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Literature summary for 5.4.99.50 extracted from

  • Souza-Moreira, T.M.; Alves, T.B.; Pinheiro, K.A.; Felippe, L.G.; De Lima, G.M.; Watanabe, T.F.; Barbosa, C.C.; Santos, V.A.; Lopes, N.P.; Valentini, S.R.; Guido, R.V.; Furlan, M.; Zanelli, C.F.
    Friedelin synthase from Maytenus ilicifolia leucine 482 plays an essential role in the production of the most rearranged pentacyclic triterpene (2016), Sci. Rep., 6, 36858 .
    View publication on PubMedView publication on EuropePMC
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Cloned(Commentary)

Cloned (Comment) Organism
OCS sequence comparisons and phylogenetic analysis, FRS quantitative real-time reverse transcription PCR enzyme expression analysis, recombinant expression in Saccharomyces cerevisiae strain VZL 1303, NMR spectroscopic identification of metabolites Monteverdia ilicifolia

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
(3S)-2,3-epoxy-2,3-dihydrosqualene Monteverdia ilicifolia
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 friedelin
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 ?

Organism

Organism UniProt Comment Textmining
Monteverdia ilicifolia A0A1L3HE30
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Source Tissue

Source Tissue Comment Organism Textmining
leaf friedelin synthase is the most expressed 2,3-oxidosqualene cyclases (OSC) sequence in Maytenus ilicifolia leaves. The enzyme shows the highest expression level in summer, then declining to the lowest level in spring, plants are maintained at the School of Pharmaceutical Sciences, Sao Paulo State University, Araraquara, Brazil Monteverdia ilicifolia
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additional information friedelin is synthesized after oxidosqualene cyclization in the leaves of Maytenus aquifolium and Salacia campestris and is transported to their roots where it is converted by oxidoreductases to maytenin and pristimerin Monteverdia ilicifolia
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Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(3S)-2,3-epoxy-2,3-dihydrosqualene
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 Monteverdia ilicifolia friedelin
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 ?

Synonyms

Synonyms Comment Organism
FRS
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 Monteverdia ilicifolia

General Information

General Information Comment Organism
evolution the enzyme belongs to the 2,3-oxidosqualene cyclases (OSCs) in the terpenoid cyclases/protein prenyltransferases superfamily. Among terpenes, triterpenes are directly derived from the enzymatic cyclization of 30-carbon squalene in bacteria or from the cyclization of derived 2,3-oxidosqualene in eukaryotes and are catalysed by oxidosqualene cyclases (OSCs). OSCs are product specific and compete for the substrate oxidosqualene to produce triterpenes. The cyclization of oxidosqualene is initiated by the formation of a carbocation, which undergoes several rearrangements leading to the formation of a variety of compounds. Among plant pentacyclic triterpenes, germanicol is the molecule with the smallest number of rearrangements, while friedelin has the highest number. Multiple sequence alignments demonstrate the presence of a leucine residue two positions upstream of the friedelin synthase Asp-Cys-Thr-Ala-Glu (DCTAE) active site motif, while the vast majority of OSCs identified so far have a valine or isoleucine residue at the same position Monteverdia ilicifolia
physiological function the friedelin molecule has antimicrobial activity against the Gram-positive and -negative bacteria Mycobacterium bovis, Mycobacterium tuberculosis, Mycobacterium madagascariense, and Mycobacterium indicus pranii, as well as the ability to affect growth inhibition in Candida spp., Trichophyton, and Aspergillus niger. Friedelin also shows vasodilation, anti-histaminic, anti-inflammatory, analgesic and antipyretic properties, gastroprotective, antioxidant, and liver protective activities, and the ability to inhibit some cancer cell lines. Friedelin is claimed to be the precursor of antitumoural quinone methide triterpenoids, including maytenin and pristimerin in the Celastraceae and Hippocrateacea families Monteverdia ilicifolia