New esters from the essential oil of dry flowers of elder (Sambucus nigra L.).

Sambucus nigra L. chemical composition elderflower essential oil

Journal

Journal of the science of food and agriculture
ISSN: 1097-0010
Titre abrégé: J Sci Food Agric
Pays: England
ID NLM: 0376334

Informations de publication

Date de publication:
27 Sep 2023
Historique:
revised: 15 09 2023
received: 03 08 2023
accepted: 28 09 2023
pubmed: 28 9 2023
medline: 28 9 2023
entrez: 28 9 2023
Statut: aheadofprint

Résumé

Elder (Sambucus nigra L.) has relevance for the food, fragrance and pharmaceutical industries. Flowers of this species emit a very pleasant scent; for processing purposes, inflorescences are either collected from the wild or harvested from a cultivated crop. The study of elderflower-derived volatiles bears both phytochemical and commercial importance. Three samples of dry elderflower essential oil obtained from laboratory-scale hydrodistillations were analyzed. By use of gas chromatography-mass spectrometry, synthesis and NMR studies of chromatographic fractions of a distillation water extract prepared in a semi-industrial scale steam distillation, 252 constituents of the oil were identified; 115 compounds were not previously reported as elderflower volatiles, seven of which were new natural esters. Particularly interesting were those of isosenecioic (3-methylbut-3-enoic) acid because these were never before found in the plant kingdom. With these identifications, the known essential oil constituents accounted for 89.0-93.0% of the analyzed samples. Although the number of known S. nigra flower-derived volatiles is now quite high, further research (both analytical and olfactory) is needed to unveil all of the relevant contributions to the unique odor of elderflowers. © 2023 Society of Chemical Industry.

Sections du résumé

BACKGROUND BACKGROUND
Elder (Sambucus nigra L.) has relevance for the food, fragrance and pharmaceutical industries. Flowers of this species emit a very pleasant scent; for processing purposes, inflorescences are either collected from the wild or harvested from a cultivated crop. The study of elderflower-derived volatiles bears both phytochemical and commercial importance.
RESULTS RESULTS
Three samples of dry elderflower essential oil obtained from laboratory-scale hydrodistillations were analyzed. By use of gas chromatography-mass spectrometry, synthesis and NMR studies of chromatographic fractions of a distillation water extract prepared in a semi-industrial scale steam distillation, 252 constituents of the oil were identified; 115 compounds were not previously reported as elderflower volatiles, seven of which were new natural esters. Particularly interesting were those of isosenecioic (3-methylbut-3-enoic) acid because these were never before found in the plant kingdom.
CONCLUSION CONCLUSIONS
With these identifications, the known essential oil constituents accounted for 89.0-93.0% of the analyzed samples. Although the number of known S. nigra flower-derived volatiles is now quite high, further research (both analytical and olfactory) is needed to unveil all of the relevant contributions to the unique odor of elderflowers. © 2023 Society of Chemical Industry.

Identifiants

pubmed: 37759401
doi: 10.1002/jsfa.13012
doi:

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Subventions

Organisme : Ministry of Science, Technological Development and Innovation of the Republic of Serbia
ID : 451-03-47/2023-01/200125
Organisme : Ministry of Science, Technological Development and Innovation of the Republic of Serbia
ID : 451-03-47/2023-01/200124

Informations de copyright

© 2023 Society of Chemical Industry.

