Isolation of methyl syringate as a specific aflatoxin production inhibitor from the essential oil of Betula alba and aflatoxin production inhibitory activities of its related compounds

• Published in: International journal of food microbiology 2012-02, Vol.153 (3), p.339-344
• Main Authors: Jermnak, Usuma, Yoshinari, Tomoya, Sugiyama, Yasumasa, Tsuyuki, Rie, Nagasawa, Hiromichi, Sakuda, Shohei
• Format: Article
• Language: English
• Subjects: Aflatoxin; aflatoxins; Aflatoxins - antagonists & inhibitors; Aflatoxins - biosynthesis; Aflatoxins - genetics; Aspergillus flavus; Aspergillus flavus - drug effects; Aspergillus flavus - genetics; Aspergillus flavus - metabolism; Aspergillus parasiticus; Betula - chemistry; Betula alba; Betula pubescens; Biphenyl Compounds; DPPH radical scavenger; essential oils; free radical scavengers; Gallic acid; Gallic Acid - analogs & derivatives; Gallic Acid - isolation & purification; Gallic Acid - pharmacology; Gene Expression Regulation, Bacterial - drug effects; mechanism of action; messenger RNA; Methyl syringate; microbial growth; Oils, Volatile - metabolism; Picrates; RNA, Messenger - drug effects; RNA, Messenger - metabolism; syringic acid
• ISSN: 0168-1605; 1879-3460
• DOI: 10.1016/j.ijfoodmicro.2011.11.023

Methyl syringate was isolated from the essential oil of Betula alba as an aflatoxin production inhibitor. It inhibited aflatoxin production of Aspergillus parasiticus and Aspergillus flavus with IC50 values of 0.9 and 0.8mM, respectively, without significantly inhibiting fungal growth. Methyl syringate reduced mRNA levels of genes (aflR, pksA, and omtA) encoding proteins required for aflatoxin biosynthesis. Methyl gallate, methyl 3,4,5-trimethoxybenzoate, and methyl 3-O-methylgallate inhibited both aflatoxin production and fungal growth of A. parasiticus and A. flavus. However, their acids and syringic acid did not inhibit aflatoxin production and growth of A. parasiticus significantly, although gallic acid inhibited aflatoxin production of A. flavus with selectivity. The 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity of methyl syringate was much weaker than that of gallic acid. These results showed that methyl syringate has a unique inhibitory activity toward aflatoxin production with a different mode of action from that of gallic acid. ► Methyl syringate was isolated as an aflatoxin production inhibitor from Betula alba. ► It inhibited aflatoxin production of A. parasiticus and A. flavus with selectivity. ► It suppressed transcription of aflR in a dose-dependent manner. ► Among gallic acid derivatives, only methyl syringate showed selectivity. ► Its activity did not correlate to DPPH radical scavenging activity.