Cerumen of Australian stingless bees (Tetragonula carbonaria): Gas chromatography-mass spectrometry fingerprints and potential anti-inflammatory properties

Naturwissenschaften

Volumn 98, Issue 4, 2011, Pages 329-337

  Massaro, Flavia Carmelina ^a   Brooks, Peter Richard ^a   Wallace, Helen Margaret ^a   Russell, Fraser Donald ^a  

^a UNIVERSITY OF THE SUNSHINE COAST   (Australia)

Author keywords

5 Lipoxygenase; Diterpenic acids; GC MS; Honeypots; Propolis; Resins

Indexed keywords

ANTIINFLAMMATORY AGENT; ARACHIDONATE 5 LIPOXYGENASE; ENZYME INHIBITOR; PROPOLIS;

APICULTURE; COLONY; ENZYME ACTIVITY; GAS CHROMATOGRAPHY; HONEYBEE; MASS SPECTROMETRY; NEST; PHENOLIC COMPOUND; POLLINATOR; RESIN; SCANNING ELECTRON MICROSCOPY;

ANIMAL; ARTICLE; AUSTRALIA; BEE; CHEMISTRY; DRUG EFFECT; ENZYME ACTIVATION; IC 50; MASS FRAGMENTOGRAPHY; METABOLISM; PHYSIOLOGY;

ANIMALS; ANTI-INFLAMMATORY AGENTS; ARACHIDONATE 5-LIPOXYGENASE; AUSTRALIA; BEES; ENZYME ACTIVATION; ENZYME INHIBITORS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; INHIBITORY CONCENTRATION 50; PROPOLIS;

AUSTRALIA; QUEENSLAND;

APIS MELLIFERA; APOIDEA; MELIPONINAE;

EID: 79954423401     PISSN: 00281042     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00114-011-0770-7     Document Type: Article

References (49)

