TY - JOUR
T1 - Modulation of polyketide biosynthetic pathway of the endophytic fungus, Anteaglonium sp. FL0768, by copper (II) and anacardic acid
AU - Mafezoli, Jair
AU - Xu, Ya ming
AU - Hilário, Felipe
AU - Freidhof, Brandon
AU - Espinosa-Artiles, Patricia
AU - dos Santos, Lourdes C.
AU - de Oliveira, Maria C.F.
AU - Gunatilaka, A. A.Leslie
N1 - Funding Information:
Financial support for this work was provided by the U.S. National Cancer Institute (Grant R01 CA090265), U.S. National Institute of General Medical Sciences (Grant P41 GM094060) and CNPq, Brazil [Fellowship awards to JM (Process: 236451/2012-0) and MCFO (Process: 233171/2012-6)]. We are thankful to Drs. A. Elizabeth Arnold and Jana M. UʹRen (University of Arizona) for their help with collection and identification of the fungal strain, Prof. Diego L. V. Oliveira (Departamento de Química Orgânica e Inorgânica, Universidade Federal do Ceará Brazil) for providing anacardic acid, Prof. Lijiang Xuan (Shanghai Institute of Materia Medica, PR China) for HRESIMS data, and Ms. Mangping X. Liu (University of Arizona) for conducting cytotoxicity assays.
Funding Information:
Financial support for this work was provided by the U.S. National Cancer Institute (Grant R01 CA090265 ), U.S. National Institute of General Medical Sciences (Grant P41 GM094060 ) and CNPq, Brazil [Fellowship awards to JM (Process: 236451/2012-0) and MCFO (Process: 233171/2012-6)]. We are thankful to Drs. A. Elizabeth Arnold and Jana M. UʹRen (University of Arizona) for their help with collection and identification of the fungal strain, Prof. Diego L. V. Oliveira (Departamento de Química Orgânica e Inorgânica, Universidade Federal do Ceará, Brazil) for providing anacardic acid, Prof. Lijiang Xuan (Shanghai Institute of Materia Medica, PR China) for HRESIMS data, and Ms. Mangping X. Liu (University of Arizona) for conducting cytotoxicity assays.
Publisher Copyright:
© 2018 Phytochemical Society of Europe
PY - 2018/12
Y1 - 2018/12
N2 - In an attempt to explore the biosynthetic potential of endosymbiotic fungi, the secondary metabolite profiles of the endophytic fungus, Anteaglonium sp. FL0768, cultured under a variety of conditions were investigated. In potato dextrose broth (PDB) medium, Anteaglonium sp. FL0768 produced the heptaketides, herbaridine A (1), herbarin (2), 1-hydroxydehydroherbarin (3), scorpinone (4), and the methylated hexaketide 9S,11R-(+)-ascosalitoxin (5). Incorporation of commonly used epigenetic modifiers, 5-azacytidine and suberoylanilide hydroxamic acid, into the PDB culture medium of this fungus had no effect on its secondary metabolite profile. However, the histone acetyl transferase inhibitor, anacardic acid, slightly affected the metabolite profile affording scorpinone (4) as the major metabolite together with 1-hydroxydehydroherbarin (3) and a different methylated hexaketide, ascochitine (6). Intriguingly, incorporaion of Cu2+ into the PDB medium enhanced production of metabolites and drastically affected the biosynthetic pathway resulting in the production of pentaketide dimers, palmarumycin CE4 (7), palmarumycin CP4 (8), and palmarumycin CP1 (9), in addition to ascochitine (6). The structure of the new metabolite 7 was established with the help of spectroscopic data and by MnO2 oxidation to the known pentaketide dimer, palmarumycin CP3 (10). Biosynthetic pathways to some metabolites in Anteaglonium sp. FL0768 are presented and possible effects of AA and Cu2+ on these pathways are discussed.
AB - In an attempt to explore the biosynthetic potential of endosymbiotic fungi, the secondary metabolite profiles of the endophytic fungus, Anteaglonium sp. FL0768, cultured under a variety of conditions were investigated. In potato dextrose broth (PDB) medium, Anteaglonium sp. FL0768 produced the heptaketides, herbaridine A (1), herbarin (2), 1-hydroxydehydroherbarin (3), scorpinone (4), and the methylated hexaketide 9S,11R-(+)-ascosalitoxin (5). Incorporation of commonly used epigenetic modifiers, 5-azacytidine and suberoylanilide hydroxamic acid, into the PDB culture medium of this fungus had no effect on its secondary metabolite profile. However, the histone acetyl transferase inhibitor, anacardic acid, slightly affected the metabolite profile affording scorpinone (4) as the major metabolite together with 1-hydroxydehydroherbarin (3) and a different methylated hexaketide, ascochitine (6). Intriguingly, incorporaion of Cu2+ into the PDB medium enhanced production of metabolites and drastically affected the biosynthetic pathway resulting in the production of pentaketide dimers, palmarumycin CE4 (7), palmarumycin CP4 (8), and palmarumycin CP1 (9), in addition to ascochitine (6). The structure of the new metabolite 7 was established with the help of spectroscopic data and by MnO2 oxidation to the known pentaketide dimer, palmarumycin CP3 (10). Biosynthetic pathways to some metabolites in Anteaglonium sp. FL0768 are presented and possible effects of AA and Cu2+ on these pathways are discussed.
KW - Anacardic acid
KW - Anteaglonium
KW - Copper (II)
KW - Endophytic fungus
KW - Polyketide biosynthesis
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U2 - 10.1016/j.phytol.2018.10.011
DO - 10.1016/j.phytol.2018.10.011
M3 - Article
AN - SCOPUS:85055324451
SN - 1874-3900
VL - 28
SP - 157
EP - 163
JO - Phytochemistry Letters
JF - Phytochemistry Letters
ER -