The Use of Enzyme Systems of the Genus Prunus for the Production of Benzaldehyde

Dočolomanský, P.; Sitkey, V.; Čičová, I.

doi:10.2478/afpuc-2022-0017

Abstract

Aim

Benzaldehyde occurs in a number of plants, especially in the family Rosaceae and in particular in the genus Prunus. In nature, there are more than 100 genera and 3,000 species in the Rosaceae family. The objective of this study was to investigate the chemical composition of leaf essential oil of peach (Prunus persica L.) and cherry laurel (Prunus laurocerasus L.) as a new potential source of natural benzaldehyde.

Methods

The essential oil was prepared by hydrodistillation, and chemical constituents were determined by GC-FID, GC-MS and chromatographic profiles were compared with each other.

Results

The results show that essential oil obtained from peach and cherry laurel leaves appear to be a promising source of natural benzaldehyde. Under laboratory conditions the benzaldehyde content in peach and cherry laurel leaves reached 95.5% and 99.7%, respectively.

Conclusions

Laboratory and pilot experiments confirmed that by processing of 200–300 kg of green leaves of various species of the genus Prunus, especially peach and cherry laurel, 1 kg of benzaldehyde can be obtained.

References

Andersen A. Final report on the safety assessment of benzaldehyde. Int J Toxicol. 2006;25(suppl 1):11–27.
Search in Google Scholar Back to article
Benediková D. Direction of apricot breeding in the world. Will apricots return to our orchards? (in Slovak). Sady a vinice. 2017;12(1):15–17.
Search in Google Scholar Back to article
Benediková D, Zetochová E. New trends and directions of peach breedings in the world (in Slovak). Sady a vinice. 2017;12(4):14–16.
Search in Google Scholar Back to article
Aprea E, Biasioli F, Gasperi F. Volatile compounds of raspberry fruit: From analytical methods to biological role and sensory impact. Molecules. 2015;20:2,445–2,474.
Search in Google Scholar Back to article
Bicas JL, Silva JC, Dionísio AP, Pastore GM. Biotechnological production of bioflavors and functional sugars, Ciênc Tecnol Aliment. 2010;30:7–18.
Search in Google Scholar Back to article
Bishop J. Toxicology and carcinogenesis studies of benzaldehyde. National toxicology program technical report series no. 378. NIH Publication No. 90-2833 U.S. Department of Health and Human Services, Public Health Service, National Institutes of Health, March 1990.
Search in Google Scholar Back to article
Bonesi M, Tenuta MC, Loizzo MR, Sicari V, Tundis R. Potential application of Prunus armeniaca L. and P. domestica L. leaf essential oils as antioxidant and of cholinesterases inhibitors. Antioxidants. 2019;8(1):2.
Search in Google Scholar Back to article
Brenna E, Fronza G, Fuganti C, Gatti FC, Serra S. Biotechnological tools to produce natural flavours and methods to authenticate their origin. In: Passos ML, Ribeiro CP. Innovation in Food Engineering: New Techniques and Products. CRC Press, Taylor & Francis Group; 2016.
Search in Google Scholar Back to article
Burdock GA, ed. Fenaroli's Handbook of Flavor Ingredients. CRC Press, Taylor & Francis Group; 2010.
Search in Google Scholar Back to article
Craig T. Strategies for Enhanced Bioproduction of Benzaldehyde Using Pichia Pastoris in a Solid-liquid Partitioning Bioreactor and Integrated Product Removal by In Situ Pervaporation [dissertation]. Kingston, Ontario, Canada: Queen's University; 2013.
Search in Google Scholar Back to article
Commission Directive 91/71/EEC of 16 January 1991. Official Journal L 042. 15/02/1991.
Search in Google Scholar Back to article
