Chemotaxonomy of Plantago. Iridoid glucosides and caffeoyl phenylethanoid glycosides

N. Rønsted, E. Göbel, Henrik Franzyk, Søren Rosendal Jensen, C. E. Olsen

    Research output: Contribution to journalJournal articleResearchpeer-review

    Abstract

    Data for 34 species of Plantago (Plantaginaceae), including subgen. Littorella (=Littorella uniflora), have been collected with regard to their content of iridoid glucosides and caffeoyl phenylethanoid glycosides (CPGs). In the present work, 21 species were investigated for the first time and many known compounds were found together with three new iridoid glucosides. Of these, arborescoside and arborescosidic acid, both of the uncommon type with an 8,9-double bond, were present in several species, while 6-deoxymelittoside was found only in P, subulata. The known compounds deoxyloganic acid, caryoptoside and rehmannioside D were isolated from the genus for the first time. The earlier reported occurrence of sorbitol in the family was confirmed, and this compound was shown by NMR spectroscopy to be the main sugar in the three species investigated for this. The combined data show that CPGs are present in all species investigated. With regard to the iridoids, the distribution patterns showed a good correlation with the classification of Rahn. Thus, aucubin is typical for the whole genus, while bartsioside and catalpol as well as 5-substituted iridoids are each characteristic for a subgenus in the family. Finally, the close relationship between Plantago and Veronica suggested by chloroplast DNA sequence analysis, could be corroborated by the common occurrence of the rare 8,9-unsaturated iridoids in these two genera. (C) 2000 Elsevier Science Ltd. All rights reserved.
    Original languageEnglish
    JournalPhytochemistry
    Volume55
    Issue number4
    Pages (from-to)337-348
    ISSN0031-9422
    DOIs
    Publication statusPublished - 2000

    Cite this

    Rønsted, N. ; Göbel, E. ; Franzyk, Henrik ; Jensen, Søren Rosendal ; Olsen, C. E. / Chemotaxonomy of Plantago. Iridoid glucosides and caffeoyl phenylethanoid glycosides. In: Phytochemistry. 2000 ; Vol. 55, No. 4. pp. 337-348.
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    title = "Chemotaxonomy of Plantago. Iridoid glucosides and caffeoyl phenylethanoid glycosides",
    abstract = "Data for 34 species of Plantago (Plantaginaceae), including subgen. Littorella (=Littorella uniflora), have been collected with regard to their content of iridoid glucosides and caffeoyl phenylethanoid glycosides (CPGs). In the present work, 21 species were investigated for the first time and many known compounds were found together with three new iridoid glucosides. Of these, arborescoside and arborescosidic acid, both of the uncommon type with an 8,9-double bond, were present in several species, while 6-deoxymelittoside was found only in P, subulata. The known compounds deoxyloganic acid, caryoptoside and rehmannioside D were isolated from the genus for the first time. The earlier reported occurrence of sorbitol in the family was confirmed, and this compound was shown by NMR spectroscopy to be the main sugar in the three species investigated for this. The combined data show that CPGs are present in all species investigated. With regard to the iridoids, the distribution patterns showed a good correlation with the classification of Rahn. Thus, aucubin is typical for the whole genus, while bartsioside and catalpol as well as 5-substituted iridoids are each characteristic for a subgenus in the family. Finally, the close relationship between Plantago and Veronica suggested by chloroplast DNA sequence analysis, could be corroborated by the common occurrence of the rare 8,9-unsaturated iridoids in these two genera. (C) 2000 Elsevier Science Ltd. All rights reserved.",
    author = "N. R{\o}nsted and E. G{\"o}bel and Henrik Franzyk and Jensen, {S{\o}ren Rosendal} and Olsen, {C. E.}",
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    Chemotaxonomy of Plantago. Iridoid glucosides and caffeoyl phenylethanoid glycosides. / Rønsted, N.; Göbel, E.; Franzyk, Henrik; Jensen, Søren Rosendal; Olsen, C. E.

    In: Phytochemistry, Vol. 55, No. 4, 2000, p. 337-348.

    Research output: Contribution to journalJournal articleResearchpeer-review

    TY - JOUR

    T1 - Chemotaxonomy of Plantago. Iridoid glucosides and caffeoyl phenylethanoid glycosides

    AU - Rønsted, N.

    AU - Göbel, E.

    AU - Franzyk, Henrik

    AU - Jensen, Søren Rosendal

    AU - Olsen, C. E.

    PY - 2000

    Y1 - 2000

    N2 - Data for 34 species of Plantago (Plantaginaceae), including subgen. Littorella (=Littorella uniflora), have been collected with regard to their content of iridoid glucosides and caffeoyl phenylethanoid glycosides (CPGs). In the present work, 21 species were investigated for the first time and many known compounds were found together with three new iridoid glucosides. Of these, arborescoside and arborescosidic acid, both of the uncommon type with an 8,9-double bond, were present in several species, while 6-deoxymelittoside was found only in P, subulata. The known compounds deoxyloganic acid, caryoptoside and rehmannioside D were isolated from the genus for the first time. The earlier reported occurrence of sorbitol in the family was confirmed, and this compound was shown by NMR spectroscopy to be the main sugar in the three species investigated for this. The combined data show that CPGs are present in all species investigated. With regard to the iridoids, the distribution patterns showed a good correlation with the classification of Rahn. Thus, aucubin is typical for the whole genus, while bartsioside and catalpol as well as 5-substituted iridoids are each characteristic for a subgenus in the family. Finally, the close relationship between Plantago and Veronica suggested by chloroplast DNA sequence analysis, could be corroborated by the common occurrence of the rare 8,9-unsaturated iridoids in these two genera. (C) 2000 Elsevier Science Ltd. All rights reserved.

    AB - Data for 34 species of Plantago (Plantaginaceae), including subgen. Littorella (=Littorella uniflora), have been collected with regard to their content of iridoid glucosides and caffeoyl phenylethanoid glycosides (CPGs). In the present work, 21 species were investigated for the first time and many known compounds were found together with three new iridoid glucosides. Of these, arborescoside and arborescosidic acid, both of the uncommon type with an 8,9-double bond, were present in several species, while 6-deoxymelittoside was found only in P, subulata. The known compounds deoxyloganic acid, caryoptoside and rehmannioside D were isolated from the genus for the first time. The earlier reported occurrence of sorbitol in the family was confirmed, and this compound was shown by NMR spectroscopy to be the main sugar in the three species investigated for this. The combined data show that CPGs are present in all species investigated. With regard to the iridoids, the distribution patterns showed a good correlation with the classification of Rahn. Thus, aucubin is typical for the whole genus, while bartsioside and catalpol as well as 5-substituted iridoids are each characteristic for a subgenus in the family. Finally, the close relationship between Plantago and Veronica suggested by chloroplast DNA sequence analysis, could be corroborated by the common occurrence of the rare 8,9-unsaturated iridoids in these two genera. (C) 2000 Elsevier Science Ltd. All rights reserved.

    U2 - 10.1016/S0031-9422(00)00306-X

    DO - 10.1016/S0031-9422(00)00306-X

    M3 - Journal article

    VL - 55

    SP - 337

    EP - 348

    JO - Phytochemistry

    JF - Phytochemistry

    SN - 0031-9422

    IS - 4

    ER -