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Review
. 2022 Apr 21;27(9):2673.
doi: 10.3390/molecules27092673.

Ergothioneine, Ovothiol A, and Selenoneine-Histidine-Derived, Biologically Significant, Trace Global Alkaloids

Geoffrey A Cordell  1   2 , Sujeewa N S Lamahewage  3   4
Affiliations
Review

Ergothioneine, Ovothiol A, and Selenoneine-Histidine-Derived, Biologically Significant, Trace Global Alkaloids

Geoffrey A Cordell et al. Molecules. .

Abstract

The history, chemistry, biology, and biosynthesis of the globally occurring histidine-derived alkaloids ergothioneine (10), ovothiol A (11), and selenoneine (12) are reviewed comparatively and their significance to human well-being is discussed.

Keywords: biology; biosynthesis; chemistry; distribution; ergothioneine; ovothiol A; selenoneine.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Representative histidine-derived alkaloids.
Figure 2
Figure 2
Structures of 2-sulfanylhistidine (14), histidine (1), histamine (15), methionine (16), and L-cysteine (17).
Figure 3
Figure 3
Structures of S-alanylergothioneine (18) and 19.
Figure 4
Figure 4
Structures of γ-glutamylcysteine (20), 21, glutathione (22), and 19.
Figure 5
Figure 5
Structures of N,N-dimethyl-L-histidine (23), S-adenosylhomocysteine (24), L-tryptophan (25), 26, and 27.
Figure 6
Figure 6
Postulated mechanism and transition states for EgtB based on QM/MM calculations (adapted from ref. [105]).
Figure 7
Figure 7
Incubation of EgtE with the thioether 36 and the sulfoxide 19 (adapted from ref. [108]).
Figure 8
Figure 8
Postulated pathway from hercynine (13) to ergothioneine (10) involving PLP (adapted from ref. [38]).
Figure 9
Figure 9
Structures of 5-sulfanylhistidine (38), 1-methyl-5-sulfanylhistidine (39), ovothiol A (11), ovothiol B (40), ovothiol C (41), and imbricatine (42).
Figure 10
Figure 10
Formation of the sulfoxide intermediate 43 from L-histidine (1) and L-cysteine (17) by OvoA (adapted from ref. [101]).
Figure 11
Figure 11
Structures of D-histidine (44) and 2-fluoro-L-histidine (45).
Figure 12
Figure 12
Reaction of L-cysteine (17) in the presence of Fe(III) (adapted from ref. [102]).
Figure 13
Figure 13
Structures of cysteine sulfinic acid (46), cytisine (47), and N,N-dimethyl-L-histidine (14).
Figure 14
Figure 14
Structure of thiolurocanic acid (48).
Figure 15
Figure 15
Proposed alternative mechanistic pathways a and b for the interaction of hercynine (13) and polysulfur in the presence of EanB to form ergothioneine (10) (adapted from ref. [162]).
Figure 16
Figure 16
Structures of selenoneine (12) and selenocysteine (52).
Figure 17
Figure 17
Structures of 43 and 19.
Figure 18
Figure 18
Structures of selenocysteine (52), selenomethionine (53), selenocystine (54), and the Se-Se-linked dimer of selenoneine (55).
Figure 19
Figure 19
Divergent biosynthetic pathways from histidine (1) to ergothioneine (10) and selenoneine (12) through 19 and 56 (adapted from ref. [100]).
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References

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