Discovery and Biosynthetic Origin of Quinolizidomycins A and B, Two Quinolizidine Alkaloids from sp. KIB-1714.

Org Lett

State Key Laboratory of Phytochemistry and Plant Resources in West China and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China.

Published: March 2023

AI Article Synopsis

  • Quinolizidomycins A and B are newly discovered quinolizidine alkaloids with a unique tricyclic ring structure, isolated from the *Streptomyces* species KIB-1714.
  • Their chemical structures were determined through detailed spectroscopic analyses and X-ray diffraction techniques.
  • Research indicates that these compounds are synthesized using lysine, ribose 5-phosphate, and acetate, suggesting a novel assembly process in their biosynthesis; Quinolizidomycin A has shown activity in inhibiting acetylcholinesterase.

Article Abstract

Quinolizidomycins A () and B (), two unprecedented quinolizidine alkaloids featuring a tricyclic 6/6/5 ring system, were isolated from sp. KIB-1714. Their structures were assigned by detailed spectroscopic data analyses and X-ray diffraction. Stable isotope labeling experiments suggested that compounds and are derived from lysine, ribose 5-phosphate, and acetate units, which indicates an unprecedented manner of assembly of the quinolizidine (1-azabicyclo[4.4.0]decane) scaffold in quinolizidomycin biosynthesis. Quinolizidomycin A () was active in an acetylcholinesterase inhibitory assay.

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http://dx.doi.org/10.1021/acs.orglett.3c00478DOI Listing

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