Abstract
Itaconic acid possessing a vinylidene group, which is mainly produced by fungi, is used as a biobased platform chemical and shows distinctive bioactivities. On the other hand, some fungi and lichens produce itaconic acid derivatives possessing itaconic acid skeleton, and the number of the derivatives is currently more than seventy. Based on the molecular structures, they can be categorized into two groups, alkylitaconic acids and α-methylene-γ-butyrolactones. Interestingly, some itaconic acid derivatives show versatile functions such as antimicrobial, anti-inflammatory, antitumor, and plant growth-regulating activities. The vinylidene group of itaconic acid derivatives likely participates in these functions. It is suggested that α-methylene-γ-butyrolactones are biosynthesized from alkylitaconic acids which are first biosynthesized from acyl-CoA and oxaloacetic acid. Some modifying enzymes such as hydroxylase and dehydratase are likely involved in the further modification after biosynthesis of their precursors. This contributes to the diversity of itaconic acid derivatives. In this review, we summarize their structures, functions, and biosynthetic pathways together with a discussion of a strategy for the industrial use.
Key points
• Itaconic acid derivatives can be categorized into alkylitaconic acids and α-methylene-γ-butyrolactones.
• The vinylidene group of itaconic acid derivatives likely participates in their versatile function.
• It is suggested that α-methylene-γ-butyrolactones are biosynthesized from alkylitaconic acids which are first synthesized from acyl-CoA and oxaloacetic acid.
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This work was supported by JSPS KAKENHI Grant Number 19K05767 and Grant-in-Aid for JSPS Fellows Number 18J13414. The funders had no role in study design and interpretation or the decision to submit the work for publication.
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General writing of the manuscript, investigation, literature search, and editing: Mei Sano and Yuji Aso. Supervision: Tomonari Tanaka and Hitomi Ohara. All authors contributed to the study conception and design and approved the final manuscript.
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Sano, M., Tanaka, T., Ohara, H. et al. Itaconic acid derivatives: structure, function, biosynthesis, and perspectives. Appl Microbiol Biotechnol 104, 9041–9051 (2020). https://doi.org/10.1007/s00253-020-10908-1
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DOI: https://doi.org/10.1007/s00253-020-10908-1