Alkaloids Derived from Tryptophan: A Focus on Ergot Alkaloids

Mai, Peter; Li, Shu-Ming

doi:10.1007/978-3-642-22144-6_24

Cited by 8 publications

(4 citation statements)

References 123 publications

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“…Usually, the numbering of carbons into the ergot alkaloid backbone is established according to the original ergoline system [20]. Nevertheless, in their first report, the 8-chlororugulovasines were named from a different counting system [17], where the new halogenated rugulovasines were named on the basis of their known analogues.…”

Section: Introductionmentioning

confidence: 99%

Dichlorinated and Brominated Rugulovasines, Ergot Alkaloids Produced by Talaromyces wortmannii

et al. 2015

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UHPLC-DAD-HRMS based dereplication guided the detection of new halogenated alkaloids co-produced by Talaromyces wortmannii. From the fungal growth in large scale, the epimers 2,8-dichlororugulovasines A and B were purified and further identified by means of a HPLC-SPE/NMR hyphenated system. Brominated rugulovasines were also detected when the microbial incubation medium was supplemented with bromine sources. Studies from 1D/2D NMR and HRMS spectroscopy data allowed the structural elucidation of the dichlorinated compounds, while tandem MS/HRMS data analysis supported the rationalization of brominated congeners. Preliminary genetic studies revealed evidence that FADH2 dependent halogenase can be involved in the biosynthesis of the produced halocompounds.

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Section: Introductionmentioning

confidence: 99%

Dichlorinated and Brominated Rugulovasines, Ergot Alkaloids Produced by Talaromyces wortmannii

et al. 2015

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“…Tryptophan is a key residue in numerous important natural products including daptomycin, the calcium dependent antibiotic, , conotoxin, and the uridyl peptide antibiotics . Tryptophan is also a biosynthetic precursor in notable bioactive compounds such as the anticancer agent staurosporine, the ergot alkaloids, indole alkaloids such as vindoline and vinblastine, and epipolythiodiketopiperazine alkaloids such as (+)-gliocladins and (+)-bionectins . The 7-halotryptophan motif is found in a number of biologically active natural products, such as rebeccamycin and pyrrolnitrin .…”

mentioning

confidence: 99%

The First One-Pot Synthesis of l-7-Iodotryptophan from 7-Iodoindole and Serine, and an Improved Synthesis of Other l-7-Halotryptophans

et al. 2014

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“…As a result, the production of such mixed (or hybrid) fungal BGCs results in chimeric secondary metabolites such as NRPS/PKS, NRPS/terpenoid, PKS/terpenoid, or alkaloid/terpenoid hybrids ( Figure 1 e–h) [ 67 , 160 , 207 ]. Some (but not all) alkaloids also use core enzymes for their construction [ 208 , 209 ]; for example, ergot alkaloids use NRPS [ 210 , 211 ]. In rare cases, secondary metabolites in fungi result from crosstalk between two separate BGCs [ 212 ].…”

Section: Biosynthetic Gene Clusters (Bgcs) For the Production Of Fung...mentioning

confidence: 99%

Fungal BGCs for Production of Secondary Metabolites: Main Types, Central Roles in Strain Improvement, and Regulation According to the Piano Principle

Zhgun

2023

IJMS

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Filamentous fungi are one of the most important producers of secondary metabolites. Some of them can havse a toxic effect on the human body, leading to diseases. On the other hand, they are widely used as pharmaceutically significant drugs, such as antibiotics, statins, and immunosuppressants. A single fungus species in response to various signals can produce 100 or more secondary metabolites. Such signaling is possible due to the coordinated regulation of several dozen biosynthetic gene clusters (BGCs), which are mosaically localized in different regions of fungal chromosomes. Their regulation includes several levels, from pathway-specific regulators, whose genes are localized inside BGCs, to global regulators of the cell (taking into account changes in pH, carbon consumption, etc.) and global regulators of secondary metabolism (affecting epigenetic changes driven by velvet family proteins, LaeA, etc.). In addition, various low-molecular-weight substances can have a mediating effect on such regulatory processes. This review is devoted to a critical analysis of the available data on the “turning on” and “off” of the biosynthesis of secondary metabolites in response to signals in filamentous fungi. To describe the ongoing processes, the model of “piano regulation” is proposed, whereby pressing a certain key (signal) leads to the extraction of a certain sound from the “musical instrument of the fungus cell”, which is expressed in the production of a specific secondary metabolite.

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Alkaloids Derived from Tryptophan: A Focus on Ergot Alkaloids

Cited by 8 publications

References 123 publications

Dichlorinated and Brominated Rugulovasines, Ergot Alkaloids Produced by Talaromyces wortmannii

Dichlorinated and Brominated Rugulovasines, Ergot Alkaloids Produced by Talaromyces wortmannii

The First One-Pot Synthesis of l-7-Iodotryptophan from 7-Iodoindole and Serine, and an Improved Synthesis of Other l-7-Halotryptophans

Fungal BGCs for Production of Secondary Metabolites: Main Types, Central Roles in Strain Improvement, and Regulation According to the Piano Principle

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