Formation of 4-Hydroxy-2,5-Dimethyl-3[2H]-Furanone by Zygosaccharomyces rouxii : Identification of an Intermediate

Abstract

13 C]FBP to the nutrient medium revealed that only exogenously supplied FBP was transformed to HDMF (6). It was assumed that at least one metabolic step takes place in the cell wall or membrane of the yeast. However, the biosynthesis in plants and microorganisms is still unclear since no enzyme or intermediate involved in HDMF formation has been identified so far. Recently, the chemical formation of HDMF from FBP in the presence of NAD(P)H was reported (11). The authors proposed the dicarbonyl compound 1-deoxy-2,3-hexodiulose-6-phosphate as a possible intermediate which is subsequently reduced by NAD(P)H to the final product, HDMF. A similar biosynthetic pathway is anticipated in plants and microorganisms.Prior to the usage of Z. rouxii for the biotechnological production of the economically important flavor compound HDMF, it is of utmost significance to know the biosynthetic pathway of HDMF. The objective of this study was to obtain detailed information about HDMF formation from FBP by the yeast Z. rouxii. Here, we report on potential intermediates, such as ␣-dicarbonyls in the culture medium. Employment of the ␣-dicarbonyl-trapping reagent o-phenylenediamine revealed three highly reactive ␣-dicarbonyl structures derived from FBP in the nutrient medium. Structure elucidation of the corresponding quinoxaline derivatives demonstrated the chemical formation of the often postulated but never identified intermediate * Corresponding author. Present address: Biomolekulare Lebensmitteltechnologie,

Determination of Key Volatile Compounds Related to Long‐Term Fermentation of Soy Sauce

“…The bioformation pathway of HDMF during fermentation is proposed by Z. rouxii from D-fructose-1,6-bisphosphate (Hara, Kusaka, Inagaki, Takahashi, & Wada, 2000). In addition, some previous studies showed that the formation of HDMF was significantly higher in soy sauce fermented by the combination of T. halophilus and Z. rouxii, compared to the single culture (Hauck, Brühlmann, & Schwab, 2003).…”

2,5-dimethyl-4-hydroxy-3(2H)-furanone (DMHF); antimicrobial compound with cell cycle arrest in nosocomial pathogens

“…2,5-dimethyl-4-hydroxy-3(2H)-furanone (DMHF), also known as furaneol, is an aroma compound found in strawberries, mangos, pineapples, raspberries, and various processed foodstuffs (Rodin et al, 1965;Ohloff, 1969;Larsen et al, 1992;Wein et al, 2002), and is extensively used as a food flavoring due to its low odor threshold and flavor-enhancing properties (Hauck et al, 2003). This compound is formed mainly as a result of the operation of the Maillard reactions between sugars and amino acids (Hayase et al, 1985;Blank and Fay, 1996).…”

Bioactive compound that inhabit quorum sensing system in gram negative bacteria

“…Pada kecoa jantan , furanon digunakan sebagai sex pheromone. Furanon ini terdapat secara alami pada nanas dan strawberry dan membuat senyawa cita rasa pada keju dan wine (Martinelli et al, 2004;Hauck et al, 2003).…”