Davidson AR. A Study of the Potential Evidential Value of Perfumes, Antiperspirants and Deodorants in Forensic Science [dissertation]. Staffordshire University; 2017.
Search in Google Scholar Back to article
Dionísio AP, Molina G, Souza de Carvalho D, dos Santos R, Bicas JL, Pastore GM. Natural flavourings from biotechnology for foods and beverages. In: Baines D, Seal R. Woodhead Publishing Series in Food Science, Technology and Nutrition. Cambridge: Woodhead Publishing; 2012.
Search in Google Scholar Back to article
Franklin LM, Mitchell A. Review of the sensory and chemical characterization of almond (Prunus dulcis) flavor. J Agric Food Chem. 2019;67:2,743–2,753.
Search in Google Scholar Back to article
Geng H, Yu X, Lu A, et al. Extraction, chemical composition, and antifungal activity of essential oil of bitter almond. Int J Mol. Sci. 2016;17:1,421.
Search in Google Scholar Back to article
Helmig D, Klinger LF, Guenther A, Vierling L, Geron C, Zimmerman P. Biogenic volatile organic compound emissions (BVOCs). I. Identifications from three continental sites in the U.S. Chemosphere. 1999;38:2,163–87.
Search in Google Scholar Back to article
Ho CL, Wang EIC, Su YC. Composition of the leaf oils of Prunus phaeosticta var. phaeosticta from Taiwan. J Essent Oil Res. 2009;21:345–347.
Search in Google Scholar Back to article
INC International Nuts and Dried Fruit Statistical Yearbook 2017/2018. Reus, Spain:INC.
Search in Google Scholar Back to article
Jain AN, Khan TR, Daugulis AJ. Bioproduction of benzaldehyde in a solid-liquid two-phase partitioning bioreactor using Pichia pastoris. Biotechnol Lett. 2010;32:1,649–54.
Search in Google Scholar Back to article
Jaszczak-Wilke E, Polkowska Z, Koprowski M, Owsianik K, Mitchell AE, Bałczewski P. Amygdalin: Toxicity, anticancer activity and analytical procedures for its determination in plant seeds. Molecules. 2021;26:2,253.
Search in Google Scholar Back to article
Karaagac EH, Çavuş F, Kadioğlu B, Ugur N, Tokat E, Şahan Y. Evaluation of nutritional, color and volatiles properties of currant (Ribes spp.) cultivars in Turkey. Food Sci Technol (Campinas). 2021;41:304–313.
Search in Google Scholar Back to article
Klatt BK, Burmeister C, Westphal C, Tscharntke T, von Fragstein M. Flower volatiles, crop varieties and bee responses. PLoS One. 2013;8:e72724.
Search in Google Scholar Back to article
Knudsen JT, Eriksson R, Gershenzon J, Stahl B. Diversity and distribution of floral scent. Bot Rev. 2006;72:1–120.
Search in Google Scholar Back to article
Kosmider L, Sobczak A, Prokopowicz A, et al. Cherry-flavoured electronic cigarettes expose users to the inhalation irritant, benzaldehyde. Thorax. 2016;71:376–7.
Search in Google Scholar Back to article
Kristiawan M, Sobolik V, Allaf K. Isolation of Indonesian Cananga oil by instantaneous controlled pressure drop. J Essent Oil Res. 2008;20:135–146.
Search in Google Scholar Back to article
Lee HH, Ahn JH, Kwon AR, Lee ES, Kwak JH, Min YH. Chemical composition and antimicrobial activity of the essential oil of apricot seed. Phytother Res. 2014; 28:1,867–72.
Search in Google Scholar Back to article
Luo KK, Kim DA, Mitchell-Silbaugh KC, Huang G, Mitchell AE. Comparison of amygdalin and benzaldehyde levels in California almond (Prunus dulcis) varietals. Acta Hortic. 2018;1,219:1–8.
Search in Google Scholar Back to article
Maatallah S, Dabbou S, Castagna A, et al. Prunus persica byproducts: A source of minerals, phenols and volatile compounds, Sci Hortic. 2020;261:109,016.
Search in Google Scholar Back to article
