Plants Utilize a Protection/Deprotection Strategy in Limonoid Biosynthesis: A "Missing Link" Carboxylesterase Boosts Yields and Provides Insights into Furan Formation

J Am Chem Soc. 2024 Oct 30;146(43):29305-29310. doi: 10.1021/jacs.4c11213. Epub 2024 Oct 17.

Abstract

The furan ring is a defining feature of limonoids, a class of highly rearranged and bioactive plant tetranortriterpenoids. We recently reported an apparent complete biosynthetic pathway to these important natural furanoids. Herein, we disclose the subsequent discovery of a yield-boosting "missing link" carboxylesterase that selectively deprotects a late-stage intermediate, so triggering more efficient furan biosynthesis. This has allowed, for the first time, the isolation and structural elucidation of unknown intermediates, refining our understanding of furan formation in limonoid biosynthesis.

MeSH terms

  • Carboxylesterase* / chemistry
  • Carboxylesterase* / metabolism
  • Furans* / chemistry
  • Furans* / metabolism
  • Limonins* / biosynthesis
  • Limonins* / chemistry
  • Limonins* / metabolism
  • Molecular Structure

Substances

  • Limonins
  • Furans
  • Carboxylesterase
  • furan