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Oliver Kayser
TU Dortmund University, Faculty of Biochemical and Chemical Engineering, Chair of Technical Biochemistry, Emil‐Figge‐Strasse 66 44227 Dortmund Germany

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Research article
Published: 26 July 2021 in Pest Management Science
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BACKGROUND Cannabis sativa L. (C. sativa; hemp) is a medicinal plant producing various cannabinoids. Its consumption is legalized for medical use due to their alleged positive health effects. To satisfy the demand C. sativa plants are grown in contained growth chambers. During indoor propagation pesticides are usually used for an efficient production. However, pesticide registration and safe application in C. sativa has not been investigated in detail. RESULTS With this study the metabolic degradation of pesticides in recently established C. sativa callus cultures is examined. Tebuconazole, metalaxyl-M fenhexamid, flurtamone and spirodiclofen were applied at 10 μM for 21 days. Results were compared with metabolism data obtained from Brassica napus L., Glycine max (L.) Merr., Zea mays L. and Tritium aestivum L. callus cultures as well as in metabolism guideline studies. The successfully established C. sativa callus cultures were able to degrade pesticides by oxidation, demethylation, cleavage of ester bonds in phase I as well as glycosylation and conjugation with malonic acid in phase II and III. Initial metabolites were detected after 7 days and were traced during the 21 day. CONCLUSION The resulting pathways demonstrate the same main degradation strategies as crop plants. Since metabolites could be the main residue, the exposure of consumers to these residues will be of high importance. We present here an in vitro assay for a first estimation of pesticide metabolism in C. sativa.

ACS Style

Leonie Hillebrands; Marc Lamshoeft; Andreas Lagojda; Andreas Stork; Oliver Kayser. In vitro metabolism of Tebuconazole, Flurtamone, Fenhexamid, Metalaxyl‐M and Spirodiclofen in Cannabis sativa L. (hemp) callus cultures. Pest Management Science 2021, 1 .

AMA Style

Leonie Hillebrands, Marc Lamshoeft, Andreas Lagojda, Andreas Stork, Oliver Kayser. In vitro metabolism of Tebuconazole, Flurtamone, Fenhexamid, Metalaxyl‐M and Spirodiclofen in Cannabis sativa L. (hemp) callus cultures. Pest Management Science. 2021; ():1.

Chicago/Turabian Style

Leonie Hillebrands; Marc Lamshoeft; Andreas Lagojda; Andreas Stork; Oliver Kayser. 2021. "In vitro metabolism of Tebuconazole, Flurtamone, Fenhexamid, Metalaxyl‐M and Spirodiclofen in Cannabis sativa L. (hemp) callus cultures." Pest Management Science , no. : 1.

Journal article
Published: 21 July 2021 in Plants
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The metabolite 20-Hydroxymaytenin (20-HM) is a member of the quinone-methide pentacyclic triterpenoids (QMTs) group. This metabolite group is present only in Celastraceae plants, and it has shown various biological activities from antioxidant to anticancer properties. However, most QMTs metabolites including 20-HM cannot be synthesized in a laboratory. Therefore, we optimized a plant tissue culture protocol and examined the potential of Gymnosporia heterophylla (synonym. Maytenus heterophylla) to produce 20-HM in an in vitro experiment. For the first time, we reported the optimum callus induction medium with a high percentage success rate of 82% from the combination of 1 mg/L indole-3-butyric acid and 5 mg/L naphthalene acetic acid. Later, our cell suspension culture cultivated in the optimum medium provided approximately 0.35 mg/g fresh weight of 20-HM. This concentration is roughly 87.5 times higher than a concentration of 20-HM presenting in Elaeodendron croceum (Celastraceae) leaves. In addition, we also found that 20-HM presented in a cultivation medium, suggesting that G. heterophylla cells secreted 20-HM as an exudate in our experiment. Noticeably, 20-HM was missing when Penicillium cf. olsonii occurred in the medium. These findings hint at an antifungal property of 20-HM.

ACS Style

Thanet Pitakbut; Michael Spiteller; Oliver Kayser. In Vitro Production and Exudation of 20-Hydroxymaytenin from Gymnosporia heterophylla (Eckl. and Zeyh.) Loes. Cell Culture. Plants 2021, 10, 1493 .

