“Reuterin”的意思、由来-开放百科全书

Reuterin (3-hydroxypropionaldehyde) is the organic compound with the formula HOCH₂CH₂CHO. It is a bifunctional molecule, containing both a hydroxy and aldehyde functional groups.

The name reuterin is derived from Lactobacillus reuteri, which produces the compound biosynthetically from glycerol as a broad-spectrum antibiotic.^[1] L. reuteri itself is named after the microbiologist Gerhard Reuter, who did early work in distinguishing it as a district species.

Solution structure

In aqueous solution 3-hydroxypropionaldehyde exists in equilibrium with its hydrate, in which the aldehyde group converts to a geminal diol:

The hydrate is also in equilibrium with its dimer, which dominates at high concentrations. These three components - the aldehyde, its dimer, and the hydrate are therefore in a dynamic equilibrium.^[2]

Synthesis and biosynthesis

3-Hydroxypropionaldehyde is formed by the condensation of acetaldehyde and formaldehyde. This reaction, when conducted in the gas-phase, was the basis for a now obsolete industrial route acrolein:^[3]

Presently 3-hydroxypropionaldehyde is an intermediate in the production of pentaerythritol.

Reuterin is an intermediate in the metabolism of glycerol to 1,3-propanediol catalysed by the coenzyme B12-dependent diol dehydrase.

Biological activity

Reuterin is a potent antimicrobial compound produced by Lactobacillus reuteri. It is an intermediate in the metabolism of glycerol to 1,3-propanediol catalysed by the coenzyme B12-dependent diol dehydrase.

Reuterin inhibits the growth of some harmful Gram-negative and Gram-positive bacteria, along with yeasts, molds, and protozoa.^[4] L. reuteri can secrete sufficient amounts of reuterin to inhibit the growth of harmful gut organisms, without killing beneficial gut bacteria, allowing L. reuteri to remove gut invaders while keeping normal gut flora intact.^[5]

Reuterin is water-soluble, effective in a wide range of pH, resistant to proteolytic and lipolytic enzymes, and has been studied as a food preservative or auxiliary therapeutic agent.^[6]^[7]^[8]

Reuterin as an extracted compound has been shown capable of killing H7 and Listeria monocytogenes, with the addition of lactic acid increasing its efficacy.^[9] It has also been demonstrated to kill H7 when produced by L. reuteri.^[10]^[11]

References

1. ^{{cite journal |last1=Talarico |first1=T L |last2=Casas |first2=I A |last3=Chung |first3=T C |last4=Dobrogosz |first4=W J |title=Production and isolation of reuterin, a growth inhibitor produced by Lactobacillus reuteri. |journal=Antimicrobial Agents and Chemotherapy |date=1 December 1988 |volume=32 |issue=12 |pages=1854–1858 |doi=10.1128/AAC.32.12.1854}}
2. ^{{cite journal|doi=10.1021/jf021086d |pmid=12744656 |authors=Vollenweider, Sabine; Grassi, Guido; König, Iwo; Puhan, Zdenko |title=Purification and Structural Characterization of 3-Hydroxypropionaldehyde and Its Derivatives|journal=Journal of Agricultural and Food Chemistry |pages=3287–3293|volume=51 |issue=11 |year=2003}}
3. ^{{Ullmann|authors=Dietrich Arntz, Achim Fischer, Mathias Höpp, Sylvia Jacobi, Jörg Sauer, Takashi Ohara, Takahisa Sato, Noboru Shimizu and Helmut Schwind|title=Acrolein and Methacrolein||year=2012|doi=10.1002/14356007.a01_149.pub2}}
4. ^{{cite journal |vauthors=Talarico TL, Dobrogosz WJ |title=Chemical characterization of an antimicrobial substance produced by Lactobacillus reuteri |journal=Antimicrob. Agents Chemother. |volume=33 |issue=5 |pages=674–9|date=May 1989 |pmid=2751282 |pmc=172512 |doi=10.1128/aac.33.5.674}}
5. ^{{cite journal |vauthors=Casas IA, Dobrogosz WJ |title=Validation of the Probiotic Concept: Lactobacillus reuteri Confers Broad-spectrum Protection against Disease in Humans and Animals |journal=Microbial Ecology in Health and Disease |volume=12 |issue=4 |pages=247–285 |date=December 1, 2000 |doi=10.1080/08910600050216246-1 }}
6. ^Vollenweider S, Lacroix C: 3-hydroxypropionaldehyde: applications and perspectives of biotechnological production. Appl Microbiol Biotechnol 2004, 64(1):16-27.
7. ^Axelsson LT, Chung TC, Dobrogosz WJ, Lindgren SE: Production of a broad spectrum antimicrobial substance by Lactobacillus reuteri. Microb Ecol Health Dis 1989, 2:131-136.
8. ^El-Ziney MG, van den Tempel T, Debevere J, Jakobsen M: Application of reuterin produced by Lactobacillus reuteri 12002 for meat decontamination and preservation. J Food Prot 1999, 62(3):257-261.
9. ^{{cite journal|vauthors=El-Ziney MG, van den Tempel T, Debevere J, Jakobsen M |title=Application of reuterin produced by Lactobacillus reuteri 12002 for meat decontamination and preservation.|journal=Journal of Food Protection|date=March 1999|volume=62|issue=3|pages=257–61|pmid=10090245|doi=10.4315/0362-028X-62.3.257}}
10. ^{{cite journal|last=Muthukumarasamy|first=P|author2=Han, JH |author3=Holley, RA |title=Bactericidal effects of Lactobacillus reuteri and allyl isothiocyanate on Escherichia coli O157:H7 in refrigerated ground beef.|journal=Journal of Food Protection|date=November 2003|volume=66|issue=11|pages=2038–44|pmid=14627280|doi=10.4315/0362-028X-66.11.2038}}
11. ^{{cite journal|doi=10.1038/srep36246 |pmid=27819285 |pmc=5098142 |vauthors=Engels C, Schwab C, Zhang J, Stevens MJ, Bieri C, Ebert MO, McNeill K, Sturla SJ, and Lacroix C |title=Acrolein contributes strongly to antimicrobial and heterocyclic amine transformation activities of reuterin. |journal=Scientific Reports|volume=6 |pages=36246 |year=2016|bibcode=2016NatSR...636246E }}