Methylobamine, a UVA-absorbing compound from the plant-associated bacteria methylobacterium sp.

Tsunashi Kamo, Syuntaro Hiradate, Ken Suzuki, Ichiro Fujita, Shinji Yamaki, Tadashi Yoneda, Motoo Koitabashi, Shigenobu Yoshida

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)141-143
Number of pages3
JournalNatural product communications
Volume13
Issue number2
DOIs
Publication statusPublished - 2018

All Science Journal Classification (ASJC) codes

  • Pharmacology
  • Plant Science
  • Drug Discovery
  • Complementary and alternative medicine

Fingerprint Dive into the research topics of 'Methylobamine, a UVA-absorbing compound from the plant-associated bacteria methylobacterium sp.'. Together they form a unique fingerprint.

Cite this