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<p><i>Exiguobacterium</i> bacteria produce yellowish‒orange pigments, but their detailed characteristics have not been fully elucidated. Here, we report that the newly isolated <i>Exiguobacterium</i> strain oki7 from the surface of seaweed collected from Senaga-Jima Island, Okinawa, Japan, produces a rare C<sub>30</sub> carotenoid. The major orange carotenoid was purified from oki7 using thin-layer chromatography and high-performance liquid chromatography. Structural analysis using nuclear magnetic resonance and high-resolution mass spectrometry revealed that the major carotenoid produced by oki7 was methyl 5′-(6-iso-C<sub>13:0</sub>)-glucosyl-5′,6′-dihydro-4,4′-diapolycopenoate (methyl 5′-[6-<i>O</i>-(11-methyldodecanoyl)-β-D-glucopyranosyl]-5′,6′-dihydro-4,4′-diapo-ψ,ψ-caroten-4-oate), the first carotenoid to be identified from the genus <i>Exiguobacterium</i>. Furthermore, several derivatives with different fatty acids bound to this C<sub>30</sub> carotenoid glycoside backbone were also predicted by mass spectrometry/mass spectrometry analysis. Compared with naturally abundant β-carotene and zeaxanthin, methyl 5′-(6-iso-C<sub>13:0</sub>)-glucosyl-5′,6′-dihydro-4,4′-diapolycopenoate showed stronger singlet oxygen-quenching activity. Furthermore, methyl 5′-(6-iso-C<sub>13:0</sub>)-glucosyl-5′,6′-dihydro-4,4′-diapolycopenoate inhibited the overproduction of the inflammatory cytokine interleukin-6 and the inflammatory mediator nitric oxide in lipopolysaccharide-stimulated RAW264.7 macrophages through the downregulation of their gene expression. This study provides fundamental insights into the potential of <i>Exiguobacterium</i> bacteria as a source of health-beneficial carotenoids and the application of C<sub>30</sub> carotenoids as nutraceuticals and pharmaceuticals.</p>

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Structural determination of the carotenoid glycoside ester produced by the marine bacterium Exiguobacterium sp. strain oki7 and its antioxidant and anti-inflammatory effects

  • 期刊论文

  • 发表日期：

    2025年7月1日

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  • Naoki Takatani,
  • Takashi Maoka,
  • Misaki Aoike,
  • Munekimi Nanao,
  • Tomoo Sawabe,
  • Fumiaki Beppu,
  • Masashi Hosokawa

摘要

Exiguobacterium bacteria produce yellowish‒orange pigments, but their detailed characteristics have not been fully elucidated. Here, we report that the newly isolated Exiguobacterium strain oki7 from the surface of seaweed collected from Senaga-Jima Island, Okinawa, Japan, produces a rare C30 carotenoid. The major orange carotenoid was purified from oki7 using thin-layer chromatography and high-performance liquid chromatography. Structural analysis using nuclear magnetic resonance and high-resolution mass spectrometry revealed that the major carotenoid produced by oki7 was methyl 5′-(6-iso-C13:0)-glucosyl-5′,6′-dihydro-4,4′-diapolycopenoate (methyl 5′-[6-O-(11-methyldodecanoyl)-β-D-glucopyranosyl]-5′,6′-dihydro-4,4′-diapo-ψ,ψ-caroten-4-oate), the first carotenoid to be identified from the genus Exiguobacterium. Furthermore, several derivatives with different fatty acids bound to this C30 carotenoid glycoside backbone were also predicted by mass spectrometry/mass spectrometry analysis. Compared with naturally abundant β-carotene and zeaxanthin, methyl 5′-(6-iso-C13:0)-glucosyl-5′,6′-dihydro-4,4′-diapolycopenoate showed stronger singlet oxygen-quenching activity. Furthermore, methyl 5′-(6-iso-C13:0)-glucosyl-5′,6′-dihydro-4,4′-diapolycopenoate inhibited the overproduction of the inflammatory cytokine interleukin-6 and the inflammatory mediator nitric oxide in lipopolysaccharide-stimulated RAW264.7 macrophages through the downregulation of their gene expression. This study provides fundamental insights into the potential of Exiguobacterium bacteria as a source of health-beneficial carotenoids and the application of C30 carotenoids as nutraceuticals and pharmaceuticals.