The Bite of the Honeybee: 2-Heptanone Secreted from Honeybee Mandibles during a Bite Acts as a Local Anaesthetic in Insects and Mammals
Publication Date
October 16, 2012
Journal
PLOS ONE
Authors
Alexandros Papachristoforou, Alexia Kagiava, Chrisovalantis Papaefthimiou, Aikaterini Termentzi, et al
Volume
7
Issue
10
Pages
e47432
DOI
https://dx.plos.org/10.1371/journal.pone.0047432
Publisher URL
http://journals.plos.org/plosone/article?id=10.1371%2Fjournal.pone.0047432
PubMed
http://www.ncbi.nlm.nih.gov/pubmed/23091624
PubMed Central
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3472974
Europe PMC
http://europepmc.org/abstract/MED/23091624
Web of Science
000310135800047
Scopus
84867593308
Mendeley
http://www.mendeley.com/research/bite-honeybee-2heptanone-secreted-honeybee-mandibles-during-bite-acts-local-anaesthetic-insects-mamm
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Mendeley | Further Information

{"title"=>"The Bite of the Honeybee: 2-Heptanone Secreted from Honeybee Mandibles during a Bite Acts as a Local Anaesthetic in Insects and Mammals", "type"=>"journal", "authors"=>[{"first_name"=>"Alexandros", "last_name"=>"Papachristoforou", "scopus_author_id"=>"14521493100"}, {"first_name"=>"Alexia", "last_name"=>"Kagiava", "scopus_author_id"=>"23972871000"}, {"first_name"=>"Chrisovalantis", "last_name"=>"Papaefthimiou", "scopus_author_id"=>"6507648362"}, {"first_name"=>"Aikaterini", "last_name"=>"Termentzi", "scopus_author_id"=>"12807241200"}, {"first_name"=>"Nikolas", "last_name"=>"Fokialakis", "scopus_author_id"=>"6602292126"}, {"first_name"=>"Alexios Leandros", "last_name"=>"Skaltsounis", "scopus_author_id"=>"7006891205"}, {"first_name"=>"Max", "last_name"=>"Watkins", "scopus_author_id"=>"53983503900"}, {"first_name"=>"Gérard", "last_name"=>"Arnold", "scopus_author_id"=>"7202727363"}, {"first_name"=>"George", "last_name"=>"Theophilidis", "scopus_author_id"=>"7003885349"}], "year"=>2012, "source"=>"PLoS ONE", "identifiers"=>{"sgr"=>"84867593308", "doi"=>"10.1371/journal.pone.0047432", "pui"=>"365872687", "pmid"=>"23091624", "scopus"=>"2-s2.0-84867593308", "issn"=>"19326203", "isbn"=>"1932-6203"}, "id"=>"9af7bce9-978c-3fb9-98ee-083de2caf759", "abstract"=>"Honeybees secrete 2-heptanone (2-H) from their mandibular glands when they bite. Researchers have identified several possible functions: 2-H could act as an alarm pheromone to recruit guards and soldiers, it could act as a chemical marker, or it could have some other function. The actual role of 2-H in honeybee behaviour remains unresolved. In this study, we show that 2-H acts as an anaesthetic in small arthropods, such as wax moth larva (WML) and Varroa mites, which are paralysed after a honeybee bite. We demonstrated that honeybee mandibles can penetrate the cuticle of WML, introducing less than one nanolitre of 2-H into the WML open circulatory system and causing instantaneous anaesthetization that lasts for a few minutes. The first indication that 2-H acts as a local anaesthetic was that its effect on larval response, inhibition and recovery is very similar to that of lidocaine. We compared the inhibitory effects of 2-H and lidocaine on voltage-gated sodium channels. Although both compounds blocked the hNav1.6 and hNav1.2 channels, lidocaine was slightly more effective, 2.82 times, on hNav.6. In contrast, when the two compounds were tested using an ex vivo preparation-the isolated rat sciatic nerve-the function of the two compounds was so similar that we were able to definitively classify 2-H as a local