Reaction participants Show >> << Hide
- Name help_outline peregrinol diphosphate Identifier CHEBI:138232 Charge -3 Formula C20H35O8P2 InChIKeyhelp_outline BXBWAHVSCRSIHO-UEHSRLBXSA-K SMILEShelp_outline [C@@]1(CC/C(/C)=C/COP(OP(=O)([O-])[O-])(=O)[O-])([C@@H](CC[C@@]2([C@]1(C)CCCC2(C)C)[H])C)O 2D coordinates Mol file for the small molecule Search links Involved in 4 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline labd-13(16),14-diene-9-ol Identifier CHEBI:145549 Charge 0 Formula C20H34O InChIKeyhelp_outline PDMYSSCHAFCEEN-LCLWPZTBSA-N SMILEShelp_outline [C@]1([C@@H](CC[C@@]2([C@]1(C)CCCC2(C)C)[H])C)(CCC(C=C)=C)O 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
- Name help_outline diphosphate Identifier CHEBI:33019 (Beilstein: 185088) help_outline Charge -3 Formula HO7P2 InChIKeyhelp_outline XPPKVPWEQAFLFU-UHFFFAOYSA-K SMILEShelp_outline OP([O-])(=O)OP([O-])([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 1,211 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:62184 | RHEA:62185 | RHEA:62186 | RHEA:62187 | |
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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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Biosynthesis of bioactive diterpenoids in the medicinal plant Vitex agnus-castus.
Heskes A.M., Sundram T.C.M., Boughton B.A., Jensen N.B., Hansen N.L., Crocoll C., Cozzi F., Rasmussen S., Hamberger B., Hamberger B., Staerk D., Moeller B.L., Pateraki I.
Vitex agnus-castus L. (Lamiaceae) is a medicinal plant historically used throughout the Mediterranean region to treat menstrual cycle disorders, and is still used today as a clinically effective treatment for premenstrual syndrome. The pharmaceutical activity of the plant extract is linked to its ... >> More
Vitex agnus-castus L. (Lamiaceae) is a medicinal plant historically used throughout the Mediterranean region to treat menstrual cycle disorders, and is still used today as a clinically effective treatment for premenstrual syndrome. The pharmaceutical activity of the plant extract is linked to its ability to lower prolactin levels. This feature has been attributed to the presence of dopaminergic diterpenoids that can bind to dopamine receptors in the pituitary gland. Phytochemical analyses of V. agnus-castus show that it contains an enormous array of structurally related diterpenoids and, as such, holds potential as a rich source of new dopaminergic drugs. The present work investigated the localisation and biosynthesis of diterpenoids in V. agnus-castus. With the assistance of matrix-assisted laser desorption ionisation-mass spectrometry imaging (MALDI-MSI), diterpenoids were localised to trichomes on the surface of fruit and leaves. Analysis of a trichome-specific transcriptome database, coupled with expression studies, identified seven candidate genes involved in diterpenoid biosynthesis: three class II diterpene synthases (diTPSs); three class I diTPSs; and a cytochrome P450 (CYP). Combinatorial assays of the diTPSs resulted in the formation of a range of different diterpenes that can account for several of the backbones of bioactive diterpenoids observed in V. agnus-castus. The identified CYP, VacCYP76BK1, was found to catalyse 16-hydroxylation of the diol-diterpene, peregrinol, to labd-13Z-ene-9,15,16-triol when expressed in Saccharomyces cerevisiae. Notably, this product is a potential intermediate in the biosynthetic pathway towards bioactive furan- and lactone-containing diterpenoids that are present in this species. << Less
Plant J. 93:943-958(2018) [PubMed] [EuropePMC]
This publication is cited by 10 other entries.