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Phytochemistry Reviews

, Volume 18, Issue 3, pp 871–891 | Cite as

Volatile organic compounds as artefacts derived from natural phytochemicals sourced form plants and honey

  • Igor JerkovićEmail author
  • Piotr Marek Kuś
  • Ángel A. Carbonell-Barrachina
Article
  • 186 Downloads

Abstract

The review presents typical pathways of artefacts generation from the plant and honey phytochemicals: (a) cutting of the fresh plant material (with or without characteristic aroma release); (b) drying process of the plant material; (c) distillation or extraction; (d) thermal processing; (e) storage; (f) gas chromatography and mass spectrometry analysis. Major reactions of artefacts formation were presented (oxidation, hydrolysis, H2O addition, degradation, rearrangement, others) in order to point out general mechanisms of the artefacts formation that could occur in any sample containing particular phytochemical molecular structures. Degradation of phytochemicals and formation of the artefacts depends on several chemical and external factors (such as temperature, water, light, accessibility to atmospheric oxygen, chemical composition, compound structures, or presence of impurities). Most common examples of volatile artefacts generation were presented. Detail analysis, based on different preparative methods, should be performed as a part of the analytical toolbox to obtain more complete understanding on the artefacts formation.

Keywords

Phytochemicals Essential oils Volatile organic compounds Artefacts Gas chromatography mass spectrometry (GC–MS) 

Notes

Acknowledgements

Funding was provided by Ministry of Science and Education of the Republic of Croatia.

