New pyrrole alkaloids with bulky N-alkyl side chains containing stereogenic centers from Lycium chinense

Ui Joung Youn, Yun Seo Kil, Joo Won Nam, Yoo Jin Lee, Jinwoong Kim, Dongho Lee, Je Hyun Lee, Eun Kyoung Seo

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Four new pyrrole alkaloids, methyl 2-[2-formyl-5-(methoxymethyl)-1H-pyrrol- 1-yl]propanoate (1), methyl 2-[2-formyl-5-(methoxymethyl)-1H-pyrrol-1-yl]-3-(4- hydroxyphenyl)propanoate (2), dimethyl 2-[2-formyl-5-(methoxymethyl)-1H-pyrrol- 1-yl]butanedioate (3), and dimethyl 2-[2-formyl-5-(methoxymethyl)-1H-pyrrol-1- yl]pentanedioate (4), were isolated from the AcOEt extract of the fruits of Lycium chinense Miller (Solanaceae). The stereogenic center C(2) in the bulky N-alkyl side chain in each of 1-4 seems to hold the H-atoms of nearby CH 2 groups, CH2(7′) and CH2(3) (if R≠H), leading to two different chemical shifts in the 1H-NMR spectrum due to their diastereotopic characteristics. In the 1H-NMR data of each of 2-4, the enhancement of H-C(2) signal was inhibited by the R group, probably due to steric hindrance, and its chemical shift was influenced by the anisotropy effect. The structures of 1-4 were elucidated by analysis of various spectroscopic data, including 1D- and 2D-NMR.

Original languageEnglish
Pages (from-to)1482-1487
Number of pages6
JournalHelvetica Chimica Acta
Volume96
Issue number8
DOIs
Publication statusPublished - 2013 Aug 1

Keywords

  • Alkaloids
  • Lycium chinense
  • Pyrrole alkaloids

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Catalysis
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Inorganic Chemistry

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  • Cite this

    Joung Youn, U., Kil, Y. S., Nam, J. W., Jin Lee, Y., Kim, J., Lee, D., Lee, J. H., & Seo, E. K. (2013). New pyrrole alkaloids with bulky N-alkyl side chains containing stereogenic centers from Lycium chinense. Helvetica Chimica Acta, 96(8), 1482-1487. https://doi.org/10.1002/hlca.201200608