Ergothioneine

Ergothioneine (EGT) is a sulfur-containing histidine derivative (figure 1). To date, ergothioneine biosynthesis is documented in several non‐yeast fungal species including Neurospora crassa and other filamentous fungi. The precise role of ergothioneine is not yet known but there is growing evidence that it plays a role as an antioxidant protecting human cells from oxidative stress and pathogenic bacteria from host defenses.

Fig. 1 Structures of ergothioneine

Biosynthesis of Ergothioneine

There are two main reactions in the ergothioneine biosynthesis, namely the oxidative C‐S bond formation and the subsequent C‐S bond cleavage reaction, which result in the net transfer of the sulfur atom from cysteine or γ‐glutamyl cysteine to the imidazole side chain of histidine. According to the reaction conditions, the ergothioneine biosynthetic pathways can be divided into two types, the aerobic and anaerobic biosynthetic pathways (Figure 2)^[1].

Fig. 2 Biosynthesis pathway of ergothioneine. (A) Aerobic synthesis pathway of ergothioneine (EgtB-EgtC-EgtE-catalysis in mycobacteria, and Egt1-Egt2-catalysis in fungi); (B) Anaerobic synthesis pathway of ergothioneine (EanB-catalysis in sulfur bacteria).

• Aerobic synthesis pathway

Basically, there are two known aerobic biosynthesis pathways: the Mycobacterium smegmatis pathway and the Neurospora crassa pathway. In the aerobic ergothioneine biosynthetic pathway, histidine, cysteine and methionine are used as the precursors to synthesize EGT by EgtABCE or Egt1/Egt2.

• Anaerobic synthesis pathway

In anaerobic synthesis pathway, oxygen is independent and two-step reactions are involved for ergothioneine biosynthesis. Firstly, EanA (a methyltransferase) transfers three methyl groups from S-adenosylmethionine (SAM) to histidine to produce hercynine. Then, EanB (a rhodanese-like enzyme) transfers sulfur to the imidazole ring of hercynine to form ergothioneine^[2].

Roles of Ergothioneine

The structure of ergothioneine shows that it is a tautomer in both a thiol and a thione form. Although it is a thiol, the thione tautomer is predominant at physiological pH, and this makes it unusually resistant to autoxidation. Hence, ergothioneine has been shown to possess antioxidant and cytoprotective effects in vitro and a few in vivo (Fig. 3), including free radical scavenger activity, radioprotective properties, anti-inflammatory actions and protection against UV radiation or neuronal injury^[3].

Fig. 3 Possible roles and interactions of ergothioneine (EGT) in vivo. Functional roles as an antioxidant are highlighted in yellow, anti-inflammatory agent in green, protectant against radiation in blue and roles in disease in orange.

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References

1. Ronghai Cheng, Lian Wu, Rui Lai, et al. Single-step Replacement of an Unreactive C-H Bond by a C-S Bond Using Polysulfide as the Direct Sulfur Source in the Anaerobic Ergothioneine Biosynthesis. ACS Catal. 2020 Aug 21;10(16):8981-8994.
2. Han, Y., Tang, X., Zhang, Y., Hu, X., & Ren, L.-J. The current status of biotechnological production and the application of a novel antioxidant ergothioneine. Critical Reviews in Biotechnology, 2021, 41(4), 580–593.
3. Cheah, I. K., & Halliwell, B. Ergothioneine; antioxidant potential, physiological function and role in disease. Biochimica et Biophysica Acta (BBA) - Molecular Basis of Disease, 2012, 1822(5), 784–793.

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