Mayu Hakamada, Chihiro Tokairin, Hayate Ishizuka, Kanna Adachi, Toma Osawa, Shiori Aonuma, Ryosuke Hirozumi, Shigeki Tsuchiya, Yuko Cho, Yuta Kudo, Keiichi Konoki, Yasukatsu Oshima, Kazuo Nagasawa, Mari Yotsu-Yamashita
Saxitoxin (STX, 1) is a representative compound of paralytic shellfish toxins (PSTs) that are produced by marine dinoflagellates and freshwater cyanobacteria. Although several pathways have been proposed for the biosynthesis of STX, the order of ring and side chain hydroxylation, and formation of the tricyclic skeleton have not been well established. In this study, 12,12-dideoxy-decarbamoyloxySTX (dd-doSTX, 2), the most reduced STX analogue having the tricyclic skeleton, and its analogues, 12β-deoxy-doSTX (12β-d-doSTX, 3), 12α-deoxy-doSTX (12α-d-doSTX, 4), and doSTX (5), were synthesized, and these compounds were screened in the toxic microalgae using high-resolution LCMSMS...
January 25, 2024: Chemistry: a European Journal