Acylated Flavonoid Glycosides are the Main Pigments that Determine the Flower Colour of the Brazilian Native Tree Tibouchina pulchra (Cham.) Cogn

Molecules. 2019 Feb 16;24(4):718. doi: 10.3390/molecules24040718.

Abstract

Tibouchina pulchra (Cham.) Cogn. is a plant native to Brazil whose genus and family (Melastomataceae) are poorly studied with regards to its metabolite profile. Phenolic pigments of pink flowers were studied by ultra-performance liquid chromatography with a photodiode array detector and electrospray ionization quadrupole time-of-flight mass spectrometry. Therein, twenty-three flavonoids were identified with eight flavonols isolated by preparative high-performance liquid chromatography and analysed by one- and two-dimensional nuclear magnetic resonance. Kaempferol derivatives were the main flavonols, encompassing almost half of the detected compounds with different substitution patterns, such as glucoside, pentosides, galloyl-glucoside, p-coumaroyl-glucoside, and glucuronide. Concerning the anthocyanins, petunidin p-coumaroyl-hexoside acetylpentoside and malvidin p-coumaroyl-hexoside acetylpentoside were identified and agreed with previous reports on acylated anthocyanins from Melastomataceae. A new kaempferol glucoside was identified as kaempferol-(2''-O-methyl)-4'-O-α-d-glucopyranoside. Moreover, twelve compounds were described for the first time in the genus with five being new to the family, contributing to the chemical characterisation of these taxa.

Keywords: Melastomataceae; anthocyanin; flavonol; kaempferol.

MeSH terms

  • Chromatography, High Pressure Liquid
  • Flavonoids / chemistry*
  • Flowers / chemistry*
  • Glycosides / chemistry*
  • Magnetic Resonance Spectroscopy
  • Melastomataceae / chemistry*
  • Pigmentation*
  • Plant Extracts / chemistry
  • Spectrometry, Mass, Electrospray Ionization
  • Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
  • Trees*

Substances

  • Flavonoids
  • Glycosides
  • Plant Extracts