Barricyclin D1-a dimeric ellagitannin with a macrocyclic structure-and accompanying tannins from Barringtonia racemosa

Biosci Biotechnol Biochem. 2021 Jun 24;85(7):1609-1620. doi: 10.1093/bbb/zbab073.

Abstract

Our examination of high molecular weight polyphenolic constituents in the leaves of Barringtonia racemosa of the family Lecythidaceae uncovered 5 previously undescribed ellagitannins. One, barringtin M1 (1), among them was a hydrolysable tannin monomer, while remaining 4, barringtins D1 (2), D2 (3), D3 (4), and barricyclin D1 (5), were all dimers. Barricyclin D1 had a first macrocyclic structure formed from casuarictin (6) and tellimagrandin I (7), and the other ellagitannins had structures related to 5. Two additional known phenolics, valoneic acid dilactone (8) and schimawalin A (9), were also isolated from the leaves. These results suggested that the leaves of B. racemosa are a natural resource rich in hydrolysable tannin oligomers.

Keywords: Barringtonia racemosa; Lecythidaceae; barricyclin D1; ellagitannin; macrocyclic structure.

MeSH terms

  • Barringtonia / chemistry*
  • Chromatography, High Pressure Liquid / methods
  • Dimerization
  • Hydrolyzable Tannins / chemistry
  • Hydrolyzable Tannins / isolation & purification*
  • Molecular Structure
  • Plant Leaves / chemistry
  • Spectrum Analysis / methods

Substances

  • Hydrolyzable Tannins
  • ellagitannin

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