γ-Linolenic and Stearidonic Acids from Boraginaceae of Diverse Mediterranean Origin.
Boraginaceae
principal component analysis
seed oil
stearidonic acid
γ-linolenic acid
Journal
Chemistry & biodiversity
ISSN: 1612-1880
Titre abrégé: Chem Biodivers
Pays: Switzerland
ID NLM: 101197449
Informations de publication
Date de publication:
Dec 2020
Dec 2020
Historique:
received:
29
07
2020
accepted:
12
10
2020
pubmed:
13
10
2020
medline:
24
6
2021
entrez:
12
10
2020
Statut:
ppublish
Résumé
Thirty Boraginaceae species from different tribes were evaluated in a search of γ-linolenic (GLA, 18:3n-6) and stearidonic acid (SDA, 18:4n-3)-rich oils. The high GLA percentages were found in the seed oils of Symphytum bulbosum and S. tuberosum subsp. tuberosum (27.6 and 27.2 % of total fatty acids (FA)), which are unusually high values for GLA-oils in the current literature. On the whole seed, noticeable GLA percentages were found in S. grandiflorum, S. tuberosum subsp. tuberosum and Borago officinalis (7.43, 4.90, and 4.51 g/100 g, respectively). The main SDA-taxa detected in this study were Buglossoides arvensis, B. incrassata and Glandora oleifolia (21.3, 18.9, and 16.3 % of total fatty acids). On total seed weight, Glandora rosmarinifolia showed the highest SDA content (3.57 g/100 g). Finally, the higher FA contents were found in S. grandiflorum and Paramoltkia doerfleri seeds (35.2 and 37.0 g/100 g, respectively). Principal component analysis showed that similarities in FA profiles allow grouping species as botanical criteria for Boraginaceae tribes do, while the FA groupings confirm the metabolic activities of desaturase and elongase enzymes. Data on the FA composition of the seed oils analyzed here suggest their potential use as functional foods and can be considered as novel sources of SDA and GLA.
Identifiants
pubmed: 33045128
doi: 10.1002/cbdv.202000627
doi:
Substances chimiques
Fatty Acids, Omega-3
0
Plant Oils
0
gamma-Linolenic Acid
78YC2MAX4O
stearidonic acid
P4CEK3495O
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e2000627Subventions
Organisme : University of Almería
ID : 301046
Organisme : 'Asociación Universitaria Iberoamericana de Postgrado' (AUIP)
Organisme : 'Consejería de Economía y Conocimiento de la Junta de Andalucía'
Informations de copyright
© 2020 Wiley-VHCA AG, Zurich, Switzerland.
Références
F. Attar, S. Esfandani-Bozchaloyi, M. Mirtadzadini, F. Ullah, ‘Taxonomic identification in the tribe Cynoglosseae (Boraginaceae) using palynological characteristics’, Flora 2018, 249, 97-110.
S. Dresler, G. Szymczak, M. Wójcik, ‘Comparison of some secondary metabolite content in the seventeen species of the Boraginaceae family’, Pharm. Biol. 2017, 55, 691-695.
J. L. Guil-Guerrero, ‘Stearidonic acid (18:4n-3): Metabolism, nutritional importance, medical uses and natural sources’, Eur. J. Lipid Sci. Technol. 2007, 109, 1226-1236.
L. Menghini, C. Ferrante, G. Zengin, M. F. Mahomoodally, L. Leporini, M. Locatelli, F. Cacciagrano, L. Recinella, A. Chiavaroli, S. Leone, L. Brunetti, ‘Multiple pharmacological approaches on hydroalcoholic extracts from different parts of Cynoglossum creticum Mill. (Boraginaceae)’, Plant Biosyst. 2019, 633-639.
D. Jakovljević, S. Vasić, M. Stanković, M. Topuzović, L. Comić, ‘The content of secondary metabolites and In Vitro biological activity of Anchusa officinalis L. (Boraginaceae)’, Indian J. Tradit. Know. 2016, 15, 587-593.
