Publications by authors named "Maaria Kortesniemi"

24 Publications

  • Page 1 of 1

Oxidative stability, oxidation pattern and α-tocopherol response of docosahexaenoic acid (DHA, 22:6n-3)-containing triacylglycerols and ethyl esters.

Food Chem 2022 Sep 3;387:132882. Epub 2022 Apr 3.

Food Chemistry and Food Development, Department of Life Technologies, University of Turku, FI-20014 Turun yliopisto, Turku, Finland. Electronic address:

DHA is most often used in supplements either in its triacylglycerol or ethyl ester form. Currently, there is only little published data on the differences in the oxidative stability and α-tocopherol response between the two lipid structures, as well as on the oxidation patterns of pure DHA. This study investigated the oxidative stability, α-tocopherol response and oxidation pattern of DHA incorporated in triacylglycerols and as ethyl esters with an untargeted approach after oxidation at 50 °C in the dark. Liquid and gas chromatographic methods with mass spectrometric detection and nuclear magnetic resonance spectroscopy were applied. DHA was more stable in triacylglycerols than as ethyl esters without α-tocopherol addition. With α-tocopherol added the opposite was observed. The oxidation products formed during triacylglycerol and ethyl ester oil oxidation were mostly similar, but also some structure-related differences were detected in both volatile and non-volatile oxidation products.
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http://dx.doi.org/10.1016/j.foodchem.2022.132882DOI Listing
September 2022

Effects of acylated and nonacylated anthocyanins extracts on gut metabolites and microbiota in diabetic Zucker rats: A metabolomic and metagenomic study.

Food Res Int 2022 03 7;153:110978. Epub 2022 Feb 7.

Food Chemistry and Food Development, Department of Life Technologies, University of Turku, FI-20014 Turun yliopisto, Finland. Electronic address:

Anthocyanins have been shown to have prebiotic properties. This study investigated the impact of nonacylated anthocyanins and acylated anthocyanins on fecal and cecal metabolites and colonic gut microbiota in diabetic state using H nuclear magnetic resonance (NMR) metabolomics and metagenomic sequencing. Zucker diabetic fatty rats fed with high-fat diet were gavaged with nonacylated anthocyanins extracted from bilberries (NAAB) or acylated anthocyanins extracted from purple potatoes (AAPP) at daily doses of 25 and 50 mg/kg body weight for 8 weeks. Lean Zucker rats fed with normal diet (ND) and high-fat diet (Con) were used as healthy controls groups. Binned NMR spectra and sequenced gene abundance were used for data analysis. Dysbiosis of colonic microbiota and gut metabolites in the diabetic rats were observed compared to the lean Zucker rats. Both anthocyanin extracts increased cecal sugar levels and the abundance of Peptostreptococcaceae sp. and decreased the abundance of Parabacteroides spp. in colon. In addition to the increased fecal short-chain fatty acids, AAPP decreased colonic Ruminococcus torques and Lachnospiraceae bacterium 4_1_37FAA abundances and increased oxidative phosphorylation. The anthocyanin extracts modulated the gut metabolism and microbiota in diabetes, with AAPP showing more regulatory and beneficial effects on diabetes.
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http://dx.doi.org/10.1016/j.foodres.2022.110978DOI Listing
March 2022

Sensory and chemical characterization of Chinese bog bilberry wines using Check-all-that-apply method and GC-Quadrupole-MS and GC-Orbitrap-MS analyses.

Food Res Int 2022 01 14;151:110809. Epub 2021 Nov 14.

Food Chemistry and Food Development, Department of Life Technologies, University of Turku, FI-20014 Turun yliopisto, Finland. Electronic address:

The sensory and chemical profiles of commercial bog bilberry (BB) wines were investigated using a multi-analytical approach. Sensory test included scaling and check-all-that-apply (CATA) method with questions on liking of BB wine. The sensory data was correlated with their volatile compound profiles determined using gas chromatography coupled with quadrupole and orbitrap mass spectrometry (GC-Quadrupole/Orbitrap-MS). In general, all BB wines were characterized with "fruity", "blueberry" and "floral" odors and "sour", "mouth puckering" and "sweet" flavors. Samples more frequently characterized as "fruity" and "floral" in CATA were preferred by the panelists (n = 93). High relative proportions of o-cymene, p-cymenene, 1-octen-3-one and 3-ethylphenol in a sample (described as "ginger" and "chili") resulted in a lower liking rating. Similarly, generally disliked sample described with "Chinese herbs" and "licorice" was characterized by compounds 3-methylpentan-1-ol, 1,1,6-trimethyl-1,2-dihydronaphthalene, and 4-vinylphenol. The data will give novel information for berry wine and beverage industry on the quality factors of BB wines linked to higher acceptance.
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http://dx.doi.org/10.1016/j.foodres.2021.110809DOI Listing
January 2022

Human milk metabolome is associated with symptoms of maternal psychological distress and milk cortisol.

