EC Number   |
General Information |
Reference |
|---|
   4.2.3.135 | metabolism |
6-protoilludene is the exclusive reaction product of protoilludene synthase |
719998 |
| 4.2.3.135 | metabolism |
in the presence of Ca2+, DELTA6-protoilludene synthases catalyze diverse cyclization reactions. DELTA6-Protoilludene and (E)-beta-caryophyllene result from a 1,11 cyclization of (2E,6E)-farnesyl diphosphate ((2E,6E)-FPP) following metal ion mediated ionization. The intermediate trans-humulyl cation may undergo a hydride shift followed by two cyclizations and a deprotonation to yield DELTA6-protoilludene. Alternatively, a direct 2,10 cyclization of the trans-humulyl cation leads to (E)-beta-caryophyllene. On the other hand, beta-elemene, 4,11-selinadiene, beta-selinene and alpha-selinene are derived from a 1,10 cyclization of (2E,6E)-FPP. A direct deprotonation of the intermediate (E,E)-germacradienyl cation results in germacrene A. beta-Elemene is the heat-induced Cope rearrangement product. A 2,7 cyclization of the (E,E)-germacradienyl cation is followed by deprotonation yields 4,11-selinadiene. Finally, a hydride shift, followed by a 2,7 cyclization of the (E,E)-germacradienyl cation and deprotonation leads to beta-selinene and alpha-selinene. Therefore DELTA6-protoilludene synthases are capable of catalyzing simultaneously a 1,10 and a 1,11 cyclization in the presence of an alternative metal ion |
747535 |
| 4.2.3.135 | metabolism |
in the presence of Ca2+, DELTA6-protoilludene synthases catalyze diverse cyclization reactions. DELTA6-Protoilludene and (E)-beta-caryophyllene result from a 1,11 cyclization of (2E,6E)-farnesyl diphosphate ((2E,6E)-FPP) following metal ion mediated ionization. The intermediate trans-humulyl cation may undergo a hydride shift followed by two cyclizations and a deprotonation to yield DELTA6-protoilludene. Alternatively, a direct 2,10-cyclization of the trans-humulyl cation leads to (E)-beta-caryophyllene. On the other hand, beta-elemene, 4,11-selinadiene, beta-selinene and alpha-selinene are derived from a 1,10 cyclization of (2E,6E)-FPP. A direct deprotonation of the intermediate (E,E)-germacradienyl cation results in germacrene A. beta-Elemene is the heat-induced Cope rearrangement product. A 2,7 cyclization of the (E,E)-germacradienyl cation is followed by deprotonation yields 4,11-selinadiene. Finally, a hydride shift, followed by a 2,7 cyclization of the (E,E)-germacradienyl cation and deprotonation leads to beta-selinene and alpha-selinene. Therefore DELTA6-protoilludene synthases are capable of catalyzing simultaneously a 1,10- and a 1,11-cyclization in the presence of an alternative metal ion |
747535 |
| 4.2.3.135 | metabolism |
the three cytochrome P450 monooxygenases CYP5344B1, CYP5348E1, and CYP5348J3 show substantial activities against DELTA6-protoilludene catalyzing the hydroxylation reaction of DELTA6-protoilludene to produce DELTA6-protoilludene-8-ol and DELTA6-protoilludene-5-ol |
748574 |