M. Assadi-Samani, M. Bahmani, M. Rafieian-Kopaei, ‘The chemical composition, botanical characteristic and biological activities of Borago officinalis: a review’, Asian Pac. J. Trop. Med. 2014, 7 (Suppl 1), S22-S28.
N. Siriwardhana, N. S. Kalupahana, N. Moustaid-Moussa, ‘Health benefits of n-3 polyunsaturated fatty acids: eicosapentaenoic acid and docosahexaenoic acid’, Adv. Food Nutr. Res. 2012, 65, 211-222.
C. Cardoso, J. P. Martinho, P. A. Lopes, S. Martins, J. Correia, C. Afonso, F. J. Alarcón, M. J. González-Fernández, R. M. Pinto, J. A. Prates, N. M. Bandarra, J. L. Guil-Guerrero, ‘Stearidonic Acid Combined with Alpha-Linolenic Acid Improves Lipemic and Neurological Markers in a Rat Model Subject to a Hypercaloric Diet’, Prostaglandins Leukotrienes Essent. Fatty Acids 2018, 135, 137-146.
J. L. Guil-Guerrero, R. P. Ramos-Bueno, F. Gómez-Mercado, M. A. Rincón-Cervera, ‘Positional distribution assessment of essential fatty acids in several fats and oils including plant, fish, and microbial sources and subcutaneous fat of Galician horse’, Eur. J. Lipid Sci. Technol. 2015, 117, 701-709.
J. L. Guil-Guerrero, F. Gómez-Mercado, F. García-Maroto, P. Campra-Madrid, ‘Occurrence and characterization of oils rich in γ-linolenic acid Part I: Echium seeds from Macaronesia’, Phytochemistry 2000, 53, 451-456.
N. Lefort, R. LeBlanc, M. E. Surette, ‘Dietary Buglossoides arvensis Oil Increases Circulating n-3 Polyunsaturated Fatty Acids in a Dose-Dependent Manner and Enhances Lipopolysaccharide-Stimulated Whole Blood Interleukin-10-A Randomized Placebo-Controlled Trial’, Nutrients 2017, 9, 261.
J. L. Guil-Guerrero, F. Gómez-Mercado, R. P. Ramos-Bueno, M. J. González-Fernández, M. Urrestarazu, M. A. Rincón-Cervera, ‘Sardinian Boraginaceae are new potential sources of gamma-linolenic acid’, Food Chem. 2017, 218, 435-439.
J. L. Guil-Guerrero, F. Gómez-Mercado, R. P. Ramos-Bueno, M. J. González-Fernández, M. Urrestarazu, S. Jiménez-Becker, G. de Bélair, ‘Fatty acid profiles and sn-2 fatty acid distribution of γ-linolenic acid-rich Borago species’, J. Food Compos. Anal. 2018, 66, 74-80.
J. L. Guil-Guerrero, J. C. López-Martínez, F. Gómez-Mercado, P. Campra-Madrid, ‘Gamma-linolenic and stearidonic acids from Moroccan Boraginaceae’, Eur. J. Lipid Sci. Technol. 2006, 108, 43-47.
K. Kuhnt, Ch. Degen, A. Jaudszus, G. Jahreis, ‘Searching for health beneficial n-3 and n-6 fatty acids in plant seeds’, Eur. J. Lipid Sci. Technol. 2012, 114, 153-160.
J. L. Guil-Guerrero, F. Gómez-Mercado, I. Rodríguez-García, P. Campra-Madrid, F. García-Maroto, ‘Occurrence and characterization of oils rich in γ-linolenic acid (III): the taxonomical value of the fatty acids in Echium (Boraginaceae)’, Phytochemistry 2001, 58, 117-120.