Food Chem 2021 Sep 20;356:129628. Epub 2021 Mar 20.

FinnBrain Birth Cohort Study, Turku Brain and Mind Center, Department of Clinical Medicine, University of Turku, Finland.

The composition of human milk is subject to considerable variation, but the effects of maternal stress are largely unknown. We studied differences in human milk metabolome between Finnish mothers (n = 120, secretors) with symptoms of prenatal symptoms of psychological distress and milk cortisol concentrations. Human milk samples acquired at 2.5 months postpartum were analyzed using targeted H NMR metabolomics. Self-reported scores for depression (EPDS), overall anxiety (SCL-90), and pregnancy-related anxiety (PRAQ) were used to evaluate psychological distress. Prenatal psychological distress was positively associated with concentrations of short-chain fatty acids, caprate, and hypoxanthine (q < 0.0012). Milk cortisol was positively associated with lactate concentration (q < 0.05). Changes in the human milk metabolome were shown to be associated with maternal psychological distress and concentration of milk cortisol in a dissimilarly, suggesting alterations in bacterial and energy metabolism of the mother, respectively.
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http://dx.doi.org/10.1016/j.foodchem.2021.129628DOI Listing
September 2021

H NMR Metabolomics and Full-Length RNA-Seq Reveal Effects of Acylated and Nonacylated Anthocyanins on Hepatic Metabolites and Gene Expression in Zucker Diabetic Fatty Rats.

J Agric Food Chem 2021 Apr 9;69(15):4423-4437. Epub 2021 Apr 9.

Food Chemistry and Food Development, Department of Life Technologies, University of Turku, FI-20014 Turun yliopisto, Finland.

Anthocyanins have been reported to possess antidiabetic effects. Recent studies indicate acylated anthocyanins have better stability and antioxidative activity compared to their nonacylated counterparts. This study compared the effects of nonacylated and acylated anthocyanins on hepatic gene expression and metabolic profile in diabetic rats, using full-length transcriptomics and H NMR metabolomics. Zucker diabetic fatty (ZDF) rats were fed with nonacylated anthocyanin extract from bilberries (NAAB) or acylated anthocyanin extract from purple potatoes (AAPP) at daily doses of 25 and 50 mg/kg body weight for 8 weeks. Both anthocyanin extracts restored the levels of multiple metabolites (glucose, lactate, alanine, and pyruvate) and expression of genes (, , , and ) involved in glycolysis and gluconeogenesis. AAPP decreased the hepatic glutamine level. NAAB regulated the expression of , , and , whereas AAPP modified the expression of , , , and . This study indicated different effects of AAPP and NAAB on the hepatic transcriptomic and metabolic profiles of diabetic rats.
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http://dx.doi.org/10.1021/acs.jafc.1c00130DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8154569PMC
April 2021

Effects of Anthocyanin Extracts from Bilberry ( L.) and Purple Potato ( L. var. 'Synkeä Sakari') on the Plasma Metabolomic Profile of Zucker Diabetic Fatty Rats.

J Agric Food Chem 2020 Sep 20;68(35):9436-9450. Epub 2020 Aug 20.

Food Chemistry and Food Development, Department of Biochemistry, University of Turku, Turun yliopisto, Turku FI-20014, Finland.

This study compared the effects of the nonacylated and acylated anthocyanin-rich extracts on plasma metabolic profiles of Zucker diabetic fatty rats. The rats were fed with the nonacylated anthocyanin extract from bilberries (NAAB) or the acylated anthocyanin extract from purple potatoes (AAPP) at daily doses of 25 and 50 mg/kg body weight for 8 weeks. H NMR metabolomics was used to study the changes in plasma metabolites. A reduced fasting plasma glucose level was seen in all anthocyanin-fed groups, especially in the groups fed with NAAB. Both NAAB and AAPP decreased the levels of branched-chain amino acids and improved lipid profiles. AAPP increased the glutamine/glutamate ratio and decreased the levels of glycerol and metabolites involved in glycolysis, suggesting improved insulin sensitivity, gluconeogenesis, and glycolysis. AAPP decreased the hepatic and messenger RNA level, suggesting regulation of gluconeogenesis and lipogenesis. This study indicated that AAPP and NAAB affected the plasma metabolic profile of diabetic rats differently.
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http://dx.doi.org/10.1021/acs.jafc.0c04125DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7586333PMC
September 2020

Interactions between cortisol and lipids in human milk.

Int Breastfeed J 2020 07 20;15(1):66. Epub 2020 Jul 20.

The FinnBrain Birth Cohort Study, Turku Brain and Mind Center, Institute of Clinical Medicine, University of Turku, Turku, Finland.

