Natural products from the integument of nonavian reptiles

Weldon, Paul J.; Flachsbarth, Birte; Schulz, Stefan

doi:10.1039/b509854h

Cited by 118 publications

(136 citation statements)

References 144 publications

(417 reference statements)

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“…Similar fatty acids, but in much lower proportions, have been found in secretions of most other lizard species examined (Weldon et al, 2008). Moreover, it is notorious to fi nd in tegu lizards such a high proportion of octadecanoic and octadecadienoic acids.…”

Section: Discussionmentioning

confidence: 79%

“…steroids and fatty acids) seem to be the main compounds involved in pheromonal communication (Mason, 1992;Martín and López, 2006a, 2010a, 2011. Although the types of compounds in secretions are similar in different lizard species, the presence and abundance of specifi c compounds vary widely between species (Weldon et al, 2008), which might be due to phylogenetic or environmental differences (Alberts, 1992;Escobar et al, 2003;Martín and López, 2006b). However, the chemical composition of femoral gland secretions has been analysed in only a few lizard species (reviewed in Weldon et al, 2008).…”

Section: Introductionmentioning

confidence: 99%

“…Although the types of compounds in secretions are similar in different lizard species, the presence and abundance of specifi c compounds vary widely between species (Weldon et al, 2008), which might be due to phylogenetic or environmental differences (Alberts, 1992;Escobar et al, 2003;Martín and López, 2006b). However, the chemical composition of femoral gland secretions has been analysed in only a few lizard species (reviewed in Weldon et al, 2008). Most information relates to European lizards of the family Lacertidae (López and Martín, 2005b, c, 2006López, 2006b, c, 2010b;Gabirot el al., 2008;Kopena et al, 2009), American lizards of the families Iguanidae (Weldon et al, 1990;Alberts et al, 1992) and Liolaemidae (Escobar et al, 2001(Escobar et al, , 2003, and an African cordylid lizard (Louw et al, 2007).…”

Section: Introductionmentioning

confidence: 99%

“…Most information relates to European lizards of the family Lacertidae (López and Martín, 2005b, c, 2006López, 2006b, c, 2010b;Gabirot el al., 2008;Kopena et al, 2009), American lizards of the families Iguanidae (Weldon et al, 1990;Alberts et al, 1992) and Liolaemidae (Escobar et al, 2001(Escobar et al, , 2003, and an African cordylid lizard (Louw et al, 2007). However, there are many lizard species within other taxonomic lineages and geographical areas that have femoral pores with abundant secretions, which have never been chemically analysed, in spite of secretions being often related to chemical communication (see reviews by Weldon et al, 2008;Mason and Parker, 2010). To understand the composition and role of femoral gland secretions of lizards, we need more studies that deal with a wider range of lizard taxa and consider a larger variety of environmental conditions.…”

Section: Introductionmentioning

confidence: 99%

“…Males of many lizard species secrete chemical compounds from the femoral or precloacal glands (Alberts, 1993;Weldon et al, 2008) that may function as pheromones (Mason and Parker, 2010;Martín and López, 2011). Multiple pheromone compounds in femoral gland secretions seem to inform about the characteristics and health state of a male Martín et al, 2007a).…”

Section: Introductionmentioning

confidence: 99%

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Chemical Constituents of the Femoral Gland Secretions of Male Tegu Lizards (Tupinambis merianae) (Family Teiidae)

Martı́n

Chamut

Manes

et al. 2011

Zeitschrift Für Naturforschung C

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In spite of the importance of chemical signals (pheromones) in the reproductive behaviour of lizards, the chemical compounds secreted by their femoral glands, which may be used as sexual signals, are only known for a few lizard species. Based on mass spectra, obtained by GC-MS, we found 49 lipophilic compounds in femoral gland secretions of male tegu lizards (Tupinambis merianae) (fam. Teiidae), including a very high proportion of carboxylic acids and their esters ranging between n-C 8 and n-C 20 (mainly octadecanoic and 9,12-octadecadienoic acids), with much less proportions of steroids, tocopherol, aldehydes, and squalene. We discuss the potential function of these compounds in secretions, and compare the compounds found here with those documented for other lizard species.

