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Hedycaryol - Central Intermediates in Sesquiterpene Biosynthesis, Part II.
Xu H, Dickschat JS. Xu H, et al. Chemistry. 2022 May 6;28(26):e202200405. doi: 10.1002/chem.202200405. Epub 2022 Mar 21. Chemistry. 2022. PMID: 35239190 Free PMC article. Review.
The known sesquiterpenes that arise biosynthetically from hedycaryol are summarised. Reasonings for the assignments of their absolute configurations are discussed. The analysis provided here suggests that reprotonations at the C1=C10 double bond of hedycaryol are di …
The known sesquiterpenes that arise biosynthetically from hedycaryol are summarised. Reasonings for the assignments of their absolute …
Isotopic Labeling Experiments Solve the Hedycaryol Problem.
Xu H, Lackus ND, Köllner TG, Dickschat JS. Xu H, et al. Org Lett. 2022 Jan 21;24(2):587-591. doi: 10.1021/acs.orglett.1c04021. Epub 2022 Jan 5. Org Lett. 2022. PMID: 34985289
Hedycaryol is a widespread sesquiterpene alcohol and important biosynthetic intermediate toward eudesmols and guaiols. ...This problem was solved through the enzymatic synthesis of isotopically labeled materials using a mutated plant and a bacterial enzyme for access to bo …
Hedycaryol is a widespread sesquiterpene alcohol and important biosynthetic intermediate toward eudesmols and guaiols. ...This proble …
Hedycaryol synthase in complex with nerolidol reveals terpene cyclase mechanism.
Baer P, Rabe P, Citron CA, de Oliveira Mann CC, Kaufmann N, Groll M, Dickschat JS. Baer P, et al. Chembiochem. 2014 Jan 24;15(2):213-6. doi: 10.1002/cbic.201300708. Epub 2014 Jan 7. Chembiochem. 2014. PMID: 24399794
The biosynthesis of terpenes is catalysed by class I and II terpene cyclases. Here we present structural data from a class I hedycaryol synthase in complex with nerolidol, serving as a surrogate for the reaction intermediate nerolidyl diphosphate. ...
The biosynthesis of terpenes is catalysed by class I and II terpene cyclases. Here we present structural data from a class I hedycaryol …
Identification of a novel hedycaryol synthase gene isolated from Camellia brevistyla flowers and floral scent of Camellia cultivars.
Hattan J, Shindo K, Ito T, Shibuya Y, Watanabe A, Tagaki C, Ohno F, Sasaki T, Ishii J, Kondo A, Misawa N. Hattan J, et al. Planta. 2016 Apr;243(4):959-72. doi: 10.1007/s00425-015-2454-6. Epub 2016 Jan 7. Planta. 2016. PMID: 26744017
A novel terpene synthase (Tps) gene isolated from Camellia brevistyla was identified as hedycaryol synthase, which was shown to be expressed specifically in flowers. ...Spectroscopic data of elemol were also determined. These results indicated that the CbTps1 gene encodes …
A novel terpene synthase (Tps) gene isolated from Camellia brevistyla was identified as hedycaryol synthase, which was shown to be ex …
Essential Oils from the Malaysian Citrus (Rutaceae) Medicinal Plants.
Md Othman SNA, Hassan MA, Nahar L, Basar N, Jamil S, Sarker SD. Md Othman SNA, et al. Medicines (Basel). 2016 Jun 3;3(2):13. doi: 10.3390/medicines3020013. Medicines (Basel). 2016. PMID: 28930124 Free PMC article. Review.
In addition, citronellal (20) (61.7%-72.5%), linalool (18) (56.5%), and hedycaryol (23) (19.0%) were identified as the major components in the oil of C. hystrix leaves, C. grandis blossom and C. microcarpa leaves, respectively. ...
In addition, citronellal (20) (61.7%-72.5%), linalool (18) (56.5%), and hedycaryol (23) (19.0%) were identified as the major componen …
Functional characterisation of twelve terpene synthases from actinobacteria.
