Plumeridoid C from the Amazonian traditional medicinal plant Himatanthus sucuuba

Acta Crystallogr C. 2011 Oct;67(Pt 10):o409-12. doi: 10.1107/S0108270111035761. Epub 2011 Sep 29.

Abstract

The stereochemistry of the iridoid plumeridoid C, C(15)H(18)O(7), was established by X-ray single-crystal structure analysis, giving (2'R,3R,4R,4aS,7aR)-methyl 3-hydroxy-4'-[(S)-1-hydroxyethyl]-5'-oxo-3,4,4a,7a-tetrahydro-1H,5'H-spiro[cyclopenta[c]pyran-7,2'-furan]-4-carboxylate. The absolute structure of the title compound was determined on the basis of the Flack x parameter and Bayesian statistics on Bijvoet differences. The hydrogen-bond donor and acceptor functions of the two hydroxy groups are employed in the formation of O-H···O-bonded helical chains.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Apocynaceae / chemistry*
  • Crystallography, X-Ray
  • Furans / chemistry*
  • Hydrogen Bonding
  • Molecular Structure
  • Pyrans / chemistry*
  • Spiro Compounds / chemistry*
  • Stereoisomerism

Substances

  • (2'R,3R,4R,4aS,7aR)-methyl-3-hydroxy-4'-((S)-1-hydroxyethyl)-5'-oxo-3,4,4a,7a-tetrahydro-1H,5'H-spiro(cyclopenta(c)pyran-7,2'-furan)-4-carboxylate
  • Furans
  • Pyrans
  • Spiro Compounds