anaesthetic. Using the same method, we showed that 2-H has the fastest inhibitory effect of all alkyl-ketones tested, including the isomers 3- and 4-heptanone. This suggests that natural selection may have favoured 2-H over other, similar compounds because of the associated fitness advantages it confers. Our results reveal a previously unknown role of 2-H in honeybee defensive behaviour and due to its minor neurotoxicity show potential for developing a new local anaesthetic from a natural product, which could be used in human and veterinary medicine.", "link"=>"http://www.mendeley.com/research/bite-honeybee-2heptanone-secreted-honeybee-mandibles-during-bite-acts-local-anaesthetic-insects-mamm", "reader_count"=>65, "reader_count_by_academic_status"=>{"Professor > Associate Professor"=>2, "Librarian"=>2, "Researcher"=>11, "Student > Doctoral Student"=>4, "Student > Ph. D. Student"=>18, "Student > Postgraduate"=>2, "Student > Master"=>6, "Other"=>1, "Student > Bachelor"=>9, "Lecturer"=>2, "Lecturer > Senior Lecturer"=>1, "Professor"=>7}, "reader_count_by_user_role"=>{"Professor > Associate Professor"=>2, "Librarian"=>2, "Researcher"=>11, "Student > Doctoral Student"=>4, "Student > Ph. D. Student"=>18, "Student > Postgraduate"=>2, "Student > Master"=>6, "Other"=>1, "Student > Bachelor"=>9, "Lecturer"=>2, "Lecturer > Senior Lecturer"=>1, "Professor"=>7}, "reader_count_by_subject_area"=>{"Unspecified"=>1, "Agricultural and Biological Sciences"=>43, "Veterinary Science and Veterinary Medicine"=>2, "Chemistry"=>3, "Computer Science"=>1, "Engineering"=>1, "Environmental Science"=>3, "Biochemistry, Genetics and Molecular Biology"=>2, "Medicine and Dentistry"=>1, "Neuroscience"=>4, "Pharmacology, Toxicology and Pharmaceutical Science"=>1, "Physics and Astronomy"=>1, "Psychology"=>1, "Social Sciences"=>1}, "reader_count_by_subdiscipline"=>{"Medicine and Dentistry"=>{"Medicine and Dentistry"=>1}, "Social Sciences"=>{"Social Sciences"=>1}, "Physics and Astronomy"=>{"Physics and Astronomy"=>1}, "Psychology"=>{"Psychology"=>1}, "Unspecified"=>{"Unspecified"=>1}, "Environmental Science"=>{"Environmental Science"=>3}, "Pharmacology, Toxicology and Pharmaceutical Science"=>{"Pharmacology, Toxicology and Pharmaceutical Science"=>1}, "Engineering"=>{"Engineering"=>1}, "Chemistry"=>{"Chemistry"=>3}, "Neuroscience"=>{"Neuroscience"=>4}, "Agricultural and Biological Sciences"=>{"Agricultural and Biological Sciences"=>43}, "Computer Science"=>{"Computer Science"=>1}, "Biochemistry, Genetics and Molecular Biology"=>{"Biochemistry, Genetics and Molecular Biology"=>2}, "Veterinary Science and Veterinary Medicine"=>{"Veterinary Science and Veterinary Medicine"=>2}}, "reader_count_by_country"=>{"United States"=>2, "United Kingdom"=>1, "Mexico"=>1, "Germany"=>1}, "group_count"=>1}

Scopus | Further Information

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Figshare

  • {"files"=>["https://ndownloader.figshare.com/files/557756"], "description"=>"<p>. <b>a)</b> The amplitude of the nCAP, baseline to peak, was used as the main parameter to quantify the vitality of the sciatic nerve fibres during exposure to 2-H. The record presents the decrease in the amplitude nCAP during exposure of the sciatic nerve to 3.41 mg/mL 2-H. The first arrow indicates the beginning of the application and the second arrow indicates the time when the nerve was washed and bathed in normal saline. During exposure to 2-H, records were taken at a rate of 1 nCAP per 20s. After 2-H was replaced with normal saline, measurements were taken