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      Comparison of some secondary metabolite content in the seventeen species of the Boraginaceae family

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          Abstract

          Context: The Boraginaceae family comprises plants that have important therapeutic and cosmetic applications. Their pharmacological effect is related to the presence of naphthaquinones, flavonoids, terpenoids, phenols, or purine derivative – allantoin.

          Objective: In the present study, comparison of some secondary metabolite content and phytochemical relationship between 17 species of the Boraginaceae family were analyzed.

          Materials and methods: High performance capillary electrophoresis (HPCE) was used to perform a chemometric analysis in the following Boraginaceae species: Anchusa azurea Mill., Anchusa undulata L., Borago officinalis L., Buglossoides purpurocaerulea (L.) I.M. Johnst., Cerinthe minor L., Cynoglossum creticum Mill, Echium italicum L., Echium russicum J.F. Gmel., Echium vulgare L., Lindelofia macrostyla (Bunge) Popov (syn. Lindelofia anchusoides (Lindl.) Lehm.), Lithospermum officinale L., Nonea lutea (Desr.) DC., Omphalodes verna Moench (syn. Cynoglossum omphaloides L.), Pulmonaria mollis Wulfen ex Hornem., Pulmonaria obscura Dumort., Symphytum cordatum Waldst. & Kit ex Willd., and Symphytum officinale L.

          Results: Six active compounds in shoot extracts (allantoin, p-hydroxybenzoic acid, rutin, hydrocaffeic acid, rosmarinic acid, and chlorogenic acid) and four compounds in root extracts (allantoin, hydrocaffeic acid, rosmarinic acid, and shikonin) were identified. The presence and abundance of these compounds were used for the characterization of the species and for revealing their phytochemical similarity and differentiation.

          Discussion and conclusion: The present study provides the first comprehensive report of the extraction and quantification of several compounds in Boraginaceae species (some of them for the first time). Among the 17 species studied, species with potentially high pharmacological activity were recognized.

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          Most cited references16

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          The Chemistry and Biology of Alkannin, Shikonin, and Related Naphthazarin Natural Products

          Wound healing properties of plant extracts that contain the naphthoquinone natural products alkannin (1) and shikonin (2) have been known for many centuries. More recently, the biological properties of 1, 2, and related derivatives have been demonstrated experimentally, and their production both by cell cultures and chemical synthesis has been studied extensively.
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            Evolution of rosmarinic acid biosynthesis.

            Rosmarinic acid and chlorogenic acid are caffeic acid esters widely found in the plant kingdom and presumably accumulated as defense compounds. In a survey, more than 240 plant species have been screened for the presence of rosmarinic and chlorogenic acids. Several rosmarinic acid-containing species have been detected. The rosmarinic acid accumulation in species of the Marantaceae has not been known before. Rosmarinic acid is found in hornworts, in the fern family Blechnaceae and in species of several orders of mono- and dicotyledonous angiosperms. The biosyntheses of caffeoylshikimate, chlorogenic acid and rosmarinic acid use 4-coumaroyl-CoA from the general phenylpropanoid pathway as hydroxycinnamoyl donor. The hydroxycinnamoyl acceptor substrate comes from the shikimate pathway: shikimic acid, quinic acid and hydroxyphenyllactic acid derived from l-tyrosine. Similar steps are involved in the biosyntheses of rosmarinic, chlorogenic and caffeoylshikimic acids: the transfer of the 4-coumaroyl moiety to an acceptor molecule by a hydroxycinnamoyltransferase from the BAHD acyltransferase family and the meta-hydroxylation of the 4-coumaroyl moiety in the ester by a cytochrome P450 monooxygenase from the CYP98A family. The hydroxycinnamoyltransferases as well as the meta-hydroxylases show high sequence similarities and thus seem to be closely related. The hydroxycinnamoyltransferase and CYP98A14 from Coleus blumei (Lamiaceae) are nevertheless specific for substrates involved in RA biosynthesis showing an evolutionary diversification in phenolic ester metabolism. Our current view is that only a few enzymes had to be "invented" for rosmarinic acid biosynthesis probably on the basis of genes needed for the formation of chlorogenic and caffeoylshikimic acid while further biosynthetic steps might have been recruited from phenylpropanoid metabolism, tocopherol/plastoquinone biosynthesis and photorespiration.
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              Distribution and function of allantoin (5-ureidohydantoin) in rice grains.

              Despite increasing knowledge of allantoin as a phytochemical involved in rice, relatively little is known about its distribution and function in rice grains. In this study, allantoin was quantified in 15 Chinese rice grains, and its contents varied with grain fraction, cultivar, and genotype. Bran always had the highest allantoin level, followed by brown rice and milled rice. Hull contained the lowest allantoin content. Allantoin in japonica bran ranged from 70 to 171 μg/g but rarely exceeded 100 μg/g in indica bran. There was a positive relationship between allantoin level in grains and seedling survival in seedbeds under low temperature or water deficit. Exogenous allantoin stimulated plant growth, increased soluble sugar and free proline contents, and decreased malondialdehyde content in rice seedlings. However, allantoin did not show any antioxidant activity through free radical-scavenging capacity, reducing power, linoleic acid peroxidation inhibition, and chelating activity. The results suggest that allantoin in rice grains may play some roles in providing plant stress protection but not serving as a beneficial health antioxidant.
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                Author and article information

                Journal
                Pharm Biol
                Pharm Biol
                IPHB
                iphb20
                Pharmaceutical Biology
                Taylor & Francis
                1388-0209
                1744-5116
                2017
                31 January 2017
                : 55
                : 1
                : 691-695
                Affiliations
                [a ]Department of Plant Physiology, Maria Curie-Skłodowska University , Lublin, Poland;
                [b ]Botanical Garden of Maria Curie-Skłodowska University , Lublin, Poland
                Author notes
                CONTACT Sławomir Dresler slawomir.dresler@ 123456poczta.umcs.lublin.pl Department of Plant Physiology, Maria Curie-Skłodowska, University , Akademicka 19, 20-033Lublin, Poland
                Article
                1265986
                10.1080/13880209.2016.1265986
                6130574
                28140740
                171453a3-f675-4b99-95f2-c4ae999fd83b
                © 2017 The Author(s). Published by Informa UK Limited, trading as Taylor & Francis Group.

                This is an Open Access article distributed under the terms of the Creative Commons Attribution License ( http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

                History
                : 15 February 2016
                : 22 August 2016
                : 22 November 2016
                Page count
                Pages: 5, Words: 3707
                Categories
                Research Article

                chemometrics,capillary electrophoresis,allantoin,rosmarinic acid,shikonin,rutin

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