J. Smolanoff, J. M. Demange, J. Meinivald, and T. Eisner.
1,4-Benzoquinones in African Millipeds.
Psyche 82(1):78-80, 1975.

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1,4BENZOQUINONES IN AFRICAN MILLIPEDS1
The defensive glands of millipeds have been the subject of con- siderable recent chemical and biological investigation. Compounds identified from the secretions have included hydrogen cyanide, ace- tate esters, aldehydes, phenols, 1,4-benzoquinones, quinazolinones, and nitrogen-containing terpenes (references in Eisner et al., 1975). The most widespread of these components are the 1,4-benzoquinones which have been found in the secretion of species of the orders Julida, Spiro- bolida, and Spirostreptida. We here report the isolation of 1,4-ben- zoquinones from three species of Spirostreptida from Africa: Archi- spirostreptus turnultporus, Peridontopyge conani, and P. rubescens. The millipeds were collected in Senegal, in the region of Kaolack (Sine-Saloum), where they are known to damage agricultural crops, particularly peanuts. Peridontopyge conuni and P. rubescens can be especially abundant. At the beginning of the rainy season the milli- peds swarm over the soil surface in large numbers in search of food and mates.
The animals were shipped live to Ithaca, N. Y., where they were "milked" of secretions on arrival. Individual animals were handled and tapped gently with a small metal mallet, until the golden-brown secretion oozed from their glands. The effluent was soaked up in pieces of filter paper, and transferred to carbon disulfide. Examina- tion of the secretion from the two species of Peridontopyge by gas- liquid chromatography (6 ft. column, 15% SE-30, 200å¡C revealed the presence of a single component. Comparison with an authentic sample (gas-liquid chromatography, infrared spectroscopy, proton magnetic resonance spectroscopy) showed this component to be 2- methyl-3-methoxy-I ,4-benzoquinone.
The secretion from A. tumuliporus was shown by gas-liquid chro- matography to contain two components, which by chromatographic and spectroscopic comparison with authentic samples were shown to *Paper No. XLIV of the series Defense Mechanisms of Arthropods. department of Chemistry, Spencer T. Olin Laboratory, Cornell Univer- sity, Ithaca, New York 14853.
Museum National d'Histoire Naturelle, Laboratoire de Zoologic, 61 Rue de Buffon, Paris - Ve.
"'Section of Neurobiology and Behavior, Division of Biological Sciences, Cornell University, Ithaca, New York 14853. Manuscript received by the editor April 3,1975 Pwht Ìö2:78-8 (1075). hup //psyche einclub org/82/82-078 html



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19751 Sm~olanoff, Demange, Meinwald, & Eisner 79 be 2-methyl-3-methoxy-I ,4-benzoquinone and 2-methyl-I ,4-benzoqui- none. Gas-liquid chromatography indicated the presence of a third minor component, pr,esent as a shoulder On the downward side of the 2-methyl-I ,4-benzoquinone peak.
Individual milkings from males and females of the three species showed no qualitative sexual differences in quinone content, although the ratio of the two quinones in A. tunzuZiporus showed considerable individual variability.
The two quinones here identified are the most common ones found in millipeds ( references in Eisner et at., I 975 ) . Fifteen spirostreptoid species have been previously studied. Of these, eight resemble Arch- ispirostreptus tumuliporus in that they produce both quinones (Arch- ispirostreptus gigus, Cambala hubrichti, Collostreptus fulvus, Dora- togonus annulipes, Orthoporus flavior, 0. punctilliger, Prionopetalum frundsbergi, P. tricuspis) (Eisner et al., 1975; Perks6 and Salles, I 970 ; Wood,
I 974). One species resembles Peridontopyge conani and P. rubescens in that it produces 2-methyl-3-methoxy-1,4-benzo- quinone only (Orthoporus conifer) (Eisner et al., 1965). Five spe- cies, including two other Peridontopyge, produce only 2-methyl-1,4- benzoquinone (Auglonopygus aculeatus, Peridontopyge aberrans, P. vachoni, Spirostreptus multisulcatus, Rhupidostreptus (5'pirostreptus) virgator) (Barbier, 1959 ; Barbier and Lederer, 1957). One species produces the unsubstituted quinone, 1,4-benzoquinone (Spirostreptus castaneus) ( Barbier and Lederer, 1957). This study has been supported by grants AI-02908 from the Na- tional Institutes of Health and BMS-74-15084 from the National Science Foundation.
BARBIER, M.
1959. Separations de p-benzoquinones naturelles par chromatoplaques. J. Chromatography 2, 649-651.
BARRIER, M. AND LEDERER, E.
1957. On the benzoquinones of the venom of three species of myria- pods. Blokhimya 22, 221-225.
EISNER, T., ALSOP, D., HICKS, K., AND MEINWALD, J. 1975. Defensive secretions of millipeds. In "Arthropod Venoms" (S. Bettini, ed.). Springer VerIag (in press). EISNER, T., HURST, J. J., KEETON, W. T., AND MEINWALD, Y. 1965. Defense mechanisms of arthropods. XVI. P,ara-benzoquinones in the secretion of spirostreptoid millipeds. Ann. Ent. Soc. Amer, 58, 247-248.




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Psyche
[March
PERISSE, A. C. M., AND SALLES, C. A.
1970. Estudo quimico de Diplopoda Brasileiros. 111. Collostreptus fulvus (Schubert, 1960). Atlas Sac. Biol. Rio de Janeiro 13, 95-99.
WOOD, W. F.
1974. Toluquinone and 2-methoxy-3-methyl benzoquinone from the de- fensive secretions of three African millipeds. Ann. Ent. Soc. Amer. 67, 988-989.




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