References

  1. Alissandrakis E, Daferera D, Tarantilis PA, Polissiou M, Harizanis PC (2003) Ultrasound-assisted extraction of volatile compounds from citrus flowers and citrus honey. Food Chem 82(4):575–582Google Scholar
  2. Alissandrakis E, Tarantilis PA, Harizanis PC, Polissiou M (2005) Evaluation of four isolation techniques for honey aroma compounds. J Sci Food Agric 85(1):91–97Google Scholar
  3. Alissandrakis E, Tarantilis PA, Harizanis PC, Polissiou M (2007) Aroma investigation of unifloral Greek citrus honey using solid-phase microextraction coupled to gas chromatographic–mass spectrometric analysis. Food Chem 100(1):396–404Google Scholar
  4. Ames BN (1983) Dietary carcinogens and anticarcinogens oxygen radicals and degenerative diseases. Science 221(4617):1256–1264Google Scholar
  5. Asekun OT, Grierson DS, Afolayan AJ (2006) Effects of drying methods on the quality and quantity of the essential oil of Mentha longifolia L. subsp. Capensis. Food Chem 101(3):995–998Google Scholar
  6. Asfaw N, Storesund HJ, Skattebøl L, Aasen AJ (2001) Coexistence of chrysanthenone, filifolone and (Z)-isogeranic acid in hydrodistillates. Artefacts! Phytochemistry 58(3):489–492Google Scholar
  7. Bäcktorp C, Wass JRTJ, Panas I, Sköld M, Börje A, Nyman G (2006) Theoretical investigation of linalool oxidation. J Phys Chem A 110(44):12204–12212Google Scholar
  8. Baldwin EA, Scott JW, Shewmaker CK, Schuch W (2000) Flavor trivia and tomato aroma: biochemistry and possible mechanisms for control of important aroma components. HortScience 35(6):1013–1022Google Scholar
  9. Barrett DM, Beaulieu JC, Shewfelt R (2010) Color, flavor, texture, and nutritional quality of fresh-cut fruits and vegetables: desirable levels, instrumental and sensory measurement, and the effects of processing. Crit Rev Food Sci Nutr 50(5):369–389Google Scholar
  10. Baser KHC, Buchbauer G (2010) Handbook of essential oils: science, technology and applications, 1st edn. CRC Press, Boca RatonGoogle Scholar
  11. Baser KHC, Buchbauer G (2016) Handbook of essential oils: science, technology, and applications, 2nd edn. CRC Press, Boca RatonGoogle Scholar
  12. Bastos DM, Monaro É, Siguemoto É, Séfora M (2012) Maillard reaction products in processed food: pros and cons. In: Valdez B (ed) Food industrial processes—methods and equipment. IN TECH d.o.o., RijekaGoogle Scholar
  13. Bates RB, Onore MJ, Paknikar SK, Steelink C (1967) d- and l-Filifolones, monoterpenoid cyclobutanones with the bicyclo[3.2.0]heptane ring system. Chem Commun 20:1037–1038Google Scholar
  14. Beaulieu J, Baldwin E (2002) Flavor and aroma of fresh-cut fruits and vegetables. In: Lamikanra O (ed) Fresh-cut fruits and vegetables. Science, technology and market. CRC Press, Boca RatonGoogle Scholar
  15. Beaulieu JC, Gorny JR (2002) Fresh-cut fruits. In: Gross KC, Wang CY, Saltveit ME (eds) The commercial storage of fruits, vegetables, and florist and nursery stocks. Agricultural Research Service, WashingtonGoogle Scholar
  16. Bernhard RA, Marr AG (1960) The oxidation of terpenes. I. Mechanism and reaction products of d-limonene autoxidation. J Food Sci 25:517–530Google Scholar
  17. Block E, Cai X-J, Uden PC, Zhang X, Quimby BD, Sullivan JJ (1996) Allium chemistry: natural abundance of organoselenium compounds from garlic, onion and related plants and in human garlic breath. Pure Appl Chem 68(4):937–944Google Scholar
  18. Bogdanov S, Ruoff K, Persano Oddo L (2004) Physico-chemical methods for the characterisation of unifloral honeys: a review. Apidologie 35(S1):S4–S17Google Scholar
  19. Boonprab K, Matsui K, Akakabe Y, Yoshida M, Yotsukura N, Chirapart A, Kajiwara T (2006) Formation of aldehyde flavor (n-hexanal, 3Z-nonenal and 2E-nonenal) in the brown alga, Laminaria angustata. J Appl Phycol 18(3–5):409–412Google Scholar
