The Biotransformation of Two 3,15-Oxygenate <i>ent</i>-Kaurane Derivatives by <i>Gibberella fujikuroi</i>

Fraga, Braulio M.; Hernández, Melchor G.; Guillermo, Ricardo

doi:10.1021/np960405q

Cited by 23 publications

(26 citation statements)

References 17 publications

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“…Fraga and co-workers [75,93] showed that the biotransformation of ent-15β,16β-dihydroxy-or ent-15β,16β-epoxy-kauranes by Gibberella fujikuroi produced selective hydroxylation at the ent-7β and ent-11α positions, and inhibited the oxidation of C-19. Similar results were also obtained in kauranes having the ent-16β,17-diol [94], ent-15α-hydroxyl or 15-oxo [95] groups. Besides, an ent-11α-hydroxylation seems to be directed by the presence of a 7-oxo group [96].…”

Section: Microbiological Methodssupporting

confidence: 82%

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Occurrence, Biological Activities and Synthesis of Kaurane Diterpenes and their Glycosides

2007

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This paper presents a review on kaurane diterpenes and their glycoside derivatives, covering aspects of their occurrence, biological activities and the synthesis of these natural products and their analogues. First, it shows and classifies diterpenes, in accordance with the already established structural criteria in the literature. Then, kaurane diterpenes are presented, focusing on their chemical structures, occurrence in the plant kingdom and their main, recently described, biological activities. Moreover, the most significant works, published between 1964 and November 2006, which describe the total synthesis or structural transformations of some kaurane diterpenes, including either semisynthetic and/or microbiological methodologies, are consisely reviewed. At this point, some general considerations on glycosides are introduced, and kaurane glycosides are presented and discussed on the basis of their toxic importance and occurrence in the plant kingdom, having focused on related aspects of their biological activities and the relationships between these activities and the structural factors of their molecules. Finally, the principal methods of glycosidation by enzymatic and chemical processes are both presented, and a few papers on the synthesis of kaurane glycosides are succinctly discussed. Molecules 2007, 12 456

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Section: Microbiological Methodssupporting

confidence: 82%

“…Besides, an ent-11α-hydroxylation seems to be directed by the presence of a 7-oxo group [96]. The non-oxidation of C-19 by this microorganism was also observed in kauranes having one ent-3β-hydroxyl or one carbonyl at C-3 [75,95].…”

Section: Microbiological Methodsmentioning

confidence: 67%

Occurrence, Biological Activities and Synthesis of Kaurane Diterpenes and their Glycosides

2007

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“…Transformation was carried out as previously described (Tudzynski et al, 1996). About 10 7 protoplasts were transformed with about 10 μg of the amplified replacement cassettes for generating the knock-outs.…”

Section: Methodsmentioning

confidence: 99%

Lack of the COMPASS Component Ccl1 Reduces H3K4 Trimethylation Levels and Affects Transcription of Secondary Metabolite Genes in Two Plant–Pathogenic Fusarium Species

Studt

Janevska²,

Arndt

et al. 2017

Front. Microbiol.

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In the two fungal pathogens Fusarium fujikuroi and Fusarium graminearum, secondary metabolites (SMs) are fitness and virulence factors and there is compelling evidence that the coordination of SM gene expression is under epigenetic control. Here, we characterized Ccl1, a subunit of the COMPASS complex responsible for methylating lysine 4 of histone H3 (H3K4me). We show that Ccl1 is not essential for viability but a regulator of genome-wide trimethylation of H3K4 (H3K4me3). Although, recent work in Fusarium and Aspergillus spp. detected only sporadic H3K4 methylation at the majority of the SM gene clusters, we show here that SM profiles in CCL1 deletion mutants are strongly deviating from the wild type. Cross-complementation experiments indicate high functional conservation of Ccl1 as phenotypes of the respective △ccl1 were rescued in both fungi. Strikingly, biosynthesis of the species-specific virulence factors gibberellic acid and deoxynivalenol produced by F. fujikuroi and F. graminearum, respectively, was reduced in axenic cultures but virulence was not attenuated in these mutants, a phenotype which goes in line with restored virulence factor production levels in planta. This suggests that yet unknown plant-derived signals are able to compensate for Ccl1 function during pathogenesis.

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“…2) H (8), and HÀC(8)/HÀC(7) indicated that they were on the same side of the molecule, and they were arbitrarily assigned as b-oriented. The correlations H a ÀC(2)/Me(14), Me(14)/ H a ÀC (9), and H a ÀC(9)/HÀC(11) indicated a-orientation. Thus, 2 is a rare natural ciseudesmane derivative [12].…”

mentioning

confidence: 99%

“…1) experiments provided the gross structure of 1 as a kaurane-type diterpenoid or its enantiomer [8] with a ketone and three OH groups. The HMBC of Me (17) (7) is a-oriented, and the OH groups at C(11) and C(14), and the Me group at C(16) are b-oriented, which was supported by the chemical shifts and splitting patterns of corresponding H-atoms [8] [9].…”

mentioning

confidence: 99%

Terpenoids from the Chinese Liverwort Chiloscyphus polyanthus

Xie

Sun

Guo

et al. 2011

Helvetica Chimica Acta

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The Biotransformation of Two 3,15-Oxygenate ent-Kaurane Derivatives by Gibberella fujikuroi

Cited by 23 publications

References 17 publications

Occurrence, Biological Activities and Synthesis of Kaurane Diterpenes and their Glycosides

Occurrence, Biological Activities and Synthesis of Kaurane Diterpenes and their Glycosides

Lack of the COMPASS Component Ccl1 Reduces H3K4 Trimethylation Levels and Affects Transcription of Secondary Metabolite Genes in Two Plant–Pathogenic Fusarium Species

Terpenoids from the Chinese Liverwort Chiloscyphus polyanthus

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