Diastereoisomeric macrocyclic polydisulfides from the mangrove Bruguiera gymnorrhiza.

The uncommon macrocyclic polydisulfides, trans-3,3'-dihydroxy-1,5,1',5'-tetrathiacyclodecane (1), cis-3,3'-dihydroxy-1,5,1',5'-tetrathiacyclodecane (2), along with five known related cyclic disulfides, gymnorrhizol (3), neogymnorrhizol (4), bruguiesulfurol (5), brugierol (6), and isobrugierol (7), were isolated from the mangrove Bruguiera gymnorrhiza collected from Guangdong Province, China. Structures of compounds 1 and 2 were determined by extensive analysis of their spectroscopic data, by comparison of their NMR spectroscopic data with those of the co-occurring known compounds, as well as by single-crystal X-ray diffraction analysis. A possible biogenetic origin was also proposed.