T. Özcan, ‘Differentiation of Symphytum Species Using RAPD and Seed Fatty Acid Patterns’, Nat. Prod. Commun. 2010, 5, 587-596.
M. Urrestarazu, V. M. Gallegos-Cedillo, F. Ferron-Carrillo, J. L. Guil-Guerrero, M. T. Lao, J. E. Alvaro, ‘Effects of the electrical conductivity of a soilless culture system on gamma linolenic acid levels in borage seed oil’, PLoS One 2019, 14, e0207106.
K. Jaffel-Hamza, S. Sai-Kachout, J. Harrathi, M. Lachaal, B. Marzouk, ‘Growth and Fatty Acid Composition of Borage (Borago officinalis L.) Leaves and Seeds Cultivated in Saline Medium’, J. Plant Growth Regul. 2013, 32, 200-207.
R. El Hafid, S. F. Blade, Y. Hoyano, ‘Seeding date and nitrogen fertilization effects on the performance of borage (Borago officinalis L.)’, Ind. Crops Prod. 2002, 16, 193-199.
A. De Haro, V. Domínguez, M. del Río, ‘Variability in the Content of Gamma-Linolenic Acid and Other Fatty Acids of the Seed Oil of Germplasm of Wild and Cultivated Borage (Borago officinalis L.)’, J. Herbs Spices Med. Plants 2002, 9, 297-304.
E. Bagci, L. Bruehl, K. Aitzetmuller, Y. Altan, ‘Fatty acid and tocochromanol patterns of some Turkish Boraginaceae-a chemotaxonomic approach’, Nordic J. Bot. 2002, 22, 719-726.
S. Lyashenko, M. J. González-Fernández, F. Gómez-Mercado, S. Yunusova, O. Denisenko, J. L. Guil-Guerrero, ‘Ribes taxa: A promising source of γ-linolenic acid-rich functional oils’, Food Chem. 2019, 301, 125309.
T. Greupner, E. Koch, L. Kutzner, A. Hahn, N. Helge Schebb, J. P. Schuchardt, ‘Single-Dose SDA-Rich Echium Oil Increases Plasma EPA, DPAn3, and DHA Concentrations’, Nutrients 2019, 11, 2346.
S. L. Lemke, J. L. Vicini, H. Su, D. A. Goldstein, M. A. Nemeth, E. S. Krul, W. S. Harris, ‘Dietary intake of stearidonic acid-enriched soybean oil increases the omega-3 index: randomized, double-blind clinical study of efficacy and safety’, Am. J. Clin. Nutr. 2010, 92, 766-775.
A. K. Duttaroy, ‘Regulation of functional foods in European Union: assessment of health claim by the European Food Safety Authority’, in ‘Nutraceutical and Functional Food Regulations in the United States and Around the World’, Ed. D. Bagchi, Elsevier, 2019, Chapt. 19.
A. J. Stein, E. Rodriguez Cerezo, ‘Functional Food in the European Union’, JRC European Commission, 2008.
Regulation (EC) No. 1924/2006 of the European Parliament and of the Council of 20 December 2006 on nutrition and health claims made on foods.
C. Tan, ‘Virgin avocado oil: An emerging source of functional fruit oil’, J. Funct. Foods 2019, 54, 381-392.
D. Fabrikov, J. L. Guil-Guerrero, M. J. González-Fernández, I. Rodríguez-García, F. Gómez-Mercado, M. Urrestarazu, M. T. Lao, M. Á. Rincón-Cervera, J. E. Álvaro, S. Lyashenko, ‘Borage oil: Tocopherols, sterols and squalene in farmed and endemic-wild Borago species’, J. Food Compos. Anal. 2019, 83, 103299.
Regulation (EU) No. 2015/2283 of the European Parliament and of the Council of 25 November 2015 on novel foods, amending Regulation (EU) No. 1169/2011 of the European Parliament and of the Council and repealing Regulation (EC) No. 258/97 of the European Parliament and of the Council and Commission Regulation (EC) No. 1852/2001 (Text with EEA relevance).
