Identification of a novel saxitoxin analogue, 12β-deoxygonyautoxin 3, in the cyanobacterium, anabaena circinalis (TA04)

Takashi Minowa, Yuko Cho, Yasukatsu Oshima, Keiichi Konoki, Mari Yotsu-Yamashita

    Research output: Contribution to journalArticlepeer-review

    10 Citations (Scopus)

    Abstract

    Saxitoxin (STX) and its analogues, the potent voltage-gated sodium channel blockers, are biosynthesized by freshwater cyanobacteria and marine dinoflagellates. We previously identified several biosynthetic intermediates in the extract of the cyanobacterium, Anabaena circinalis (TA04), that are primarily produced during the early and middle stages in the biosynthetic pathway to produce STX. These findings allowed us to propose a putative biosynthetic pathway responsible for STX production based on the structures of these intermediates. In the present study, we identified 12β-deoxygonyautoxin 3 (12β-deoxyGTX3), a novel STX analogue produced by A. circinalis (TA04), by comparing the retention time and MS/MS fragmentation pattern with those of synthetic standards using LC-MS. The presence of this compound in A. circinalis (TA04) is consistent with stereoselective enzymatic oxidations at C11 and C12, and 11-O-sulfation, during the late stage of STX biosynthesis, as proposed in previous studies.

    Original languageEnglish
    Article numbertoxins11090539
    JournalToxins
    Volume11
    Issue number9
    DOIs
    Publication statusPublished - 2019 Sep 16

    Keywords

    • Anabaena circinalis
    • Biosynthesis
    • Gonyautoxin
    • Paralytic shellfish toxins
    • Saxitoxin

    ASJC Scopus subject areas

    • Toxicology
    • Health, Toxicology and Mutagenesis

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