Ljubodrag Vujisić

Defensive Secretions in Three Species of Polydesmids (Diplopoda, Polydesmida, Polydesmidae)

Nine compounds were detected in three different millipede species: Polydesmus complanatus (L.), Brachydesmus (Stylobrachydesmus) avalae Ćurčić & Makarov, and Brachydesmus (Stylobrachydesmus) dadayi Verhoeff. Benzaldehyde, benzyl alcohol, benzoylnitrile, benzyl methyl ketone, benzoic acid, benzyl ethyl ketone, mandelonitrile, and mandelonitrile benzoate were identified by GC-FID and GC-MS analyses. Hydrogen cyanide was detected qualitatively by the picric acid test. Benzyl ethyl ketone, benzyl methyl ketone, and benzyl alcohol were detected for the first time in polydesmidan millipedes. Benzoylnitrile was the major component in all three hexane extracts. These compounds are suspected to be active in the defensive secretions of these millipede species.

Composition of the Defensive Secretion in Three Species of European Millipedes

Three European julid species, Cylindroiulus boleti, Leptoiulus trilineatus, and Megaphyllum bosniense, secrete mixtures of up to 12 different quinones. The major components in these species are 2-methoxy-3-methyl-1,4-benzoquinone and 2-methyl-1,4-benzoquinone. 2-Methoxy-5-methylhydroquinone is detected for the first time in the Class Diplopoda. 2-Hydroxy-3-methyl-1,4-benzoquinone, 2,3-dimethoxyhydroquinone, 2-methyl-3,4-methylendioxyphenol, and 2,3-dimethoxy-5-methylhydroquinone are registered for the first time in representatives of the family Julidae. The similar chemical composition of defense secretions in all analyzed European julids and Pacific spirobolids supports the idea of the chemical consistency of defensive compounds in juliform millipedes.

Preliminary Data on Essential Oil Composition of the Moss Rhodobryum ontariense (Kindb.) Kindb.

ABSTRACT The essential oil composition of the moss Rhodobryum ontariense obtained by hydrodistillation was preliminary analyzed by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). Thirteen compounds (86.41% of the total oil) were identified. The main chemical constituents were phytol (31.95%) and 1-octen-3-ol (15.44%). Such an abundance of phytol has not yet been reported in other mosses. Four chemicals (cis-decahydronaphthalene, allo-hedycaryol, jasmone and 2,5,5,8a-tetramethyl1,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid, methyl ester) are first records, not only for the genus Rhodobryum and mosses in general, but also for the group of bryophytes as a whole.

Defensive Secretions in Three Ground-Beetle Species (Insecta: Coleoptera: Carabidae)

The adults of three ground-beetle species were induced to discharge defensive secretions into vials. The secretions were obtained by CH2Cl2 extraction. Altogether 11 compounds were identified by GC-MS analysis. Calosoma sycophanta possesses 10 defensive compounds, Carabus ullrichii seven, while Abax parallelepipedus has six compounds. Methacrylic, tiglic and isobutyric acids were present in all samples. The first two organic compounds were predominant in the extracts of Abax parallelepipedus. Methacrylic acid and salicylaldehyde were the major compounds in extracts of Calosoma sycophanta. Methacrylic and angelic acids were the major components in extracts of Carabus ullrichii. Propanoic acid was detected for the first time in the family Carabidae and in all animals. 2-Methyl butyric, angelic and benzoic acids were found for the first time in the subfamily Carabinae. Our finding of butyric acid is its first precise identification in the Carabinae subfamily. 2-Methyl butyric, angelic, crotonic, senecioic and benzoic acids were found for the first time in a European groundbeetle species. The compounds detected in the defensive secretions serve as protection against predators.