1. US Akula B Odhav 2008 In vitro 5-lipoxygenase inhibition of polyphenolic antioxidants from undomesticated plants of South Africa J Med Plants Res 2 9 207 212
2. GE Anthon DM Barrett 2001 Colorimetric method for the determination of lipoxygenase activity J Agric Food Chem 49 32 37 11170556 10.1021/jf000871s 1:CAS:528:DC%2BD3cXosFWmtLg%3D (Pubitemid 32104484)
3. V Bankova 2009 Chemical diversity of propolis makes it a valuable source of new biologically active compounds J ApiProd ApiMed Sci 1 23 28 10.3896/IBRA.4.01.2.01
4. VS Bankova M Popova 2007 Propolis of stingless bees: a promising source of biologically active compounds Pharm Rev 1 88 92 1:CAS:528:DC%2BD2sXhtVSit7zF
5. AH Banskota Y Tezuka S Kadota 2001 Recent progress in pharmacological research of propolis Phytother Res 15 561 571 11746834 10.1002/ptr.1029 1:CAS:528:DC%2BD3MXovVGqtbc%3D (Pubitemid 33021859)
6. S Cremer M Sixt 2009 Analogies in the evolution of individual and social immunity Phil Trans R Soc B 364 129 142 10.1098/rstb.2008.0166 18926974 10.1098/rstb.2008.0166
7. CS Creaser MR Koupai-Abyazani GR Stephenson 1991 Mass spectra of trimethylsilyl derivatives of naturally occurring flavonoid aglycones and chalcones Org Mass Spectrom 26 157 160 10.1002/oms.1210260310 1:CAS:528:DyaK3MXit1ymurg%3D
8. M Curini F Epifano S Genovese L Menghini D Ricci D Fraternale L Giamperi A Bucchini E Bellacchio 2006 Lipoxygenase inhibitory activity of boropinic acid, active principle of boronia pinnata Nat Prod Comm 1 12 1141 1145 1:CAS:528:DC%2BD2sXhsFaksr4%3D
9. EC de Almeida H Menezes 2002 Anti-inflammatory activity of propolis extracts: a review J Venom Anim Toxins 8 191 212
10. CG dos Santos FL Megiolaro JE Serrão B Blochtein 2009 Morphology of the head salivary and intramandibular glands of the stingless bee Plebeia emerina (Hymenoptera: Meliponini) workers associated with propolis Morphol Histol Fine Struct 102 137 143
11. AP Farnesi R Aquino-Ferreira D De Jong JK Bastos AE Soares 2009 Effects of stingless bee and honey bee propolis on four species of bacteria Gen Mol Res 8 635 640 10.4238/vol8-2kerr023 1:CAS:528:DC%2BD1MXntV2rtb8%3D
12. W Greenaway T Scaysbrook FR Whatley 1987 The analysis of bud exudate of Populus × Euramericana, and of propolis, by gas chromatography-mass spectrometry Proc R Soc Lond B Biol Sci 232 249 272 10.1098/rspb.1987.0073 1:CAS:528:DyaL1cXkvV2lurc%3D
13. TA Heard 1999 The role of stingless bees in crop pollination Ann Rev Entomol 44 183 206 10.1146/annurev.ento.44.1.183 1:CAS:528:DyaK1MXpvFKhug%3D%3D (Pubitemid 29096971)
14. HT Inoue EA De Sousa OR de Oliveira SR Cunha Funari LMR Carelli Barreto AP Da Silva Dib 2007 Produção de própolis por diferentes métodos de coleta Arch Latinoam Prod Anim 15 65 69
15. T Kaneko N Baba M Matsuo 2001 Structure-activity relationship of antioxidants for inhibitors of linoleic acid hydroperoxide-induced toxicity in cultured human umbilical vein endothelial cells Cytotechnology 35 43 55 19003280 10.1023/A:1008139412588 1:CAS:528:DC%2BD3MXjsVWgt7s%3D (Pubitemid 32304976)
16. VD Kortenska MP Velikova NV Yanishlieva IR Totzeva VS Bankova MC Marcucci 2002 Kinetics of lipid oxidation in the presence of cinnamic acid derivatives Eur J Lipid Sci Technol 104 19 28 10.1002/1438-9312(200201)104:1<19::AID- EJLT19>3.0.CO;2-Q 1:CAS:528:DC%2BD38XhtV2hsrc%3D (Pubitemid 34848660)
17. MV Kumaraswamy S Satish 2008 Antioxidant and anti-lipoxygenase activity of Thespesia lampas Dalz & Gibs Adv Biol Res 2 56 59
18. L Lehmberg K Dworschak N Blüthgen 2008 Defensive behavior and chemical deterrence against ants in the stingless bee genus Trigona (Apidae, Meliponini) J Apicult Res 47 17 21 (Pubitemid 351439996)
19. SD Leonhardt N Blüthgen 2009 A sticky affair: resin collection by Bornean stingless bees Biotropica 41 730 736 10.1111/j.1744-7429.2009.00535.x
20. SD Leonhardt N Blüthgen T Schmitt 2009 Smelling like resin: terpenoids account for species-specific cuticular profiles in Southeast-Asian stingless bees Insect Soc 56 157 170 10.1007/s00040-009-0007-3
21. Leonhardt SD, Wallace HM, Schmitt T (2010a) The cuticular profiles of Australian stingless bees are shaped by resin of the eucalypt tree Corymbia torelliana. Austral Ecol (in press)
22. Leonhardt SD, Zeilhofer S, Blüthgen N, Schmitt T (2010b) Stingless bees use terpenes as olfactory cues to find resin sources. Chem Senses. doi: 10.1093/chemse/bjq058
23. KR Markham KA Mitchell AL Wilkins JA Daldy Y Lu 1996 HPLC and GC-MS identification of the major organic constituents in New Zealand propolis Phytochemistry 42 1 205 211 10.1016/0031-9422(96)83286-9 1:CAS:528: DyaK28XisFGgt7Y%3D (Pubitemid 126686184)
24. SV McLennan J Bonner S Milne L Lo A Charlton S Kurup J Jia DK Yue SM Twigg 2008 The anti-inflammatory agent propolis improves wound healing in a rodent model of experimental diabetes Wound Repair Regen 16 706 713 19128266 10.1111/j.1524-475X.2008.00421.x
25. BV Milborrow JM Kennedy LJ Dollin 1987 Composition of wax made by the Australian stingless bee Trigona australis Aust J Biol Sci 40 15 25 1:CAS:528:DyaL2sXktVCltb4%3D
