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Quantitation of Oleuropein and Related Phenolics in Cured Spanish-Style Green, California- Style Black Ripe, and Greek-Style Natural Fermentation Olives

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Quantitation of Oleuropein and Related Phenolics in Cured Spanish-Style Green, California- Style Black Ripe, and Greek-Style Natural Fermentation Olives UC Davis UC Davis Previously Published Works Title Quantitation of Oleuropein and Related Phenolics in Cured Spanish-Style Green, California- Style Black Ripe, and Greek-Style Natural Fermentation Olives. Permalink https://escholarship.org/uc/item/3t34332d Journal Journal of agricultural and food chemistry, 66(9) ISSN 0021-8561 Authors Johnson, Rebecca Melliou, Eleni Zweigenbaum, Jerry et al. Publication Date 2018-03-01 DOI 10.1021/acs.jafc.7b06025 Peer reviewed eScholarship.org Powered by the California Digital Library University of California Article Cite This: J. Agric. Food Chem. 2018, 66, 2121−2128 pubs.acs.org/JAFC Quantitation of Oleuropein and Related Phenolics in Cured Spanish-Style Green, California-Style Black Ripe, and Greek-Style Natural Fermentation Olives † ‡ § Rebecca Johnson, Eleni Melliou, Jerry Zweigenbaum, and Alyson E. Mitchell* † Department of Food Science and Technology, University of California, Davis, One Shields Avenue, Davis, California 95616, United States ‡ Department of Pharmacognosy and Natural Products Chemistry, Faculty of Pharmacy, University of Athens, Panepistimiopolis Zografou, GR-15771 Athens, Greece § Agilent Technologies, 2850 Centerville Road, Wilmington, Delaware 19808, United States *S Supporting Information ABSTRACT: Oleuropein, ligstroside, and related hydrolysis products are key contributors to olive bitterness, and several of these phenolics are implicated in the prevention of lifestyle age-related diseases. While table olive processing methods are designed to reduce oleuropein, the impact of processing on ligstroside and related hydrolysis products (e.g., oleacein, oleocanthal, hydroxytyrosol glucoside, ligstroside aglycone, and oleuropein aglycone) is relatively unknown. Herein, levels of these com- pounds were measured in Spanish-style green (SP), Californian-style black ripe (CA), and Greek-style natural fermentation (GK) olives using rapid ultrahigh-performance liquid chromatography (UHPLC) tandem mass spectrometry (MS/MS). GK olives had the highest concentration of all compounds measured, with the exception of oleocanthal, which was highest in SP olives (0.081 mg kg−1 wet weight (w.wt)). CA olives had the lowest levels of most compounds measured, including ligstroside (0.115 mg kg−1 w.wt) and oleuropein (0.974 mg kg−1 w.wt). Hydroxytyrosol was the predominate compound in all three styles of commercial olives, with similar concentrations observed for GK and SP olives (134.329 and 133.685 mg kg−1 w.wt, respectively) and significantly lower concentrations observed for CA olives (19.981 mg kg−1 w.wt). KEYWORDS: olives, Olea europaea, phenolics, UHPLC, MS/MS, oleuropein, oleocanthal, ligstroside, oleacein, oleuropein aglycone ■ INTRODUCTION of endogenous β-glucosidases and esterases,13 which can hydro- 15 Olives, the edible drupes from the olive tree (Olea europaea), are lyze oleuropein and ligstroside into a range of compounds. a popular food consumed worldwide. Table olives and olive oil Hydrolysis can also continue after harvest due to the action of enzymes from lactic acid bacteria that proliferate during are a major component of the Mediterranean diet: a diet linked to 16 β reducing cardiovascular disease,1 Alzheimer’sdisease,2,3 and other storage. Hydrolysis by -glucosidase results in the formation age-related conditions.4 Olives are an important part of this diet of oleuropein aglycone and ligstroside aglycone (Figure 1). The not just for their monounsaturated fatty acids, but also a phenolic aglycones can undergo further ester hydrolysis to produce composition that is unique to Olea europaea.5 Olive oil contains elenolic acid and hydroxytyrosol or tyrosol. Decarboxylation of Downloaded via UNIV OF CALIFORNIA DAVIS on July 18, 2018 at 20:50:29 (UTC). phenolic compounds including oleuropein, hydroxytyrosol, and the aglycones with no ester hydrolysis results in formation of tyrosol which have demonstrated antioxidant,6 anti-inflamma- oleacein and oleocanthal (Figure 1). Direct ester hydrolysis of See https://pubs.acs.org/sharingguidelines for options on how to legitimately share published articles. 7 8 9 oleuropein or ligstroside (i.e., loss of hydroxytyrosol or tyrosol) tory, anticancer, antimicrobial, and antiviral properties. The 17 olive phenolic oleocanthal exhibits ibuprofen-like activity and is results in formation on oleoside methyl ester (Figure 1). active toward inflammatory diseases including neurodegenerative Although oleuropein is considered the primary bitter fi 7,10 compound in olives, ligstroside aglycone, oleuropein aglycone, diseases, joint-degenerative diseases, and some speci c cancers. 