Chemical defense in the cave-dwelling millipede Brachydesmus troglobius Daday, 1889 (Diplopoda, Polydesmidae)

10Faculty of Veterinary Medicine, University of Belgrade, Bulevar Oslobodjenja 18, 11000 Belgrade, Serbia (iris@vet.bg.ac.rs) Makarov S.E. , Vujisić L.V., Ćurčić B.P.M., Ilić B.S., Tešević V.V., Vajs V.E., Vučković I.M., Mitić B.M., Lučić L.R. and Đorđević I.Ž. 2012. Chemical defense in the cave-dwelling millipede Brachydesmus troglobius Daday, 1889 (Diplopoda, Polydesmidae). International Journal of Speleology, 41(1), 95-100. Tampa, FL (USA). ISSN 0392-6672. http://dx.doi.org/10.5038/1827-806X.41.1.10

Cytotoxic Guaianolide from Anthemis segetalis (Asteraceae)

Two epimeric guaianolides were isolated from the aerial parts of Anthemis segetalis. These compounds have not been detected in any Anthemis species so far. One of them was tested for cytotoxicity against human cervical cancer (HeLa) and murine melanoma (B16) cell lines showing appreciable activity. Copyright

Molecular Diversity of Compounds from Pygidial Gland Secretions of Cave-Dwelling Ground Beetles: The First Evidence

Three adult cave-dwelling ground beetle species were induced to discharge secretions of their pygidial glands into vials. Dichloromethane extraction was used to obtain the secretions. In total, 42 compounds were identified by GC/MS analysis. Pheggomisetes ninae contained 32 glandular compounds, Laemostenus (Pristonychus) punctatus 13, whereas Duvalius (Paraduvalius) milutini had nine compounds. Caproic, oleic, palmitic, and stearic acids were present in the samples of all analyzed species. Undecane was predominant in the extract of L. punctatus. Palmitic acid was the major component in the secretion of D. milutini. Finally, the most abundant compounds in P. ninae secretion were heptacosene and nonacosadienes. Herein, we present the first data on the identification of pygidial gland secretion components in both troglophilous and troglobite cave-dwelling ground beetles. Some compounds are reported for the first time in the secretions of ground beetles and other higher or lower taxa. The adaptation to underground life has not led to a reduction or changes in the chemical defense mechanism in the analyzed troglophilous and troglobitic Platyninae and Trechinae taxa.

Chemical Defense in Millipedes (Myriapoda, Diplopoda): Do Representatives of the Family Blaniulidae Belong to the ‘Quinone’ Clade?

The defensive secretions of two blaniulid millipedes, Nopoiulus kochii and Cibiniulus phlepsii, were characterized by GC‐FID and GC/MS analyses, which showed the presence of a complex mixture of benzoquinones, hydroquinones, and oleates. Altogether, 13 compounds were identified. The major compound in the secretions of both analyzed species was 2‐methyl‐1,4‐benzoquinone (toluquinone). The second major constituent in the N. kochii secretion was 2‐methyl‐3,4‐(methylenedioxy)phenol, while in that of C. phlepsii, it was 2‐methoxy‐3‐methyl‐1,4‐benzoquinone. The defensive secretion of N. kochii also showed a high content of hydroquinones (13.5%) in comparison to that of C. phlepsii (0.8%). Hexyl oleate and octyl oleate were detected for the first time in defensive millipede fluids. The chemical composition of the defensive secretions supports the chemotaxonomic position of the family Blaniulidae in the ‘quinone’ millipede clade.

Identification of Secretory Compounds from the European Callipodidan Species Apfelbeckia insculpta

Defensive secretions of the callipodidan species Apfelbeckia insculpta contain a p-cresol as the main component and phenol in traces. This is the first identification of these compounds in a European callipodidan species. The repugnatory glands of A. insculpta are of the spirobolid type and consist of a spherical reservoir, a simple duct, and a valvular cuticular infolding that opens onto the lateral surface of the millipede via a pore.

Pyrrolizidine Alkaloids and Fatty Acids from the Endemic Plant Species Rindera umbellata and the Effect of Lindelofine-N-oxide on Tubulin Polymerization

The examination of the aerial parts, roots, and seeds of the endemic plant Rindera umbellata is reported in this paper for the first time. Phytochemical investigation of R. umbellata led to the isolation and characterization of ten pyrrolizidine alkaloids and eleven fatty acids in the form of triglycerides. Pyrrolizidine alkaloids 1–9 were found in the aerial parts, 7 and 8 in the roots, and 6–10, together with eleven fatty acids, in the seeds of this plant species. The structures of compounds 1–10 were established based on spectroscopic studies (1H- and 13C-NMR, 2D NMR, IR and CI-MS). After trans-esterification, methyl esters of the fatty acids were analyzed using GC-MS. The effect of lindelofine-N-oxide (7) on tubulin polymerization was determined.