Microbial transformation of cannabinoids. Part 3: Major metabolites of (3R, 4R)‐Δ1‐tetrahydrocannabinol

Binder, Michael; Popp, A.

doi:10.1002/hlca.19800630846

Cited by 8 publications

(3 citation statements)

References 12 publications

(5 reference statements)

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“…Biotransformation of cannabinoids to glucosylated forms by plant tissues (Tanaka et al 1997) and various oxidized derivatives by microorganisms (Robertson et al 1978;Binder and Popp 1980) have been reported; as well as biotransformations for olivetol (McClanahan and Robertson 1984). However, the best studied biotransformations are in animals and humans (Mechoulam 1970;Watanabe et al 2007).…”

Section: Cannabinoid Biosynthesismentioning

confidence: 97%

Secondary metabolism in cannabis

2008

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Cannabis sativa L. is an annual dioecious plant from Central Asia. Cannabinoids, flavonoids, stilbenoids, terpenoids, alkaloids and lignans are some of the secondary metabolites present in C. sativa. Earlier reviews were focused on isolation and identification of more than 480 chemical compounds; this review deals with the biosynthesis of the secondary metabolites present in this plant. Cannabinoid biosynthesis and some closely related pathways that involve the same precursors are disscused.

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Section: Cannabinoid Biosynthesismentioning

confidence: 97%

Secondary metabolism in cannabis

2008

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“…It is well known that microorganisms such as fungi are capable to perform oxidation, reduction, isomerization reactions enzymatically, among other specific reactions. According to previous reports, Thamnidium elegans is used in biotransformations due to its allylic hydroxylase activity [28]. Also, it is known that bisabolol oxides may be vulnerable to allylic hydroxylation [29].…”

Section: Microbial Transformation and Analysis Of Metabolitesmentioning

confidence: 99%

Microbial Transformation of (–)-α-Bisabolol Towards Bioactive Metabolites

Fırat¹,

Demirci²,

Demırcı³

et al. 2021

Rec.Nat.Prod.

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Bisabolol is one of the bioactive constituents of chamomile. It was aimed to biotransform (–)-α-bisabolol by different fungi for the production of new bioactive metabolites, which was converted to α-bisabolol oxide A and B by Thamnidium elegans. Additionally, the biotransformation by Penicillium neocrassum yielded a new metabolite, which was characterized as 2-(5-methyl-5-(6-methyl-7-oxabicyclo[4.1.0]heptan-3-yl)tetrahydrofuran-2-yl)propan-2-ol = bisafuranol. The substrate and its metabolite mixtures were tested using antioxidant DPPH• scavenging assay. Antimicrobial activity was evaluated by an in vitro microdilution assay against a panel of human pathogenic bacteria and yeasts resulting in the lowest MIC and MFC values of 150 μg/mL. (–)-α-Bisabolol was effective against Propionibacterium acnes and Staphylococcus epidermidis (75, 37.5 μg/mL, respectively). The antioxidant activity of the metabolites was found to be more effective in scavenging free radicals.

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“…The introduction of hydroxyl, carbonyl, carboxyl or glycosyl groups enhances the solubility of molecules in general. In 1980s, fungal and bacterial strains were already used to transform THC into polar derivatives (Binder and Meisenberg 1978 ; Binder and Popp 1980 ; Fukuda, Archer and Abbott 1977 ), as well as plant cell suspension cultures were used for the biotransformation of cannabinoids (Akhtar, Mustafa and Verpoorte 2015 ; Braemer and Paris 1987 ; Hartsel, Loh and Robertson 1983 ). Nevertheless, the overall yield of the metabolites was too low for pharmacological evaluation of the activity.…”

Section: Heterologous Systems For the Biosynthesis Of Cannabinoidsmentioning

confidence: 99%

Designing microorganisms for heterologous biosynthesis of cannabinoids

Carvalho

Hansen

Kayser

et al. 2017

FEMS Yeast Research

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During the last decade, the use of medical Cannabis has expanded globally and legislation is getting more liberal in many countries, facilitating the research on cannabinoids. The unique interaction of cannabinoids with the human endocannabinoid system makes these compounds an interesting target to be studied as therapeutic agents for the treatment of several medical conditions. However, currently there are important limitations in the study, production and use of cannabinoids as pharmaceutical drugs. Besides the main constituent tetrahydrocannabinolic acid, the structurally related compound cannabidiol is of high interest as drug candidate. From the more than 100 known cannabinoids reported, most can only be extracted in very low amounts and their pharmacological profile has not been determined. Today, cannabinoids are isolated from the strictly regulated Cannabis plant, and the supply of compounds with sufficient quality is a major problem. Biotechnological production could be an attractive alternative mode of production. Herein, we explore the potential use of synthetic biology as an alternative strategy for synthesis of cannabinoids in heterologous hosts. We summarize the current knowledge surrounding cannabinoids biosynthesis and present a comprehensive description of the key steps of the genuine and artificial pathway, systems biotechnology needs and platform optimization.

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Microbial transformation of cannabinoids. Part 3: Major metabolites of (3R, 4R)‐Δ¹‐tetrahydrocannabinol

Cited by 8 publications

References 12 publications

Secondary metabolism in cannabis

Secondary metabolism in cannabis

Microbial Transformation of (–)-α-Bisabolol Towards Bioactive Metabolites

Designing microorganisms for heterologous biosynthesis of cannabinoids

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