Background: Human breast milk is one of the key early postnatal biological exposures for the developing child. It includes bioactive compounds, such as cortisol and fatty acids, which may be linked via the mother's lipid metabolism.

Methods: This study investigated the associations between cortisol and lipids in human milk at the infant age of 2.5 months. Human milk cortisol concentrations were measured using luminescence immunoassay, and two groups of milks (n = 50 each) were formed based on either high (> 10 nmol/L) or low (< 3 nmol/L) cortisol levels. Lipids, as fatty acid content and composition of neutral (triacylglycerol-rich) and polar (phospholipid-rich) lipids, were measured with gas chromatography. The samples originated from the FinnBrain Birth Cohort Study.

Results: The percentage of phospholipid-rich lipids of total lipids was 33.08% ± 1.33%. In triacylglycerol-rich lipids, high cortisol level in milk was associated with higher lauric (12:0, mass % and mg/mL), myristic (14:0, mass % and mg/mL), eicosenoic (20:1n - 9, mass %), docosenoic (22:1n - 9, mass %, and mg/mL) acids, and to lower palmitic acid (16:0, mass %) compared with low cortisol levels in milk. In phospholipid-rich lipids, high cortisol level was associated with higher myristic (14:0, mass %) and docosenoic (22:1n - 9, mass %) acids. After adjusting for pre-pregnancy BMI and sampling time by linear regression, the milk cortisol remained a significant predictor for lauric and myristic acids in triacylglycerol-rich lipids, and myristic and docosenoic acid in phospholipid-rich lipids (β = 0.23 to 0.38 and p < 0.05 for each).

Conclusions: This study revealed certain significant associations between milk cortisol and the fatty acid composition of human milk, indicating that cortisol might be one of the factors affecting the origin of the lipids in human milk.
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http://dx.doi.org/10.1186/s13006-020-00307-7DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7370511PMC
July 2020

Characterization and Quantification of Nonanthocyanin Phenolic Compounds in White and Blue Bilberry () Juices and Wines Using UHPLC-DAD-ESI-QTOF-MS and UHPLC-DAD.

J Agric Food Chem 2020 Jul 14;68(29):7734-7744. Epub 2020 Jul 14.

Food Chemistry and Food Development, Department of Biochemistry, University of Turku, FI-20014 Turku, Finland.

The nonanthocyanin phenolic compounds in juice and wine produced from fruits of white bilberry, a nonpigmented mutant of , and blue bilberry (pigmented variety) were analyzed using liquid chromatography with a diode array detector (LC-DAD) and LC-DAD-electrospray ionization-quadrapole/time of flight hybrid mass spectrometry (ESI-QTOF-MS). On the basis of elution order, UV-vis spectra, accurate mass data, and fragmentation pattern and standards, 42 compounds including 22 phenolic acids, 15 flavonols, and 5 flavan-3-ols, were identified in juices and wines prepared from the two bilberry varieties. The levels of most individual nonanthocyanin phenolic compounds in white bilberry products were significantly lower than those in pigmented ones. In bilberry juices, phenolic acids were the most predominant, accounting for approximately 80% of total phenolic content, with -coumaroyl monotropeins and caffeic acid hexoside being the major phenolic acids. After fermentation, the total contents of phenolic acids, flavonols, and nonanthocyanin phenolic compounds significantly increased, while the content of total flavan-3-ols decreased significantly. -Coumaroyl monotropeins still dominated in the wine products, while caffeic acid content showed dramatic elevation with the significant drop of caffeic acid hexoside.
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http://dx.doi.org/10.1021/acs.jafc.0c02842DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7497633PMC
July 2020

Evaluation of the composition and oxidative status of omega-3 fatty acid supplements on the Finnish market using NMR and SPME-GC-MS in comparison with conventional methods.

Food Chem 2020 Nov 6;330:127194. Epub 2020 Jun 6.

Food Chemistry and Food Development, Department of Biochemistry, University of Turku, 20014 Turun yliopisto, Turku, Finland. Electronic address:

Previous studies disagree on the oxidative status of omega-3 supplements. The great deviation raises concerns about quality and the methods used to monitor it. This study investigated 49 omega-3 products for their fatty acid content, lipid class and oxidative status using official methods, gas and liquid chromatography with mass spectrometry and nuclear magnetic resonance spectroscopy. With minor deviations, omega-3 fatty acid content and lipid class of all products were as declared. 24% of studied products exceeded thresholds set by The Global Organization for EPA and DHA Omega-3s for peroxide and/or p-anisidine value suggesting a compromised oxidative status. However, peroxide and/or p-anisidine value were only suitable for detection of lipid oxidation in 90% or 73%, respectively, of the products. Analysis of volatile oxidation compounds can be an alternative method for p-anisidine value. Nuclear magnetic resonance spectroscopy was shown to be a rapid method for determination of oil type and lipid class.
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http://dx.doi.org/10.1016/j.foodchem.2020.127194DOI Listing
November 2020

Hops compounds modulatory effects and 6-prenylnaringenin dual mode of action on GABA receptors.