every 15 min. Vertical scale bar: 3 mV. Horizontal scale bar: 6 ms. <b>b)</b>. Diagrammatic representation of the three-chamber recording bath made of Plexiglass. It consists of the recording (R), the perfusion (P) and the stimulating chambers (S), separated by two partitions. The sciatic nerve was placed along the three chambers which were filled with oxygenated saline to cover the nerve. The dimensions of each chamber were 26×26×10 mm (length. width, depth), total volume 10 mL. The cover (c) made of Plexiglass was used to close hermitically the whole recording system, while the air inside the bath was saturated with 2-H, to eliminate the evaporation of 2-H in the perfusion chamber.</p>", "links"=>[], "tags"=>["evoked", "ncap", "sciatic", "exposed", "saline"], "article_id"=>228237, "categories"=>["Biochemistry", "Neuroscience", "Pharmacology", "Evolutionary Biology"], "users"=>["Alexandros Papachristoforou", "Alexia Kagiava", "Chrisovalantis Papaefthimiou", "Aikaterini Termentzi", "Nikolas Fokialakis", "Alexios-Leandros Skaltsounis", "Max Watkins", "Gérard Arnold", "George Theophilidis"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0047432.g005", "stats"=>{"downloads"=>1, "page_views"=>11, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_The_evoked_nCAP_from_the_isolated_rat_sciatic_nerve_exposed_to_saline_and_2_H_/228237", "title"=>"The evoked nCAP from the isolated rat sciatic nerve exposed to saline and 2-H", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2012-10-16 02:17:17"}
  • {"files"=>["https://ndownloader.figshare.com/files/557966"], "description"=>"a,b<p>Significant difference (p<0.05) for the IT<sub>0</sub> comparison between 2-heptanone, 3-heptanone and 4-heptanone.</p>", "links"=>[], "tags"=>["anaesthetic", "properties", "2-heptanone"], "article_id"=>228446, "categories"=>["Biochemistry", "Neuroscience", "Pharmacology", "Evolutionary Biology"], "users"=>["Alexandros Papachristoforou", "Alexia Kagiava", "Chrisovalantis Papaefthimiou", "Aikaterini Termentzi", "Nikolas Fokialakis", "Alexios-Leandros Skaltsounis", "Max Watkins", "Gérard Arnold", "George Theophilidis"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0047432.t003", "stats"=>{"downloads"=>2, "page_views"=>14, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Comparing_the_local_anaesthetic_properties_of_2_heptanone_with_the_other_ketones_/228446", "title"=>"Comparing the local anaesthetic properties of 2-heptanone with the other ketones.", "pos_in_sequence"=>0, "defined_type"=>3, "published_date"=>"2012-10-16 02:20:46"}
  • {"files"=>["https://ndownloader.figshare.com/files/557673"], "description"=>"<p>. Data represent tonic (a and c) and phasic (b and d) effects. Solid curves represent when data are fitted with a logistic equation with minimum and maximum effects fixed at 0 and 100% (n = 6).</p>", "links"=>[], "tags"=>["2-heptanone"], "article_id"=>228163, "categories"=>["Biochemistry", "Neuroscience", "Pharmacology", "Evolutionary Biology"], "users"=>["Alexandros Papachristoforou", "Alexia Kagiava", "Chrisovalantis Papaefthimiou", "Aikaterini Termentzi", "Nikolas Fokialakis", "Alexios-Leandros Skaltsounis", "Max Watkins", "Gérard Arnold", "George Theophilidis"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0047432.g004", "stats"=>{"downloads"=>1, "page_views"=>10, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_The_effect_of_2_heptanone_on_hNav1_2_a_and_hNav1_6_b_sodium_channels_/228163", "title"=>"The effect of 2-heptanone on hNav1.2 (a) and hNav1.6 (b) sodium channels", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2012-10-16 02:16:03"}
