Reaction participants Show >> << Hide
- Name help_outline (2E)-geraniol Identifier CHEBI:17447 (Beilstein: 1722456; CAS: 106-24-1) help_outline Charge 0 Formula C10H18O InChIKeyhelp_outline GLZPCOQZEFWAFX-JXMROGBWSA-N SMILEShelp_outline CC(C)=CCC\C(C)=C\CO 2D coordinates Mol file for the small molecule Search links Involved in 10 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline O2 Identifier CHEBI:15379 (CAS: 7782-44-7) help_outline Charge 0 Formula O2 InChIKeyhelp_outline MYMOFIZGZYHOMD-UHFFFAOYSA-N SMILEShelp_outline O=O 2D coordinates Mol file for the small molecule Search links Involved in 2,648 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
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Namehelp_outline
reduced [NADPH—hemoprotein reductase]
Identifier
RHEA-COMP:11964
Reactive part
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- Name help_outline FMNH2 Identifier CHEBI:57618 (Beilstein: 6258176) help_outline Charge -2 Formula C17H21N4O9P InChIKeyhelp_outline YTNIXZGTHTVJBW-SCRDCRAPSA-L SMILEShelp_outline Cc1cc2Nc3c([nH]c(=O)[nH]c3=O)N(C[C@H](O)[C@H](O)[C@H](O)COP([O-])([O-])=O)c2cc1C 2D coordinates Mol file for the small molecule Search links Involved in 771 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline (6E)-8-hydroxygeraniol Identifier CHEBI:64235 (CAS: 26488-97-1) help_outline Charge 0 Formula C10H18O2 InChIKeyhelp_outline PREUOUJFXMCMSJ-TXFIJWAUSA-N SMILEShelp_outline C\C(CO)=C/CC\C(C)=C\CO 2D coordinates Mol file for the small molecule Search links Involved in 6 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline H+ Identifier CHEBI:15378 Charge 1 Formula H InChIKeyhelp_outline GPRLSGONYQIRFK-UHFFFAOYSA-N SMILEShelp_outline [H+] 2D coordinates Mol file for the small molecule Search links Involved in 9,176 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline H2O Identifier CHEBI:15377 (Beilstein: 3587155; CAS: 7732-18-5) help_outline Charge 0 Formula H2O InChIKeyhelp_outline XLYOFNOQVPJJNP-UHFFFAOYSA-N SMILEShelp_outline [H]O[H] 2D coordinates Mol file for the small molecule Search links Involved in 6,048 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
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Namehelp_outline
oxidized [NADPH—hemoprotein reductase]
Identifier
RHEA-COMP:11965
Reactive part
help_outline
- Name help_outline FMN Identifier CHEBI:58210 Charge -3 Formula C17H18N4O9P InChIKeyhelp_outline ANKZYBDXHMZBDK-SCRDCRAPSA-K SMILEShelp_outline C12=NC([N-]C(C1=NC=3C(N2C[C@@H]([C@@H]([C@@H](COP(=O)([O-])[O-])O)O)O)=CC(=C(C3)C)C)=O)=O 2D coordinates Mol file for the small molecule Search links Involved in 781 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
RHEA:32495 | RHEA:32496 | RHEA:32497 | RHEA:32498 | |
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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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Geraniol 10-hydroxylase, a cytochrome P450 enzyme involved in terpenoid indole alkaloid biosynthesis.
Collu G., Unver N., Peltenburg-Looman A.M., van der Heijden R., Verpoorte R., Memelink J.
