3-(allyltrisulfanyl)-2-aminopropanoic acid, a novel nonvolatile water-soluble antimicrobial sulfur compound in heated garlic.
A nonvolatile and slightly water-soluble antimicrobial sulfur compound newly isolated from heated garlic extract was characterized. The compound was generated most when heated at 120°C for 30 minutes and completely disappeared after 90 minutes of heating. It has a molecular mass of 225 daltons with an elemental ratio of C₆H₁₁N₁O₂S₃, and the interpretation of ¹H- and ¹³C-nuclear magnetic resonance and Fourier transform-infrared data showed that the compound was CH₂=CH-CH₂-S-S-S-CH₂-CH(NH₂)COOH, 3-(allyltrisulfanyl)-2-aminopropanoic acid, a derivative of cysteine, presumably derived from alliin (S-allyl-L-cysteine sulfoxide). This novel compound has comparatively potent anti-yeast activity and rather weak antibacterial activity, similar to other antimicrobial compounds in garlic.
Kang
Seung-Sik
SS
Department of Food Science, Sejong University, Seoul, Republic of Korea.
Lim
Dong Ryul
DR
Kyung
Kyu Hang
KH
D000890:Anti-Infective Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D005737:Garlic / Q000737:chemistry*; D006358:Hot Temperature; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D008970:Molecular Weight; D012995:Solubility; D017550:Spectroscopy, Fourier Transform Infrared; D013438:Sulfhydryl Compounds / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D014835:Volatilization; D014867:Water; D015003:Yeasts / Q000187:drug effects; D015091:beta-Alanine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology
C554999:3-(allyltrisulfanyl)-2-aminopropanoic acid; D000890:Anti-Infective Agents; D013438:Sulfhydryl Compounds; D014867:Water; D015091:beta-Alanine