Chhalodia AK, Xu H, Tabekoueng GB, Gu B, Taizoumbe KA, Lauterbach L, Dickschat JS. Chhalodia AK, et al. Beilstein J Org Chem. 2023 Sep 15;19:1386-1398. doi: 10.3762/bjoc.19.100. eCollection 2023. Beilstein J Org Chem. 2023. PMID: 37736393 Free PMC article.
The characterised enzymes include a new epi-isozizaene synthase with monoterpene synthase side activity, a 7-epi-alpha-eudesmol synthase that also produces hedycaryol and germacrene A, and four more sesquiterpene synthases that produce mixtures of hedycaryol and ger …
The characterised enzymes include a new epi-isozizaene synthase with monoterpene synthase side activity, a 7-epi-alpha-eudesmol synthase tha …
Probing Enzymatic Structure and Function in the Dihydroxylating Sesquiterpene Synthase ZmEDS.
Liang J, Wang L, Liu J, Shen Q, Fu J, Peters RJ, Wang Q. Liang J, et al. Biochemistry. 2020 Jul 21;59(28):2660-2666. doi: 10.1021/acs.biochem.0c00395. Epub 2020 Jun 28. Biochemistry. 2020. PMID: 32558549 Free PMC article.
This production of dual hydroxyl groups is presumably enabled by protonation of the singly hydroxylated transient stable intermediate hedycaryol. To probe the enzymatic structure-function relationships underlying this unusual reaction, protein modeling and docking were use …
This production of dual hydroxyl groups is presumably enabled by protonation of the singly hydroxylated transient stable intermediate hed …
Gene Networks Underlying Cannabinoid and Terpenoid Accumulation in Cannabis.
Zager JJ, Lange I, Srividya N, Smith A, Lange BM. Zager JJ, et al. Plant Physiol. 2019 Aug;180(4):1877-1897. doi: 10.1104/pp.18.01506. Epub 2019 May 28. Plant Physiol. 2019. PMID: 31138625 Free PMC article.
In addition to cloning variants of previously characterized genes, specifically CsTPS14CT [(-)-limonene synthase] and CsTPS15CT (beta-myrcene synthase), we functionally evaluated genes that encode enzymes with activities not previously described in cannabis, namely CsTPS18VF and …
In addition to cloning variants of previously characterized genes, specifically CsTPS14CT [(-)-limonene synthase] and CsTPS15CT (beta-myrcen …
Brazilian essential oils as source for the discovery of new anti-COVID-19 drug: a review guided by in silico study.
Amparo TR, Seibert JB, Silveira BM, Costa FSF, Almeida TC, Braga SFP, da Silva GN, Dos Santos ODH, de Souza GHB. Amparo TR, et al. Phytochem Rev. 2021;20(5):1013-1032. doi: 10.1007/s11101-021-09754-4. Epub 2021 Apr 13. Phytochem Rev. 2021. PMID: 33867898 Free PMC article. Review.
(E)-alpha-atlantone; 14-hydroxy-alpha-muurolene; allo-aromadendrene epoxide; amorpha-4,9-dien-2-ol; aristochene; azulenol; germacrene A; guaia-6,9-diene; hedycaryol; humulene epoxide II; alpha-amorphene; alpha-cadinene; alpha-calacorene and alpha-muurolene showed by a mole …
(E)-alpha-atlantone; 14-hydroxy-alpha-muurolene; allo-aromadendrene epoxide; amorpha-4,9-dien-2-ol; aristochene; azulenol; germacrene A; gua …
Direct production of dihydroxylated sesquiterpenoids by a maize terpene synthase.
Liang J, Liu J, Brown R, Jia M, Zhou K, Peters RJ, Wang Q. Liang J, et al. Plant J. 2018 Jun;94(5):847-856. doi: 10.1111/tpj.13901. Epub 2018 Apr 17. Plant J. 2018. PMID: 29570233 Free PMC article.
Evidence for the proposed mechanism was provided by labeling studies, as well as site-directed mutagenesis, based on structural modeling, which identified an active site phenylalanine required for the protonation and further elaboration of hedycaryol. This dihydroxylated s …
Evidence for the proposed mechanism was provided by labeling studies, as well as site-directed mutagenesis, based on structural modeling, wh …
25 results