RT journal article
T1 Identification of the Sesquiterpene Cyclase Involved in the Biosynthesis of (+)-4-Epi-eremophil-9-en-11-ol Derivatives Isolated from Botrytis cinerea
A1 Suárez Cáceres, Ivonne Rocío
A1 González Rodríguez, Victoria Eugenia
A1 Viaud, Muriel
A1 Garrido Crespo, Carlos
A1 González Collado, Isidro
A2 BiomedicinaBiotecnología y Salud Pública
A2 Química Orgánica
AB Cultivation of the phytopathogenic fungus Botrytis cinereausing sublethal amounts of copper sulfate yielded a crypticsesquiterpenoids family, which displayed the basic chemical structureof (+)-4-epi-eremophil-9-ene. The biosynthesis pathway was established,and the route involved the likely transformation of the diphosphate offarnesyl (FDP), to give a cis-fused eudesmane cation, through (S)-hedycaryol, finally yielding the (+)-4-epi-eremophil-9-enol derivatives.An expression study of genes that code for the sesquiterpene cyclases(STC), including the recently reported gene Bcstc7 present in the B.cinerea genome, was performed in order to establish the STC involved inthis biosynthesis. The results showed a higher expression level for theBcstc7 gene with respect to the other stc1−5 genes in both wild-type strains, B05.10 and Botrytis cinerea UCA992. Deletion of theBcstc7 gene eliminated (+)-4-epi-eremophilenol biosynthesis, which could be re-established by complementing the null mutant withthe Bcstc7 gene. Chemical analysis suggested that STC7 is the principal enzyme responsible for the key step of cyclization of FDP toeremophil-9-en-11-ols. Furthermore, a thorough study of the two wild-types and the complemented mutant revealed four neweremophilenol derivatives whose structures are reported here.
SN 10.1021/acschembio.0c00561
YR 2020
FD 2020-09-21
LK http://hdl.handle.net/10498/33285
UL http://hdl.handle.net/10498/33285
LA eng
DS Repositorio Institucional de la Universidad de Cádiz
RD 05-nov-2026