Selaginellin A and B, two novel natural pigments isolated from Selaginella tamariscina

Chem Pharm Bull (Tokyo). 2008 Jul;56(7):982-4. doi: 10.1248/cpb.56.982.

Abstract

Two new unusual natural pigments were first isolated from the whole herbs of Selaginella tamariscina. The structure of selaginellin A (1) was established as (R,S)-4-[(4'-hydroxy-3-((4-hydroxyphenyl)ethynyl)biphenyl-2-yl)(4-hydroxyphenyl)methylene]-2,5-cyclohexadien-1-one and selaginellin B (2) as (R,S)-4-[(4'-methoxy-4-(methyl)-3-((4-methoxyphenyl)ethynyl)biphenyl-2-yl)(4-methoxyphenyl)methylene]-2,5-cyclohexadien-1-one, along with four known biflavonoids, amentoflavone (3), hinokiflavone (4), heveaflavone (5), and 7''-O-methylamentoflavone (6). Their chemical structures were elucidated by spectral analysis of electrospray ionization mass spectroscopy (ESI-MS), one-dimensional nuclear magnetic resonance spectroscopy (1D-NMR) and two-dimensional-nuclear magnetic resonance spectroscopy (2D-NMR) including (1)H-NMR, (13)C-NMR, distortionless enhancement by polarization transfer (DEPT) and heteronuclear multiple bond coherence (HMBC), and single-crystal X-ray diffraction techniques.

MeSH terms

  • Biphenyl Compounds / chemistry
  • Biphenyl Compounds / isolation & purification*
  • Cyclohexanones / chemistry
  • Cyclohexanones / isolation & purification*
  • Magnetic Resonance Spectroscopy
  • Pigments, Biological / chemistry
  • Pigments, Biological / isolation & purification*
  • Selaginellaceae / chemistry*

Substances

  • (R,S)-4-((4'-hydroxy-3-((4-hydroxyphenyl)ethynyl)biphenyl-2-yl)(4-hydroxyphenyl)methylene)-2,5-cyclohexadien-1-one
  • (R,S)-4-((4'-methoxy-4-(methyl)-3-((4-methoxyphenyl)ethynyl)biphenyl-2-yl)(4-methoxyphenyl)methylene)-2,5-cyclohexadien-1-one,
  • Biphenyl Compounds
  • Cyclohexanones
  • Pigments, Biological