The Bite of the Honeybee: 2-Heptanone Secreted from Honeybee Mandibles during a Bite Acts as a Local Anaesthetic in Insects and Mammals

PLoS ONE

Volumn 7, Issue 10, 2012, Pages

  Papachristoforou, Alexandros ^a,b,c,d   Kagiava, Alexia ^a,e   Papaefthimiou, Chrisovalantis ^a   Termentzi, Aikaterini ^f   Fokialakis, Nikolas ^f   Skaltsounis, Alexios Leandros ^f   Watkins, Max ^g   Arnold, Gérard ^b,c   Theophilidis, George ^a  

^a ARISTOTLE UNIVERSITY OF THESSALONIKI   (Greece)

^b CNRS   (France)

^c UNIVERSITÉ PARIS SACLAY   (France)

^d CYPRUS UNIVERSITY OF TECHNOLOGY   (Cyprus)

^e CYPRUS INSTITUTE OF NEUROLOGY AND GENETICS   (Cyprus)

^f UNIVERSITY OF ATHENS   (Greece)

^g Vita (Europe) Limited   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

2 HEPTANONE; 3 HEPTANONE; 4 HEPTANONE; ALKANONE; LIDOCAINE; SODIUM CHANNEL NAV1.2; SODIUM CHANNEL NAV1.6; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; BEE STING; CONTROLLED STUDY; EX VIVO STUDY; FEMALE; GALLERIA MELLONELLA; HONEYBEE; LOCAL ANESTHESIA; MALE; MANDIBLE; NONHUMAN; RAT; SCIATIC NERVE; VARROA;

ANESTHETICS, LOCAL; ANIMALS; BEES; BITES AND STINGS; FEMALE; KETONES; LARVA; LIDOCAINE; MALE; MOTHS; MOTOR ACTIVITY; PHEROMONES; RATS; SCIATIC NERVE; VARROIDAE;

EID: 84867593308     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0047432     Document Type: Article

References (45)