AMA Style

Thanet Pitakbut, Michael Spiteller, Oliver Kayser. In Vitro Production and Exudation of 20-Hydroxymaytenin from Gymnosporia heterophylla (Eckl. and Zeyh.) Loes. Cell Culture. Plants. 2021; 10 (8):1493.

Chicago/Turabian Style

Thanet Pitakbut; Michael Spiteller; Oliver Kayser. 2021. "In Vitro Production and Exudation of 20-Hydroxymaytenin from Gymnosporia heterophylla (Eckl. and Zeyh.) Loes. Cell Culture." Plants 10, no. 8: 1493.

Mini review
Published: 12 October 2020 in Applied Microbiology and Biotechnology
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Heterologous biosynthesis of tetrahydrocannabinolic acid (THCA) in yeast is a biotechnological process in Natural Product Biotechnology that was recently introduced. Based on heterologous genes from Cannabis sativa and Streptomyces spp. cloned into Saccharomyces cerevisiae, the heterologous biosynthesis was fully embedded as a proof of concept. Low titer and insufficient biocatalytic rate of most enzymes require systematic optimization of recombinant catalyst by protein engineering and consequent C-flux improvement of the yeast chassis for sufficient precursor (acetyl-CoA), energy (ATP), and NADH delivery. In this review basic principles of in silico analysis of anabolic pathways towards olivetolic acid (OA) and cannabigerolic acid (CBGA) are elucidated and discussed to identify metabolic bottlenecks. Based on own experimental results, yeasts are discussed as potential platform organisms to be introduced as potential cannabinoid biofactories. Especially feeding strategies and limitations in the committed mevalonate and olivetolic acid pathways are in focus of in silico and experimental studies to validate the scientific and commercial potential as a realistic alternative to the plant Cannabis sativa. Key points • First time critical review of the heterologous process for recombinant THCA/CBDA production and critical review of bottlenecks and limitations for a bioengineered technical process • Integrative approach of protein engineering, systems biotechnology, and biochemistry of yeast physiology and biosynthetic cannabinoid enzymes • Comparison of NphB and CsPT aromatic prenyltransferases as rate-limiting catalytic steps towards cannabinoids in yeast as platform organisms

ACS Style

Fabian Thomas; Christina Schmidt; Oliver Kayser. Bioengineering studies and pathway modeling of the heterologous biosynthesis of tetrahydrocannabinolic acid in yeast. Applied Microbiology and Biotechnology 2020, 104, 9551 -9563.

AMA Style

Fabian Thomas, Christina Schmidt, Oliver Kayser. Bioengineering studies and pathway modeling of the heterologous biosynthesis of tetrahydrocannabinolic acid in yeast. Applied Microbiology and Biotechnology. 2020; 104 (22):9551-9563.

Chicago/Turabian Style

Fabian Thomas; Christina Schmidt; Oliver Kayser. 2020. "Bioengineering studies and pathway modeling of the heterologous biosynthesis of tetrahydrocannabinolic acid in yeast." Applied Microbiology and Biotechnology 104, no. 22: 9551-9563.

Chapter
Published: 10 October 2020 in Grain Legumes
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Cultivation and breeding of Cannabis sativa L. for medicinal purposes is of actual importance since in many countries the legalization allows its use by patients. So far, Cannabis sativa L. and its various strains, optimized for their cannabinoids, have mostly been bred and cultivated under illegal conditions to provide an illicit drug without integration of any pharmaceutical standards according to GAP. The situation has changed now, and many professional breeders introduced the rational concepts for growing cannabis mostly indoor under strict control of drug agencies and international pharmaceutical standards. Here, we report and summarize the actual status of analytics, phytochemistry, and phytoengineering of cannabinoid optimization. Special focus is set on legislation, pharmaceutical standardization, and basic concepts for industrial growing and breeding of cannabis plants.

ACS Style

Paweł Rodziewicz; Oliver Kayser. Cannabis sativa L. –Cannabis. Grain Legumes 2020, 233 -264.

AMA Style

Paweł Rodziewicz, Oliver Kayser. Cannabis sativa L. –Cannabis. Grain Legumes. 2020; ():233-264.