Eur J Pharmacol 2020 Apr 27;873:172962. Epub 2020 Jan 27.

Integrative Physiology and Pharmacology, Institute of Biomedicine, University of Turku, Finland. Electronic address:

Hops (Humulus lupulus L.), a major component of beer, contain potentially neuroactive compounds that made it useful in traditional medicine as a sleeping aid. The present study aims to investigate the individual components in hops acting as allosteric modulators in GABA receptors and bring further insight into the mode of action behind the sedative properties of hops. GABA-potentiating effects were measured using [H]ethynylbicycloorthobenzoate (EBOB) radioligand binding assay in native GABA receptors. Flumazenil sensitivity of GABA-potentiating effects, [H]Ro 15-4513, and [H]flunitrazepam binding assays were used to examine the binding to the classical benzodiazepines site. Humulone (alpha acid) and 6-prenylnaringenin (prenylflavonoid) were the most potent compounds displaying a modulatory activity at low micromolar concentrations. Humulone and 6-prenylnaringenin potentiated GABA-induced displacement of [H]EBOB binding in a concentration-dependent manner where the IC values for this potentiation in native GABA receptors were 3.2 μM and 3.7 μM, respectively. Flumazenil had no significant effects on humulone- or 6-prenylnaringenin-induced displacement of [H]EBOB binding. [H]Ro 15-4513 and [H]flunitrazepam displacements were only minor with humulone but surprisingly prominent with 6-prenylnaringenin despite its flumazenil-insensitive modulatory activity. Thus, we applied molecular docking methods to investigate putative binding sites and poses of 6-prenylnaringenin at the GABA receptor α1β2γ2 isoform. Radioligand binding and docking results suggest a dual mode of action by 6-prenylnaringenin on GABA receptors where it may act as a positive allosteric modulator at α+β- binding interface as well as a null modulator at the flumazenil-sensitive α+γ2- binding interface.
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http://dx.doi.org/10.1016/j.ejphar.2020.172962DOI Listing
April 2020

Untargeted metabolic fingerprinting reveals impact of growth stage and location on composition of sea buckthorn (Hippophaë rhamnoides) leaves.

J Food Sci 2020 Feb 24;85(2):364-373. Epub 2020 Jan 24.

Food Chemistry and Food Development, Dept. of Biochemistry, Univ. of Turku, FI-20014, Turku, Finland.

Sea buckthorn (Hippophaë rhamnoides) is increasingly cultivated to produce raw materials for food and nutraceuticals. There is little knowledge on composition of sea buckthorn leaves (SBLs) and the key factors influencing the composition. This research aims to unravel the metabolic profile of SBLs and the effects of cultivar, location and stage of growth, and climatic conditions on the metabolic profile of SBLs. Leaves of two sea buckthorn cultivars grown in the south and north of Finland during two consecutive growth seasons were studied using untargeted nuclear magnetic resonance (NMR) metabolomics. The highest variance in the metabolic profile was linked to the growth stage, wherein leaves from the first 7 weeks of harvest were characterized with higher abundance of polyphenols, while relatively higher abundance of carbohydrates and sugars was observed in the later weeks. The growth location attributed for the second highest variation, wherein the north-south comparison identified fatty acids and sugars as discriminatory metabolites, and the potential association of metabolome to natural abiotic stressors was revealed. An inverse correlation between carbohydrate/sugar content as well as fatty acids of higher carbon chain length with the temperature variables was evident. The supervised chemometric models with high sensitivity and specificity classified and predicted the samples based on growth stage and location, and cultivar. Nontargeted NMR-metabolomics revealed the metabolic profile of SBLs and their variation associated with various biotic and abiotic factors. Cultivar and growth stage are key factors to consider when harvesting SBLs for use in food and nutraceuticals. PRACTICAL APPLICATION: Globally, sea buckthorn cultivation has been rapidly increasing due to the known health-promoting benefits of the berries and leaves of the plant. The current research obtained new comprehensive information on the compositional profile of sea buckthorn leaves as well as the impact of major contributory factors, such as cultivars, the advancement of growth stage, geographical location, and weather parameters. The findings of this research provide new knowledge and guidance for plant breeding, cultivation and commercial utilization of sea buckthorn leaves as raw materials for food, feed, and nutraceuticals.
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http://dx.doi.org/10.1111/1750-3841.15025DOI Listing
February 2020

Anthocyanin-rich extract from purple potatoes decreases postprandial glycemic response and affects inflammation markers in healthy men.