1. Robinson GE, (1985) Effects of a juvenile hormone analogue on honey bee foraging behaviour and alarm pheromone production. J Insect Physiol 31: 277-282.
2. Vallet A, Cassier P, Lensky Y, (1991) Ontogeny of the fine structure of the mandibular glands of the honeybee (Apis mellifera L.) workers and the pheromonal activity of 2-heptanone. J Insect Physiol 37: 789-804.
3. Engels W, Rosenkranz P, Adler A, Taghizadeh T, Lubke G, et al. (1997) Mandibular gland volatiles and their ontogenetic patterns in queen honey bees, Apis mellifera carnica. J Insect Physiol 43: 307-313.
4. Shearer DA, Boch R, (1965) 2-heptanone in the mandibular gland secretion of the honey-bee. Nature 206: 530.
5. Free JB, Simpson J, (1968) The alerting pheromones of the honeybee. Z Vergl Physiol 61: 361-365.
6. Boch R, Shearer DA, Petrasovits A, (1970) Efficacies of two alarm substances of honey bee. J Insect Physiol 16: 17-24.
7. Boch R, Shearer DA, (1971) Chemical releasers of alarm behaviour in the honeybee, Apis mellifera. J Insect Physiol 17: 2277-2285.
8. Free JB, Pickett JA, Ferguson AW, Simpkins JR, Smith MC, (1985) Repelling foraging honeybees with alarm pheromones. J Agric Sci 105: 225-260.
9. Reith JP, Wilson WT, Levin MD, (1986) Repelling honey bees from insecticide-treated flowers with 2-heptanone. J Apicult Res 25: 78-84.
10. Couvillon JM, Barton NS, Cohe AJ, Fabricius KO, Kärcher HM, et al. (2010) Alarm pheromones do not mediate rapid shifts in honeybee guard acceptance threshold. J Chem Ecol 36: 1306-1308.
11. Breed DM, Guzmán-Novoa E. Hunt JG, (2004) Defensive behaviour of honeybees: Organization, genetics, and comparisons with other bees. Annu Rev Entomol 49: 271-98.
12. Eischen FA, Rinderer TE, Dietz A, (1986) Nocturnal defensive responses of Africanized and European honey bees to the greater wax moth (Galleria mellonella L). Anim Behav 34: 1070-1077.
13. Boecking O, Spivak M, (1999) Behavioral defenses of honeybees against Varroa jacobsoni Oud. Apidologie 30: 141-158.
14. Paterson BA, Anikin IM, Krans JK, (2010) Hysteresis in the production of force by larval dipteran muscle. J Exp Biol 231: 2483-2493.
15. Papachristoforou A, Papaefthimiou C, Zafeiridou G, Goundy V, Watkins M, et al. (2011) Monitoring the gravitational reflex of the ectoparasitic mite Varroa destructor: a novel bioassay for assessing toxic effects of acaricides. Pestic Biochem Phys 101: 109-117.
16. Song W, Silver KS, Du Y, Liu Z, Dong K, (2011) Analysis of the action of lidocaine on insect sodium channels. Insect Biochem Molec 41: 36-41.
17. Sheets LP, Jarecki WB, Cummins RT, (2011) Lidocaine reduces the transition to slow inactivation in Nav1.7 voltage-gated sodium channels. Br J Pharmacol 164: 719-730.
18. Leterrier C, Brachet A, Fache MP, Dargent B, (2010) Voltage-gated sodium channel organization in neurons: Protein interactions and trafficking pathways. Neurosci Lett 486: 92-100.
19. Kagiava A, Theophilidis G, (2011) High concentrations of dichloroacetate (DCA) have minor effects on the vitality of the mammalian nerve fibres: An ex vivo electrophysiological study. Anti-cancer Drugs 22 3: 273-276.
20. Patte F, Etcheto M, Marfaing P, Laffort P, (1989) Electroantennogram stimulus-response curves for 59 odourants in the honey bee, Apis mellifica J Insect Physiol. 35: 667-675.
21. Lensky Y, Cassier P, (1995) The alarm pheromones of queen and worker honey bees. Bee World 76: 119-129.
22. Feyereisen R, (2006) Evolution of insect P450. Biochem Soc Trans 34: 1252-1255.
23. Albro PW, Corbett JT, Schroeder JL, (1984) Metabolism of methyl n-amyl ketone (2-heptanone) and its binding to DNA of rat liver in vivo and in vitro. Chem Biol Interact 51: 295-308.
24. Imaoka S, Enomoto K, Oda Y, Asada A, Fujimori M, et al. (1990) Lidocaine Metabolism by Human Cytochrome P-450s Purified from Hepatic Microsomes: Comparison of Those with Rat Hepatic Cytochrome P-450s. J Pharmacol Exp Ther 255: 1385-1391.
25. Marder E, Bucher D, Schulz JD, Taylor LA, (2005) Invertebrate central pattern generation moves along. Curr Biol 15: R685-R699.
26. Ruttner F, Hänel H, (1992) Active defence against Varroa mites in a Carniolan strain of honeybee (Apis mellifera carnica Pollmann). Apidologie 23: 173-187.
27. Aumeier P, (2001) Bioassay for grooming effectiveness towards Varroa destructor mites in Africanized and Carniolan honey bees. Apidologie 32: 81-90.
28. Cummins TR, (2007) Setting up for the block: the mechanism underlying lidocaine's use-dependent inhibition of sodium channels. J. Phys. 582: 11.
29. Moschou M, Kosmidis EK, Kaloyianni M, Geronikaki A, Dabarakis N, et al. (2008) In vitro assessment of the neurotoxic and neuroprotective effects of N-acetyl-l-cysteine (NAC) on the rat sciatic nerve fibers. Toxicol In Vitro 22: 267-274.
30. Kagiava A, Tsingotjidou A, Emmanouilides C, Theophilidis G, (2008) The effects of oxaliplatin, an anticancer drug, on potassium channels of the peripheral myelinated nerve fibres of the adult rat. Neurotoxicology 29: 1100-1106.
31. Hung YC, Suzuki S, Chen CC, Pan YY, Wang TY,et al. 2009 Calcium chloride prolongs the effects of lidocaine and bupivacaine in rat sciatic nerve. Reg Anesth Pain Med 34: 333-339.
32. Kanai Y, Katsuki H, Takasaki M, (2009) Lidocaine Disrupts Axonal Membrane of Rat Sciatic Nerve In Vitro. Anesth Analg 91: 944-948.
33. Geronikaki A, Vicini P, Dabarakis N, Lagunin A, Poroikov V, et al. (2009) Evaluation of the local anesthetic activity of 3-aminobenzo[d]isothiazole derivatives using the rat sciatic nerve model. Eur J Med Chem 44: 473-481.
34. Kroin J, Buvanendran A, Williams DK, Wagenaar B; Moric M, et al. (2010) Local anesthetic sciatic nerve block and nerve fiber damage in diabetic rats. Reg Anesth Pain Med 35: 343-350.
35. Jianguo T, Soderlund MD, (2009) Human and Rat Nav1.3 Voltage-Gated Sodium Channels Differ in Inactivation Properties and Sensitivity to the Pyrethroid Insecticide Tefluthrin Neurotoxicology. 30: 81-89.
36. Nielsen CK, Lewis JR, Alewood D, Drinkwater R, Palant E, et al. (2005) Anti-allodynic efficacy of the c-conopeptide, Xen2174 in rats with neuropathic pain. Pain 118: 112-124.
37. Koh YC, Kini MR, (2012) From snake venom toxins to therapeutics - Cardiovascular examples Toxicon. 4: 497-506.
38. Misumi J, Nagano M, (1984) Neurophysiological studies on the relation between the structural properties and neurotoxicity of aliphatic hydrocarbon compounds in rats. Br J Ind Med 41: 526-532.
39. Myers RR, Kalichman MW, Reisner LS, Powell HC, (1986) Neurotoxicity of local anesthetics: altered perineurial permeability, edema, and nerve fiber injury. Anesthesiology 64: 29-35.
40. Kalichman MW, Powell HC, Myers RR, (1988) Pathology of local anesthetic-induced nerve injury. Acta Neuropathol. 75: 583-589.
41. Lambert LA, Lambert DH, Strichartz GR, (1994) Irreversible conduction block in isolated nerve by high concentrations of local anesthetics. Anesthesiology 80: 1082-1093.
42. Lewis JR, (2012) Discovery and development of the χ-conopeptide class of analgesic peptides Toxicon. 59: 524-528.
43. Struye MH, Mortier HL, Arnold G, Miniggio C, Borneck R, (1994) Microprocessor-controlled monitoring of honeybee flight activity at the hive entrance. Apidologie 25: 384-395.
44. Slama K, (1984) Recording of haemolymph pressure pulsations from the insect body surface J Comp Physiol B. 154: 635-643.
45. Schmalbruch H, (1986) Fiber composition of the rat sciatic nerve. Anat Rec 215: 71-81.