Study on the Preparation and Chemical Structure Characterization of Melanin from Boletus griseus

Int J Mol Sci. 2018 Nov 23;19(12):3736. doi: 10.3390/ijms19123736.

Abstract

In this study, melanin (BgM) was obtained from Boletus griseus. The chemical composition and structure of BgM were characterized by UV-visible absorption spectrum, Fourier transform infrared spectrum, elemental analysis, nuclear magnetic resonance, pyrolysis gas chromatography mass spectrometry, and ultra-performance liquid chromatography⁻high resolution mass spectrometry. The percentage contents of C, H, N, S and O elements were 56.38%, 5.86%, 6.17%, 2.44%, and 28.04%, and the S/N and C/N ratios were 0.17 and 10.66, respectively. The UV-vis spectrum of BgM showed a maximum absorption peak at 214 nm. Characteristic absorption peaks were observed at 3426, 1600 and 1105 cm-1, and BgM contained phenolic hydroxyl, amidogen, carbonyl, methylene, and methyl groups. Moreover, BgM is an eumelanin, and its main skeleton has both a benzene ring and an indole, and the branched chain mainly consists of alkanes, alcohols, and fatty acids. BgM was hydrolyzed by H₂O₂ and four compounds were tentatively analyzed from the UPLC-MS/MS profile. The chemical structure of BgM was characterized as 5,6-dihydroxyindole eumelanin, and the condensed molecular formula is [C28(OR₁)₄(OR₂)₃H11O₆N₄]n.

Keywords: Boletus griseus; chemical structure; mass spectrometry; melanin.

MeSH terms

  • Basidiomycota / chemistry*
  • Gas Chromatography-Mass Spectrometry
  • Magnetic Resonance Spectroscopy
  • Melanins / chemistry*
  • Melanins / isolation & purification*
  • Molecular Structure*
  • Solubility
  • Spectrum Analysis
  • Tandem Mass Spectrometry

Substances

  • Melanins