Chemo-enzymatic syntheses of drimane-type sesquiterpenes and the fundamental core of hongoquercin meroterpenoid by recombinant squalene-hopene cyclase.

Yukie Yonemura, Takuro Ohyama, Tsutomu Hoshino

Department of Applied Biological Chemistry, Faculty of Agriculture, and Graduate School of Science and Technology, Niigata University, Nishi-ku, Ikarashi 2-8050, Niigata, 950-2181, Japan.

Organic & biomolecular chemistry 2012 Jan 14

filter terms:

Squalene-hopene cyclase (SHC) converts squalene (C(30)) into pentacyclic triterpenes of hopene and hopanol. A linear sesquiterpene, (6E,10E)-2,6,10-trimethyldodeca-2,6,10-triene, underwent cyclization catalyzed by SHC, affording the following six bicyclic sesquiterpenes (drimane skeleton) in relatively high yield (68%): drim-7(8)-ene, drim-8(12)-ene, drim-8(9)-ene, driman-8α-ol, driman-8β-ol, and the novel sesquiterpene, named quasiclerodane, the skeleton of which is analogous to that of clerodane diterpene. To extend the scope of the enzymatic syntheses, acyclic sesquiterpenes to which a phenol moiety was appended were subjected to the enzymatic reaction catalyzed by SHC. The cyclic meroterpene core present in hongoquercins A and B was successfully prepared. The formation mechanisms of drimane-type sesquiterpenes and the cyclic meroterpene core of hongoquercins A and B are discussed.

Citation

Yukie Yonemura, Takuro Ohyama, Tsutomu Hoshino. Chemo-enzymatic syntheses of drimane-type sesquiterpenes and the fundamental core of hongoquercin meroterpenoid by recombinant squalene-hopene cyclase. Organic & biomolecular chemistry. 2012 Jan 14;10(2):440-6