26. CV Nunez ML de Oliveira R Duarte Lima IEC Diaz E Collantes EJ Sargentini OLJ Pereira LM Araújo 2008 Chemical analyses confirm a rare case of seed dispersal by bees Apidologie 39 618 626 10.1051/apido:2008047 1:CAS:528:DC%2BD1MXivFWjt7w%3D
27. LP Oddo TA Heard A Rodriguez-Malaver RA Perez M Fernandez-Muino MT Sancho G Sesta L Lusco P Vit 2008 Composition and antioxidant activity of Trigona carbonaria honey from Australia J Med Food 11 789 794 19012514 10.1089/jmf.2007.0724 1:CAS:528:DC%2BD1cXhsVKjtrzE
28. EF Patricio L Cruz-Lopez R Maile J Tentschert GR Jones ED Morgan 2002 The propolis of stingless bees: terpenes from the tibia of three Frieseomelitta species J Insect Physiol 48 249 254 12770125 10.1016/S0022-1910(01)00170-6 1:CAS:528:DC%2BD38XhsFagtbs%3D (Pubitemid 34194464)
29. AS Pereira EA Nascimento FR Aquino Neto 2002 Lupeol alkanoates in Brazilian propolis Z Naturforsch C 57 721 726 12241003 1:CAS:528: DC%2BD38XmvVCis70%3D (Pubitemid 35008536)
30. AS Pereira B Bicalho FR de Aquino Neto 2003 Comparison of propolis from Apis mellifera and Tetragonisca angustula Apidologie 34 291 298 10.1051/apido:2003023 10.1051/apido:2003023 (Pubitemid 36647103)
31. EM Pferschy-Wenzig O Kunert A Presser R Bauer 2008 In vitro anti-inflammatory activity of larch (Larix decidua L.) sawdust J Agric Food Chem 56 24 11688 11693 19049343 10.1021/jf8024002 1:CAS:528:DC%2BD1cXhsVCrurfI
32. AL Piccinelli L Campone F Dal Piaz O Cuesta-Rubio L Rastrelli 2009 Fragmentation pathways of polycyclic polyisoprenylated benzophenones and degradation profile of nemorosone by multiple-stage tandem mass spectrometry J Am Soc Mass Spectrom 20 1688 1698 19540134 10.1016/j.jasms.2009.05.004 1:CAS:528:DC%2BD1MXhtV2nt7vN
33. Polya GM (2003) Biochemical targets of plant bioactive compounds. A pharmacological reference guide to sites of action and biological effects. CRC, Boca Raton
34. JA Rankin 2004 Biological mediators of acute inflammation AACN Clin Issues 15 317
35. DW Roubik 2006 Stingless bee nesting biology Apidologie 37 124 143 10.1051/apido:2006026 (Pubitemid 44033085)
36. AC Sawaya DM Tomazela IB Cunha VS Bankova MC Marcucci AR Custodio MN Eberlin 2004 Electrospray ionization mass spectrometry fingerprinting of propolis Analyst 129 739 744 15284918 10.1039/b403873h 1:CAS:528: DC%2BD2cXmtFOju7k%3D (Pubitemid 39120520)
37. M Simone JD Evans M Spivak 2009 Resin collection and social immunity in honey bees Evolution 11 3016 3022 10.1111/j.1558-5646.2009.00772.x
38. M Simone-Finstrom M Spivak 2010 Propolis and bee health: the natural history and significance of resin use by honey bees Apidologie 41 295 311 10.1051/apido/2010016 10.1051/apido/2010016
39. A Stow D Briscoe M Gillings M Holley S Smith R Leys T Silberbauer C Turnbull A Beattie 2007 Antimicrobial defences increase with sociality in bees Biol Lett 3 423 424 10.1098/rsbl.2007.0178
40. GF Sud'ina OK Mirzoeva MA Pushkareva GA Korshunova NV Sumbatyan SD Varfolomeev 1993 Caffeic acid phenethyl ester as a lipoxygenase inhibitor with antioxidant properties FEBS Lett 329 21 24 7689063 10.1016/0014-5793(93)80184-V (Pubitemid 23248240)
41. AC Teixeira D Message G Negri A Salatino 2006 Bauer-7-en-3â-yl acetate: a major constituent of unusual samples of Brazilian propolis Quimica Nova 29 245 246 1:CAS:528:DC%2BD28XjtV2rtrs%3D (Pubitemid 43536083)
42. E Temaru S Shimura K Amano T Karasawa 2007 Antibacterial activity of honey from stingless honeybees (Hymenoptera; Apidae; Meliponinae) Pol J Microbiol 56 281 285 18254500 (Pubitemid 351171170)
43. NN Ulusu D Ercil MK Sakar EF Tezcan 2002 Abietic acid inhibits lipoxygenase activity Phytother Res 16 88 90 11807975 10.1002/ptr.983 1:CAS:528:DC%2BD38Xhs1Wisbk%3D (Pubitemid 34116705)
44. A Urzúa MC Rezende C Mascayano L Vásquez 2008 A structure-activity study of antibacterial diterpenoids Molecules 13 882 891 18463590 10.3390/molecules13040822
45. M Velikova V Bankova MC Marcucci I Tsvetkova A Kujumgiev 2000 Chemical composition and biological activity of propolis from Brazilian Meliponinae Z Naturforsch C 55 785 789 11098831 1:CAS:528:DC%2BD3cXoslyrt7g%3D
46. M Velikova V Bankova I Tsvetkova A Kujumgiev MC Marcucci 2000 Antibacterial ent-kaurene from Brazilian propolis of native stingless bees Fitoterapia 71 6 693 696 11077178 10.1016/S0367-326X(00)00213-6 1:CAS:528:DC%2BD3cXotlGitLg%3D
47. HM Wallace SJ Trueman 1995 Dispersal of Eucalyptus torelliana seeds by the resin-collecting stingless bee, Trigona carbonaria Oecologia 104 12 16 10.1007/BF00365556 10.1007/BF00365556 (Pubitemid 26452248)
48. HM Wallace DJ Lee 2010 Resin-foraging by colonies of Trigona sapiens and T. hockingsi (Hymenoptera: Apidae, Meliponini) and consequent seed dispersal of Corymbia torelliana (Myrtaceae) Apidologie 41 428 435 10.1051/apido/20079074 10.1051/apido/2009074
49. HM Wallace GM Howell DJ Lee 2008 Standard yet unusual mechanisms of long-distance dispersal: seed dispersal of Corymbia torelliana by bees Divers Distrib 14 87 94 10.1111/j.1472-4642.2007.00427.x (Pubitemid 350256039)