Food Chem 2020 Apr 26;310:125797. Epub 2019 Oct 26.

Food Chemistry and Food Development, Department of Biochemistry, University of Turku, FI-20014 Turun yliopisto, Turku, Finland. Electronic address:

Our recent clinical study suggested that polyphenol-rich purple potatoes lowered postprandial glycemia and insulinemia compared to yellow potatoes. Here, 17 healthy male volunteers consumed yellow potatoes with or without purple potato extract (PPE, extracted with water/ethanol/acetic acid) rich in acylated anthocyanins (152 mg) and other phenolics (140 mg) in a randomized cross-over trial. Ethanol-free PPE decreased the incremental area under the curve for glucose (p = 0.019) and insulin (p = 0.015) until 120 min after the meal, glucose at 20 min (p = 0.015) and 40 min (p = 0.004), and insulin at 20 min (p = 0.003), 40 min (p = 0.004) and 60 min (p = 0.005) after the meal. PPE affected some of the studied 90 inflammation markers after meal; for example insulin-like hormone FGF-19 levels were elevated at 240 min (p = 0.001). These results indicate that PPE alleviates postprandial glycemia and insulinemia, and affects postprandial inflammation.
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http://dx.doi.org/10.1016/j.foodchem.2019.125797DOI Listing
April 2020

Enzymatic acylation of blackcurrant (Ribes nigrum) anthocyanins and evaluation of lipophilic properties and antioxidant capacity of derivatives.

Food Chem 2019 May 3;281:189-196. Epub 2019 Jan 3.

Food Chemistry and Food Development, Department of Biochemistry, University of Turku, FI-20014 Turku, Finland. Electronic address:

Anthocyanin-rich fractions isolated from blackcurrant (Ribes nigrum L.) including delphinidin-3-O-glucoside, delphinidin-3-O-rutinoside, cyanidin-3-O-glucoside and cyanidin-3-O-rutinoside were enzymatically acylated with lauric acid. All the four anthocyanins were successfully monoacylated, and their relative proportions did not affect the conversion yield. The acylation occurred at the 6″-OH position of the glucosides and at the rhamnose 4‴-OH of the rutinosides. The rutinoside moieties of the anthocyanins were successfully acylated for the first time, and the corresponding acylation sites were verified by NMR analysis. The acylation enhanced the lipophilicity. The hydrophilic anthocyanin rutinosides were more lipophilic after acylation. Introducing lauric acid into the anthocyanins significantly improved the thermostability and capacity to inhibit lipid peroxidation and maintained UV-vis absorbance and antioxidant activity. This research provides important insights into acylation of mixed anthocyanins with different glycosyl moieties.
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http://dx.doi.org/10.1016/j.foodchem.2018.12.111DOI Listing
May 2019

Chemical composition of bilberry wine fermented with non-Saccharomyces yeasts (Torulaspora delbrueckii and Schizosaccharomyces pombe) and Saccharomyces cerevisiae in pure, sequential and mixed fermentations.

Food Chem 2018 Nov 4;266:262-274. Epub 2018 Jun 4.

Food Chemistry and Food Development, Department of Biochemistry, University of Turku, FI-20014 Turku, Finland. Electronic address:

This study evaluated the effects of fermentation with pure cultures of Torulaspora delbrueckii (TD291 and TD70526) and Schizosaccharomyces pombe (SP3796 and SP70572), as well as in sequential and mixed inoculations with Saccharomyces cerevisiae, on the chemical composition of bilberry wine. In comparison to the bilberry wines produced by pure and sequential fermentations, mixed cultures produced bilberry wines with more ethanol, higher pH values, higher percentages of red and yellow shade, but less glycerol and acetaldehyde. Higher values of color intensity and bluish parameter were found in products of pure fermentations with non-Saccharomyces yeasts. Compared to S. cerevisiae, T. delbrueckii contributed to the reduction of ethanol and acetic acid while increasing the content of succinic acid, lactic acid and higher alcohols; S. pombe consumed malic acid almost completely and produced more glycerol, acetaldehyde and/or pyruvic acid. Fermentation with SP70572 had the highest amounts of anthocyanins and hydroxycinnamic acids derivatives.
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http://dx.doi.org/10.1016/j.foodchem.2018.06.003DOI Listing
November 2018

Profiles of Volatile Compounds in Blackcurrant ( Ribes nigrum) Cultivars with a Special Focus on the Influence of Growth Latitude and Weather Conditions.

J Agric Food Chem 2018 Jul 9;66(28):7485-7495. Epub 2018 Jul 9.

Food Chemistry and Food Development, Department of Biochemistry , University of Turku , FI-20014 Turun yliopisto , Finland.