18 Oleuropein (Figure 1) is the most prevalent phenolic present oleacein, and oleocanthal also correlate with olive oil bitterness. in olives at harvest, and levels in mature olives can reach concen- Sensory evaluation of isolated forms of these compounds trations as high as 140 mg g−1 dry weight (d.wt).11 Oleuropein is indicate that they are bitter, astringent, and or pungent with fi taste thresholds that vary from 0.05 to 1.6 mM, whereas tyrosol is an intensely bitter compound, and levels need to be signi cantly 19 reduced before olives become edible.12 Oleuropein and its nonbitter. Oleocanthal is characterized as a stinging irritant at the back of the throat and contributes to bitterness perception in biosynthetic precursor, ligstroside (Figure 1), are phenolic esters 20 of glycosylated elenolic acid that undergo hydrolysis to form a olive oil. Isolated ligstroside has not been directly evaluated for range of related phenolic compounds. Different styles of olive sensorial bitterness but the high structural similarity to curing will result in a different complement of hydrolysis prod- ucts13 and impact both the flavor and health-promoting prop- Received: December 21, 2017 erties of various styles of cured table olives. Revised: February 8, 2018 Oleuropein and ligstroside accumulate during olive matura- Accepted: February 9, 2018 tion.14 Damage to the fruit during ripening can result in the release Published: February 9, 2018 © 2018 American Chemical Society 2121 DOI: 10.1021/acs.jafc.7b06025 J. Agric. Food Chem. 2018, 66, 2121−2128 Journal of Agricultural and Food Chemistry Article Figure 1. Structures of oleuropein, ligstroside, and related hydrolysis products. oleuropein and oleocanthal suggest that this compound is also reported for olive phenolics using mass spectrometric methods bitter.21 are 10−100× more sensitive than spectrophotometric meth- Olives are cured (i.e., processed) to reduce bitterness and ods,26,40,42 with the exception of oleuropein which has a LOD of create edible products. The most common commercial methods 200−800 μg/L for DAD detection,35,43 140 μg/L for fluores- used to produce table olives are GK, SP, and CA.46 GK methods cence,41 and 3 and 10 μg/L for ion trap MS42 and MS/MS detec- use ripe olives that are either gradually fermented in brine, dry tion, respectively.26 cured with salt, sun cured on the tree, or cured in oil.22,23 SP Mass spectrometry methods sensitive enough to measure the methods use unripe green olives that are cured briefly in lye hydrolysis products of oleuropein and ligstroside at concen- (sodium hydroxide), then fermented, and finally pasteurized.24,25 trations present in processed table olives have focused primarily 31,32 CA methods use green unripe olives that are cured over several on olive oil. Although hydroxytyrosol, tyrosol, oleuropein days in lye, with air oxidation, and then followed by steril- aglycone, oleuropein, hydroxytyrosol glucoside, 3,4-dihydrox- ization.26,27 Lye promotes the base-catalyzed hydrolysis of yphenyl acetic acid, elenolic acid, and ligstroside aglycone have 26,44,45 oleuropein and ligstroside into nonbitter products. Fermenta- been measured in processed table olives, oleacein, oleo- tion-based processing relies on the action of endogenous and canthal, and ligstroside, have not. Oleocanthal and oleacein are microbial enzymes in addition to the acid-catalyzed hydrolysis of bitter compounds, and there is a strong indication ligstroside is as oleuropein and ligstroside.28 To date, it is not clear how differing well. Additionally, ligstroside is both a precursor of oleuropein processing methods influence the range of these related phenolic and a source of the bitter compounds ligstroside aglycone and ff oleocanthal. However, only a direct sensory study can confirm compounds in di erent olive products. 47−50 Phenolic compounds in olives have been quantitated using a the bitterness of ligstroside. variety of instrumentational methods. HPLC methods employ- Herein a UHPLC-(ESI) MS/MS method was developed to ing spectrophotometric detection (e.g., ultraviolet/visible (UV/vis) measure 11 compounds related to olive bitterness at high sensitivity fi and diode array detection [DAD]) have been used to measure and selectivity. Compounds were quanti ed in CA, SP, and GK table oleuropein, ligstroside, oleuropein aglycone, ligstroside aglycone, olives. Characterizing oleuropein and ligstroside as well as the full oleacein, oleocanthal, hydroxytyrosol, tyrosol, elenolic acid, and range of their hydrolysis products in response to curing will pro- − hydroxytyrosol glucoside,29 32 as well as other phenolics present vide a greater understanding of how these compounds respond to − fl in olives including phenolic acids,30,33 36 anthocyanins,29,37 processing conditions and possibly allow for tighter control of avor 30,33,35 fl 29,34,35 (i.e., bitterness), while developing table olives products with target lignans, and avonoids.
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