Itaconic acid derivatives: structure, function, biosynthesis, and perspectives
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MINI-REVIEW
Itaconic acid derivatives: structure, function, biosynthesis, and perspectives Mei Sano 1 & Tomonari Tanaka 1 & Hitomi Ohara 1 & Yuji Aso 1 Received: 21 August 2020 / Revised: 21 August 2020 / Accepted: 13 September 2020 # Springer-Verlag GmbH Germany, part of Springer Nature 2020
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.
Keywords Alkylitaconic acids . Biosynthesis . Function . Itaconic acid derivatives . α-Methylene-γ-butyrolactones . Structure
Introduction Itaconic acid (IA) consists of two carboxy groups and a vinylidene group (R1=R2=R3=H in Fig. 1). IA is mainly produced by fungi, such as Aspergillus terreus, and is used as a biobased platform chemical as a feedstock for synthetic polymers (Marvel and Shepherd 1959; Bednarz et al. 1975; Bednarz et al. 2015; Robert and Friebel 2016; Bednarz et al. 2017; Electronic supplementary material The online version of this article (https://doi.org/10.1007/s00253-020-10908-1) contains supplementary material, which is available to authorized users. * Yuji Aso [email protected] 1
Department of Biobased Materials Science, Kyoto Institute of Technology, 1 Hashigami-cho, Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan
Cho et al. 2018; Teleky and Vodnar 2019) and surfactants (Okada et al. 2009; Abruzzo et al. 2017). It has recently been found that mammalian macrophages produce IA (Mao et al. 2013; Michelucci et al. 2013; Hooftman and O’Neill 2019). Furthermore, IA has bioactivities, such as antimicrobial (Cordes et
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