Chicago/Turabian Style

Paweł Rodziewicz; Oliver Kayser. 2020. "Cannabis sativa L. –Cannabis." Grain Legumes , no. : 233-264.

Journal article
Published: 17 March 2020 in Indonesian Journal of Chemistry
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Trichomes of Cannabis sativa are the main tissue for synthesizing and storing cannabinoids, the most interesting compounds in this plant. In this report, metabolic changes in the trichomes of C. sativa var. bedrobinol were investigated by 1H-NMR-based metabolomics over the flowering session. Three cannabinoids, including Δ9-tetrahydrocannabinolic acid (THCA), cannabichromenic acid (CBCA), and Δ9-tetrahydrocannabinol (THC), were successfully identified in the chloroform extracts of the Cannabis trichomes. Meanwhile, 20 non-cannabinoid compounds, including sugars, amino acids, and other acidic constituents, were detected in the water extracts. Metabolic changes of the Cannabis trichomes during the monitoring time were successfully revealed using the models of partial least squares discriminant analysis (PLSDA) and 1H-NMR quantitative analysis. Score plots of the PLSDA models classified metabolomes based on the harvest time. Discriminant metabolites for the differentiation were detected in the loading plots of the models. THCA was found as an important discriminant compound in the chloroform extracts, while all quantified water-soluble compounds were detected, contributing to the metabolic changes of the water extracts. The obtained results shed more light on the biosynthesis of metabolites in the Cannabis trichomes over the flowering season.

ACS Style

Nizar Happyana; Oliver Kayser. Metabolic Changes in the Trichomes of Cannabis sativa var. bedrobinol Analyzed by 1H-NMR-Based Metabolomics. Indonesian Journal of Chemistry 2020, 20, 1246 -1254.

AMA Style

Nizar Happyana, Oliver Kayser. Metabolic Changes in the Trichomes of Cannabis sativa var. bedrobinol Analyzed by 1H-NMR-Based Metabolomics. Indonesian Journal of Chemistry. 2020; 20 (6):1246-1254.

Chicago/Turabian Style

Nizar Happyana; Oliver Kayser. 2020. "Metabolic Changes in the Trichomes of Cannabis sativa var. bedrobinol Analyzed by 1H-NMR-Based Metabolomics." Indonesian Journal of Chemistry 20, no. 6: 1246-1254.

Journal article
Published: 30 September 2019 in Journal of Medical Science
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Cannabinoids from Cannabis sativa L. play an important role as natural products in clinics. The major cannabinoids compromise tetrahydrocannabinolic acid (THCA) and cannabidiolic acid (CBDA) and its decarboxylated analogs. In this review, we focus on often neglected minor cannabinoids and discuss biosynthetic and chemical degradation routes to other neglected cannabinoids in Cannabis sativa starting from THCA, CBDA and cannabichromenic acid (CBCA). Based on the literature, patents and scientific reports, essential routes for the chemical modification of cannabinoids are discussed to explain chemical diversity chemical conversion and degradation by UV light, as well as temperature and pH leading to the formation of structurally unusual cannabinoids in planta called as minor cannabinoids. Based on known bioorganic reaction schemes and organic chemistry, principles for minor cannabinoid formation like [2+2] cycloaddition, Markonov condensation, radical introduction, or aromatization are discussed. Finally, the non-aqueous environment in Cannabis sativa trichomes is analyzed to clarify their role of a miniaturized bioreactors the light-induced conversion in a non-aqueous enviroment. The overall objective is to bridge from metabolic profiling via cannabinomics to structural and chemical diversity that allows the definition of patterns with consequences also to pharmacology and plant breeding.

ACS Style

Fabian Johannes Thomas; Oliver Kayser. Minor Cannabinoids of Cannabis sativa L. Journal of Medical Science 2019, 88, 141 -149.

AMA Style

Fabian Johannes Thomas, Oliver Kayser. Minor Cannabinoids of Cannabis sativa L. Journal of Medical Science. 2019; 88 (3):141-149.

