Skip to main content

Propolis and Geopropolis Volatiles

  • Chapter
  • First Online:
Bee Products - Chemical and Biological Properties

Abstract

Propolis and geopropolis are bee products (from honeybees and stingless bees, respectively) which are receiving increasing attention due to their reputed biological properties. Although several works have examined the chemical variability of propolis (in general), not so much is known about their volatile chemical profiles. The composition of volatile compounds in propolis can be affected in a number of ways, starting from the raw material used by different types of bees (honeybees or stingless bees) to the techniques used for their final isolation and analysis. This work gives an overview of the existing literature on propolis volatiles, their origin, bee producing species, plant sources and methodologies of extraction and analysis.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 149.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 199.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 199.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  • Agüero MB, Svetaz L, Sánchez M, Luna L, Lima B, López ML, Zacchino S, Palermo J, Wunderlin D, Feresin GE, Tapia A (2011) Argentinean Andean propolis associated with the medicinal plant Larrea nitida Cav. (Zygophyllaceae). HPLC–MS and GC–MS characterization and antifungal activity. Food Chem Toxicol 49:1970–1978

    Article  PubMed  Google Scholar 

  • de Albuquerque IL, Alves LA, Lemos TLG, Dorneles CA, de Morais MO (2008) Constituents of the essential oil of Brazilian green propolis from Brazil. J Essent Oil Res 20:414–415

    Google Scholar 

  • Alqarni AS, Rushdi AI, Owayss AA, Raweh HS, El-Mubarak AH, Simoneit BRT (2015) Organic tracers from asphalt in propolis produced by urban honey bees, Apis mellifera Linn. PLoS One 10:e0128311

    Article  PubMed  PubMed Central  Google Scholar 

  • Atungulu G, Miura M, Atungulu E, Satou Y, Suzuki K (2007) Activity of gaseous phase steam distilled propolis extracts on peroxidation and hydrolysis of rice lipids. J Food Eng 80:850–858

    Article  CAS  Google Scholar 

  • Bankova V, Popova M (2007) Propolis of stingless bees: a promising source of biologically active compounds. Pharmacogn Rev 1:88–92

    CAS  Google Scholar 

  • Bankova V, Christov R, Popov S, Pureb O, Bocari G (1994) Volatile constituents of propolis. Z Naturforsch 49c:6–10

    Google Scholar 

  • Bankova V, Christov R, Kujumgiev A, Marcuccic MC, Popov S (1995) Chemical composition and antibacterial activity of Brazilian propolis. Z Naturforsch 50c:167–172

    Google Scholar 

  • Bankova V, Boudourova-Krasteva G, Popov S, Sforcin J, Funari SC (1998a) Seasonal variations in essential oil from Brazilian propolis. J Essent Oil Res 10:693–696

    Article  CAS  Google Scholar 

  • Bankova VS, Christov RS, Delgado Tejera A (1998b) Lignans and other constituents of propolis from the Canary islands. Phytochemistry 49:1411–1415

    Article  CAS  Google Scholar 

  • Bankova V, Christov R, Popov S, Marcucci MC, Tsvetkovac I, Kujumgiev A (1999) Antibacterial activity of essential oils from Brazilian propolis. Fitoterapia 70:190–193

    Article  CAS  Google Scholar 

  • Bankova V, de Castro SL, Marcucci MC (2000) Propolis: recent advances in chemistry and plant origin. Apidologie 31:3–15

    Article  CAS  Google Scholar 

  • Bankova V, Popova M, Trusheva B (2014) Propolis volatile compounds: chemical diversity and biological activity: a review. Chem Cent J 8:28

    Article  PubMed  PubMed Central  Google Scholar 

  • Bittencourt MLF, Ribeiro PR, Franco RLP, Hilhorst HWM, de Castro RD, Fernandez LG (2015) Metabolite profiling, antioxidant and antibacterial activities of Brazilian propolis: use of correlation and multivariate analyses to identify potential bioactive compounds. Food Res Int 76:449–457

    Article  CAS  PubMed  Google Scholar 

  • Bonvehí JS, Coll FC, Jordà RE (1994) The composition active components of bacteriostatic activity of propolis in dietetics. JAOCS 71:529–532