  20. Braun M, Franz G (1999) Quality criteria of bitter fennel oil in the German pharmacopoeia. Pharm Pharmacolo Lett 9(2):48–51Google Scholar
  21. Brodnitz MH, Pascale JV (1971) Thiopropanal 5-oxide: a lachrymatory factor in onions. J Agric Food Chem 19(2):269–272Google Scholar
  22. Buttery RG (1981) Vegetable and fruit flavors. In: Teranishi R, Flath RA, Sugisawa H (eds) Flavor research-recent advances. Marcel Dekker, New YorkGoogle Scholar
  23. Carson JF (1987) Chemistry and biological properties of onions and garlic. Food Rev Int 3(1–2):71–103Google Scholar
  24. Castro-Vázquez L, Pérez-Coello MS, Cabezudo MD (2003) Analysis of volatile compounds of rosemary honey. Comparison of different extraction techniques. Chromatographia 57(3–4):227–233Google Scholar
  25. Chis A, Purcarea C (2014) The influence of storage conditions on the freshness of selected monofloral honey. Analele Univ Din Oradea Fasc Ecotoxicol Zooteh Si Tehnol de Ind Aliment 13(1):141–148Google Scholar
  26. Choe E, Min DB (2006) Mechanisms and factors for edible oil oxidation. Compr Rev Food Sci Food Saf 5(4):169–186Google Scholar
  27. Colquhoun TA, Verdonk JC, Schimmel BC, Tieman DM, Underwood BA, Clark DG (2010) Petunia floral volatile benzenoid/phenylpropanoid genes are regulated in a similar manner. Phytochem 71(2–3):158–167Google Scholar
  28. Cookson RC, Hudec J, Knight SA, Whitear B (1962) Cyclization of citral by light. Tetrahed Lett 3(2):79–81Google Scholar
  29. Cornwell CP, Reddy N, Leach DN, Wyllie SG (2000) Hydrolysis of hedycaryol: the origin of the eudesmols in the Myrtaceae. Flav Fragr J 15(6):421–431Google Scholar
  30. Cuevas-Glory LF, Pino JA, Santiago LS, Sauri-Duch E (2007) A review of volatile analytical methods for determining the botanical origin of honey. Food Chem 103(3):1032–1043Google Scholar
  31. da Silva PM, Gauche C, Gonzaga LV, Costa ACO, Fett R (2016) Honey: chemical composition, stability and authenticity. Food Chem 196(1):309–323Google Scholar
  32. Dewick PM (2009) Medicinal natural products: a biosynthetic approach, 3rd edn. Wiley, ChicesterGoogle Scholar
  33. Dignum MJW, der Heijden R, Kerler J, Winkel K, Verpoorte R (2004) Identification of glucosides in green beans of Vanilla planifolia Andrews and kinetics of vanilla β-glucosidase. Food Chem 85(2):199–205Google Scholar
  34. Ding SH, Ana KJ, Zhao CP, Li Y, Guo YH, Wang ZF (2012) Effect of drying methods on volatiles of Chinese ginger (Zingiber officinale Roscoe). Food Bioprod Process 90:515–524Google Scholar
  35. Dudareva N, Andersson S, Orlova I, Gatto N, Reichelt M, Rhodes D, Boland W, Gershenzon J (2005) The nonmevalonate pathway supports both monoterpene and sesquiterpene formation in snapdragon flowers. Proc Natl Acad Sci USA 102(3):933–938Google Scholar
  36. Dudareva N, Klempien A, Muhlemann JK, Kaplan I (2013) Biosynthesis, function and metabolic engineering of plant volatile organic compounds. New Phytol 198(1):16–32Google Scholar
  37. Erman WF (1967) Photochemical transformations of unsaturated icyclic ketones. Verbenone and its photodynamic products of ultraviolet irradiation. J Am Chem Soc 89(15):3828–3841Google Scholar
  38. Espino-Díaz M, Sepúlveda DR, González-Aguilar G, Olivas GI (2016) Biochemistry of apple aroma: a review. Food Technol Biotechnol 54(4):375–397Google Scholar
  39. European Comission (2002) European Commission council directive 2001/110/EC of 20 December 2001 relating to honey. OJEC 70:10–47.  https://doi.org/10.1093/jac/dkv056 Google Scholar
  40. Farag SEA, Abo-Zeid M (1997) Degradation of the natural mutagenic compound safrole in spices by cooking and irradiation. Nahrung 41(6):359–361Google Scholar
