Isolation, ECD assisted structural analyses, biosynthetic discussions, and biological activities of epi-cochlioquinones D and its derivatives

Miki Arayama, Tatsuo Nehira, Hayato Maeda, Kazuaki Tanaka, Hisashi Miyagawa, Tamio Ueno, Seijiro Hosokawa, Masaru Hashimoto

    Research output: Contribution to journalArticle

    7 Citations (Scopus)

    Abstract

    epi-Cochlioquinone D (1) and its 12-α-hydroxyderivative (2) were isolated from Helminthosporium velutinum TS28 based on antifungal screening against Cochliobolus miyabeanus. Relative configurations were established by the NMR analyses except for C5 locating far from the other asymmetric centers. ECD discussions involving spectral comparison with those of other related molecules as well as those based on theoretical calculations disclosed not only the C5 configuration but also the chirality for C12-C22 polycyclic moiety. H. velutinum TS28 also afforded precochlioquinol D (3), just the side chain component, which led us to discuss their biosynthetic pathway. Although 1 and 2 inhibit C. miyabeanus effectively, the C-14 epimeric cochlioquinones scarcely inhibited in spite of very close structures. Present study further revealed that C. miyabeanus tightly recognizes both the polycyclic moiety and the side chain. In contrast, both cochlioquinones and epi-cochlioquinones exhibited potent cytotoxicity against human colon adenocarcinoma (COLO 201) cells regardless of the C14 configuration as well as type of side chains.

    Original languageEnglish
    Pages (from-to)4788-4794
    Number of pages7
    JournalTetrahedron
    Volume71
    Issue number29
    DOIs
    Publication statusPublished - 2015

    Fingerprint

    Helminthosporium
    Ascomycota
    Chirality
    Biosynthetic Pathways
    Cytotoxicity
    Bioactivity
    Screening
    Colon
    Adenocarcinoma
    Nuclear magnetic resonance
    Derivatives
    Molecules

    Keywords

    • Absolute configuration
    • Biological properties
    • Biosynthetic discussions
    • Calculations of ECD spectra
    • Difference ECD spectra
    • SAR study

    ASJC Scopus subject areas

    • Biochemistry
    • Organic Chemistry
    • Drug Discovery

    Cite this

    Isolation, ECD assisted structural analyses, biosynthetic discussions, and biological activities of epi-cochlioquinones D and its derivatives. / Arayama, Miki; Nehira, Tatsuo; Maeda, Hayato; Tanaka, Kazuaki; Miyagawa, Hisashi; Ueno, Tamio; Hosokawa, Seijiro; Hashimoto, Masaru.

    In: Tetrahedron, Vol. 71, No. 29, 2015, p. 4788-4794.

    Research output: Contribution to journalArticle

    Arayama, Miki ; Nehira, Tatsuo ; Maeda, Hayato ; Tanaka, Kazuaki ; Miyagawa, Hisashi ; Ueno, Tamio ; Hosokawa, Seijiro ; Hashimoto, Masaru. / Isolation, ECD assisted structural analyses, biosynthetic discussions, and biological activities of epi-cochlioquinones D and its derivatives. In: Tetrahedron. 2015 ; Vol. 71, No. 29. pp. 4788-4794.
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