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Section: Discussionmentioning

confidence: 79%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Chemical Constituents of the Femoral Gland Secretions of Male Tegu Lizards (Tupinambis merianae) (Family Teiidae)

Martı́n

Chamut

Manes

et al. 2011

Zeitschrift Für Naturforschung C

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Anatomical, Histological, and Histochemical Analyses of the Scent Glands of the Scorpion Mud Turtle (Kinosternon scorpioides scorpioides)

Bezerra

Rebelo

Sousa

et al. 2019

The Anatomical Record

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Fossil evidence suggests that scent glands are basal features of Testudines. However, we know little about the structure of these glands in the Brazilian Kinosternidae. In this study, we described the macroscopic anatomy, histology, and histochemistry of the scent glands of three males and three females of Kinosternon scorpioides scorpioides from the Marajó mesoregion, Pará State, Brazil. In all of the specimens analyzed, regardless of sex, we found four scent glands, including two axillary and two inguinal glands that were structurally similar to each other. Each gland consisted of a single holocrine secretory lobule, a large lumen surrounded by relatively thin glandular secretory epithelium, an adjacent narrow layer of loose connective tissue, and a thick layer of skeletal striated muscle tissue surrounded by a serous tunic. The secretory epithelium produced a characteristic malodorous yellowish substance that was passed via a single duct through a bone channel in the bridge connecting the carapace to the plastron and excreted through an outer pore in the plate of each respective gland. Histologically, the secretory epithelium presented cells with two types of secretory vacuoles. Type 1 vacuoles stained red were the largest and most frequently found, and stained positively with Periodic acid-Schiff (PAS), suggesting they contained glycoproteic complexes. Type 2 vacuoles were translucent, smaller in size and fewer in number, and negative for PAS staining. Because they are very primitive structures, scent glands must play important roles in the lives of chelonians, but their real function remains unknown. Several hypotheses suggest that they can act as protection against ectoparasites, as a repellent of predators, in addition to attracting mates and eliciting other pheromonal responses. In this study, all animals reacted by exuding malodorous substances when handled, as a form of defense. However, these are just assumptions that need to be clarified with additional studies on animal behavior.

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Composition of the Cloacal Gland Secretion of Tuatara, Sphenodon punctatus

Flachsbarth

Fritzsche

Weldon

et al. 2009

Chemistry & Biodiversity

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The lipophilic content of the cloacal gland secretion of the tuatara (Sphenodon punctatus) was investigated. GC/EI-MS Analysis of CH2Cl2 extracts of the secretions revealed triacylglycerols as major glandular constituents. Twelve major medium-chain fatty acids were found to be conjugated to glycerol in different combinations, resulting in complex mixtures. These acids were identified by transesterification and subsequent derivatization of natural samples, and their structures were verified by synthesis. The natural glycerides contain predominantly three of the following acids: octanoic (A), (E)- and (Z)-oct-4-enoic (B and C, resp.), (4E,6Z)-octa-4,6-dienoic (tuataric acid; D), (R)-2,6-dimethylheptanoic (E), (R)-2,6-dimethylhept-5-enoic (F), (Z)-dec-4-enoic (G), (4Z,7Z)-deca-4,7-dienoic (H), (R)-3,7-dimethyloct-6-enoic (I), (R)-4,8-dimethylnon-7-enoic (J), (2R,6S)-2,6,10-trimethylundec-9-enoic (K), and (2R,5E)-2,6,10-trimethylundeca-5,9-dienoic acids (L). Several additional acids, occurring in trace amounts only, were tentatively identified by MS. The elucidation of the absolute configuration of the acids was performed by GC on chiral phases. Individual tuatara show specific mixtures of glycerides with up to 100 components. The individual mixtures may permit individual recognition because the bouquets seem to be stable over years.

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Natural products from the integument of nonavian reptiles

Abstract: This review describes the epidermal and glandular chemistry of nonavian reptiles in relation to proposed functions, and includes more than 170 references. The results are presented according to the different reptile taxa.

Cited by 118 publications

References 144 publications

Chemical Constituents of the Femoral Gland Secretions of Male Tegu Lizards (Tupinambis merianae) (Family Teiidae)

Chemical Constituents of the Femoral Gland Secretions of Male Tegu Lizards (Tupinambis merianae) (Family Teiidae)

Anatomical, Histological, and Histochemical Analyses of the Scent Glands of the Scorpion Mud Turtle (Kinosternon scorpioides scorpioides)

Composition of the Cloacal Gland Secretion of Tuatara, Sphenodon punctatus

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