  41. Feussner I, Wasternack C (2002) The lipoxygenase pathway. Annu Rev Plant Biol 53:275–297Google Scholar
  42. Fischer N, Nib S, Drawert F (1987) Original flavour compounds and the essential oil composition of marjoram (Majorana hortensis Moench). Flav Fragr J 2:55–61Google Scholar
  43. Fritsch RM, Keusgen M (2006) Occurrence and taxonomic significance of cysteine sulphoxides in the genus Allium L. (Alliaceae). Phytochemistry 67(11):1127–1135Google Scholar
  44. Gardner HW (1995) Biological roles and biochemistry of the lipoxygenase pathway. HortScience 30(2):197–205Google Scholar
  45. Gopalakrishnan N (1994) Studies on the storage quality of CO2-extracted cardamom and clove bud oils. J Agric Food Chem 42(3):796–798Google Scholar
  46. Guyot-Declerck C, Sarah R, Bouseta A, Collin S (2002) Floral quality and discrimination of Lavandula stoechas, Lavandula angustifolia, and Lavandula angustifolia × latifolia honeys. Food Chem 79(4):453–459Google Scholar
  47. Hamberg M, Samuelsson B (1967) On the specificity of the oxygenation of unsaturated fatty acids catalyzed by soybean lipoxidase. J Biol Chem 242(22):5329–5335Google Scholar
  48. Hodge LC (1953) Chemistry of browning reactions in model systems. J Agric Food Chem 1:928–943Google Scholar
  49. Holman RT, Egwim PO, Christie WW (1969) Substrate specificity of soybean lipoxidase. J Biol Chem 244:1149–1151Google Scholar
  50. Imai S, Tsuge N, Tomotake M, Nagatome Y, Sawada H, Nagata T, Kumagai H (2002) An onion enzyme that makes the eyes water. Nature 419(6908):685Google Scholar
  51. Järvenpää EP, Zhang Z, Huopalahti R, King JW (1998) Determination of fresh onion (Allium cepa L.) volatiles by solid phase microextraction combined with gas chromatography–mass spectrometry. Eur Food Res Technol 207(1):39–43Google Scholar
  52. Jerković I, Kuś PM (2014) Terpenes in honey: occurrence, origin and their role as chemical biomarkers. RSC Advances 4(60):31710–31728Google Scholar
  53. Jerković I, Marijanović Z (2009) A short review of headspace extraction and ultrasonic solvent extraction for honey volatiles fingerprinting. Croat J Food Sci Technol 1(2):28–34Google Scholar
  54. Jerković I, Mastelić J, Marijanović Z, Klein Ž, Jelić M (2007) Comparison of hydrodistillation and ultrasonic solvent extraction for the isolation of volatile compounds from two unifloral honeys of Robinia pseudoacacia L. and Castanea sativa L. Ultrason Sonochem 14(6):750–756Google Scholar
  55. Jerković I, Tuberoso CIG, Ksum A, Marijanović Z (2011) Volatile compounds of Asphodelus microcarpus Salzm. et. Viv. honey obtained by HS-SPME and USE analyzed by GC/MS. Chem Biodivers 8(4):587–598Google Scholar
  56. Jerković I, Kranjac M, Šuste M, Kuś PM, Svečnjak L (2015) Rhamnus frangula L. honey: screening of volatile organic compounds and their composition after short-term heating. Chem Natl Comp 51(6):1174–1177Google Scholar
  57. Kanisawa T, Tokoro K, Kawahara S (1994) Flavor development in the beans of Vanilla planifolia. In: Kurihara K, Suzuki N, Ogawa H (eds) Olfaction and taste XI. Springer, TokyoGoogle Scholar
  58. Keusgen M (2011) Volatile compounds of the genus Allium L. (onions). In: Qian MC, Fan X, Mahattanatawee K (eds) Volatile sulfur compounds in food. American Chemical Society, New YorkGoogle Scholar
  59. Kirillov V, Stikhareva T, Atazhanova G, Mukasheva F, Yrymgali M (2015) Chemical composition of the essential oil of the boreal relict of Pyrola rotundifolia L. from Northern Kazakhstan. J Oleo Sci 4(10):1065–1073Google Scholar
  60. Krest I, Glodek J, Keusgen M (2000) Cysteine sulfoxides and alliinase activity of some Allium species. J Agric Food Chem 48(8):3753–3760Google Scholar
