Spirostomin, Defense Toxin of the Ciliate Spirostomum teres: Isolation, Structure Elucidation, and Synthesis

The defense toxins, spirostomins A and B, have been isolated as a diastereomeric mixture from the ciliate microorganism Spirostomum teres. The structure of spirostomin was elucidated through a number of NMR experiments which allowed assigning the unprecedented spiro[(2,5-dimethyl-5,6,7,8-tetrahydron...

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Published inChemistry letters Vol. 44; no. 5; pp. 633 - 635
Main Authors Sera, Yoshihiko, Masaki, Miyuki Eiraku, Doe, Matsumi, Buonanno, Federico, Miyake, Akio, Usuki, Yoshinosuke, Iio, Hideo
Format Journal Article
LanguageEnglish
Published TOKYO Chemical Soc Japan 05.05.2015
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
STENTOR-COERULEUS
CHEMICAL DEFENSE
BLEPHARISMA-JAPONICUM
PHOTORECEPTOR
OXYBLEPHARISMIN
UNICELLULAR ORGANISM
PIGMENT GRANULES
STENOSTOMUM-SPHAGNETORUM
DERIVATIVES
CLIMACOSTOMUM-VIRENS
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Summary:The defense toxins, spirostomins A and B, have been isolated as a diastereomeric mixture from the ciliate microorganism Spirostomum teres. The structure of spirostomin was elucidated through a number of NMR experiments which allowed assigning the unprecedented spiro[(2,5-dimethyl-5,6,7,8-tetrahydronaphthalene-1,4-dione)-8,6'-(pyrane-2',5'-di-one)] skeleton to this natural compound. The total syntheses of the racemic spirostomins confirmed their structure and relative configurations.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.150044