  • {"files"=>["https://ndownloader.figshare.com/files/558011"], "description"=>"<p>Values are the mean IC<sub>50</sub>± SEM. <i>n</i> = 6 in all cases. 2-H and lidocaine both blocked the two channels that we tested. In the tonic experiments, 2-H was 3.97 (for hNav1.2) and 2.82 (for hNav1.6) times less active than lidocaine. In the phasic experiments, 2-heptanone was 7.50 (for hNav1.2) and 7.57 (for hNav1.6) times less active than lidocaine. The exposure time for 2-H was limited to 3 min.</p>", "links"=>[], "tags"=>["2-h", "lidocaine", "applied", "ion"], "article_id"=>228493, "categories"=>["Biochemistry", "Neuroscience", "Pharmacology", "Evolutionary Biology"], "users"=>["Alexandros Papachristoforou", "Alexia Kagiava", "Chrisovalantis Papaefthimiou", "Aikaterini Termentzi", "Nikolas Fokialakis", "Alexios-Leandros Skaltsounis", "Max Watkins", "Gérard Arnold", "George Theophilidis"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0047432.t001", "stats"=>{"downloads"=>7, "page_views"=>5, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_IC_50_of_2_H_and_lidocaine_applied_to_hNav1_2_and_hNav1_6_ion_channels_/228493", "title"=>"IC<sub>50</sub> of 2-H and lidocaine applied to hNav1.2 and hNav1.6 ion channels.", "pos_in_sequence"=>0, "defined_type"=>3, "published_date"=>"2012-10-16 02:21:33"}
  • {"files"=>["https://ndownloader.figshare.com/files/557602"], "description"=>"<p>. <b>a</b>) Response of small-size wax moth larvae (WML) bitten by a honeybee, <b>b</b>) Response of large-size WML injected with 2.5 µL of 2-H, <b>c</b>) response of large-size WML injected with 1.63 mg of lidocaine <b>d, e)</b> modification of the gravitation reflex of <i>Varroa</i> exposed to 0.025 µL and 0.061 µL of 2-H (respectively), Vertical scale bar: a 3.4 mN, b 9.8 mN, c 75 μΝ, d 9.8 mN.</p>", "links"=>[], "tags"=>["locomotory", "tethered", "wax", "moth", "larvae", "gravitational", "reflex"], "article_id"=>228085, "categories"=>["Biochemistry", "Neuroscience", "Pharmacology", "Evolutionary Biology"], "users"=>["Alexandros Papachristoforou", "Alexia Kagiava", "Chrisovalantis Papaefthimiou", "Aikaterini Termentzi", "Nikolas Fokialakis", "Alexios-Leandros Skaltsounis", "Max Watkins", "Gérard Arnold", "George Theophilidis"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0047432.g003", "stats"=>{"downloads"=>1, "page_views"=>14, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_The_locomotory_pattern_of_tethered_wax_moth_larvae_and_the_gravitational_reflex_of_Varroa_mites_/228085", "title"=>"The locomotory pattern of tethered wax moth larvae and the gravitational reflex of <i>Varroa</i> mites", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2012-10-16 02:14:45"}
  • {"files"=>["https://ndownloader.figshare.com/files/296458"], "description"=>"<div><p>Honeybees secrete 2-heptanone (2-H) from their mandibular glands when they bite. Researchers have identified several possible functions: 2-H could act as an alarm pheromone to recruit guards and soldiers, it could act as a chemical marker, or it could have some other function. The actual role of 2-H in honeybee behaviour remains unresolved. In this study, we show that 2-H acts as an anaesthetic in small arthropods, such as wax moth larva (WML) and Varroa mites, which are paralysed after a honeybee bite. We demonstrated that honeybee mandibles can penetrate the cuticle of WML, introducing less than one nanolitre of 2-H into the WML open circulatory system and causing instantaneous