  61. Kubec R, Svobodová M, Velíšek J (2000) Distribution of S-alk(en)ylcysteine sulfoxides in some Allium species. Identification of a new flavor precursor: S-ethylcysteine sulfoxide (ethiin). J Agric Food Chem 48(2):428–433Google Scholar
  62. Kubeczka KH (1974) Pregeijeren, hauptkomponente des ätherischen wurzelöls von Ruta graveolens. Phytochemistry 13(9):2017–2018Google Scholar
  63. Kubeczka KH (1993) Möglichkeiten und Grenzen der Qualitätsbeurteilung arzneilich verwendeter ätherischer öle. In: Carle R (ed) Ätherische Öle—Anspruch und Wirklichkeit. Wissenschaftliche Verlagsgesellschaft, StuttgartGoogle Scholar
  64. Kubeczka KH, Bohn I, Schultze W (1989) The compositions of the essential root oils from Pimpinella saxifraga s.l. and chemotaxonomic implications. Z Naturforsch C Biosci 44(3–4):177–182Google Scholar
  65. Lanzotti V (2006) The analysis of onion and garlic. J Chromatogr A 1112(1–2):3–22Google Scholar
  66. Le Quere JL, Latrasse A (1990) Composition of the essential oils of black currant buds (Ribes nigrum L.). J Agric Food Chem 38:3–10Google Scholar
  67. Løkke MM, Edelenbos M, Larsen E, Feilberget A (2012) Investigation of volatiles emitted from freshly cut onions (Allium cepa L.) by real time proton-transfer reaction-mass spectrometry (PTR-MS). Sensors 12(12):16060–16076Google Scholar
  68. Lu SL, Liu H, Chen GY, Han CR, Zang WX (2014) Chemical composition of leaf essential oil of Synsepalum dulcificum and evaluation of its antibacterial and antitumoral activities in vitro. Chem Indust Forest Prod 34(1):121–127Google Scholar
  69. Maffei ME, Gertsch J, Appendino G (2011) Plant volatiles: production, function and pharmacology. Nat Prod Rep 28(8):1359–1380Google Scholar
  70. Maignial L, Pibarot P, Bonetti G, Chaintreau A, Marion JP (1992) Simultaneous distillation–extraction under static vacuum: isolation of volatile compounds at room temperature. J Chromatogr A 606(1):87–94Google Scholar
  71. Manyi-Loh CE, Ndip RN, Clarke AM (2011) Volatile compounds in honey: a review on their involvement in aroma, botanical origin determination and potential biomedical activities. Int J Mol Sci 12(12):9514–9532Google Scholar
  72. Marrez DA, Sultan YY (2016) Antifungal activity of the cyanobacterium Microcystis aeruginosa against mycotoxigenic fungi. J Appl Pharm Sci 6(11):191–198Google Scholar
  73. Martins SIFS, Jongen WMF, Van Boekel MAJS (2001) A review of Maillard reaction in food and implications to kinetic modeling. Trends Food Sci Technol 11:364–373Google Scholar
  74. Mastelić J (2001) The essential oil co-distillation by superheated vapour of organic solvents from aromatic plants. Flav Fragr J 16(5):370–373Google Scholar
  75. Mastelić J, Jerković I (2003) Application of co-distillation with superheated pentane vapour to the isolation of unstable essential oils. Flav Fragr J 18(6):521–526Google Scholar
  76. Mastelić J, Miloš M, Kuštrak D (2000) Free and glycosidically bound volatiles of Mentha citrata ehrh. Croat Chem Acta 73(3):781–794Google Scholar
  77. McGraw GW, Hemingway RW, Ingram LL Jr, Canady CS, McGraw WB (1999) Thermal degradation of terpenes: camphene, Δ-3-carene, limonene, and α-terpinene. Environ Sci Technol 33:4029–4033Google Scholar
  78. Miething H, Seger V, Hänsel R (1990) Determination of photoanethole from a stored essential oil of anise fruits as 4,4-dimethoxystilbene by high performance liquid chromatography—ultraviolet coupling. Pytother Res 4:121–123Google Scholar
  79. Min SS, Dong GK, Lee SH (2005) Isolation and characterization of a jasmonic acid carboxyl methyltransferase gene from hot pepper (Capsicum annuum L.). J Plant Biol 48(3):292–297Google Scholar
