethylalkanes, alkenes, and secondary alcohol wax esters. This composition did not reflect that of the Dufour gland, hence eggs are not being coated with Dufour gland components during oviposition.

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Section: Resultsmentioning

confidence: 87%

Novel diterpenoids and hydrocarbons in the Dufour gland of the ectoparasitoid Habrobracon hebetor (Say) (Hymenoptera: Braconidae)

Howard¹,

Baker²,

Morgan

2003

Arch Insect Biochem Physiol

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“…These values are consistent with (4E,6E, 10E)-3,7,11,15-tetramethylhexadeca-1,4,6,10,14-pentaene, an isomer not previously reported from nature, although additional spectral data are needed to confirm this structure. Isomers of springene are known from a variety of natural sources, including a plant (Uegaki et al, 1980), insects (Billen et al, 1988;Fukushima et al, 1990), a crocodilian (Avery et al, 1989), and another mamma/, the springbok antelope (Antidorcas marsupialis, Bovidae) (Burger et al, 1978(Burger et al, , 1981. In the springbok antelope, (3E,6E,(3Z,6E,and ~-springene are the volatile products of a skin gland also called the dorsal gland; this organ also is situated on the midline of the dorsum and is hypothesized to release alarm pheromones (Burger et al, 1981).…”

Section: Resultsmentioning

confidence: 98%

Volatile components in dorsal gland secretions of the collared peccary,Tayassu tajacu (Tayassuidae, mammalia)

Waterhouse

Jia

Pickett³

et al. 1996

J Chem Ecol

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Secretions of the dorsal gland of free-ranging adult male and female collared peccaries (Tayassu tajacu) were analyzed by gas chromatography-mass spectrometry. Both sexes contain (2E,6E,10E)-geranylgeraniol; squalene (allE isomer); and the following isomers of springene, a diterpene homolog of β-farnesene: (3E,6E,10E)-α-springene, (3Z,6E,10E)-α-springene, and (6E,10E)-β-springene. A diterpene alcohol and an additional isomer each of squalene and springene also were observed. Straight- and branched-chain esters abound in the secretions of females, but they were not detected in males.

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“…The β-springene was first discovered by Zimmermann in the secretion of the dorsal glands of the antelope Antidorcas marsupialis (Burger et al, 1978), and later in the secretions of cloacal glands of crocodiles (Weldon et al, 1988;Avery et al, 1993), in the Dufour glands of ants (Billen et al, 1988), braconid wasps (Fukushima et al, 1990), and stingless bees (Cruz-Lopez et al, 2001) and in the essential oils of the leaves of Heracleum persicum Desf. (Mojab et al, 2002).…”

Section: Discussionmentioning

confidence: 99%

Cephalic secretions of the bumblebee subgenus Sibiricobombus Vogt suggest Bombus niveatus Kriechbaumer and Bombus vorticosus Gerstaecker are conspecific (Hymenoptera, Apidae, Bombus)

et al. 2005

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-Three taxa of the subgenus Sibiricobombus live in the Near-East mountain steppes: Bombus niveatus, B. sulfureus and B. vorticosus. The latter is also present in the Balkan. B. niveatus and B. vorticosus can only be distinguished based on color pattern. B. sulfureus differs in coat color and in genitalia. We identified 40 compounds in the secretions of the labial glands of these taxa, among which 7 were detected for the first time in labial cephalic gland secretions of bumblebee males. Whereas the secretions of the male cephalic labial glands of B. sulfureus are very different from those of B. niveatus and B. vorticosus, we found no significant difference between the latter. We conclude that B. sulfureus is a valid species, whereas B. vorticosus is a mere subspecies of B. niveatus: Bombus niveatus ssp. vorticosus Gerstaecker nov. status. cephalic secretions / Sibiricobombus / Bombus / taxonomic status / chemical composition

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β-Springene in the paracloacal gland secretions of the smooth-fronted caiman (Paleosuchus trigonatus)

Cited by 13 publications

References 6 publications

Novel diterpenoids and hydrocarbons in the Dufour gland of the ectoparasitoid Habrobracon hebetor (Say) (Hymenoptera: Braconidae)

Novel diterpenoids and hydrocarbons in the Dufour gland of the ectoparasitoid Habrobracon hebetor (Say) (Hymenoptera: Braconidae)

Volatile components in dorsal gland secretions of the collared peccary,Tayassu tajacu (Tayassuidae, mammalia)

Cephalic secretions of the bumblebee subgenus Sibiricobombus Vogt suggest Bombus niveatus Kriechbaumer and Bombus vorticosus Gerstaecker are conspecific (Hymenoptera, Apidae, Bombus)

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