    Google Scholar 

  • Borčić I, Radonić A, Grzunov K (1996) Comparison of the volatile constituents of propolis gathered in different regions of Croatia. Flavour Fragr J 11:311–313

    Article  Google Scholar 

  • Bracho JC (2000) Constituyentes volátiles del propóleo, una realidade acerca de su rica composición química. Bol Soc Quim Peru 66:198–209

    CAS  Google Scholar 

  • Bracho JC, Rosado A, Pino JA (1996) Comparison of isolation methods for propolis volatiles. J Essent Oil Res 8:665–668

    Article  CAS  Google Scholar 

  • Cheng H, Qin ZH, Guo XF, Hu XS, Wu JH (2013) Geographical origin identification of propolis using GC–MS and electronic nose combined with principal component analysis. Food Res Int 51:813–822

    Article  CAS  Google Scholar 

  • Clair G, Peyron L (1981) Contribuition à l’étude de l’huile essentille de propolis. Riv ital EPPOS 63:168–170

    CAS  Google Scholar 

  • Corsi M (1981) Les huilles essentielles de la propolis. In: Meletinov C (ed) XXVIIIth international congress of apiculture. Apimondia, Acapulco, Mexico, pp 407–411

    Google Scholar 

  • Council of Europe (2010) European Pharmacopoeia, 7th edn. Strasbourg, France, p. 241

    Google Scholar 

  • Falcão SI, Freire C, Figueiredo AC, Villas-Boas M (2016) The volatile composition of Portuguese propolis towards its origin discrimination. Rec Nat Prod 10:176–188

    Google Scholar 

  • Fernandes FH, Guterres ZR, Violante IMP, Lopes TFS, Garcez WS, Garcez FR (2015) Evaluation of mutagenic and antimicrobial properties of brown propolis essential oil from the Brazilian Cerrado biome. Toxicol Rep 2:1482–1488

    Article  CAS  Google Scholar 

  • Fernandes-Silva CC, Lima CA, Negri G, Salatini MLF, Salatino A, Mayworm MAS (2015) Composition of the volatile fraction of a sample of Brazilian green propolic and its phytotoxic activity. J Sci Food Agric 95:3091–3095

    Article  CAS  PubMed  Google Scholar 

  • Fu Y-X, Xu Y-J, Chen B, Li Y, Luo L-P (2009) Analysis of volatile components from inner Mongolia propolis by gas chromatography-mass spectrometry. Chin J Anal Chem 37:745–748

    CAS  Google Scholar 

  • Greenaway W, Scaysbrook T, Whatley FR (1989) Headspace volatiles from propolis. Flavour Fragr J 4:173–175

    Article  CAS  Google Scholar 

  • Greenaway W, May J, Scaysbrook T, Whatley FR (1991) Identification by gas chromatography-mass spectrometry of 150 compounds in propolis. Z Naturforsch 46c:111–121

    Google Scholar 

  • Haile K, Kebede T, Dekebo A (2012) A comparative study of volatile components of propolis (bee glue) collected from Haramaya University and Assela Beekeeping Centers, Ethiopia. Bull Chem Soc Ethiop 26:353–360

    Article  CAS  Google Scholar 

  • Hames-Kocabas EE, Demirci B, Uzel A, Demirci F (2013) Volatile composition of Anatolian propolis by headspace-solid-phase microextraction (HS-SPME), antimicrobial activity against food contaminants and antioxidant activity. J Med Plant Res 7:2140–2149

    Article  CAS  Google Scholar 

  • Huang S, Zhang C-P, Wang K, Li GQ, Hu F-L (2014) Recent advances in the chemical composition of propolis. Molecules 19:19610–19632

    Article  PubMed  Google Scholar 

  • Ioshida MDM, Young MCM, Lago JHG (2010) Chemical composition and antifungal activity of essential oil from Brazilian propolis. J Essent Oil Bear Pl 13:633–637

