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 | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
---|---|---|---|---|---|---|
(3S)-2,3-epoxy-2,3-dihydrosqualene | Monteverdia ilicifolia | - |
friedelin | - |
? |
Organism | UniProt | Comment | Textmining |
---|---|---|---|
Monteverdia ilicifolia | A0A1L3HE30 | - |
- |
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 | - |
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 | - |
Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
---|---|---|---|---|---|---|
(3S)-2,3-epoxy-2,3-dihydrosqualene | - |
Monteverdia ilicifolia | friedelin | - |
? |
Synonyms | Comment | Organism |
---|---|---|
FRS | - |
Monteverdia ilicifolia |
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 |