Chicago/Turabian Style

Fabian Johannes Thomas; Oliver Kayser. 2019. "Minor Cannabinoids of Cannabis sativa L." Journal of Medical Science 88, no. 3: 141-149.

Review article
Published: 14 September 2019 in Journal of Ethnopharmacology
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The pharmacology, toxicology and pharmacokinetics of bioactive preparations derived from natural sources has become a flourishing field of research. However, researching complex extracts and natural products faces numerous challenges. More broadly in recent years the critique of pharmacological research, and specifically its design, the methods used and reporting has intensified. This consensus document provides a perspective on what constitutes best practice in pharmacological research on bioactive preparations derived from natural sources, providing a perspective of what the leading specialist journals in the field consider as the core characteristics of good research. The editors-in-chief of seven journals developed this best practice statement in an iterative process. A first draft of the guidelines (prepared by MH) was then discussed and amended by the other editors. Core to this contribution is a table which provides detailed advice including simple points like a use of appropriate controls and the full taxonomic validity of the material under investigation (see also below), to the relevance of the model for the question being researched (e.g., can specific in silico or in vitro models really address the species anti-inflammatory activity?). Therefore, obviously, researchers must pay detailed attention to reporting and discussing such studies. This information must be discussed critically (as much as it is possible based on the published papers) in terms of their scientific quality and validity. While these points are obvious, as editors, we are aware that they are often not properly implemented. We call for an approach which incorporates a careful design, meticulous execution and a detailed reporting of studies focusing on the pharmacology/bioactivity of bioactive preparations. Clearly testable research questions must be developed and investigated experimentally. As the founder of pharmacology Claude Bernard put it already in 1865: ‘…. either the experimenter's hypothesis will be disproved or it will be proved by experiment. When experiment disproves its preconceived ideas, the experimenter must discard or modify it.‘

ACS Style

Michael Heinrich; Giovanni Appendino; Thomas Efferth; Robert Fürst; Angelo A. Izzo; Oliver Kayser; John M. Pezzuto; Alvaro Viljoen. Best practice in research – Overcoming common challenges in phytopharmacological research. Journal of Ethnopharmacology 2019, 246, 112230 .

AMA Style

Michael Heinrich, Giovanni Appendino, Thomas Efferth, Robert Fürst, Angelo A. Izzo, Oliver Kayser, John M. Pezzuto, Alvaro Viljoen. Best practice in research – Overcoming common challenges in phytopharmacological research. Journal of Ethnopharmacology. 2019; 246 ():112230.

Chicago/Turabian Style

Michael Heinrich; Giovanni Appendino; Thomas Efferth; Robert Fürst; Angelo A. Izzo; Oliver Kayser; John M. Pezzuto; Alvaro Viljoen. 2019. "Best practice in research – Overcoming common challenges in phytopharmacological research." Journal of Ethnopharmacology 246, no. : 112230.

Review
Published: 01 June 2019 in Phytochemistry Reviews
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ACS Style

Tajammul Hussain; Richard Espley; Jürg Gertsch; Tracey Whare; Felix Stehle; Oliver Kayser. Demystifying the liverwort Radula marginata, a critical review on its taxonomy, genetics, cannabinoid phytochemistry and pharmacology. Phytochemistry Reviews 2019, 18, 953 -965.

AMA Style

Tajammul Hussain, Richard Espley, Jürg Gertsch, Tracey Whare, Felix Stehle, Oliver Kayser. Demystifying the liverwort Radula marginata, a critical review on its taxonomy, genetics, cannabinoid phytochemistry and pharmacology. Phytochemistry Reviews. 2019; 18 (3):953-965.

Chicago/Turabian Style

Tajammul Hussain; Richard Espley; Jürg Gertsch; Tracey Whare; Felix Stehle; Oliver Kayser. 2019. "Demystifying the liverwort Radula marginata, a critical review on its taxonomy, genetics, cannabinoid phytochemistry and pharmacology." Phytochemistry Reviews 18, no. 3: 953-965.

