The biosynthesis of the fungal meroterpenoids boviquinone-3 and -4 follows two different pathways

Mühlbauer, Andrea; Beyer, Jürgen; Steglich, Wölfgang

doi:10.1016/s0040-4039(98)01039-9

Cited by 23 publications

(20 citation statements)

References 10 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It has been shown, by biosynthetic labeling studies, that isoprenoids of the yeast Rhodotorula glutinis and of four fungal species are synthesized exclusively via the MVA pathway (23)(24)(25). A central enzyme of the MVA pathway, 3-hydroxy-3-methylglutaryl-CoA reductase, has been cloned and characterized from the fungus Gibberella fujikuroi (26).…”

Section: Resultsmentioning

confidence: 99%

Isoprenoid biosynthesis: The evolution of two ancient and distinct pathways across genomes

Lange

Rujan²,

Martin³

et al. 2000

Proc. Natl. Acad. Sci. U.S.A.

744

529

View full text Add to dashboard Cite

Isopentenyl diphosphate (IPP) is the central intermediate in the biosynthesis of isoprenoids, the most ancient and diverse class of natural products. Two distinct routes of IPP biosynthesis occur in nature: the mevalonate pathway and the recently discovered deoxyxylulose 5-phosphate (DXP) pathway. The evolutionary history of the enzymes involved in both routes and the phylogenetic distribution of their genes across genomes suggest that the mevalonate pathway is germane to archaebacteria, that the DXP pathway is germane to eubacteria, and that eukaryotes have inherited their genes for IPP biosynthesis from prokaryotes. The occurrence of genes specific to the DXP pathway is restricted to plastid-bearing eukaryotes, indicating that these genes were acquired from the cyanobacterial ancestor of plastids. However, the individual phylogenies of these genes, with only one exception, do not provide evidence for a specific affinity between the plant genes and their cyanobacterial homologues. The results suggest that lateral gene transfer between eubacteria subsequent to the origin of plastids has played a major role in the evolution of this pathway.chloroplast ͉ deoxyxylulose 5-phosphate ͉ endosymbiosis ͉ mevalonate ͉ phylogeny

show abstract

Section: Resultsmentioning

confidence: 99%

Isoprenoid biosynthesis: The evolution of two ancient and distinct pathways across genomes

Lange

Rujan²,

Martin³

et al. 2000

Proc. Natl. Acad. Sci. U.S.A.

744

529

View full text Add to dashboard Cite

show abstract

“…(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008) (1) in S. variegatus. [1] Here we report these and further experiments in detail and describe new insights into the biosynthesis of boviquinone-4 and bovilactone-4,4.…”

Section: Introductionmentioning

confidence: 78%

“…In the case of dihydroxyquinone 2*, the incorporation rate was determined by 13 C NMR analysis of the corresponding dimethyl ether. [1] The outcome of these experiments was critically dependent on the amount of precursor administered. Application of [1-13 C]-labelled 4-hydroxy-(10*) or 3,4-dihydroxybenzoic acid (11*) in doses of 5 mg per fruit body yielded mainly boviquinone-4 (2*), with incorporation rates ( 13 C atom-% excess) of 1.1 and 2.6 %, respectively (Table 2, Entries 1 and 3, and Scheme 3).…”

Section: Suillus Bovinusmentioning

confidence: 99%

See 1 more Smart Citation

Studies on the Biosynthesis of Bovilactone‐4,4 and Related Fungal Meroterpenoids

et al. 2008

Self Cite

View full text Add to dashboard Cite

Keywords: Natural products / Meroterpenoids / Mushrooms / Biosynthesis / Isotopic labelling The initial step in the biosynthesis of suillin (1), boviquinone-4 (2) and bovilactone-4,4 (3) in Suillus species is the geranylgeranylation of 3,4-dihydroxybenzoic acid at the 2-position. Feeding experiments with advanced precursors have identified boviquinone-4 and deacetylsuillin (9) as building blocks for the dilactone and catechol moieties, respectively, of bovilactone-4,4 (3). In order to explain the failure of boviquinone-4 (2) to incorporate side-chain-labelled deace-

show abstract

“…(Gomphidiaceae), bovinoquinone-4 (2,5-dihydroxy-3-geranylgeranyl-1,4-benzoquinone, 53) is an example of prenylated benzoquinones found in Suillus bovinus (L.) Roussel. (Mühlbauer et al 1998). The red pigment tridentoquinone (54) is the main pigment of S. tridenticus (Bres.)…”

Section: Boletalesmentioning

confidence: 99%

Pigments of higher fungi - a review

Velı́šek¹,

Cejpek²

2011

Czech J. Food Sci.

100

View full text Add to dashboard Cite

Velíšek J., Cejpek K. (2011): Pigments of higher fungi -a review. Czech J. Food Sci., 29: 87-102.This review surveys the literature dealing with the structure of pigments produced by fungi of the phylum Basidiomycota and also covers their significant colourless precursors that are arranged according to their biochemical origin to the shikimate, polyketide and terpenoid derived compounds. The main groups of pigments and their leucoforms include simple benzoquinones, terphenylquinones, pulvinic acids, and derived products, anthraquinones, terpenoid quinones, benzotropolones, compounds of fatty acid origin and nitrogen-containing pigments (betalains and other alkaloids). Out of three orders proposed, the concern is only focused on the orders Agaricales and Boletales and the taxonomic groups (incertae sedis) Cantharellales, Hymenochaetales, Polyporales, Russulales, and Telephorales that cover most of the so called higher fungi often referred to as mushrooms. Included are only the European species that have generated scientific interest due to their attractive colours, taxonomic importance and distinct biological activity.

show abstract

The biosynthesis of the fungal meroterpenoids boviquinone-3 and -4 follows two different pathways

Cited by 23 publications

References 10 publications

Isoprenoid biosynthesis: The evolution of two ancient and distinct pathways across genomes

Isoprenoid biosynthesis: The evolution of two ancient and distinct pathways across genomes

Studies on the Biosynthesis of Bovilactone‐4,4 and Related Fungal Meroterpenoids

Pigments of higher fungi - a review

Contact Info

Product

Resources

About