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Salamon, M.; Davies, Noel W.

doi:10.1023/a:1020868528762

Cited by 27 publications

(7 citation statements)

References 33 publications

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“…The scent glands produce secretions that contain chemicals that are, for example, used as allomones to repel predators . A few short-chain nitriles have been identified in the sternal gland secretions used by the male koala, Phascolarctos cinereus , for territorial marking …”

Section: Resultsmentioning

confidence: 99%

“…(2) A few short-chain nitriles have been identified in the sternal gland secretions used by the male koala, Phascolarctos cinereus, for territorial marking. (19) Even though GC-MS analysis yielded good mass spectra for constituents 25, 31, 36, and 39, these constituents could not be identified by MS library comparison or the interpretation of their mass spectra, due to the paucity of relevant mass spectrometric information. The present investigation showed that the generation glands produce more diverse chemicals than the femoral glands, including groups of compounds (e.g., nitriles and amides) that are absent from the femoral gland secretions.(3)C.…”

Section: A/b Ring Junctions (5α-h) Have [M -H2o]mentioning

confidence: 99%

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Lizard Epidermal Gland Secretions. II. Chemical Characterization of the Generation Gland Secretion of the Sungazer, Cordylus giganteus

et al. 2011

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In lizards, the epidermal glands of the femoral and precloacal regions are involved in the production of semiochemicals. In addition to its femoral glands, the giant girdled lizard, or sungazer, Cordylus giganteus, which is endemic to South Africa, has generation glands as an additional potential source of semiochemicals. These epidermal glands are described as glandular scales that overlay the femoral glands and are included in the normal epidermal profile located in the femoral (thigh) and anterior antebrachial (fore-leg) regions of the male sungazer.GC-MS analysis of the generation gland secretions and the trimethylsilyl derivatives of some of the steroidal constituents was employed to identify 59 constituents, including alkenes, carboxylic acids, alcohols, ketones, aldehydes, esters, amides, nitriles, and steroids. The quantitative differences of the volatile constituents of the fore-and hind-leg generation glands were compared between individuals. This is the first report on the chemical composition of generation glandular material of lizards.Several potential sources of pheromones in lizards have been described, including epidermal and cloacal glands and the blood-skin barrier.(1) A comprehensive review of the natural products originating from the integument of reptiles, including a summary of the chemicals secreted from the femoral (thigh) and precloacal (preanal) glands of a number of lizard species, was recently published.(2) The chemical characterization of the secretion of the femoral glands of the giant girdled lizard, or sungazer, Cordylus giganteus (Squamata, Cordylidae), located in the ventral femoral region, has also been reported.(2, 3) López and co-workers(4-7) recently summarized the potential functions of femoral gland semiochemicals, which could, for example, include mate choice, male-male competition, and interspecific recognition.In addition to femoral glands, cordylid lizards have holocrine secretory cells located in the beta-layer of the epidermis, termed generation glands,(8, 9) which may occur in different body locations, for example, in the femoral, precloacal, antebrachial (fore-arm), and dorsal epidermal regions.(10) In most cases, the glandular material is stacked as a series of beta-layers.(10) In the case of C. giganteus, only males have generation glands, as patches of "glandular scales" anterior to the single row of femoral gland pores and on the ventral aspect of the fore-arm region ( Figure 1).(10) In other cordylid species, females may also possess generation glands, the number which may vary according to geographical region. (11,12) It has been suggested that the generation glands could have a semiochemical function in combination with other sources such as the femoral glands.(12, 13) The purpose of this study was to identify the volatile constituents secreted from the generation glands by GC-MS analysis of the secretion and the trimethylsilyl derivatives of some of its constituents. Additionally, the quantitative differences of the volatile constituents of the fore...

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Section: Resultsmentioning

confidence: 99%

Section: A/b Ring Junctions (5α-h) Have [M -H2o]mentioning

confidence: 99%

Lizard Epidermal Gland Secretions. II. Chemical Characterization of the Generation Gland Secretion of the Sungazer, Cordylus giganteus

et al. 2011

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“…strain capable of degrading aldoximes via their conversion to nitriles prompted the isolation and purification of an enzyme capable of producing the syn geometrical isomer of phenylacetaldoxime from N-hydroxy-L-phenylalanine, suggesting that amino acid-derived aldoximes are biosynthesized and metabolized in microorganisms like in plants 111 Oximes were identified in the sternal gland of male koalas. Thus, a mixture of syn and anti phenylacetaldoxime and the syn and anti forms of 3-methylthiopropanal oxime, 19, MeS(CH 2 ) 2 CH=N-OH, were found in the sternal secretion, and are thought to be involved in the scent territorial marking of koalas 112 ; syn and anti phenylacetaldoximes were also observed in the urine of male guinea pigs by Smith and colleagues, who attributed to the oxime a repellent effect on the approach of other male guinea pigs 113 . It should be noted that aldoximes, in general, can readily dehydrate to form the corresponding nitriles that may be utilized for olfactory communication between animals, as is attributed to benzyl cyanide 112 .…”

Section: A Natural Occurrence and Possible Physiological Rolementioning

confidence: 99%

“…Thus, a mixture of syn and anti phenylacetaldoxime and the syn and anti forms of 3-methylthiopropanal oxime, 19, MeS(CH 2 ) 2 CH=N-OH, were found in the sternal secretion, and are thought to be involved in the scent territorial marking of koalas 112 ; syn and anti phenylacetaldoximes were also observed in the urine of male guinea pigs by Smith and colleagues, who attributed to the oxime a repellent effect on the approach of other male guinea pigs 113 . It should be noted that aldoximes, in general, can readily dehydrate to form the corresponding nitriles that may be utilized for olfactory communication between animals, as is attributed to benzyl cyanide 112 .…”

Section: A Natural Occurrence and Possible Physiological Rolementioning

confidence: 99%

Hydroxylamines and Oximes: Biological Properties and Potential Uses as Therapeutic Agents

Ashani¹,

Silman²

2010

Patai's Chemistry of Functional Groups

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“…Interestingly, the sternal gland secretion of male koalas (Phascolarctos cinereus) contains volatile nitrile and oxime derivatives 40 . This oily gland plays a vital role in koalas' communication and is only produced by males that use it for scent marking on trees within their territorial range.…”

Section: I12 Natural Occurrence and Bioactivities Of Oximesmentioning

confidence: 99%

Expanding the chemical space of enone-containing natural products

Vágvölgyi

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Heteronanoparticles (H-NPs) consisting of conjugates characterized by a squalene tail linked to doxorubicin and ecdysteroid derivatives are presented. Biological evaluation on A2780ADR cell line confirms not only the maintenance of the activity of the parental drug but also the ability to overcome cancer resistance. The in vitro cell uptake was demonstrated, and the involvement of an endosomal-mediated pathway was suggested.

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Untitled

Cited by 27 publications

References 33 publications

Lizard Epidermal Gland Secretions. II. Chemical Characterization of the Generation Gland Secretion of the Sungazer, Cordylus giganteus

Lizard Epidermal Gland Secretions. II. Chemical Characterization of the Generation Gland Secretion of the Sungazer, Cordylus giganteus

Hydroxylamines and Oximes: Biological Properties and Potential Uses as Therapeutic Agents

Expanding the chemical space of enone-containing natural products

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