    Article  CAS  Google Scholar 

  • Isidorov VA, Bakier S, Pirożnikow E, Zambrzycka M, Swiecicka I (2016) Selective behaviour of honeybees in acquiring European propolis plant precursors. J Chem Ecol 42:475–485

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Jercović I, Marijanović Z, Kuś PM, Tuberoso CIG (2016) Comprehensive study of Mediterranean (Croatian) propolis peculiarity: headspace, volatiles, anti-Varroa-treatment residue, phenolics, antioxidant properties. Chem Biodivers 13:210–2018

    Article  Google Scholar 

  • Kaškoniene V, Kaškonas P, Maruška A, Kubiliene L (2014) Chemometric analysis of volatiles of propolis from different regions using static GC-MS. Cent Eur J Chem 12:736–746

    Article  Google Scholar 

  • Kusumoto T, Miyamoto T, Higuchi R, Doi S, Sugimoto H, Yamada H (2001) Isolation and structures of two new compounds from the essential oil of Brazilian propolis. Chem Pharm Bull 49:1207–1209

    Article  CAS  PubMed  Google Scholar 

  • Li Y-J, Xuan H-Z, Shou Q-Y, Zhan Z-G, Lu X, Hu F-L (2012) Therapeutic effects of propolis essential oil on anxiety of restraint-stressed mice. Hum Exp Toxicol 31:157–165

    Article  PubMed  Google Scholar 

  • Maciejewicz W, Scheller S, Daniewski M (1983) Gas chromatography-mass spectrometry investigation of propolis, analysis of sesquiterpenes. Acta Pol Pharm 40:251–253

    Google Scholar 

  • Maróstica Junior MR, Daufsch A, Moraes CS, Queiroga CL, Pastore GM, Park YK (2008) Comparison of volatile and polyphenolic compounds in Brazilian green propolis and its botanical origin Baccharis dracunculifolia. Ciênc Tecnol Aliment 28:178–181

    Article  Google Scholar 

  • Melliou E, Stratis E, Chinou I (2007) Volatile constituents of propolis from various regions of Greece - antimicrobial activity. Food Chem 103:375–380

    Article  CAS  Google Scholar 

  • Miguel MG, Nunes S, Cruz C, Duarte J, Antunes MD, Cavaco AM, Mendes MD, Lima AS, Pedro LG, Barroso JG, Figueiredo AC (2013) Propolis volatiles characterization from acaricide-treated and -untreated beehives maintained at Algarve (Portugal). Nat Prod Res 27:743–749

    Article  CAS  PubMed  Google Scholar 

  • Naik DG, Vaidya HS, Namjoshi TP (2013) Essential oil of Indian propolis: chemical composition and repellency against the honeybee Apis florea. Chem Biodivers 10:649–657

    Article  CAS  PubMed  Google Scholar 

  • Negri G, Salatino MLF, Salatino A (2003a) “Green propolis”: unreported constituents and a novel compound from chloroform extracts. J Apic Res 42:1–3

    Google Scholar 

  • Negri G, Salatino MLF, Salatino A (2003b) Unusual chemical composition of a sample of Brazilian propolis as assessed by analysis of a chloroform extract. J Apic Res 42:53–56

    Article  CAS  Google Scholar 

  • Nunes CA, Guerreiro M (2012) Characterization of Brazilian green propolis throughout the seasons by headspace GC/MS and ESI-MS. J Sci Food Agric 93:433–438

    Article  Google Scholar 

  • Oliveira AP, França HS, Kuster RM, Teixeira LA, Rocha LM (2010) Chemical composition and antibacterial activity of Brazilian propolis essential oil. J Venom Anim Toxins incl Trop Dis 16:121–130

    Article  CAS  Google Scholar 

  • Patricio EFLRA, Cruz-López L, Maile R, Tentschert J, Jones GR, Morgan ED (2002) The propolis of stingless bees: terpenes from the tibia of three Frieseomelitta species. J Insect Physiol 48:249–254

    Article  CAS  PubMed  Google Scholar 

  • Pellati F (2014) Innovative methods for the extraction and chromatographic analysis of honey bee products. In: Jayprakasha GK, Patil BS, Pellati F (eds) Instrumental methods for the analysis and identification of bioactive molecules, Chapter 2, ACS symposium series. American Chemical Society, Washington, pp 33–49

