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- Name help_outline (S)-2,3-epoxysqualene Identifier CHEBI:15441 Charge 0 Formula C30H50O InChIKeyhelp_outline QYIMSPSDBYKPPY-RSKUXYSASA-N SMILEShelp_outline CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C=C(/C)CC\C=C(/C)CC[C@@H]1OC1(C)C 2D coordinates Mol file for the small molecule Search links Involved in 30 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline shionone Identifier CHEBI:63459 (CAS: 10376-48-4) help_outline Charge 0 Formula C30H50O InChIKeyhelp_outline HXPXUNQUXCHJLL-LZQQOHPBSA-N SMILEShelp_outline [H][C@@]12CCC(=O)[C@H](C)[C@@]1(C)CC[C@@]1([H])[C@@]2(C)CC[C@@]2(C)C[C@](C)(CCC=C(C)C)CC[C@]12C 2D coordinates Mol file for the small molecule Search links Involved in 1 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:31847 | RHEA:31848 | RHEA:31849 | RHEA:31850 | |
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| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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Publications
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Molecular characterization of an oxidosqualene cyclase that yields shionone, a unique tetracyclic triterpene ketone of Aster tataricus.
Sawai S., Uchiyama H., Mizuno S., Aoki T., Akashi T., Ayabe S., Takahashi T.
Shionone is the major triterpenoid component of Aster tataricus possessing a unique all six-membered tetracyclic skeleton and 3-oxo-4-monomethyl structure. To clarify its biosynthetic process, an oxidosqualene cyclase cDNA was isolated from A. tataricus, and the function of the enzyme was determin ... >> More
Shionone is the major triterpenoid component of Aster tataricus possessing a unique all six-membered tetracyclic skeleton and 3-oxo-4-monomethyl structure. To clarify its biosynthetic process, an oxidosqualene cyclase cDNA was isolated from A. tataricus, and the function of the enzyme was determined in lanosterol synthase-deficient yeast. The cyclase yielded ca. 90% shionone and small amounts of β-amyrin, friedelin, dammara-20,24-dienol, and 4-epishionone and was designated as a shionone synthase (SHS). Transcripts of SHS were detected in A. tataricus organs, confirming its involvement in shionone biosynthesis. SHS was shown to have evolved in the Asteraceae from β-amyrin synthase lineages and acquired characteristic species- and product-specificities. << Less