title: Chemical defense in millipedes (Myriapoda, Diplopoda): do representatives of the family Blaniulidae belong to the 'quinone' clade?
abstract: 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.
authors.affiliation: Faculty of Chemistry, University of Belgrade, Studentski trg 12 - 16, 11000 Belgrade, Serbia.
authors.forename: Ljubodrag V
authors.initials: LV
authors.lastname: Vujisić
authors.forename: Dragan Ž
authors.initials: DŽ
authors.lastname: Antić
authors.forename: Ivan M
authors.initials: IM
authors.lastname: Vučković
authors.forename: Tatjana Lj
authors.initials: TLj
authors.lastname: Sekulić
authors.forename: Vladimir T
authors.initials: VT
authors.lastname: Tomić
authors.forename: Boris M
authors.initials: BM
authors.lastname: Mandić
authors.forename: Vele V
authors.initials: VV
authors.lastname: Tešević
authors.forename: Božidar P M
authors.initials: BP
authors.lastname: Ćurčić
authors.forename: Vlatka E
authors.initials: VE
authors.lastname: Vajs
authors.forename: Slobodan E
authors.initials: SE
authors.lastname: Makarov
mesh_terms: D000818:Animals; D001181:Arthropods / Q000737:chemistry* / Q000378:metabolism; D016227:Benzoquinones / Q000737:chemistry / Q000302:isolation & purification; D005260:Female; D008401:Gas Chromatography-Mass Spectrometry; D006873:Hydroquinones / Q000737:chemistry / Q000302:isolation & purification; D008297:Male; D008752:Methylene Chloride / Q000737:chemistry; D019301:Oleic Acid / Q000737:chemistry / Q000302:isolation & purification; D011809:Quinones / Q000737:chemistry* / Q000302:isolation & purification
chemical_list: D016227:Benzoquinones; D006873:Hydroquinones; D011809:Quinones; D019301:Oleic Acid; C004532:quinone; D008752:Methylene Chloride
keywords: Cibiniulus phlepsii; Defensive secretions; Millipedes; Nopoiulus kochii; Oleates; Quinones