Journal article
Published: 12 April 2019 in Plant Science
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Cannabinoids are terpenophenolic compounds produced by Cannabis sativa L., which accumulate in storage cavities of glandular trichomes as a part of the exudates. We investigated if tetrahydrocannabinolic acid synthase and cannabidiolic acid synthase, which are involved in the last step of cannabinoid biosynthesis, are also secreted into Cannabis trichome exudates. The exudates were collected by microsuction from storage cavities of Cannabis glandular trichomes and were subjected for proteomic and metabolomic analyses. The catalytic activity of the exudates was documented by cannabigerolic acid biotransformation studies under hydrophobic conditions. Electrophoretic separations revealed protein bands at ˜65 kDa, which were further identified as tetrahydrocannabinolic acid synthase and cannabidiolic acid synthase. The accumulation of the enzymes in trichome exudates increased substantially during the flowering period in the drug-type Cannabis plants. The content of cannabinoids increased significantly after incubating hexane-diluted trichome exudates with cannabigerolic acid. In this study, we showed that Cannabis glandular trichomes secrete and accumulate cannabinoid synthases in storage cavities, and the enzymes able to convert cannabigerolic acid under hydrophobic trichome-mimicking conditions. Metabolite profiling of the exudates revealed compounds with hydrophilic, osmoprotective and amphiphilic properties, which may play a role in providing a necessary aqueous microenvironment, which enables enzyme solubility and biocatalysis under hydrophobic conditions of glandular trichomes.

ACS Style

Paweł Rodziewicz; Stefan Loroch; Łukasz Marczak; Albert Sickmann; Oliver Kayser. Cannabinoid synthases and osmoprotective metabolites accumulate in the exudates of Cannabis sativa L. glandular trichomes. Plant Science 2019, 284, 108 -116.

AMA Style

Paweł Rodziewicz, Stefan Loroch, Łukasz Marczak, Albert Sickmann, Oliver Kayser. Cannabinoid synthases and osmoprotective metabolites accumulate in the exudates of Cannabis sativa L. glandular trichomes. Plant Science. 2019; 284 ():108-116.

Chicago/Turabian Style

Paweł Rodziewicz; Stefan Loroch; Łukasz Marczak; Albert Sickmann; Oliver Kayser. 2019. "Cannabinoid synthases and osmoprotective metabolites accumulate in the exudates of Cannabis sativa L. glandular trichomes." Plant Science 284, no. : 108-116.

Review
Published: 22 February 2019 in Molecules
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Tropane alkaloids (TA) are valuable secondary plant metabolites which are mostly found in high concentrations in the Solanaceae and Erythroxylaceae families. The TAs, which are characterized by their unique bicyclic tropane ring system, can be divided into three major groups: hyoscyamine and scopolamine, cocaine and calystegines. Although all TAs have the same basic structure, they differ immensely in their biological, chemical and pharmacological properties. Scopolamine, also known as hyoscine, has the largest legitimate market as a pharmacological agent due to its treatment of nausea, vomiting, motion sickness, as well as smooth muscle spasms while cocaine is the 2nd most frequently consumed illicit drug globally. This review provides a comprehensive overview of TAs, highlighting their structural diversity, use in pharmaceutical therapy from both historical and modern perspectives, natural biosynthesis in planta and emerging production possibilities using tissue culture and microbial biosynthesis of these compounds.

ACS Style

Kathrin Laura Kohnen-Johannsen; Oliver Kayser. Tropane Alkaloids: Chemistry, Pharmacology, Biosynthesis and Production. Molecules 2019, 24, 796 .

AMA Style

Kathrin Laura Kohnen-Johannsen, Oliver Kayser. Tropane Alkaloids: Chemistry, Pharmacology, Biosynthesis and Production. Molecules. 2019; 24 (4):796.

Chicago/Turabian Style

Kathrin Laura Kohnen-Johannsen; Oliver Kayser. 2019. "Tropane Alkaloids: Chemistry, Pharmacology, Biosynthesis and Production." Molecules 24, no. 4: 796.