The volatile profiles of three blackcurrant ( Ribes nigrum L.) cultivars grown in Finland and their responses to growth latitude and weather conditions were studied over an 8 year period by headspace solid-phase microextraction (HS-SPME) followed by gas-chromatographic-mass-spectrometric (GC-MS) analysis. Monoterpene hydrocarbons and oxygenated monoterpenes were the major classes of volatiles. The cultivar 'Melalahti' presented lower contents of volatiles compared with 'Ola' and 'Mortti', which showed very similar compositions. Higher contents of volatiles were found in berries cultivated at the higher latitude (66° 34' N) than in those from the southern location (60° 23' N). Among the meteorological variables, radiation and temperature during the last month before harvest were negatively linked with the volatile content. Storage time had a negative impact on the amount of blackcurrant volatiles.
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http://dx.doi.org/10.1021/acs.jafc.8b02070DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6221373PMC
July 2018

Enzymatic Acylation of Anthocyanins Isolated from Alpine Bearberry ( Arctostaphylos alpina) and Lipophilic Properties, Thermostability, and Antioxidant Capacity of the Derivatives.

J Agric Food Chem 2018 Mar 2;66(11):2909-2916. Epub 2018 Mar 2.

Department of Food Science and Engineering , Jinan University , Guangzhou , Guangdong 510632 , People's Republic of China.

Cyanidin-3- O-galactoside (cy-gal) isolated from alpine bearberry ( Arctostaphylos alpine L.) was enzymatically acylated with saturated fatty acids of different chain lengths with Candida antarctica lipase immobilized on acrylic resin (Novozyme 435). The acylation reaction was optimized by considering the reaction medium, acyl donor, substrate molar ratio, reaction temperature, and reaction time. The highest conversion yield of 73% was obtained by reacting cy-gal with lauric acid (molar ratio of 1:10) in tert-butanol at 60 °C for 72 h. A novel compound was synthesized, which was identified as cyanidin-3- O-(6″-dodecanoyl)galactoside by mass spectrometry and nuclear magnetic resonance. Introducing lauric acid into cy-gal significantly improved both the lipophilicity and thermostability and substantially preserved the ultraviolet-visible absorbance and antioxidant properties. The research provides important insight in expanding the application of natural anthocyanins in the cosmetic and food industries.
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http://dx.doi.org/10.1021/acs.jafc.7b05924DOI Listing
March 2018

Sensory and chemical profiles of Finnish honeys of different botanical origins and consumer preferences.

Food Chem 2018 Apr 12;246:351-359. Epub 2017 Oct 12.

Food Chemistry and Food Development, Department of Biochemistry, University of Turku, FI-20014 Turun yliopisto, Finland.

The sensory-chemical profiles of Finnish honeys (labeled as buckwheat, cloudberry-bog, lingonberry, sweet clover, willowherb and multifloral honeys) were investigated using a multi-analytical approach. The sensory test (untrained panel, n = 62) was based on scaling and check-all-that-apply (CATA) methods accompanied with questions on preference and usage of honey. The results were correlated with corresponding profiles of odor-active compounds, determined using gas chromatography coupled with mass spectrometry/olfactometry (GC-MS/O). Botanical origins and chemical compositions including sugars were evaluated using NMR spectroscopy. A total of 73 odor-active compounds were listed based on GC-O. Sweet and mild honeys with familiar sensory properties were preferred by the panelists (PCA, RX(1) = 0.7) while buckwheat and cloudberry-bog honeys with strong odor, flavor and color were regarded as unfamiliar and unpleasant. The data will give the honey industry novel information on honey properties in relation to the botanical origin, and consumer preference.
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http://dx.doi.org/10.1016/j.foodchem.2017.10.069DOI Listing
April 2018

NMR metabolomics demonstrates phenotypic plasticity of sea buckthorn (Hippophaë rhamnoides) berries with respect to growth conditions in Finland and Canada.

Food Chem 2017 Mar 20;219:139-147. Epub 2016 Sep 20.

Food Chemistry and Food Development, Department of Biochemistry, University of Turku, FI-20014 Turun yliopisto, Finland; The Kevo Subarctic Research Institute, University of Turku, FI-20014 Turun yliopisto, Finland.

The berries of sea buckthorn (Hippophaë rhamnoides ssp. rhamnoides) cultivars 'Terhi' and 'Tytti' were studied with respect to their growth location, 60° and 68°N latitude in Finland and 46°N in Canada, using H NMR metabolomics. The berries of 'Terhi' were characterised by stronger signals of quinic acid, while 'Tytti' had higher levels of O-ethyl β-d-glucopyranoside. The metabolic profile of the northernmost berries was distinctly different from those grown in southern Finland or Canada. Berries from northern Finland had relatively higher levels of quinic acid, glucose, l-quebrachitol and ascorbic acid. Ethyl glucoside was shown to accumulate by several fold at the late stage of maturation in the south as it correlated with degree days (r=0.63) and global radiation (r=0.59), but not in the north. The variance in the composition of the sea buckthorn berries demonstrates plasticity in the acclimatisation to growth environments.
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http://dx.doi.org/10.1016/j.foodchem.2016.09.125DOI Listing
March 2017

Comparison of the postprandial effects of purple-fleshed and yellow-fleshed potatoes in healthy males with chemical characterization of the potato meals.

