Cannabidiolic‐acid synthase, the chemotype‐determining enzyme in the fiber‐type <i>Cannabis sativa</i>

Taura, Futoshi; Sirikantaramas, Supaart; Yoshikai, Kazuyoshi; Shoyama, Yukihiro; Morimoto, Satoshi

doi:10.1016/j.febslet.2007.05.043

Cited by 211 publications

(238 citation statements)

References 30 publications

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“…CBDA), and CBG total (= CBG ? CBGA) (Swift et al 2013;Taura et al 2007a) between sample replicates were typically \5 % RSD. One way analysis of variance (ANOVA) calculated using GenStat 64-bit Release 16.1 (VSN International 2014) indicated that there was no significant difference in THC total F 1, 130 = 0.01, P = 0.936, CBD total F 1, 130 = 0.00, P = 0.985, and CBG total F 1, 122 = 0.02, P = 0.898 between replicates.…”

Section: Linearity and Reproducibilitymentioning

confidence: 99%

“…In a single (B) locus model, chemotype II individuals are assumed to be heterozygote for the codominant B T (THCAS) and B D (CBDAS) alleles (De Meijer et al 2003). These alleles encode functional sequence variants of THCA and CBDA synthase, and therefore the efficiency (Pacifico et al 2006) with which CBG(V)A is converted to THC(V)A (B T ) and CBD(V)A (B D ) (Sirikantaramas et al 2004;Taura et al 2007b) (Fig. 1).…”

Section: Chemotype II Variabilitymentioning

confidence: 99%

“…B Tabsent haplotype. THCA and CBDA synthase are considered isoforms of the same enzyme (De Meijer et al 2003;Taura et al 2007a), sharing 83.9 % amino acid identity (Taura et al 2007b). Residues of THCA in chemotype III are thought to be due to an imperfect capacity of CBDA synthase to form CBDA (De Meijer et al 2003).…”

Section: Characterisation Of Chemotypementioning

confidence: 99%

“…THCVA (THC(V)A) and CBDA ? CBDVA (CBD(V)A) respectively (Sirikantaramas et al 2004;Taura et al 2007b) (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

“…The pentyl-alkyl-cannabinoids THCA and cannabidiolic acid (CBDA) are the major constituents found in plants ( De Backer et al 2009;Swift et al 2013), although a series of propyl-alkyl-cannabinoid homologues [delta-9-tetrahydrocannabivarinic acid (THCVA) and cannabidivarinic acid (CBDVA)] also occur in plants from specific geographical regions (Baker et al 1980;Hillig and Mahlberg 2004). Pentyl-cannabinoids are formed from cannabigerolic acid (CBGA) (Taura et al 2007b), while propyl-cannabinoids are formed from cannabigerovarinic acid (CBGVA) (Shoyama et al 1984). Oxidocyclization reactions catalysed by THCA and CBDA synthase (Shoyama et al 1984), form THCA ?…”

Section: Introductionmentioning

confidence: 99%

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Characterisation of cannabinoid composition in a diverse Cannabis sativa L. germplasm collection

et al. 2015

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The ability to characterise cannabinoid chemical phenotype (chemotype) accurately is important for the development of Cannabis sativa L. cultivars specific for pharmacological, hemp fibre, or seed end use. Although a number of chemotyping and genotyping methods have previously been developed to predict and characterise cannabinoid composition, only a subset of the gene pool has been examined. A representative survey from a wide range of geographically and genetically diverse C. sativa accessions using liquid chromatography-mass spectrometry (LC-MS) cannabinoid profiling together with dominant and co-dominant DNA marker assays was performed. Overall variability of chemotype across the gene pool was found to be three-fold greater within heterozygote genotypes than previously reported. Interestingly, an individual plant of East Asian origin was found to exhibit a rare propyl alkyl cannabinoid homologue and a chemotype inconsistent with the predicted genotype. We propose that in order to carry out comprehensive screening of genetic resource collections and to identify chemotypic variants specific for end-use pharmacological applications, a strategy which adopts both cannabinoid profiling and the co-dominant DNA marker assay is required. Further research with consideration of propyl-alkyl-cannabinoid homologues should explore the relationship between chemotype and genotype in greater detail.

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Section: Linearity and Reproducibilitymentioning

confidence: 99%

Section: Chemotype II Variabilitymentioning

confidence: 99%

Section: Characterisation Of Chemotypementioning

confidence: 99%

“…THCVA (THC(V)A) and CBDA ? CBDVA (CBD(V)A) respectively (Sirikantaramas et al 2004;Taura et al 2007b) (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Characterisation of cannabinoid composition in a diverse Cannabis sativa L. germplasm collection

et al. 2015

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Validating a predictive model of cannabinoid inheritance with feral, clinical, and industrial Cannabis sativa

