Fitzgerald Daniel J, Stratford Malcolm, Gasson Michael J, Narbad Arjan
Food Safety Science Division, Institute of Food Research, Norwich Research Park, Colney Lane, Norwich, Norfolk, United Kingdom.
J Agric Food Chem. 2005 Mar 9;53(5):1769-75. doi: 10.1021/jf048575t.
The aim of the present study was to evaluate which structural elements of the vanillin molecule are responsible for its observed antifungal activity. MICs of vanillin, its six direct structural analogues, and several other related compounds were determined in yeast extract peptone dextrose broth against a total of 18 different food spoilage molds and yeasts. Using total mean MICs after 4 days of incubation at 25 degrees C, the antifungal activity order was 3-anisaldehyde (1.97 mM) > benzaldehyde (3.30 mM) > vanillin (5.71 mM) > anisole (6.59 mM) > 4-hydroxybenzaldehyde (9.09 mM) > phenol (10.59 mM) > guaiacol (11.66 mM). No correlation was observed between the relative antifungal activity of the test compounds and log P(o/w). Furthermore, phenol (10.6 mM) was found to exhibit a greater activity than cyclohexanol (25.3 mM), whereas cyclohexanecarboxaldehyde (2.13 mM) was more active than benzaldehyde (3.30 mM). Finally, the antifungal order of isomers of hydroxybenzaldehyde and anisaldehyde was found to be 2- > 3- > 4- and 3- > 2- > 4-, respectively. In conclusion, the aldehyde moeity of vanillin plays a key role in its antifungal activity, but side-group position on the benzene ring also influences this activity. Understanding how the structure of natural compounds relates to their antimicrobial function is fundamentally important and may help facilitate their application as novel food preservatives.
本研究的目的是评估香草醛分子的哪些结构元素导致了其已观察到的抗真菌活性。在酵母提取物蛋白胨葡萄糖肉汤中测定了香草醛、其六种直接结构类似物以及其他几种相关化合物对总共18种不同食品腐败霉菌和酵母菌的最低抑菌浓度（MIC）。在25℃孵育4天后，使用总平均MIC得出抗真菌活性顺序为：3-茴香醛（1.97 mM）＞苯甲醛（3.30 mM）＞香草醛（5.71 mM）＞苯甲醚（6.59 mM）＞4-羟基苯甲醛（9.09 mM）＞苯酚（10.59 mM）＞愈创木酚（11.66 mM）。未观察到测试化合物的相对抗真菌活性与log P(o/w)之间存在相关性。此外，发现苯酚（10.6 mM）的活性高于环己醇（25.3 mM），而环己烷甲醛（2.13 mM）比苯甲醛（3.30 mM）更具活性。最后，发现羟基苯甲醛和茴香醛异构体的抗真菌顺序分别为2-＞3-＞4-和3-＞2-＞4-。总之，香草醛的醛基在其抗真菌活性中起关键作用，但苯环上的侧基位置也会影响这种活性。了解天然化合物的结构与其抗菌功能之间的关系至关重要，可能有助于促进它们作为新型食品防腐剂的应用。
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