β-Hydroxyergothioneine, a New Ergothioneine Derivative from the Mushroom Lyophyllum connatum, and Its Protective Activity against Carbon Tetrachloride-Induced Injury in Primary Culture Hepatocytes

Ergothioneine as an Anti-Oxidative/Anti-Inflammatory Component in Several Edible Mushrooms

“…The active compound in F3 was identified as EGT (Ergothioneine, 2-mercaptohistidine trimethylbetaine) (Fig. 2) by co-injection into HPLC and 1 H-NMR (Kimura, et al, 2005). EGT was isolated as a component from Lyophyllum connatum by Kimura et al (2005).…”

“…2) by co-injection into HPLC and 1 H-NMR (Kimura, et al, 2005). EGT was isolated as a component from Lyophyllum connatum by Kimura et al (2005). The IC 50 (inhibitory concentration) of l-EGT on the inhibitory effect of protein chlorination by HOCl was 325 µM.…”

Gastrolatathioneine, an unusual ergothioneine derivative from an aqueous extract of “tian ma”: A natural product co-produced by plant and symbiotic fungus

“…Its IR spectrum showed absorptions for hydroxy (3172 cm -1 ), carboxylic ion (1641 cm -1 ) [33], and aromatic ring (1612, 1597, and 1515 cm -1 ) functional groups. The molecular formula of 1 was determined as C 23 (Table 1) corresponding to the above units and two additional quaternary carbonyls attributable to carboxylic (δ C 166.3, C-1) and thiocarbonyl (δ C 162.4, C-2′) groups [33].…”

“…Its IR spectrum showed absorptions for hydroxy (3172 cm -1 ), carboxylic ion (1641 cm -1 ) [33], and aromatic ring (1612, 1597, and 1515 cm -1 ) functional groups. The molecular formula of 1 was determined as C 23 (Table 1) corresponding to the above units and two additional quaternary carbonyls attributable to carboxylic (δ C 166.3, C-1) and thiocarbonyl (δ C 162.4, C-2′) groups [33]. As compared with those of the previously isolated constituents from ''tian ma'' [25−27], these spectroscopic data, especially the chemical shifts of the methylene units for the two p-hydroxybenzyls, suggest that 1 possesses an unusual and unsaturated sulfur-containing hetereocylic parent structure with substitution of the two p-hydroxybenzyls at two nitrogen atoms, which was further elucidated by 2D NMR data.…”

“…In addition, the HMBC correlations from H-2 to C-4′; from H 2 -3 to C-4′ and C-5′; and from H-5′ to C-3; combined with the molecular composition, revealed that the two moieties are connected via a C-3−C-4′ bond. Accordingly, the planar structure of 1 is elucidated as an unusual ergothioneine derivative [33]. Because 1 is an optical active compound containing only one chiral center identical with that of L-ergothioneine (2) [33], similarity of the positive specific rotations suggests that the 1 has the same S-configuration as 2 [33].…”