Wenger

Dabney

ElSohly

et al. 2020

American J of Botany

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of America. This is an open access article under the terms of the Creat ive Commo ns Attri butio n-NonCo mmerc ial-NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made. • 1423 Natural genetic variation affects the composition of phytochemicals in plants and can be of great economic importance. With a record of use by humans as food, fiber, and medicine spanning thousands of years (Faeti et al., 1996), recent decades of prohibition, and a rapidly changing regulatory context, Cannabis sativa L. (Cannabaceae) was until recently among the least studied agricultural crops (Small, 2016). Prominent among the traits of C. sativa are cannabinoids, a unique class of specialized metabolites synthesized and stored in glandular trichomes that are located on the floral bracts of pistillate inflorescences (Livingston et al., 2020; Fig. 1A-C). The ratio of the two most abundant cannabinoids, tetrahydrocannabinolic acid (THCA) and cannabidiolic acid (CBDA), hereafter THC and CBD, is represented by three main classes: THC-type plants with THC:CBD ≥ 10, intermediate-type plants with THC:CBD ≈ 1, and CBD-type plants with THC:CBD ≤ 0.1 (de Meijer et al., 2003). Some authors have referred to these chemotype (chemical phenotype) classes as Type I, Type II, and Type III (Small, 2016). Here we introduce for clarity a more descriptive classification of THC-type, intermediate-type, and CBD-type plants. Descriptive terms also avoid confusion associated with recent statutory definitions of C. sativa that vary widely among political jurisdictions (e.g., "industrial hemp" and "medical marijuana"). Our findings suggest that patterns of cannabinoid inheritance render some of these popular definitions inaccurate at least from a botanical perspective.

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Neue Enzymwerkzeuge für die Biokatalyse

Vick

Schmidt‐Dannert

2011

Angewandte Chemie

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Biochemistry and Molecular Biology unterhält eine Enzymdatenbank (http://www.enzyme-database.org), um der gewaltigen Herausforderung der Klassifizierung und Kategorisierung der derzeit 5174 beschriebenen individuellen Enzymmechanismen mithilfe von Leitlinien, die die Enzyme Commission (EC) festgelegt hat, [1] Herr zu werden. Die Datenbank enthält jede Menge Enzyme, für die noch keine Untersuchungen zur Nutzung ihrer katalytischen Fähigkeiten durchgeführt worden sind. Ein Beispiel für ein in die Datenbank aufgenommenes Enzym ist das Berberin-Brücken-Enzym (BBE) [EC 1.21.3.3], [2a,b] das die Umsetzung des Tetrahydroisochinolins (S)-Reticulin (1 a) zu (S)-Scoulerin (2 a; Schema 1) katalysiert. BBE wurde erstmals 1985 aus Berberis beaniana gewonnen, [2c] die BBE-Aktivität konnte allerdings schon 1975 in einem Zellextrakt aus Macleaya microcarpa nachgewiesen werden. [2d] BBE ist eine FAD-gesteuerte Oxidase, die die Bildung intramolekularer C-C-Bindungen zwischen der N-Methylgruppe und dem 2'-Kohlenstoffatom des Benzylrests von 1 a katalysiert (Schema 1), wodurch die "Berberinbrücke" über einen für Enzyme einzigartigen Reaktionsmechanismus gebildet wird. Das C1-Enantiomer (R)-Reticulin wird von BBE nicht umgesetzt. Dieses Enzym wird besonders interessant mit Blick auf die Synthese neuartiger nichtnatürlicher Stoffe. Bei (S)-Scoulerin (2 a) handelt es sich um eine Vorstufe für eine Vielzahl nützlicher Derivate der Benzophenantridinalkaloide, die antibakterielle, antimikrobielle, blutdrucksenkende, schmerzlindernde und beruhigende Eigenschaften haben und potenziell zur Behandlung von Schizophrenie geeignet sind, wodurch die Berberin-Alkaloidfamilie für die Entwicklung einer Fülle neuartiger nichtnatürlicher Stoffe prädestiniert ist. Eine ähnliche Wirkung (z. B. krampflösend, blutdrucksenkend) wurde für die strukturell verwandte Benzylisochinolin-Alkaloidfamilie gefunden (siehe Schrittwieser et al., [2e] zit. Lit.). Schrittwieser et al. [2e] erkannten dieses Potenzial und wollten nun herausfinden, wie vielseitig sich BBE einsetzen lässt. Die chemische Synthese von Berberinen und Benzyl-isochinolinen ist sehr zeitaufwendig, die Ausbeute ist sehr gering, und es werden kaum reine Produkte erhalten. Schrittwieser et al. synthetisierten potenzielle racemische BBE-Substrate in fünf Schritten mit einer Ausbeute von 40 % und zeigten anschließend in vitro, dass aus diesen Substraten und BBE sowohl natürliche als auch nichtnatürliche BBE-Produkte im Multigrammmaßstab erzeugt werden können.Bei den nichtnatürlichen BBE-Substraten handelte es sich um die Racemate (bezüglich C1) der (S)-und (R)-Tetrahydroisochinoline 1 b-e ohne die 4'-Methoxygruppe von Reticulin (Schema 1). Es zeigte sich, dass die S-Konformere dieser vier nichtnatürlichen Tetrahydroisochinoline Substrate für BBE waren und die R-Konformere wie auch bei den natürlichen Substraten von BBE nicht umgesetzt wurden. Angesichts der Vielfalt natürlicher (S)-Scoulerinderivate und ihrer pharmakologischen Bedeutung sind diese vier neuartigen nichtnatürlichen Produkte ausgezeichne...

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Cannabidiolic‐acid synthase, the chemotype‐determining enzyme in the fiber‐type Cannabis sativa

Cited by 211 publications

References 30 publications

Characterisation of cannabinoid composition in a diverse Cannabis sativa L. germplasm collection

Characterisation of cannabinoid composition in a diverse Cannabis sativa L. germplasm collection

Validating a predictive model of cannabinoid inheritance with feral, clinical, and industrial Cannabis sativa

Neue Enzymwerkzeuge für die Biokatalyse

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