anaesthetization that lasts for a few minutes. The first indication that 2-H acts as a local anaesthetic was that its effect on larval response, inhibition and recovery is very similar to that of lidocaine. We compared the inhibitory effects of 2-H and lidocaine on voltage-gated sodium channels. Although both compounds blocked the hNav1.6 and hNav1.2 channels, lidocaine was slightly more effective, 2.82 times, on hNav.6. In contrast, when the two compounds were tested using an <em>ex vivo</em> preparation–the isolated rat sciatic nerve–the function of the two compounds was so similar that we were able to definitively classify 2-H as a local anaesthetic. Using the same method, we showed that 2-H has the fastest inhibitory effect of all alkyl-ketones tested, including the isomers 3- and 4-heptanone. This suggests that natural selection may have favoured 2-H over other, similar compounds because of the associated fitness advantages it confers. Our results reveal a previously unknown role of 2-H in honeybee defensive behaviour and due to its minor neurotoxicity show potential for developing a new local anaesthetic from a natural product, which could be used in human and veterinary medicine.</p> </div>", "links"=>[], "tags"=>["2-heptanone", "secreted", "honeybee", "mandibles", "acts", "anaesthetic", "insects", "mammals"], "article_id"=>118403, "categories"=>["Biochemistry", "Neuroscience", "Pharmacology", "Evolutionary Biology"], "users"=>["Alexandros Papachristoforou", "Alexia Kagiava", "Chrisovalantis Papaefthimiou", "Aikaterini Termentzi", "Nikolas Fokialakis", "Alexios-Leandros Skaltsounis", "Max Watkins", "Gérard Arnold", "George Theophilidis"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0047432", "stats"=>{"downloads"=>4, "page_views"=>7, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/The_Bite_of_the_Honeybee_2_Heptanone_Secreted_from_Honeybee_Mandibles_during_a_Bite_Acts_as_a_Local_Anaesthetic_in_Insects_and_Mammals/118403", "title"=>"The Bite of the Honeybee: 2-Heptanone Secreted from Honeybee Mandibles during a Bite Acts as a Local Anaesthetic in Insects and Mammals", "pos_in_sequence"=>0, "defined_type"=>3, "published_date"=>"2012-10-16 02:20:03"}
  • {"files"=>["https://ndownloader.figshare.com/files/557354"], "description"=>"<p>. No treatment (control) and doses of 0.001, 10 and 1000 µL of 2-H were applied at the colony entrance. Honeybees were recorded using Electronic BeeSCAN counters.</p>", "links"=>[], "tags"=>["honeybees", "exiting", "beehives", "2-h"], "article_id"=>227842, "categories"=>["Biochemistry", "Neuroscience", "Pharmacology", "Evolutionary Biology"], "users"=>["Alexandros Papachristoforou", "Alexia Kagiava", "Chrisovalantis Papaefthimiou", "Aikaterini Termentzi", "Nikolas Fokialakis", "Alexios-Leandros Skaltsounis", "Max Watkins", "Gérard Arnold", "George Theophilidis"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0047432.g001", "stats"=>{"downloads"=>1, "page_views"=>8, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Number_of_honeybees_exiting_beehives_following_2_H_applications_/227842", "title"=>"Number of honeybees exiting beehives following 2-H applications", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2012-10-16 02:10:42"}