    Google Scholar 

  • Pellati F, Prencipe FP, Benvenuti S (2013) Headspace solid-phase microextraction-gas chromatography–mass spectrometry characterization of propolis volatile compounds. J Pharm Biomed Anal 84:103–111

    Article  CAS  PubMed  Google Scholar 

  • Petri G, Lemberkovics E, Foldvari M (1988) Examination of differences between propolis (bee glue) produced from different floral environments. In: Lawrence BM, Mookherjee BD, Williams BJ (eds) Flavors and fragrances: a world perspective. Elsevier, Amsterdam, pp 439–446

    Google Scholar 

  • Pino JA, Marbot R, Delgado A, Zumarraga C, Sauri E (2006) Volatile constituents of propolis from honey bees and stingless bees from Yucatán. J Essent Oil Res 18:53–56

    Article  CAS  Google Scholar 

  • Rios N, Yánez C, Rojas L, Mora F, Usubillaga A, Vit P (2014) Chemical composition of essential oil of Apis mellifera propolis from Falcón State, Venezuela. Emir J Food Agric 26:639–642

    Article  Google Scholar 

  • Salatino A, Teixeira ÉW, Negri G, Message D (2005) Origin and chemical variation of Brazilian propolis. Evid Based Complement Alternat Med 2:33–38

    Article  PubMed  PubMed Central  Google Scholar 

  • Salatino A, Fernandes-Silva CC, Righi AA, Salatino MLF (2011) Propolis research and the chemistry of plant products. Nat Prod Rep 28:925–936

    Article  CAS  PubMed  Google Scholar 

  • Segueni N, Khadraoui F, Moussaoui F, Zellagui A, Gherraf N, Lahouelc M, Rhouati S (2010) Volatil constituents of Algerian propolis. Ann Biol Res 1:103–107

    Google Scholar 

  • Simionatto E, Facco JT, Morel AF, Giacomelli SR, Linares CEB (2012) Chiral analysis of monoterpenes in volatile oils from propolis. J Chil Chem Soc 57:1240–1243

    Article  CAS  Google Scholar 

  • Toreti VC, Sato HH, Pastore GM, Park YK (2013) Recent progress of propolis for its biological and chemical compositions and its botanical origin. Evid Based Complement Alternat ID 697390

    Google Scholar 

  • Torres RNS, Lopes JAD, Neto JMM, Citó AMGL (2008) Constituintes voláteis de própolis Piauiense. Quim Nova 31:479–485

    Article  CAS  Google Scholar 

  • Torres-González A, López-Rivera P, Duarte-Lisci G, López-Ramírez Á, Correa-Benítez A, Rivero-Cruz JF (2016) Analysis of volatile components from Melipona beecheii geopropolis from Southeast Mexico by headspace solid-phase microextraction. Nat Prod Res 30:237–240

    Article  PubMed  Google Scholar 

  • Woisky RG, Salatino A (1998) Analysis of propolis: some parameters and procedures for chemical quality control. J Apic Res 37:99–105

    Article  CAS  Google Scholar 

  • Yang C, Luo L, Zhang H, Yang X, Lva Y, Song H (2010) Common aroma-active components of propolis from 23 regions of China. J Sci Food Agric 90:1268–1282

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgments

The invaluable help of Dr M. Lurdes Saramago (Biblioteca da Faculdade de Ciências da Universidade de Lisboa) on providing several references is greatly acknowledged. This study was partially funded by Fundação para a Ciência e a Tecnologia (FCT), under UID/AMB/50017/2013, FEDER PT2020-Compete 2020.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Maria Graça Miguel .

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2017 Springer International Publishing AG

About this chapter

Cite this chapter

Miguel, M.G., Figueiredo, A.C. (2017). Propolis and Geopropolis Volatiles. In: Alvarez-Suarez, J. (eds) Bee Products - Chemical and Biological Properties. Springer, Cham. https://doi.org/10.1007/978-3-319-59689-1_6

Download citation

Publish with us

Policies and ethics