Review
Published: 09 January 2019 in Journal of Ethnobiology and Ethnomedicine
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The Arabian Peninsula is recognized as an arid area dominated by deserts and poor biodiversity. However, the Kingdom of Saudi Arabia (henceforth abbreviated into KSA) has a wide range of flora, consisting of different species of trees, herbs, and shrubs and containing numerous edible and medicinal plants. The KSA is characterized by its vast area of diverse geographical landscapes and climates. Consequently, there is enormous variation in the distribution of plants across the Kingdom. The traditional use of ethnomedical plants in the KSA represents a strong interconnection among familiar remedies, health, diet, and traditional healing practices characterized by specific cultures. The present paper reviews a collection of medicinal plants in KSA used in ethnomedicine. This review might be useful in developing strategies for the sustainable use of medicinal plants which are among the threatened important natural resources in folk medicine in the KSA. The present study reports 309 genera which cover 471 species from a total of 2253 known species belonging to 89 families. The most dominating families are Asteraceae, Fabaceae, Lamiaceae, Euphorbiaceae, Solanaceae, Apiaceae, Brassicaceae, Chenopodiaceae, Poaceae, Amaranthaceae, Boraginaceae, Apocynaceae, Convolvoulaceae, Asclepiadaceae, Capparaceae, Polygonaceae, and Zygophyllaceae.

ACS Style

Hanan Aati; Ali El-Gamal; Hamdy Shaheen; Oliver Kayser. Traditional use of ethnomedicinal native plants in the Kingdom of Saudi Arabia. Journal of Ethnobiology and Ethnomedicine 2019, 15, 1 -9.

AMA Style

Hanan Aati, Ali El-Gamal, Hamdy Shaheen, Oliver Kayser. Traditional use of ethnomedicinal native plants in the Kingdom of Saudi Arabia. Journal of Ethnobiology and Ethnomedicine. 2019; 15 (1):1-9.

Chicago/Turabian Style

Hanan Aati; Ali El-Gamal; Hamdy Shaheen; Oliver Kayser. 2019. "Traditional use of ethnomedicinal native plants in the Kingdom of Saudi Arabia." Journal of Ethnobiology and Ethnomedicine 15, no. 1: 1-9.

Journal article
Published: 12 November 2018 in BMC Plant Biology
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Cannabis possesses a rich spectrum of phytochemicals i.e. cannabinoids, terpenes and phenolic compounds of industrial and medicinal interests. Most of these high-value plant products are synthesised in the disk cells and stored in the secretory cavity in glandular trichomes. Conventional trichome analysis was so far based on optical microscopy, electron microscopy or extraction based methods that are either limited to spatial or chemical information. Here we combine both information to obtain the spatial distribution of distinct secondary metabolites on a single-trichome level by applying Coherent anti-Stokes Raman scattering (CARS), a microspectroscopic technique, to trichomes derived from sepals of a drug- and a fibre-type. Hyperspectral CARS imaging in combination with a nonlinear unmixing method allows to identify and localise Δ9-tetrahydrocannabinolic acid (THCA) in the secretory cavity of drug-type trichomes and cannabidiolic acid (CBDA)/myrcene in the secretory cavity of fibre-type trichomes, thus enabling an easy discrimination between high-THCA and high-CBDA producers. A unique spectral fingerprint is found in the disk cells of drug-type trichomes, which is most similar to cannabigerolic acid (CBGA) and is not found in fibre-type trichomes. Furthermore, we differentiate between different cell types by a combination of CARS with simultaneously acquired two-photon fluorescence (TPF) of chlorophyll a from chloroplasts and organic fluorescence mainly arising from cell walls enabling 3D visualisation of the essential oil distribution and cellular structures. Here we demonstrate a label-free and non-destructive method to analyse the distribution of secondary metabolites and distinguish between different cell and chemo-types with high spatial resolution on a single trichome. The record of chemical fingerprints of single trichomes offers the possibility to optimise growth conditions as well as guarantee a direct process control for industrially cultivated medicinal Cannabis plants. Moreover, this method is not limited to Cannabis related issues but can be widely implemented for optimising and monitoring all kinds of natural or biotechnological production processes with simultaneous spatial and chemical information.

ACS Style

Paul Ebersbach; Felix Stehle; Oliver Kayser; Erik Freier. Chemical fingerprinting of single glandular trichomes of Cannabis sativa by Coherent anti-Stokes Raman scattering (CARS) microscopy. BMC Plant Biology 2018, 18, 275 .

