Meroterpenoids produced by fungi

Geris, Regina; Simpson, Thomas J.

doi:10.1039/b820413f

Cited by 357 publications

(314 citation statements)

References 183 publications

(248 reference statements)

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“…A number of bioinformatics tools for genome mining (e.g. antiSMASH 2.0 [237]) have been developed for this purpose (for a recent review, see [238]), but these tools rely on algorithms trained with hidden Markov models derived from known biosynthetic genes-the majority of which come from Ascomycota and Actinomycetes. In our experience, when applied to terpenoid pathways from Basidiomycota, they tend to identify only a subset of the pathways and have difficulties identifying cluster boundaries.…”

Section: Discussionmentioning

confidence: 99%

Biosynthesis of Terpenoid Natural Products in Fungi

Schmidt‐Dannert

2014

Biotechnology of Isoprenoids

108

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Tens of thousands of terpenoid natural products have been isolated from plants and microbial sources. Higher fungi (Ascomycota and Basidiomycota) are known to produce an array of well-known terpenoid natural products, including mycotoxins, antibiotics, antitumor compounds, and phytohormones. Except for a few well-studied fungal biosynthetic pathways, the majority of genes and biosynthetic pathways responsible for the biosynthesis of a small number of these secondary metabolites have only been discovered and characterized in the past 5-10 years. This chapter provides a comprehensive overview of the current knowledge on fungal terpenoid biosynthesis from biochemical, genetic, and genomic viewpoints. Enzymes involved in synthesizing, transferring, and cyclizing the prenyl chains that form the hydrocarbon scaffolds of fungal terpenoid natural products are systematically discussed. Genomic information and functional evidence suggest differences between the terpenome of the two major fungal phyla--the Ascomycota and Basidiomycota--which will be illustrated for each group of terpenoid natural products.

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Section: Discussionmentioning

confidence: 99%

Biosynthesis of Terpenoid Natural Products in Fungi

Schmidt‐Dannert

2014

Biotechnology of Isoprenoids

108

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“…The total EtOAc-soluble fraction (35.5 g) was subjected to stepgradient silica gel column chromatography (CC) with a solvent system consisting of 0-100% petroleum ether (PE)-EtOAc to afford 14 fractions (Frs. [1][2][3][4][5][6][7][8][9][10][11][12][13][14] on the basis of TLC analysis. Fr.…”

Section: Extraction and Isolationmentioning

confidence: 99%

“…1,2 Aspergillus ustus (A. insuetus) has been proven to be a prolific producer of terpenes, containing sesquiterpenes, sesterterpenes, and meroterpenes. [3][4][5][6][7] However, most of them have been assigned only relative configurations, and their absolute configurations remain unresolved. In our ongoing program to discover new bioactive compounds from marine algae and their associated fungi, a fungus A. ustus isolated from the marine green alga Codium fragile was investigated.…”

Section: Introductionmentioning

confidence: 99%

Terretonin, ophiobolin, and drimaneterpenes with absolute configurations from an algicolous Aspergillus ustus

et al. 2013

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One new meroterpene, 1,2-dihydroterretonin F (2), five new sesterterpenes, (6a)-21-deoxyophiobolin G(3), (6a)-16,17-dihydro-21-deoxyophiobolin G (4), ophiobolin U (5), ophiobolin V (6), and ophiobolin W (7), two new sesquiterpenes, (6-strobilactone-B) esters of (E,E)-6,7-epoxy-2,4-octadienoic acids (13 and 14), and twelve known terpenes (1, 8-12, and 15-20) were isolated from Aspergillus ustus, a fungus from the fresh tissue of marine green alga Codium fragile. Their structures and absolute configurations were identified by NMR and mass spectroscopic methods as well as quantum chemical calculations. Some of the isolates exhibited antibacterial activity and brine shrimp toxicity.

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“…Meroterpenoids are hybrid natural products that are partially derived from terpenoid origins, and thus they have the prefi x "mero-", meaning "part, partial, or segment" [ 1 ]. The fusion of the structurally diverse terpenoid and non-terpenoid moieties is a characteristic of the unique and complex molecular structures of this class of natural products.…”

Section: Introductionmentioning

confidence: 99%