Geraniol 10-hydroxylase (G10H) is a cytochrome P450 monooxygenase involved in the biosynthesis of iridoid monoterpenoids and several classes of monoterpenoid alkaloids found in a diverse range of plant species. Catharanthus roseus (Madagascar periwinkle) contains monoterpenoid indole alkaloids, se ... >> More
Geraniol 10-hydroxylase (G10H) is a cytochrome P450 monooxygenase involved in the biosynthesis of iridoid monoterpenoids and several classes of monoterpenoid alkaloids found in a diverse range of plant species. Catharanthus roseus (Madagascar periwinkle) contains monoterpenoid indole alkaloids, several of which are pharmaceutically important. Vinblastine and vincristine, for example, find widespread use as anti-cancer drugs. G10H is thought to play a key regulatory role in terpenoid indole alkaloid biosynthesis. We purified G10H from C. roseus cells. Using degenerate PCR primers based on amino acid sequence information we cloned the corresponding cDNA. The encoded CYP76B6 protein has G10H activity when expressed in C. roseus and yeast cells. The stress hormone methyljasmonate strongly induced G10h gene expression coordinately with other terpenoid indole alkaloid biosynthesis genes in a C. roseus cell culture. << Less
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Cloning and functional analysis of geraniol 10-hydroxylase, a cytochrome P450 from Swertia mussotii Franch.
Wang J., Liu Y., Cai Y., Zhang F., Xia G., Xiang F.
Swertia mussotii Franch has anti-hepatitis activity and contains a high level of iridoid monoterpenoids. The cytochrome P450 monooxygenase (CYP) geraniol 10-hydroxylase (G10H) is thought to play an important role in iridoid monoterpenoid and indole alkaloid biosynthesis. Here we report the isolati ... >> More
Swertia mussotii Franch has anti-hepatitis activity and contains a high level of iridoid monoterpenoids. The cytochrome P450 monooxygenase (CYP) geraniol 10-hydroxylase (G10H) is thought to play an important role in iridoid monoterpenoid and indole alkaloid biosynthesis. Here we report the isolation of a full-length cDNA clone of S. mussotii G10H (SmG10H). The predicted gene product was a 496 residue protein designated CYP76B10, the sequence of which was highly similar to that of the CYP76 family, particularly to Catharanthus roseus G10H (80.2% homology). SmG10H transcripts were much more abundant in the leaves than in either the root or the stem, and were derived from a single copy gene. SmG10H expression was upregulated by treatment with methyljasmonate (MeJA) over a period from 6 h to 36 h after treatment. Accumulation of swertiamarin increased after elicitation by MeJA. SmG10H was heterologously expressed in both Escherichia coli and Pichia pastoris (yeast), forming a 55.5-kDa protein. Based on analysis in vitro, SmG10H was found to have catalytic activity hydroxylating geraniol. In the SmG10H overexpression plants, the level of SmG10H transcript and the contents of 10-hydroxygeraniol and swertiamarin increased simultaneously. << Less
Biosci. Biotechnol. Biochem. 74:1583-1590(2010) [PubMed] [EuropePMC]
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Functional expression of geraniol 10-hydroxylase reveals its dual function in the biosynthesis of terpenoid and phenylpropanoid.
Sung P.H., Huang F.C., Do Y.Y., Huang P.L.
Geraniol 10-hydroxylase (G10H), a cytochrome P450 monooxygenase, has been reported to be involved in the biosynthesis of terpenoid indole alkaloids. The gene for Catharanthus roseus G10H (CrG10H) was cloned and heterologously expressed in baculovirus-infected insect cells. A number of substrates w ... >> More
Geraniol 10-hydroxylase (G10H), a cytochrome P450 monooxygenase, has been reported to be involved in the biosynthesis of terpenoid indole alkaloids. The gene for Catharanthus roseus G10H (CrG10H) was cloned and heterologously expressed in baculovirus-infected insect cells. A number of substrates were subjected to assay the enzyme activity of CrG10H. As reported in a previous study, CrG10H hydroxylated the monoterpenoid geraniol at the C-10 position to generate 10-hydroxygeraniol. Interestingly, CrG10H also catalyzed 3'-hydroxylation of naringenin to produce eriodictyol. Coexpression of an Arabidopsis NADPH P450 reductase substantially increased the ability of CrG10H to hydroxylate naringenin. The catalytic activity of CrG10H was approximately 10 times more efficient with geraniol than with naringenin, judged by the k(cat)/K(m) values. Thus, G10H also plays an important role in the biosynthetic pathway of flavonoids, in addition to its previously described role in the metabolism of terpenoids. << Less
J. Agric. Food Chem. 59:4637-4643(2011) [PubMed] [EuropePMC]