Structure elucidation and chiral-total synthesis of a new indole alkaloid, (-)-9-methoxymitralactonine, isolated from Mitragyna speciosa in Malaysia

Hiromitsu Takayama, Mika Kurihara, Mariko Kitajima, Ikram M. Said, Norio Aimi

    Research output: Contribution to journalArticle

    21 Citations (Scopus)

    Abstract

    A new Corynanthe-type indole alkaloid, (-)-9-methoxymitralactonine (1), having a highly conjugated system was isolated from the young leaves of Mitragyna speciosa in Malaysia, and its structure was first deduced by spectroscopic analysis and then confirmed by chiral-total synthesis starting from optically pure epoxy-ketone and 5-methoxy-3,4-dihydro-β-carboline. The chiral HPLC analysis demonstrated that the natural 9-methoxymitralactonine contained predominantly the (-)-enantiomer over the (+)-enantiomer in the ratio of 62:38. (C) 2000 Elsevier Science Ltd.

    Original languageEnglish
    Pages (from-to)3145-3151
    Number of pages7
    JournalTetrahedron
    Volume56
    Issue number20
    DOIs
    Publication statusPublished - 12 May 2000

    Fingerprint

    Mitragyna
    Indole Alkaloids
    Carbolines
    Enantiomers
    Malaysia
    Ketones
    High Pressure Liquid Chromatography
    Spectroscopic analysis
    corynanthe

    Keywords

    • Alkaloids
    • Asymmetric synthesis
    • Indoles

    ASJC Scopus subject areas

    • Biochemistry
    • Organic Chemistry
    • Drug Discovery

    Cite this

    Structure elucidation and chiral-total synthesis of a new indole alkaloid, (-)-9-methoxymitralactonine, isolated from Mitragyna speciosa in Malaysia. / Takayama, Hiromitsu; Kurihara, Mika; Kitajima, Mariko; Said, Ikram M.; Aimi, Norio.

    In: Tetrahedron, Vol. 56, No. 20, 12.05.2000, p. 3145-3151.

    Research output: Contribution to journalArticle

    Takayama, Hiromitsu ; Kurihara, Mika ; Kitajima, Mariko ; Said, Ikram M. ; Aimi, Norio. / Structure elucidation and chiral-total synthesis of a new indole alkaloid, (-)-9-methoxymitralactonine, isolated from Mitragyna speciosa in Malaysia. In: Tetrahedron. 2000 ; Vol. 56, No. 20. pp. 3145-3151.
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