H. E. Eisner, W. F. Wood, and T. Eisner.
Hydrogen Cyanide Production in North American and African Polydesmoid Millipeds.
Psyche 82(1):20-23, 1975.

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HYDROGEN CYANIDE PRODUCTION IN
NORTH AMERICAN AND AFRICAN
POLYDESMOID MILLIPEDS1
A diversity of substances has been isolated from the defensive secre- tions of millipeds, including hydrogen cyanide, benzaldehyde, phenols, 1,4-benzoquinones, quinazolinones, and nitrogen-containing terpenes (references in Altman and Dittmer, 1973; Duffield et al., 1974; Meinwald et al., 1975; Smolanoff et al., 1975; Wood, 1974; Wood et al., 1975). Hydrogen cyanide, the first of these compounds iden- tified (Guldensteeden-Egeling, 1882), has been reported from over a dozen European and New World species, all members of the sub- order Polydesmida (Barbetta et al., 1966; Blum and Woodring, 1962 ; BIum et al., 1973 ; Casnati et al., 1963 ; Davenport et al,, 1952, Duffield et al,, 1974; Eisner et al., 1963 ; H. E. Eisner et al., 1963 ; Hall et al., 1969; Monteiro, 1961). We have demonstrated hy- drogen cyanide production in four additional polydesmoid species, strengthening the view that cyanogenesis may be of widespread, if not general, occurrence within the suborder. Three of the species, Apheloria trimaculata, A. kleinpeteri, and Pseudopolydesmus hranner'i, stemmed from the U. S. A. (the first species was from Clifton Forge, Virginia; the other two from Roanoke, Virginia) ; the fourth species, Astrodesmus laxus, was from Africa (Mombasa, Kenya). The ani- mals were tested for cyanogenesis by manipulating them and gently squeezing them, while at the same time holding beside their bodies strips of filter paper impregnated with benzidine acetate-copper ace- tate reagent (Feigl, 1966). In all instances the papers turned blue, indicating release of hydrogen cyanide vapor from their glands. In single individuals of each of the North American species, cyanogenetic output was assayed quantitively (see accompanying table), using the technique previously developed in our laboratories (H. E. Eisner et al., 1967).
report No. XLII of the series Defense Mechanisms of Arthropods. Section of Neurobiology and Behavior, Division of Biological Sciences, Cornell University, Ithaca, N. Y. 14853
international Centre of Insect Physiology and Ecology, P. 0, Box 30772, Nairobi, Kenya.
Manuscript received by editor February 25,1975 Psw-he Ìö2:20.2 (1975). hup Ytpsyche rinclub orgt8B82-020 html



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19751 Eisner, Wood ‰â Eisner - Hydrogen Cyanide 21 TABLE
CYANOGENETIC OUTPUT OF MILLIPEDS
Species Sex and Body Weight Cyanagenetic Output of individual ( ^g/individual)
Apheloria trimaculata d' (769 mg)
A. kleinpeteri ? (1053 mg)
Pseudopolydesmus branneri 8 ( I 99 mg)
Cyanogenesi* in polydesrnoid milli~eds involves simultaneous re- lease of hydrogen cyanide and aldehyde from stored cyanoh~drin (Eisner et al., 1963). The aldehyde has been shown to be benzalde- hyde in several species (Barbetta et al., 1966; Blum et a!., 1973; Blum and Woodring, 1962 ; Casnati et al., 1963 ; 'Duffield et al., 1974 ; H. E. Eisner et al., 1963 ; Monteiro, 1961 ; Weatherston and Gardiner, 1973). We made no effort to isolate the aldehyde in the three North American species, but found evidence that Astrodesmus laxus produces benzaldehyde. Gas-liquid chromatography of a sample of secretion from this milliped, obtained by wiping the discharged fluid from the gland openings with pieces of filter paper, showed a peak of identical retention time to that of authentic benzaldehyde. Some polydesmoid millipeds have ancillary phenolic components in their secretion (Blum et al., 1973 ; Duffield et al., 1974; Monteiro, 1961). We did not attempt to isolate such components in our spe- cies, although the secretion of Pseudopolydesmus branneri had a phe- nolic odor.
This study was supported by grants AI-02908 and BMS-74-15084 from the National Institutes of Health and the National Science Foundation respectively. We thank Dr. William T. Keeton, Cornell University, for supplying and identifying the North American milli- peds, and Dr. C. A. W. Jeekel, Zoologisch Museum, Amsterdam, for identifying the African species.
ALTMAN, P. L. AND D. S. DITTMER.
1973. Biology Data Book, 2nd ed., vol. I1 (section 80, part I). Fed. Amer. Soc. Exp. Biol., Bethesda, Maryland. BARBETTA, M., G. CASNATI, AND M. PAVAN.
1966. Sulla presenze di D- (+ ) -mandlelonitrile nella secrezione difensiva del miriapode Gomphodesmus puvani Dem. Mem. Soc. Entomol. Ital. 45 : 169-176.




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Psyche
[March
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1973. Phenol and benzaldehyde in the defensive secretion of a strongy- losomid millipede. Ann. Ent. Soc. Amer. 66: 235. BLUM. M. S. AND J. P. WOODRING.
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EISNER, H. E., T. EISNER, AND J, J. HURST. 1963. Hydrogen cyanide and benzaldehyde produced by millipedes,. Chem. and Ind., London 1963, 124-125.
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MEINWALD, J., J. SMOLANOFF, A. MCPHAIL, R. MILLER, T. EISNER AND K. HICKS.
1975. Nitropalyzonamine: a spirocyclic nitro compoun,d from the defensive glands of milliped (Polyzonium rosalbum) . Tetra- hedron Letters (in press).
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1961. Constituents of the secretion of Orthomorpha coarctata Schubart. Anais Assoc. Brasil. Quim. 20 : 29-31.
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1975. Polyzonimine: a novel terpenoid insect repellent produced by a milliped. Science (in press).
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1973. The defensive secretion of a polydesmoid millipede (Diplopoda). Canad. Entom. 105 : 1375-1376.




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19751
Eisner, Wood &? Elsner - Hydrogen Cyanide WOOD, W. F.
1974. Toluquinone and 2-methoxy-3-methylbenzoquinone from the de- fensive secretions of three African millipedes. Ann. Enfc Soc. Amer. 67: 988-989.
WOOD, W. F., J. SHEPHERD, B. CHONG, AND J. MEINWALD. 1975. Ubiquinone-o in the defensive secretion of an African millipede. Nature (in press).




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