Références

Atkinson MD and Atkinson E, Sambucus nigra L. J Ecol 90:895-923 (2002).
Charlebois D, Byers PL, Finn CE and Thomas AL, Elderberry: Botany, Horticulture, Potential, in Horticulture Reviews, Vol. 37, ed. by Janick J. Wiley-Blackwell, Hoboken, NJ, pp. 213-280 (2010).
Fossum G, Assessment report on Sambucus nigra L., fructus. European Medicines Agency, London, pp. 1-25 (2014).
Kaack K, Christensen LP, Hughes M and Eder R, Relationship between sensory quality and volatile compounds of elderflower (Sambucus nigra L.) extracts. Eur Food Res Technol 223:57-70 (2006).
Khan A and Abourashed EA, Leung's Encyclopedia of Common Natural Ingredients Used in Food, Drugs, and Cosmetics, 3rd edn. Wiley, Hoboken, NJ (2010).
Schmitzer V, Veberic R and Stampar F, European elderberry (Sambucus nigra L.) and American Elderberry (Sambucus canadensis L.): Botanical, chemical and health properties of flowers, berries and their products, in Berries: Properties, Consumption and Nutrition, ed. by Tuberoso C. Nova Biomedical, Hauppauge, NY, pp. 127-144 (2012).
Finn CE, Thomas AI, Byers PL and Serçe S, Evaluation of American (Sambucus canadensis) and European (S. nigra) Elderberry Genotypes Grown in Diverse Environments and Implitacions for Cultivar Development. HortScience 43:1385-1391 (2008).
Horčinová Sedláčková V, Grygorieva O, Vergun O, Vinogradova Y and Brindza J, Comparison of selected characteristics of cultivar and wild-growing genotypes of Sambucus nigra in Slovakia. Biosyst Divers 27:56-61 (2019).
Strauß E and Novak R, Obstbau-Praxis. Österreichischer Agrarverlag, Vienna (1997).
Engels G and Brinckmann J, European Elder. HerbalGram 97:1-7 (2013).
Kiprovski B, Malenčić Đ, Ljubojević M, Ognjanov V, Veberić R, Hudina M et al., Quality parameters change during ripening in leaves and fruits of wild growing and cultivated elderberry (Sambucus nigra) genotypes. Sci Hortic 277:109792 (2021).
Mratinić E and Fotirić M, Selection of black elderberry (Sambucus nigra L.) and evaluation of its fruits usability as biologically valuable food. Genetika 39:305-314 (2007).
Bošnjaković D, Ognjanov V, Ljubojević M, Barać G, Predojević M, Mladenović E et al., Biodiversity of wild fruit spiecies of Serbia. Genetika 44:81-90 (2012).
Мłynarczyk K, Walkowiak-Tomczak D and Łysiak GP, Bioactive properties of Sambucus nigra L. as a functional ingredient for food and pharmaceutical industry. J Funct Foods 40:377-390 (2018).
Ferreira SS, Silva AM and Nunes FM, Sambucus nigra L. Fruits and Flowers: Chemical Composition and Related Bioactivities. Food Rev Int 38:1237-1265 (2022).
Willuhn G and Richter W, Zur Kenntnis der Inhaltsstoffe von Sambucus nigra: II. Die lipophilen Bestandteile der Blüten. Planta Med 31:328-343 (1977).
Velisek J, Kubelka V, Pudil F, Svobodova Z and Davidek J, Volatile constituents of elder (Sambucus nigra L.). I. Flowers and leaves. Lebensm-Wiss u.-Technol 14:309-312 (1981).
Tulemonde B and Richard HMJ, Volatile Constituents of Dry Elder. J Agric Food Chem 31:365-370 (1983).
Eberhardt R and Pfannhauser W, Analyse flüchtiger Inhaltsstoffe des Holunders. 1. Mitteilung: Extraktionstechniken und Untersuchung wesentlicher Aromakomponenten. Mikrochim Acta 85:55-67 (1985).
Eberhardt R and Pfannhauser W, Analyse flüchtiger Inhaltsstoffe des Holunders, 2. Mitteilung: Untersuchung der Monoterpenverbindungen. Z Lebensm Unters Forsch 181:97-100 (1985).
Joulain D, The Composition of the Headspace from Fragrant Flowers: Further results. Flavour Fragr J 2:149-155 (1987).
Jørgensen U, Hansen M, Christensen LP, Jensen K and Kaack K, Olfactory and Quantitative Analysis of Aroma Compounds in Elder Flower (Sambucus nigra L.) Drink Processed from Five Cultivars. J Agric Food Chem 48:2376-2383 (2000).
Kaack K, Processing of aroma extracts from elder flower (Sambucus nigra L.). Eur Food Res Technol 227:375-390 (2008).
