5.4.99.50: friedelin synthase
This is an abbreviated version!
For detailed information about friedelin synthase, go to the full flat file.
Word Map on EC 5.4.99.50
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5.4.99.50
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oxidosqualene
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ilicifolia
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pentacyclic
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maytenus
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triterpene
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triterpenoids
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cyclases
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ketone
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lupeol
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kalanchoe
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cyclization
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cycloartenol
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daigremontiana
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cork
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2,3-oxidosqualene
- 5.4.99.50
- oxidosqualene
- ilicifolia
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pentacyclic
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maytenus
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triterpene
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triterpenoids
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cyclases
- ketone
- lupeol
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kalanchoe
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cyclization
- cycloartenol
- daigremontiana
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cork
- 2,3-oxidosqualene
Reaction
Synonyms
FRS, FRS2, FRS3, MiFRS, MiFRS2, MiFRS3, OSC
ECTree
5.4.99.50 friedelin synthaseAdvanced search results
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General Information on EC 5.4.99.50 - friedelin synthase
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GENERAL INFORMATION 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
evolution
metabolism
the enzyme is involved in the biosynthesis of steroidal and pentacyclic triterpenes, overview. Friedelin is a precursor for other triterpenes and quinonemethides
physiological function
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
evolution
the enzyme belongs to the terpenoid cyclases/protein prenyltransferases superfamily. Characterictic motifs for the OSC family and friedelin synthase are the four structural QW motifs (aromatic rich motifs of seven residues from Gln to Trp), the cavity site, and the Leu482. All of them are important for product specificity
physiological function
the enzyme synthesizes friedelin, a triterpene ketone with anti-inflammatory and gastroprotective activities and it is a precursor of relevant antitumor quinonemethides
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
