RT journal article
T1 The complemented mutant (compl)Delta Bcstc7(niaD), in the STC7 of Botrytis cinerea led to the characterization of 11,12,13-tri-nor-eremophilenols derivatives
A1 Suárez Cáceres, Ivonne Rocío
A1 Pinedo Rivilla, Cristina
A1 Aleu Casatejada, Josefina
A1 Durán Patrón, Rosa María
A1 Macías Sánchez, Antonio José
A1 Hernández Galán, Rosario
A1 González Collado, Isidro
A2 BiomedicinaBiotecnología y Salud Pública
A2 Química Orgánica
K1 Botrytis cinerea
K1 Sclerotiniaceae
K1 Phytopathogenic fungus
K1 STC7
K1 Eremophilenols
K1 11,12,13-Tri-nor-eremophilenes
K1 Biosynthesis
AB Botrytis cinerea has high potential for the production of specialized metabolites. The recent resequencing of the genome of the B05.10 strain using PacBio technology and the resulting update of the Ensembl Fungi (2017) database in the genome sequence have been instrumental in identifying new genes that could be involved in secondary metabolism. Thus, a new sesquiterpene cyclase (STC) coding gene (Bcstc7) has been included in the gene list from this phytopathogenic fungus. We recently constructed the null and complement transformants in STC7 which enabled us to functionally characterize this STC. Deletion of the Bcstc7 gene abolished (+)-4-epi-eremophilenol biosynthesis, and could then be re-established by complementing the null mutant with the Bcstc7 gene. Chemical analysis of the complemented transformant suggests that STC7 is the principal enzyme responsible for the key cyclization step of farnesyl diphosphate (FDP) to (+)-4-epi-eremophil-9-en-11-ols.A thorough analysis of the metabolites produced by two wild-type strains, B05.10 and UCA992, and the complemented mutant (compl)Delta Bcstc7(niaD), revealed the isolation and structural characterization of six 11,12,13-tri-nor-eremophilene derivatives, in addition to a large number of known eremophilen-11-ol derivatives. The structural characterization was carried out by extensive spectroscopic techniques. The biosynthesis of these compounds is explained by a retroaldol reaction or by dehydration and oxidative cleavage of C11-C13 carbons. This is the first time that this interesting family of degraded eremophilenols has been isolated from the phytopathogenous fungus B. cinerea.
PB ELSEVIER
SN 0031-9422
YR 2022
FD 2022-01
LK http://hdl.handle.net/10498/25822
UL http://hdl.handle.net/10498/25822
LA eng
NO This research was supported by grants from MICINN-ERDF (RTI 2018-097356-B-C21 and -B-C22). Use of NMR facilities at the Servicio Centralizado de Ciencia y Tecnologia (SCCYT) of the University of Cadiz is acknowledged.
DS Repositorio Institucional de la Universidad de Cádiz
RD 12-nov-2026