Kaack K and Christensen LP, Effect of packing materials and storage time on volatile compounds in tea processed from flowers of black elder (Sambucus nigra L.). Eur Food Res Technol 227:1259-1273 (2008).
Farré-Armengol G, Filella I, Llusià J and Peñuelas J, Pollination mode determines floral scent. Biochem. Syst. Ecol. 61:44-53 (2015).
Ağalar HG, Demirci B, Demirci F and Kırımer N, The Volatile Compounds of the Elderflower Extract and the Essential Oil. Rec Nat Prod 11:491-496 (2017).
Bajer T, Bajerová P and Ventura K, Effect of Harvest and Drying on Composition of Volatile Profile of Elderflowers (Sambucus nigra) from Wild. Nat Prod Commun 12:1937-1942 (2017).
Salvador AC, Silvestre AJD and Rocha SM, Unveiling elderflowers (Sambucus nigra L.) volatile terpenic and norisoprenoids profile: effects of different postharvest conditions. Food Chem 229:276-285 (2017).
Najar B, Ferri B, Cioni P and Pistelli L, Volatile emission and essential oil composition of Sambucus nigra L. organs during different developmental stages. Plant Biosyst 155:721-729 (2019).
Szymański M, Dudek-Makuch M, Witkowska-Banaszczak E, Bylka W and Szymański A, Comparison of the Chemical Composition and Antioxidant Activity of Essential Oils from the Leaves and Flowers of Sambucus nigra. Pharm Chem J 54:496-503 (2020).
Vujanović MD, Đurović SD and Radojković MM, Chemical Composition of the Essential Oils of Elderberry (Sambucus nigra L.) Flowers and Fruits. Acta Period Technol 52:229-237 (2021).
Basas-Jaumandreu J, de las Heras XC, Allelochemicals and esters from leaves and inflorescences of Sambucus nigra L. Phytochem Lett 30:107-115 (2019).
Radulović NS and Blagojević PD, The Most Frequently Encountered Volatile Contaminants of Essential Oils and Plant Extracts Introduced During the Isolation Procedure: Fast and Easy Profiling. Phytochem Anal 23:131-142 (2012).
Kitahara T, Takagi Y and Matsui M, Structure and the synthesis of novel constituents of yudzu peel oil and their conversion to related monoterpenes. Agric Biol Chem 44:897-901 (1980).
Aćimović MG, Cvetković MT, Stanković Jeremić JM, Pezo LL, Varga AO, Čabarkapa IS et al., Biological activity profiling of Salvia sclarea essential oil obtained by steam and hydrodistillation extraction methods via chemometrics tools. Flavour Fragr J 37:20-32 (2022).
Radulović NS, Mladenović MZ, Stojanović NM, Ranđelović PJ and Blagojević PD, Structural Elucidation of Presilphiperfolane-7α, 8α-diol, a Bioactive Sesquiterpenoid from Pulicaria vulgaris: A Combined Approach of Solvent-Induced Chemical Shifts, GIAO Calculation of Chemical Shifts, and Full Spin Analysis. J Nat Prod 82:1874-1885 (2019).
Van den Dool H and Kratz PD, A generalization of the retention index system including linear temperature programmed gas-liquid partition chromatography. J Chromatogr 11:463-471 (1963).
Wiley Registry of Mass Spectral Data, 11th edition, John Wiley & Sons, Inc., Hoboken, New Jersey, USA (2016).
NIST/EPA/NIH Mass Spectral Library V2017, National Institute of Standards and Technology, US Secretary of Commerce, Gaithersburg, Maryland, USA (2017).
Hochmuth DH, König WA, Joulain D, MassFinder 2.3. Software & Data Bank, Hamburg, Germany (2003).
Toniolo C, Synthesis and optical studies of isoleucine oligopeptides in solution. Biopolymers 10:1707-1717 (1971).
Claude-Lafontaine A, Raharivelomanana P and Bianchini J-P, Volatile Constituents of the Flower Concrete of Gardenia taitensis DC. J Essent Oil Res 4:335-343 (1992).
Shulz S, Estrada C, Yildizhan S, Boppré M and Gilbert LE, An Antiaphrodisiac in Heliconius melpomene Butterflies. J Chem Ecol 34:82-93 (2008).
Radulović NS, Mladenović MZ and Stojanović-Radić ZZ, Synthesis of small libraries of natural products: New esters of long-chain alcohols from the essential oil of Scandix pecten-veneris L. (Apiaceae), Flavour. Fragr J 29:255-266 (2014).
Remy P-A, Sarrazin E, Pérès C, Dugay J, David N and Vial J, Identification of novel compounds in rose absolute with gas chromatography/high-resolution mass spectrometry. Flavour Fragr J 37:133-143 (2022).