Mezzomo N, Mileo BR, Friedrich MT, Martinez J, Ferreira SRS. Supercritical fluid extraction of peach (Prunus persica) almond oil: Process yield and extract composition. Bioresour. Technol. 2010;101:5,622–5,632.
Search in Google Scholar Back to article
Natsch A, inventor; Givaudan SA. Compositions. US Patent 2010/0284.942A1, November 11, 2010.
Search in Google Scholar Back to article
Okrasa K, Guibe-Jampel E, Plenkiewicz J, Therisod M. In vitro bi-enzymatic synthesis of benzaldehyde from phenylalanine: practical and mechanistic studies, J Mol Catal B Enzym. 2004;31:97–101.
Search in Google Scholar Back to article
Owens A. South Haven and the Fruit Industry: A Success Story. (https://www.southhaven.org/journal/south-haven-and-the-fruit-industry-a-success-story). Published April 19, 2019.
Search in Google Scholar Back to article
Petretto GL, Mercenaro L, Urgeghe PP, Fadda C, Valentoni A, Del Caro A. Grape and wine composition in Vitis vinifera L. cv. Cannonau explored by GC-MS and sensory analysis. Foods. 2021;10:101.
Search in Google Scholar Back to article
Picuric-Jovanovic K, Milovanovic M. Analysis of volatile compounds in almond and plum kernel oils. J Am Oil Chem Soc. 1993;70:1,101–1,104.
Search in Google Scholar Back to article
Prasad R, Gill SS, Tuteja N, eds. New and Future Developments in Microbial Biotechnology and Bioengineering: Crop Improvement through Microbial Biotechnology. Elsevier; 2018.
Search in Google Scholar Back to article
Remaud G, Debon AA, Martin YL, Martin GJ. Authentication of bitter almond oil and cinnamon oil: Application of the SNIF-NMR method to benzaldehyde. J Agric Food Chem. 1997;45:4,042–4,048.
Search in Google Scholar Back to article
Soundararajan P, So Youn Won SY, Kim JS. Insight on Rosaceae family with genome sequencing and functional genomics perspective. Biomed Res Int. 2019;2019:7,519,687.
Search in Google Scholar Back to article
Stanisavljevic IT, Lazic ML, Veljkovic VB, Stojičevic SS, Veličkovic DT, Ristic MS. Kinetics of hydrodistillation and chemical composition of essential oil from cherry laurel (Prunus laurocerasus L. var. serbica Pančić) leaves. J Essent Oil Res. 2010;22:564–567.
Search in Google Scholar Back to article
Tunçel G, Nout MJR, Brimer L. Degradation of cyanogenic glycosides of bitter apricot seeds (Prunus armeniaca) by endogenous and added enzymes as affected by heat treatments and particle size. Food Chem. 1998;63:65–69.
Search in Google Scholar Back to article
Veličkovic DT, Ristic MS, Karabegović IT, Stojicevic SS, Nikolic NC, Lazic ML. Plum (Prunus domestica) and walnut (Juglans regia): volatiles and fatty oils. Adv Technol. 2016;5:10–16.
Search in Google Scholar Back to article
Verma RS, Padalia RC, Singh VR, Goswami P, Chauhan A, Bhukya B. Natural benzaldehyde from Prunus persica (L.) Batsch. Int J Food Prop. 2017;20( suppl 2):1,259–1,263.
Search in Google Scholar Back to article
Wen W, Luo J, Li P, Huang W, Wang P, Xu S. Benzaldehyde, a new absorption promoter, accelerating absorption on low bioavailability drugs through membrane permeability. Front Pharmacol. 2021;12:663,743.
Search in Google Scholar Back to article
Xing C, Zhao X, Huang Z, Liu W, Gong H, inventors; Xiamen Oamic Biotechnology, China, assignee. Method for producing benzaldehyde using microorganism. EP 3 483 257 A1. May 15, 2019.
Search in Google Scholar Back to article
Yen MS. Synthesis and solvatochromism of heterocyclic bichromophoric dyes derived from 2-aminothiazole. Pigm Resin Technol. 2012;41:216–222.
Search in Google Scholar Back to article

The Use of Enzyme Systems of the Genus Prunus for the Production of Benzaldehyde

Abstract

Aim

Methods

Results

Conclusions

Paradigm

My account