Int J Food Sci Nutr 2015 Aug 10;67(5):581-91. Epub 2016 May 10.

a Division of Food Chemistry and Food Development, Department of Biochemistry , University of Turku , Turku , Finland ;

The aim of the current study was to characterize the anthocyanin content and composition of a purple potato landrace cultivar (Solanum tuberosum 'Synkeä Sakari') and to compare the postprandial effects of purple-fleshed potatoes, yellow-fleshed potatoes and bilberries in potato starch on postprandial glycemia and insulinemia in healthy males. The purple potato meal caused smaller insulinemia than the yellow potato meal (iAUC 120 min 1347 and 2226, respectively, p = 0.012 and iAUC 240 min 1448 and 2403, p = 0.007) or the bilberry meal (iAUC 120 min 1920, p = 0.027). The purple potato meal caused a smaller plasma glucose at 40 min postprandially compared with the yellow potato meal (p = 0.044). The results of this study suggest that anthocyanin-containing purple-fleshed potatoes influence the postprandial insulinemia positively. Since potatoes are the world's largest non-grain commodity, replacing yellow-fleshed potatoes with purple-fleshed potatoes as staple food could have large potential in maintaining public health.
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http://dx.doi.org/10.1080/09637486.2016.1181157DOI Listing
August 2015

Stability of Hydroxycinnamic Acid Derivatives, Flavonol Glycosides, and Anthocyanins in Black Currant Juice.

J Agric Food Chem 2016 Jun 26;64(22):4584-98. Epub 2016 May 26.

Department of Food Science and Engineering, Jinan University , 510632 Guangzhou, China.

The stability of phenolic compounds was followed in black currant juice at ambient temperatures (in light and in dark conditions) and at +4 °C for a year. Analyses were based on high-performance liquid chromatography-diode-array detection-electrospray ionization-mass spectrometry (or tandem mass spectrometry) and high-performance liquid chromatography-diode-array detection-electrospray ionization-quadrupole time-of-flight mass spectrometry methods supported by nuclear magnetic resonance after selective high-performance liquid chromatography isolation. Altogether, 43 metabolites were identified, of which 2-(Z)-p-coumaroyloxymethylene-4-β-d-glucopyranosyloxy-2-(Z)-butenenitrile, 2-(E)-caffeoyloxymethylene-4-β-d-glucopyranosyloxy-2-(Z)-butenenitrile, 1-O-(Z)-p-coumaroyl-β-d-glucopyranose, (Z)-p-coumaric acid 4-O-β-d-glucopyranoside, and (Z)-p-coumaric acid were novel findings in black currant juice. Hydroxycinnamic acid derivatives degraded 20-40% at room temperature during one year of storage, releasing free hydroxycinnamic acids. O-Glucosides of hydroxycinnamic acid compounds were the most stable, followed by O-acylquinic acids, acyloxymethyleneglucosyloxybutenenitriles, and O-acylglucoses. Light induced the isomerization of (E)-coumaric acid compounds into corresponding Z-isomers. Flavonol glycosides stayed fairly stable. Flavonol aglycones were derived mainly from malonylglucosides. Over 90% of anthocyanins were lost at room temperature in a year, practically independent of light. Storage at low temperatures, preferably excluding light, is necessary to retain the original composition of phenolic compounds.
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http://dx.doi.org/10.1021/acs.jafc.6b01005DOI Listing
June 2016

NMR metabolomics of ripened and developing oilseed rape (Brassica napus) and turnip rape (Brassica rapa).

Food Chem 2015 Apr 16;172:63-70. Epub 2014 Sep 16.

Food Chemistry and Food Development, Department of Biochemistry, University of Turku, FI-20014 Turku, Finland.

The oilseeds of the commercially important oilseed rape (Brassica napus) and turnip rape (Brassica rapa) were investigated with (1)H NMR metabolomics. The compositions of ripened (cultivated in field trials) and developing seeds (cultivated in controlled conditions) were compared in multivariate models using principal component analysis (PCA), partial least squares discriminant analysis (PLS-DA), and orthogonal partial least squares discriminant analysis (OPLS-DA). Differences in the major lipids and the minor metabolites between the two species were found. A higher content of polyunsaturated fatty acids and sucrose were observed in turnip rape, while the overall oil content and sinapine levels were higher in oilseed rape. The genotype traits were negligible compared to the effect of the growing site and concomitant conditions on the oilseed metabolome. This study demonstrates the applicability of NMR-based analysis in determining the species, geographical origin, developmental stage, and quality of oilseed Brassicas.
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http://dx.doi.org/10.1016/j.foodchem.2014.09.040DOI Listing
April 2015

¹H NMR spectroscopy reveals the effect of genotype and growth conditions on composition of sea buckthorn (Hippophaë rhamnoides L.) berries.

