Iridoid glycoside biosynthesis in Penstemon secundiflorus. Another H-5, H-9 trans iridoid glycoside.

Robert E. Krull, Frank R. Stermitz, Henrik Franzyk, Søren Rosendal Jensen

    Research output: Contribution to journalJournal articleResearchpeer-review

    Abstract

    Isolation and characterization of the new iridoid 10-hydroxy-(5 alpha H)-6-epidihydrocornin from Penstemon secundiflorus (Scrophulariaceae) is described. In biosynthetic experiments, deoxyloganic acid was incorporated into the transfused iridoid glycosides (5 alpha H)-6-epidihydrocornin and 10-hydroxy-(5 alpha H)-6-epidihydrocornin in P. secundiflorus. Formation of the trans-fused compounds is therefore a late event in the biosynthesis and does not occur during iridoid formation by cyclization of the open chain monoterpene precursor. In the same plant, 8-epideoxyloganic acid was not incorporated into the trans-iridoids. Deoxyloganic acid was also incorporated into 10-hydroxyhastatoside (which bears an 8 beta-methyl group), while 8-epideoxyloganic acid was incorporated into penstemoside (with an 8 alpha-methyl group). Thus, iridoid biosynthetic pathways leading from both deoxyloganic acid and 8-epideoxyloganic acid were found in the same plant. (C) 1998 Elsevier Science Ltd. All rights reserved.
    Original languageEnglish
    JournalPhytochemistry
    Volume49
    Issue number6
    Pages (from-to)1605-1608
    ISSN0031-9422
    DOIs
    Publication statusPublished - 1998

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