Microbial metabolism. Part 7: Curcumin

Microbial metabolism of the cancer chemopreventive agent, curcumin [(1E, 6E)-1,7-bis (4-hydroxy-3-methoxyphenyl) hepta-1,6-diene-3,5-dione] ( 1) with Pichia anomala ( ATCC 20170) yielded four major metabolites, 5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl) heptan-3-one ( 2), 5-hydroxy-7-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl) heptan-3-one ( 3), 1,7-bis(4-hydroxy-3-methoxyphenyl) heptan-3,5-diol ( 4), 5-hydroxy-1,7-bis (4-hydroxyphenyl) heptane-3-one ( 5) and two minor products, 1-(4-hydroxy-3-methoxyphenyl)7-( 4-hydroxyphenyl) heptane-3,5-diol ( 6) and 1,7- bis(4-hydroxyphenyl) heptane- 3,5-diol ( 7). The structures of compounds 2 - 5 were established on the basis of spectroscopic data. Compounds 6 and 7 were assigned tentative structures.