M. García-Iñiguez de Ciriano, C. García-Herreros, E. Larequi, I. Valencia, D. Ansorena, I. Astiasarán, ‘Use of natural antioxidants from lyophilized water extracts of Borago officinalis in dry fermented sausages enriched in ω-3 PUFA’, Meat Sci. 2009, 83, 271-277.
C. Soto, J. Concha, M. E. Zuniga, ‘Antioxidant content of oil and defatted meal obtained from borage seeds by an enzymatic-aided cold pressing process’, Proc. Biochem. 2008, 43, 696-699.
J. L. Guil-Guerrero, M. Á. Rincón-Cervera, E. Venegas-Venegas, ‘Gamma-linolenic and stearidonic acids: Purification and upgrading of C18-PUFA oils’, Eur. J. Lipid Sci. Technol. 2010, 112, 1068-1081.
J. L. Guil-Guerrero, F. G. Maroto, A. G. Gimenez, ‘Fatty acid profiles from forty-nine plant species that are potential new sources of γ-linolenic acid’, J. Am. Oil Chem. Soc. 2001, 78, 677-684.
P. Prasad, R. V. Sreedhar, ‘Identification and functional characterization of Buglossoides arvensis microsomal fatty acid desaturation pathway genes involved in polyunsaturated fatty acid synthesis in seeds’, J. J. Biotechnol. 2020, 308, 130-140.
E. Shokri, G. Nematzadeh, J. Zolala, N. Nasiri, S. K. Kazemi-Tabar, N. Hosseinpour-Azad, ‘Delta-6 desaturase makes a different fatty acid profile of seed oil in Iranian borage (Echium amoenum Fisch. and Mey.)’, Acta Physiol. Plantar. 2012, 34, 2413-2418.
M. Li, E. Baughman, M. R. Roth, X. Han, R. Welti, X. Wang, ‘Quantitative profiling and pattern analysis of triacylglycerol species in Arabidopsis seeds by electrospray ionization mass spectrometry’, Plant J. 2014, 77, 160-172.
L. Cecchi, F. Selvi, ‘A synopsis of Boraginaceae subfam. Hydrophylloideae and Heliotropioideae in Italy’, Plant Biosyst. 2014, 148, 2-12.
L. Cecchi, F. Selvi, ‘Synopsis of Boraginaceae subfam. Boraginoideae tribe Boragineae in Italy’, Plant Biosyst. 2015, 149, 630-677.
S. Pignatti, ‘Flora d'Italia’, Vols. 1-3, Edagricole, Bologna, 1982.
G. Lepage, C. Roy, ‘Improved recovery of fatty acid through direct transesterification without prior extraction or purification’, J. Lipid Res. 1984, 25, 1391-1396.
J. Rodríguez-Ruiz, E. H. Belarbi, J. L. García Sánchez, D. López Alonso, ‘Rapid Simultaneous Lipid Extraction and Transesterification for Fatty Acid Analyses’, Biotechnol. Tech. 1998, 12, 689-691.
M. J. González-Fernández, R. P. Ramos-Bueno, I. Rodríguez-García, J. L. Guil-Guerrero, ‘Purification process for MUFA- and PUFA-based monoacylglycerols from edible oils’, Biochimie 2017, 139, 107-114.
J. L. Guil-Guerrero, F. Gómez-Mercado, R. P. Ramos-Bueno, M. Á. Rincón-Cervera, E. Venegas-Venegas, ‘Restricted-Range Boraginaceae Species Constitute Potential Sources of Valuable Fatty Acids’, J. Am. Oil Chem. Soc. 2014, 91, 301-308.
M. J. Griffiths, R. P. Van Hille, S. T. L. Harrison, ‘Selection of direct transesterification as the preferred method for assay of fatty acid content of microalgae’, Lipids 2010, 45, 1053-1060.