Andriamaharavo NR, Retention Data. NIST Mass Spectrometry Data Center, Gaithersburg, MD, USA (2014).
Taniguchi M, Koga K, Yamada S and Stereochemical Studies XVI, Deaminative Acetolyses of l-valine and l-valine benzyl ester. Chem Pharm Bull 20:1438-1444 (1972).
Molander GA, Barcellos T and Traister KM, Pd-Catalyzed Cross-Coupling of Potassim Alkenyltrifluoroborates with 2-Chloroacetates and 2-Chloroacetamides. Org Lett 15:3342-3345 (2013).
Arai T, Sugie H, Hiradate S, Kuwahara S, Itagaki N and Nakahata T, Identification of a sex pheromone component of Pseudococcus cryptus. J Chem Ecol 29:2213-2223 (2003).
Akella SVS, Kirk WDJ, Lu Y, Murai T, Walters KFA and Hamilton JGC, Identification of the Aggregation Pheromone of the Melon Thrips, Thrips palmi. PLoS One 9:e103315 (2014).
Citron CA, Rabe P and Dickschat JS, The Scent of Bacteria: Headspace Analysis for the Discovery of Natural Products. J Nat Prod 75:1765-1776 (2012).
Yoshida T, Muraki S, Kawamura H, Komatsu A and Minor Constituents of Japanese Ho-Leaf Oil, The Structures of (+)-Tagetonol and (-)-Hotrienol. Agr Biol Chem 33:343-352 (1969).
Hashimoto S, Sakoya Y, Hayashi S, Ueyama Y and Giga T, Perfume compositions containing dimethyloctatrienol optical isomers. Japan Patent 2000192073, filed 28th December 1998, issued 11th July (2000).
Pérez-Hernández N, Becerra-Martínez E and Joseph-Nathan P, Complete 1H NMR assignment of cholesteryl benzoate. Steroids 138:72-81 (2018).
Hatakeyama S, Matsui Y, Suzuki M, Sakurai K and Takano S, Enantioselective synthesis of (+)-citreoviral using asymmetric hydroxylation of tiglate esters. Tetrahedron Lett 26:6485-6488 (1985).
Srikrishna A and Anebouselvy K, Enantiospecific first total synthesis of (+)-cis,anti,cis-3-hydroxy-1,8,12,12-tetramethyl-4-oxatricyclo[6.4.0.02,6]-dodecan-9-yl senecioate, the optical antipode of a natural thapsane isolated from Thapsia villosa. Tetrahedron Lett 44:1031-1034 (2003).
Hinkens DM, McElfresh S and Millar JG, Identification and synthesis of the sex pheromone of the vine mealybug, Planococcus ficus. Tetrahedron Lett 42:1619-1621 (2001).
Pauly G, Gleizes M and Bernard-Dagan C, Identification des constituants de l'essence des aiguilles de Pinus pinaster. Phytochemistry 12:1395-1398 (1973).
Raguso RA and Roy BA, ʻFloral’ scent production by Puccinia rust fungi that mimics flowers. Mol Ecol 7:1127-1136 (1998).
Myawaki H and Yugawa C, Senecioic acid esters with unsaturated alcohols. Japan Patent 59020246, filed 28th July 1982, issued 1st February (1984).
Liu Q, Wu L, Jiao H, Fang X, Jackstell R and Beller M, Domino Catalysis: Palladium-Catalyzed Carbonylation of Allylic Alcohols to β, γ-Unsaturated Esters. Angew Chem 52:8064-8068 (2013).
Takeoka GR, Buttery RG, Ling LC, Wong RY, Dao LT, Edwards HR et al., Odor Thresholds of Various Unsaturated Branched Esters. LWT - Food Sci. Technol 31:443-448 (1998).
Nakahata T, Itagaki N, Arai T, Sugie H and Kuwahara S, Synthesis of the Sex Pheromone of the Citrus Mealybug. Biosci Biotechnol Biochem 67:2627-2631 (2003).
Pabi N, Sortendifferenzierung von Holunder über das Aroma der Blüten, Master's thesis. Graz University of Technology, Graz, Austria (2012).
Surburg H, Güntert M and Schwarze B, Volatile Constituents of European Bird Cherry Flowers (Padus avium Mill.). J Essent Oil Res 2:307-316 (1990).
Raičević V and Radulović N, Continual Misidentification of 5-Oxolinalool as 2-Methylnon-2-en-4-one in Essential Oils. J Essent Oil Res (2023). https://doi.org/10.1080/10412905.2023.2247401.

Auteurs

Vidak Raičević (V)

Faculty of Medicine, University of Novi Sad, Novi Sad, Serbia.

Marko Mladenović (M)

Department of Chemistry, Faculty of Sciences and Mathematics, University of Niš, Niš, Serbia.

Milica Aćimović (M)

Institute of Field and Vegetable Crops, Novi Sad, Serbia.

Niko Radulović (N)

Department of Chemistry, Faculty of Sciences and Mathematics, University of Niš, Niš, Serbia.

Classifications MeSH