Food Chem 2014 Mar 3;147:138-46. Epub 2013 Oct 3.

Department of Biochemistry, University of Turku, FI-20014 Turku, Finland.

¹H NMR spectroscopy and multivariate data analysis were applied to the metabolic profiling and discrimination of wild sea buckthorn (Hippophaë rhamnoides L.) berries from different locations in Finland (subspecies (ssp.) rhamnoides) and China (ssp. sinensis). Principal component analysis (PCA) and partial least squares discriminant analysis (PLS-DA) showed discrimination of the two subspecies and different growth sites. The discrimination of ssp. rhamnoides was mainly associated with typically higher temperature, radiation and humidity and lower precipitation in the south, yielding higher levels of O-ethyl β-d-glucopyranoside and d-glucose, and lower levels of malic, quinic and ascorbic acids. Significant metabolic differences (p<0.05) in genetically identical berries were observed between latitudes 60° and 67° north in Finland. High altitudes (> 2,000 m) correlated with greater levels of malic and ascorbic acids in ssp. sinensis. The NMR metabolomics approach applied here is effective for identification of metabolites, geographical origin and subspecies of sea buckthorn berries.
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http://dx.doi.org/10.1016/j.foodchem.2013.09.133DOI Listing
March 2014

Coordinate changes in gene expression and triacylglycerol composition in the developing seeds of oilseed rape (Brassica napus) and turnip rape (Brassica rapa).

Food Chem 2014 Feb 5;145:664-73. Epub 2013 Sep 5.

Department of Biochemistry, University of Turku, FI-20014 Turku, Finland.

Crop production for vegetable oil in the northern latitudes utilises oilseed rape (Brassica napus subsp. oleifera) and turnip rape (B. rapa subsp. oleifera), having similar oil compositions. The oil consists mostly of triacylglycerols, which are synthesised during seed development. In this study, we characterised the oil composition and the expression levels of genes involved in triacylglycerol biosynthesis in the developing seeds in optimal, low temperature (15 °C) and short day (12-h day length) conditions. Gene expression levels of several genes were altered during seed development. Low temperature and short day treatments increased the level of 9,12,15-octadecatrienoic acid (18:3n-3) in turnip rape and short day treatment decreased the total oil content in both species. This study gives a novel view on seed oil biosynthesis under different growth conditions, bringing together gene expression levels of the triacylglycerol biosynthesis pathway and oil composition over a time series in two related oilseed species.
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http://dx.doi.org/10.1016/j.foodchem.2013.08.108DOI Listing
February 2014

Analysis of hydrolyzable tannins and other phenolic compounds in emblic leafflower (Phyllanthus emblica L.) fruits by high performance liquid chromatography-electrospray ionization mass spectrometry.

J Agric Food Chem 2012 Sep 22;60(35):8672-83. Epub 2012 Aug 22.

Department of Biochemistry and Food Chemistry, University of Turku, Turku, Finland.

Phenolic compounds were extracted from dried emblic leafflower (Phyllanthus emblica L.) fruits with methanol and separated by Sephadex LH-20 column chromatography. The raw extracts and fractions were analyzed with HPLC coupled with diode array UV spectroscopy, electrospray ionization mass spectrometry, and tandem mass spectrometry. Mucic acid gallate, mucic acid lactone gallate, monogalloylglucose, gallic acid, digalloylglucose, putranjivain A, galloyl-HHDP-glucose, elaeocarpusin, and chebulagic acid were suggested to be the most abundant compounds in the crude methanol extracts of the fruits. In addition, 144 peaks were detected, of which 67 were tentatively identified mostly as ellagitannins, flavonoids, and simple gallic acid derivatives in the fractions. The results indicated the presence of neochebulagic acid, isomers of neochebuloyl galloylglucose, chebuloyl neochebuloyl galloylglucose, ellagic acid glycosides, quercetin glycosides, and eriodictyol coumaroyl glycosides in the fruits. The study provides a systematic report of the retention data and characteristics of UV, MS, and MS/MS spectra of the phenolic compounds in the fruits of emblic leafflower. The fruits of two varieties (Ping Dan No 1 and Fruity) from Guangxi Province differed from those of wild Tian Chuan emblic leafflower from Fujian Province in the content and profile of phenolic compounds.
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http://dx.doi.org/10.1021/jf302925vDOI Listing
September 2012
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