  80. Mockutë D, Bernotienë G, Judpentienë A (2005) Storage-induced changes in essential oil composition of Leonurus cardiaca L. plants growing wild in Vilnius and of commercial herbs. Chemija 26(2):29–32Google Scholar
  81. Mondy N, Duplat D, Christides JP, Arnault I, Auger J (2002) Aroma analysis of fresh and preserved onions and leek by dual solid-phase microextraction–liquid extraction and gas chromatography–mass spectrometry. J Chromatogr A 963(1–2):89–93Google Scholar
  82. Moyler DA (1994) Spices—recent advances. In: Charalambous G (ed) Spices, herbs and edible fungi, 1st edn. Elsevier Science, AmsterdamGoogle Scholar
  83. Nguyen H, Campi EM, Jackson WR, Patti AF (2009) Effect of oxidative deterioration on flavour and aroma components of lemon oil. Food Chem 112:388–393Google Scholar
  84. Nishimura K, Shinoda N, Hirose Y (1969) A new sesquiterpene, bicyclogermacrene. Tetrahedron Lett 10(36):3097–3100Google Scholar
  85. Odoux E (2006) Glucosylated aroma precursors and glucosidase(s) in vanilla bean (Vanilla planifolia G. Jackson). Fruits 61:171–184Google Scholar
  86. Olías JM, Perez AG, Rios JJ, Sanz LC (1993) Aroma of virgin olive oil: biogenesis of the “Green” odor notes. J Agric Food Chem 41(12):2368–2373Google Scholar
  87. Oliveira MJ, Campos IFP, Oliveira CBA, Santos MR, Souza PS, Santos SC, Seraphin JC, Ferri PH (2005) Influence of growth phase on the essential oil composition of Hyptis suaveolens. Biochem Syst Ecol 33:275–285Google Scholar
  88. Patil A, Rathod VJ (2014) GC-MS analysis of bioactive components from methanol leaf extract of Toddalia asiatica (L.). Int J Pharm Sci Rev Res 29(1):18–20Google Scholar
  89. Pérez AG, Sanz C (2008) Formation of fruit flavour. In: Brückner B, Wyllie SG (eds) Fruit and vegetable flavour. Woodhead Publishing, AbingtonGoogle Scholar
  90. Pfau M (1972) Photochemistry in the field of monoterpenes and related compounds. Flav Ind 3:89–103Google Scholar
  91. Pichersky E, Noel JP, Dudareva N (2006) Biosynthesis of plant volatiles: nature’s diversity and ingenuity. Science 311(5762):808–811Google Scholar
  92. Pratt DA, Porter NA (2003) Role of hyperconjugation in determining carbon–oxygen bond dissociation enthalpies in alkylperoxyl radicals. Org Lett 5:387–390Google Scholar
  93. Radovic BS, Careri M, Mangia A, Musci M, Gerboles M, Anklam E (2001) Contribution of dynamic headspace GC-MS analysis of aroma compounds to authenticity testing of honey. Food Chem 72(4):511–520Google Scholar
  94. Rouatbi M, Duquenoy A, Giampaoli P (2007) Extraction of the essential oil of thyme and black pepper by superheated steam. J Food Eng 78:708–714Google Scholar
  95. Safayhi H, Sabieraj J, Sailer ER, Ammon HPT (1994) Chamazulene: an antioxidant-type inhibitor of leukotriene B4 formation. Planta Med 60(5):410–413Google Scholar
  96. Sancho MT, Muniategui S, Huidobro JF, Lozano JS (1992) Aging of honey. J Agric Food Chem 40(1):134–138Google Scholar
  97. Sanz LC, Olías JM, Pérez AG (1997) Aroma biochemistry of fruits and vegetables. In: Tomas-Barberan FA, Robins RJ (eds) Phytochemistry of fruits and vegetables. Clarendon Press, OxfordGoogle Scholar
  98. Schneider C, Pratt DA, Porter NA, Brash AR (2007) Control of oxygenation in lipoxygenase and cyclooxygenase catalysis. Chem Biol 14(5):473–488Google Scholar
  99. Schweiggert U, Carle R, Schieber A (2007) Conventional and alternative processes for spice production—a review. Trends Food Sci Technol 18(5):260–268Google Scholar
  100. Setzer WN (2008) Ab initio analysis of the cope rearrangement of germacrane sesquiterpenoids. J Mol Model 14:335–342Google Scholar
