title: Chemo-enzymatic syntheses of drimane-type sesquiterpenes and the fundamental core of hongoquercin meroterpenoid by recombinant squalene-hopene cyclase.
abstract: 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.
authors: 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.
authors: Yukie
authors: Y
authors: Yonemura
authors: Takuro
authors: T
authors: Ohyama
authors: Tsutomu
authors: T
authors: Hoshino
mesh_terms: D055162:Biocatalysis; D019751:Intramolecular Transferases / Q000737:chemistry / Q000378:metabolism*; D015394:Molecular Structure; D000081223:Polycyclic Sesquiterpenes; D011994:Recombinant Proteins / Q000737:chemistry / Q000378:metabolism; D012717:Sesquiterpenes / Q000737:chemistry / Q000378:metabolism*
chemical_list: D000081223:Polycyclic Sesquiterpenes; D011994:Recombinant Proteins; D012717:Sesquiterpenes; C437376:drimane; D019751:Intramolecular Transferases; C066630:squalene-hopene cyclase