To survive in harsh environments, phyllosphere microorganisms have developed numerous adaptive strategies against stressors. One such strategy is the synthesis of compounds that absorb ultraviolet A radiation (UVA). The chemical structure of a UVA-absorbing compound from Methylobacterium sp. strain W-213 was elucidated by spectroscopic analyses. 1H, 13C, and two-dimensional nuclear magnetic resonance spectra indicated the presence of N-methyl-α-galactosamine. The entire structure was revealed by interpretation of INADEQUATE and high-resolution liquid chromatography/electrospray ionization mass spectra. The absolute configuration was established by X-ray analysis and the compound was identified as 2-((4aR,6R,7R,8R,8aR)-7,8-dihydroxy-6-hydroxymethyl-1,2-dimethyl-4aH,6H,7H,8H,8aH-pyrano[2,3-b][1,4]oxazin-3-yl)-2-iminoacetic acid and named ‘methylobamine’. Methylobamine shows promise for pharmaceutical and cosmetic applications due to its high polarity, UVA absorption properties, and stability under UVA exposure.
All Science Journal Classification (ASJC) codes
- Plant Science
- Drug Discovery
- Complementary and alternative medicine