  101. Setzer WN, Stokes SL, Penton AF, Takaku S, Haber WA, Hansell E, Caffrey CR, McKerrow JH (2007) Cruzain inhibitory activity of leaf essential oils of neotropical Lauraceae and essential oil components. Nat Prod Commun 2:1203–1210Google Scholar
  102. Stevens MA (1985) Tomato flavor: effects of genotype, cultural practices and maturity at picking. In: Pattee HE (ed) Evaluation of quality of fruits and vegetables. AVI Publishing Company, WestportGoogle Scholar
  103. Storsberg J, Schulz H, Keusgen M, Tannous F, Dehmer KJ, Keller ER (2004) Chemical characterization of interspecific hybrids between Allium cepa L. and Allium kermesinum Rchb. J Agric Food Chem 52(17):5499–5505Google Scholar
  104. Takaku S, Haber WA, Setzer WN (2007) Leaf essential oil composition of 10 species of Ocotea (Lauraceae) from Monteverde, Costa Rica. Biochem Syst Ecol 35:525–532Google Scholar
  105. Takeda K, Horibe I, Minato H (1971) Absolute configuration of bicycloelemene and conformation of bicyclogermacrene. J Chem Soc D Chem Commun 7:308Google Scholar
  106. Thrasyvoulou AT (1986) The use of HMF and diastase as criteria of quality of Greek honey. J Apic Res 25:186–195Google Scholar
  107. Toyota M, Koyama H, Mizutani M, Asakawa Y (1996) (−)-ent-Spathulenol isolated from liverworts is an artefact. Phytochemistry 41(5):1347–1350Google Scholar
  108. Treibs W (1956) Impact of different storage conditions on the quality of selected essential oils. In: Gildemeister E, Hoffmann F (eds) Die Ätherischen Öle, vol I, 4th edn. Akademie-Verlag, BerlinGoogle Scholar
  109. Turek C, Stintzing FC (2012) Impact of different storage conditions on the quality of selected essential oils. Food Res Int 46(1):341–353Google Scholar
  110. Turek C, Stintzing FC (2013) Stability of essential oils: a review. Compr Rev Food Sci Food Saf 12(1):40–53Google Scholar
  111. Velasco J, Dobarganes C (2002) Oxidative stability of virgin olive oil. Eur J Lipid Sci Technol 104:661–676Google Scholar
  112. Venditti A (2018a) What is and what should never be: artifacts, improbabale phytochemicals, contaminants and natural products. Nat Prod Res 22:1–18Google Scholar
  113. Venditti A (2018b) Artifacts in natural products studies. An old and underestimated re-emerging problem. Nat Prod Res 32:v–viGoogle Scholar
  114. Wagner Smitt U, Moldt P, Christensen SB (1986) Structure of a pro-1,4-dimethylazulene guaianolide from Thapsia garganica L. Acta Chem Scand 840:711–714Google Scholar
  115. Weil M, Shum Cheong Sing A, Méot JM, Boulanger R, Bohuon P (2017) Impact of blanching, sweating and drying operations on pungency, aroma and color of Piper borbonense. Food Chem 219:274–281Google Scholar
  116. Yang FQ, Li SP, Zhao J, Lao SC, Wang YT (2007) Optimization of GC-MS conditions based on resolution and stability of analytes for simultaneous determination of nine sesquiterpenoids in three species of Curcuma rhizomes. J Pharm Biomed Anal 43:73–82Google Scholar
  117. Zhou X, Li Z, Liang G, Zhu J, Wang D, Cai Z (2007) Analysis of volatile components of Curcuma sichuanensis X. X. Chen by gas chromatography–mass spectrometry. J Pharm Biomed Anal 43:440–444Google Scholar

Copyright information

© Springer Nature B.V. 2019

Authors and Affiliations

  • Igor Jerković
    • 1
    Email author
  • Piotr Marek Kuś
    • 2
  • Ángel A. Carbonell-Barrachina
    • 3
  1. 1.Department of Organic Chemistry, Faculty of Chemistry and TechnologyUniversity of SplitSplitCroatia
  2. 2.Department of Pharmacognosy and Herbal MedicinesWrocław Medical UniversityWrocławPoland
  3. 3.Departamento Tecnología Agroalimentaria, Grupo Calidad y Seguridad Alimentaria, Escuela Politécnica Superior de OrihuelaUniversidad Miguel Hernández de ElcheOrihuelaSpain

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