  • {"files"=>["https://ndownloader.figshare.com/files/557913"], "description"=>"<p>The effects of 2-heptanone and lidocaine on the isolated sciatic nerve of the rat.</p>", "links"=>[], "tags"=>["2-heptanone", "lidocaine", "sciatic"], "article_id"=>228400, "categories"=>["Biochemistry", "Neuroscience", "Pharmacology", "Evolutionary Biology"], "users"=>["Alexandros Papachristoforou", "Alexia Kagiava", "Chrisovalantis Papaefthimiou", "Aikaterini Termentzi", "Nikolas Fokialakis", "Alexios-Leandros Skaltsounis", "Max Watkins", "Gérard Arnold", "George Theophilidis"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0047432.t002", "stats"=>{"downloads"=>4, "page_views"=>10, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_The_effects_of_2_heptanone_and_lidocaine_on_the_isolated_sciatic_nerve_of_the_rat_/228400", "title"=>"The effects of 2-heptanone and lidocaine on the isolated sciatic nerve of the rat.", "pos_in_sequence"=>0, "defined_type"=>3, "published_date"=>"2012-10-16 02:20:00"}
  • {"files"=>["https://ndownloader.figshare.com/files/557825"], "description"=>"<p>. <b>a)</b> the effects of 2-H and lidocaine (Lido) on the nCAP of the rat sciatic nerve, the time-response curves for 3.41 mg/mL 2-H and lidocaine. <b>b</b>) the time-response curves after the preparation was washed with normal saline (recovery) and the nCAP was monitored for 24 h, <b>c</b>) the time-response curves for 3.41 mg/mL 2-H, 3H, 4H, <b>d</b>) the recovery <b>e)</b> 2-pentanone (2-Pe), 3-pentanone (2-Pe), 2-hexanone (2-He), 2-octanone (2-Oc) and 3-octanone (3-Oc) <b>f</b>) the time-response curves after the preparations were washed with normal saline (recovery) and the nCAP was monitored for 24 h.</p>", "links"=>[], "tags"=>["alkyl-ketones", "sciatic"], "article_id"=>228312, "categories"=>["Biochemistry", "Neuroscience", "Pharmacology", "Evolutionary Biology"], "users"=>["Alexandros Papachristoforou", "Alexia Kagiava", "Chrisovalantis Papaefthimiou", "Aikaterini Termentzi", "Nikolas Fokialakis", "Alexios-Leandros Skaltsounis", "Max Watkins", "Gérard Arnold", "George Theophilidis"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0047432.g006", "stats"=>{"downloads"=>1, "page_views"=>6, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_The_effect_of_2_H_lidocaine_and_other_alkyl_ketones_on_the_sciatic_nerve_of_the_rat_/228312", "title"=>"The effect of 2-H, lidocaine, and other alkyl-ketones on the sciatic nerve of the rat", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2012-10-16 02:18:32"}
  • {"files"=>["https://ndownloader.figshare.com/files/557473"], "description"=>"<p>. <b>a</b>) SEM scan of a honeybee mandible. P, the pore from which 2-H is secreted; G, groove; S, spikes; E, edges. <b>b</b>) the opening created in a wax moth larvae exoskeleton after a honeybee bite. 1, 2, and 3 are parts of the mandible that penetrate the corresponding points on the wax moth larvae exoskeleton.</p>", "links"=>[], "tags"=>["honeybee", "mandible", "biting", "wax", "moth"], "article_id"=>227955, "categories"=>["Biochemistry", "Neuroscience", "Pharmacology", "Evolutionary Biology"], "users"=>["Alexandros Papachristoforou", "Alexia Kagiava", "Chrisovalantis Papaefthimiou", "Aikaterini Termentzi", "Nikolas Fokialakis", "Alexios-Leandros Skaltsounis", "Max Watkins", "Gérard Arnold", "George Theophilidis"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0047432.g002", "stats"=>{"downloads"=>1, "page_views"=>13, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_The_honeybee_mandible_and_the_result_of_biting_wax_moth_larvae_/227955", "title"=>"The honeybee mandible and the result of biting wax moth larvae", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2012-10-16 02:12:35"}

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Relative Metric

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