Accumulation of tilianin and rosmarinic acid and expression of phenylpropanoid biosynthetic genes in Agastache rugosa

J Agric Food Chem. 2012 Jun 13;60(23):5945-51. doi: 10.1021/jf300833m. Epub 2012 Jun 4.

Abstract

Korean mint (Agastache rugosa), a perennial, medicinal plant of the Labiatae family, has many useful constituents, including monoterpenes and phenylpropanoids. Among these, tilianin and rosmarinic acid, 2 well-known natural products, have many pharmacologically useful properties. Chalcone synthase (CHS) and chalcone isomerase (CHI) catalyze the first and second committed steps in the phenylpropanoid pathway of plants, leading to the production of tilianin. In this study, cDNAs encoding CHS (ArCHS) and CHI (ArCHI) were isolated from A. rugosa using rapid amplification of cDNA ends (RACE)-PCR. Amino acid sequence alignments showed that ArCHS and ArCHI shared high sequence identity and active sites with their respective orthologous genes. Quantitative real-time PCR analysis was used to determine the expression levels of genes involved in tilianin and rosmarinic acid biosyntheses in the flowers, leaves, stems, and roots of A. rugosa. High-performance liquid chromatography (HPLC) revealed that the accumulation pattern of tilianin matched the expression patterns of ArCHS and ArCHI in different organs of A. rugosa. Moreover, acacetin, the precursor of tilianin, also demonstrated an accumulation pattern congruent with the expression of these 2 genes. The transcription levels of ArPAL, ArC4H, and Ar4CL were the highest in the leaves or flowers of the plant, which also contained a relatively high amount of rosmarinic acid. However, the roots showed a significant content of rosmarinic acid, although the transcription of ArPAL, ArC4H, and Ar4CL were low. The findings of our study support the medicinal usefulness of A. rugosa and indicate targets for increasing tilianin and rosmarinic acid production in this plant.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acyltransferases / metabolism
  • Agastache / chemistry
  • Agastache / genetics*
  • Amino Acid Sequence
  • Cinnamates / analysis*
  • Cloning, Molecular
  • DNA, Complementary / genetics
  • Depsides / analysis*
  • Flavonoids / analysis*
  • Gene Expression Regulation, Plant*
  • Glycosides / analysis*
  • Intramolecular Lyases / metabolism
  • Molecular Sequence Data
  • Plant Leaves / chemistry
  • Plant Roots / chemistry
  • Plant Roots / genetics
  • Plants, Medicinal / chemistry
  • Plants, Medicinal / genetics
  • RNA, Plant / genetics
  • Real-Time Polymerase Chain Reaction
  • Rosmarinic Acid
  • Sequence Alignment

Substances

  • Cinnamates
  • DNA, Complementary
  • Depsides
  • Flavonoids
  • Glycosides
  • RNA, Plant
  • tilianin
  • Acyltransferases
  • flavanone synthetase
  • Intramolecular Lyases
  • chalcone isomerase