title: Macrolides and alcohols as scent gland constituents of the Madagascan frog Mantidactylus femoralis and their intraspecific diversity.
abstract: Acoustic and, to a lesser degree, visual signals are the predominant means of signaling in frogs. Nevertheless, certain lineages such as the mantelline frogs from Madagascar use the chemical communication channel as well. Males possess femoral glands on the hind legs, which recently have been shown to contain volatile compounds used in communication as pheromones. Many mantelline species occur in sympatry, and so far species recognition is regarded to occur mainly by acoustic signals. The analysis of the gland constituents of Mantidactylus femoralis by GC/MS revealed the presence of volatile macrolides and secondary alcohols. The new natural products mantidactolides A (4) and B (6), as well as several methyl carbinols, were identified, and their structures were confirmed by synthesis. The analysis of individuals from different locations of Madagascar revealed the presence of two groups characterized by specific patterns of compounds. While one group contained the alcohols and mantidactolide B, the other showed specific presence of the macrolides phoracantholide I (1) and mantidactolide A (4). Genetic analysis of some individuals showed no congruence between genetic relatedness and gland constituents. Several other individuals from related species had different gland compositions. This suggests that a basic set of biosynthetic machinery might be available to a broader group of related species.
authors.affiliation: Institut für Organische Chemie, Technische Universität Braunschweig , Hagenring 30, 38106 Braunschweig, Germany.
authors.forename: Dennis
authors.initials: D
authors.lastname: Poth
authors.forename: Pardha Saradhi
authors.initials: PS
authors.lastname: Peram
authors.forename: Miguel
authors.initials: M
authors.lastname: Vences
authors.forename: Stefan
authors.initials: S
authors.lastname: Schulz
mesh_terms: D000438:Alcohols / Q000378:metabolism*; D000818:Animals; D008401:Gas Chromatography-Mass Spectrometry; D006801:Humans; D018942:Macrolides / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D008270:Madagascar; D008297:Male; D015394:Molecular Structure; D010675:Pheromones / Q000235:genetics* / Q000502:physiology*; D010802:Phylogeny; D011898:Ranidae / Q000235:genetics* / Q000502:physiology*; D012543:Scent Glands / Q000378:metabolism*; D055549:Volatile Organic Compounds / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
chemical_list: D000438:Alcohols; D018942:Macrolides; D010675:Pheromones; D055549:Volatile Organic Compounds; C584719:mantidactolide A; C584721:mantidactolide B; C584720:phoracantholide I