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      Enhanced Bioaccessibility of Crocetin Sugar Esters from Saffron in Infusions Rich in Natural Phenolic Antioxidants

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          Abstract

          The present study aims to examine whether and to what extent the bioaccessibility of the major saffron apocarotenoids, namely crocetin sugar esters (CRTSEs), is affected by the presence of strong water-soluble antioxidants, ingredients of the herbs found in commercial tea blends with saffron. An in vitro digestion model was applied to infusions from these products to investigate the possible changes. All of the studied infusions were rich in total phenols (9.9–22.5 mg caffeic acid equivalents/100 mg dry infusion) and presented strong DPPH radical scavenging activity regardless of the composition of the corresponding herbal blends. RP-HPLC-DAD and LC-MS analysis enabled the grouping of the infusions into hydroxycinnamic acid-rich and in flavan-3-ol-rich ones. CRTSEs in herbal tea infusions were found to be significantly more bioaccessible (66.3%–88.6%) than those in the reference saffron infusion (60.9%). The positive role of strong phenolic antioxidants (caffeic acid, rosmarinic acid) on the stability of CRTSEs was also evidenced in model binary mixtures. On the contrary, cinnamic acid, exerting no antioxidant activity, did not have such an effect. Our findings suggest that strong radical scavengers may protect the crocetin sugar esters from oxidation during digestion when present in excess.

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          Most cited references26

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          In vitro bioaccessibility assessment as a prediction tool of nutritional efficiency.

          The term "bioaccessibility" is a key concept to ascertain nutritional efficiency of food and food formula developed with the aim of improving human health. In this review, working definitions of bioavailability, bioaccessibility, and bioactivity are examined, taking into account the complete sequence of events that take place during the digestive transformation of food into material that can be assimilated by the body, the absorption/assimilation into the cells of the intestinal epithelium, the presystemic metabolism, and, lastly, the development of biologic actions. Comparison among in vivo and in vitro techniques to assess bioaccessibility is accomplished, considering the strengths and limitations of each experimental approach, with a complete description of in vitro procedures applied to determine bioaccessibility of carotenoids. Although a great development has been achieved on the in vitro approaches, these are especially intended for initial screening and should be complemented with in vivo studies, which will remain as the criterion standard for bioaccessibility of nutrients and bioactive compounds at specific target populations. Application of bioaccessibility assessment in foods claiming a health benefit because of their nutrients or bioactive compounds content is described. Measurement of bioaccessibility provides valuable information to select the appropriate dosage and source of food matrices to ensure nutritional efficacy of food products. In addition, in vitro bioactivity measurements to support health benefits of bioactive compounds should be accomplished with estimation of their bioaccessibility, to adequately give nutritional significance to health claims.
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            Determination of saffron (Crocus sativus L.) components in crude plant extract using high-performance liquid chromatography-UV-visible photodiode-array detection-mass spectrometry.

            The determination of saffron components in crude plant extracts by high-performance liquid chromatography-UV-visible photodiode-array detection on-line with mass spectrometry is described. The method is shown to be suitable for the determination of picrocrocin, the glycosidic precursor of safranal, safranal and flavonoids; it is the technique of choice for the analysis of crocetin glycosides (crocins) carrying one up to five glucoses and differentiation of their trans and cis isomers.
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              Crocetin esters, picrocrocin and its related compounds present in Crocus sativus stigmas and Gardenia jasminoides fruits. Tentative identification of seven new compounds by LC-ESI-MS.

              Crocetin esters present in saffron (Crocus sativus L.) stigmas and in Gardenia jasminoides Ellis fruit are the compounds responsible for their color. Of the fifteen crocetin esters identified in this study, five new compounds were tentatively identified: trans and cis isomers of crocetin (beta-D-triglucoside)-(beta-D-gentibiosyl) ester, trans and cis isomers of crocetin (beta-D-neapolitanose)-(beta-D-glucosyl) ester, and cis crocetin (beta-D-neapolitanose)-(beta-D-gentibiosyl) ester. The most relevant differences between both species were a low content of the trans crocetin (beta-D-glucosyl)-(beta-D-gentibiosyl) ester, the absence of trans crocetin di-(beta-D-glucosyl) ester in gardenia, and its higher content of trans crocetin (beta-D-gentibiosyl) ester and cis crocetin di-(beta-D-gentibiosyl) ester. With the same chromatographic method it was possible to identify, in a single run, ten glycosidic compounds in saffron extracts with a UV/vis pattern similar to that of picrocrocin; among them, 5-hydroxy-7,7-dimethyl-4,5,6,7-tetrahydro-3H-isobenzofuranone 5-O-beta-D-gentibioside and 4-hydroxymethyl-3,5,5-trimethyl-cyclohexen-2-one 4-O-beta-D-gentibioside were tentatively identified for the first time in saffron. Of these ten glycosides, only the O-beta-D-gentibiosyl ester of 2-methyl-6-oxo-2,4-hepta-2,4-dienoic acid was found in gardenia samples, but it was possible to identify the iridoid glycoside, geniposide.
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                Author and article information

                Contributors
                Role: Academic Editor
                Journal
                Molecules
                Molecules
                molecules
                Molecules
                MDPI
                1420-3049
                25 September 2015
                October 2015
                : 20
                : 10
                : 17760-17774
                Affiliations
                Laboratory of Food Chemistry and Technology, School of Chemistry, Aristotle University of Thessaloniki, Thessaloniki 54124, Greece; E-Mails: steord@ 123456chem.auth.gr (S.A.O.); ankyria@ 123456chem.auth.gr (A.K.)
                Author notes
                [* ]Author to whom correspondence should be addressed; E-Mail: tsimidou@ 123456chem.auth.gr ; Tel.: +30-2310-997796; Fax: +30-2310-997847.
                Article
                molecules-20-17760
                10.3390/molecules201017760
                6332399
                26404216
                9019051a-0c8c-49ae-921e-72e3aa559696
                © 2015 by the authors.

                Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license ( http://creativecommons.org/licenses/by/4.0/).

                History
                : 25 August 2015
                : 21 September 2015
                Categories
                Article

                crocetin sugar esters,saffron infusions,phenolic antioxidants,in vitro digestion,bioaccessibility

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