The gabosine and anhydrogabosine family of secondary metabolites

Researchers provide information regarding the natural occurrence, biogenetic origin, and biological properties of all gabosines and anhydrogabosines, along with the synthetic efforts devoted to their preparation. The compounds with anhydrogabosine structure are included in the wider category of epoxyquinols. The gabosine family comprises a group of secondary metabolites isolated from various Streptomyces strains with a closely related carba-sugar structure. All of the gabosines present a polyhydroxylated methyl cyclohexane system as the common constitutional feature. Their structural diversity is originated by differences in the substituent positions, unsaturation degree, and relative and absolute configuration of their stereogenic centers. Several known epoxyquinone natural products also possess anhydrogabosine structure and most of these compounds are phytotoxins.