Microbiological oxidation of the pentyl side chain of cannabinoids

Robertson, Larry W.; Koh, Samuel; Huff, S R; Malhotra, Ravinder; Ghosh, Anil C.

doi:10.1007/bf01915321

Cited by 19 publications

(11 citation statements)

References 7 publications

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“…It is unclear why total THCCOOH concentrations were unstable, although altered adsorption, intramolecular acyl migration, protein binding, or further molecular degradation could explain these changes. Early synthesis of cannabinoid metabolites used microbial transformation to produce certain metabolites on the pentyl side chain [28]. Skopp et al .…”

Section: Discussionmentioning

confidence: 99%

In vitro stability of free and glucuronidated cannabinoids in urine following controlled smoked cannabis

et al. 2013

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Analyte stability is an important factor in urine test interpretation, yet cannabinoid stability data are limited. A comprehensive study of Δ9-tetrahydrocannabinol (THC), 11-hydroxy-THC (11-OH-THC), 11-nor-9-carboxy-THC (THCCOOH), cannabidiol, cannabinol, THC-glucuronide, and THCCOOH-glucuronide stabilities in authentic urine was completed. Urine samples after ad libitum cannabis smoking were pooled to prepare low and high pools for each study participant; baseline concentrations were measured within 24h at room temperature (RT), 4°C and −20°C. Stability at RT, 4°C and −20°C was evaluated by Friedman tests for up to 1 year. THCCOOH, THC-glucuronide, and THCCOOH-glucuronide were quantified in baseline pools. RT THCCOOH baseline concentrations were significantly higher than −20°C, but not 4°C baseline concentrations. After 1 week at RT, THCCOOH increased, THCCOOH-glucuronide decreased, but THC-glucuronide was unchanged. In RT low pool, total THCCOOH (THCCOOH+THCCOOH-glucuronide) was significantly lower after 1 week. At 4°C, THCCOOH was stable 2 weeks, THCCOOH-glucuronide 1 month and THC-glucuronide for at least 6 months. THCCOOH was stable frozen for 1 year, but 6 months high pool results were significantly higher than baseline; THC-glucuronide and THCCOOH-glucuronide were stable for 6 months. Total THCCOOH was stable 6 months at 4°C, and frozen 6 months (low) and 1 year (high). THC, cannabidiol and cannabinol were never detected in urine; although not detected initially, 11-OH-THC was detected in 2 low and 3 high pools after one week at RT. Substantial THCCOOH-glucuronide deconjugation was observed at RT and 4°C. Analysis should be conducted within 3 months if non-hydrolyzed THCCOOH or THCCOOH-glucuronide quantification is required.

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Section: Discussionmentioning

confidence: 99%

In vitro stability of free and glucuronidated cannabinoids in urine following controlled smoked cannabis

et al. 2013

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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: 96%

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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“… 113 Ring- and side-chain hydroxylated derivatives, namely 3′′-OH-CBD,4′′,5′′-dinor, 4′′-OH-CBD, 4′′,6α-diOH-CBD, and 3′′,6-diOH-CBD,4′′,5′′-dinor, have also been produced in milligram quantities by microbial oxidation. 114 The synthesis of the 7-COOH metabolite of CBD has been described. 74 , 115 Synthesis of the side-chain terminal carboxylic acid (5′′-COOH, identified only in animals 116–119 ) has also been described.…”

Section: Synthesis Of Cbd Metabolitesmentioning

confidence: 99%

Human Metabolites of Cannabidiol: A Review on Their Formation, Biological Activity, and Relevance in Therapy

Ujváry¹,

Hanŭs

2016

Cannabis and Cannabinoid Research

235

204

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Cannabidiol (CBD), the main nonpsychoactive constituent of Cannabis sativa, has shown a wide range of therapeutically promising pharmacological effects either as a sole drug or in combination with other drugs in adjunctive therapy. However, the targets involved in the therapeutic effects of CBD appear to be elusive. Furthermore, scarce information is available on the biological activity of its human metabolites which, when formed in pharmacologically relevant concentration, might contribute to or even account for the observed therapeutic effects. The present overview summarizes our current knowledge on the pharmacokinetics and metabolic fate of CBD in humans, reviews studies on the biological activity of CBD metabolites either in vitro or in vivo, and discusses relevant drug–drug interactions. To facilitate further research in the area, the reported syntheses of CBD metabolites are also catalogued.

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Microbiological oxidation of the pentyl side chain of cannabinoids

Abstract: Syncephalastrum racemosum ATCC 18192 and Mycobacterium rhodochrous ATCC 19067 partially degrade the n-pentyl side chain of cannabidiol, cannabinol, delta8-tetrahydrocannabinol and delta9-tetrahydrocannabinol. Carboxylic acid and alcohol side chain derivatives are major metabolites.

Cited by 19 publications

References 7 publications

In vitro stability of free and glucuronidated cannabinoids in urine following controlled smoked cannabis

In vitro stability of free and glucuronidated cannabinoids in urine following controlled smoked cannabis

Secondary metabolism in cannabis

Human Metabolites of Cannabidiol: A Review on Their Formation, Biological Activity, and Relevance in Therapy

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