AMA Style

Paul Ebersbach, Felix Stehle, Oliver Kayser, Erik Freier. Chemical fingerprinting of single glandular trichomes of Cannabis sativa by Coherent anti-Stokes Raman scattering (CARS) microscopy. BMC Plant Biology. 2018; 18 (1):275.

Chicago/Turabian Style

Paul Ebersbach; Felix Stehle; Oliver Kayser; Erik Freier. 2018. "Chemical fingerprinting of single glandular trichomes of Cannabis sativa by Coherent anti-Stokes Raman scattering (CARS) microscopy." BMC Plant Biology 18, no. 1: 275.

Journal article
Published: 11 September 2018 in Saudi Pharmaceutical Journal
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The chemical composition of the essential oil from Jatropha pelargoniifolia roots was determined via GC-FID. There were 80 compounds, representing 99.99% of the total oil constituents. Among these, 77.31% were sesquiterpenes, 14.62% were fatty acids, 7.21% were other components (i.e., phenolics, hydrocarbons, etc.), and 0.85% were monoterpenes. The major compounds in the oil were γ-eudesmol (35.31%), 5-guaien-11-ol (14.43%), epi-cedrol (8.19%), oleic acid (5.23%), bulnesol (4.45%), α-linoleic acid (4.20%), 3,4-dimethoxycinnamic acid (3.83%), palmitic acid (2.69%), isolongifolanone (2.68%), eicosane (1.41%), and cedrol (1.14%). Oxygenated sesquiterpenes were found to represent more than 50% percent of the total oil content. Moreover, the essential oil was evaluated for anti-inflammatory, antioxidant, antipyretic, and antinociceptive activities using in vivo and in vitro models. Additionally, the antioxidant potential of the oil was evaluated using various in vitro antioxidant tests, including DPPH, ABTS+ and FRAP. At a dose of 240 µl/kg, the oil showed anti-inflammatory (59.12%), antipyretic (37.00 ± 0.11), and antinociceptive (47.58%) activities and showed significant (p < 0.001) effect as compared to a standard drug (phenylbutazone and indomethacin). These findings demonstrated that the essential oil of Jatropha pelargoniifolia root could be used as a natural source for their anti-inflammatory, antinociceptive, antipyretic, and antioxidant effects.

ACS Style

Hanan Aati; Ali El-Gamal; Oliver Kayser. Chemical composition and biological activity of the essential oil from the root of Jatropha pelargoniifolia Courb. native to Saudi Arabia. Saudi Pharmaceutical Journal 2018, 27, 88 -95.

AMA Style

Hanan Aati, Ali El-Gamal, Oliver Kayser. Chemical composition and biological activity of the essential oil from the root of Jatropha pelargoniifolia Courb. native to Saudi Arabia. Saudi Pharmaceutical Journal. 2018; 27 (1):88-95.

Chicago/Turabian Style

Hanan Aati; Ali El-Gamal; Oliver Kayser. 2018. "Chemical composition and biological activity of the essential oil from the root of Jatropha pelargoniifolia Courb. native to Saudi Arabia." Saudi Pharmaceutical Journal 27, no. 1: 88-95.

Journal article
Published: 28 July 2018 in Molecules
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Extensive phytochemical analysis of different root fractions of Jatropha pelargoniifolia Courb. (Euphorbiaceae) has resulted in the isolation and identification of 22 secondary metabolites. 6-hydroxy-8-methoxycoumarin-7-O-β-d-glycopyranoside (15) and 2-hydroxymethyl N-methyltryptamine (18) were isolated and identified as new compounds along with the known diterpenoid (1, 3, 4, and 7), triterpenoid (2 and 6), flavonoid (5, 11, 13, 14, and 16), coumarinolignan (8–10), coumarin (15), pyrimidine (12), indole (17, 18), and tyramine-derived molecules (19–22). The anti-inflammatory, analgesic, and antipyretic activities were evaluated for fifteen of the adequately available isolated compounds (1–6, 8–11, 13, 14, 16, 21, and 22). Seven (4, 6, 10, 5, 13, 16, and 22) of the tested compounds showed a significant analgesic effect ranging from 40% to 80% at 10 mg/kg in two in vivo models. Compound 1 could also prove its analgesic property (67.21%) when it was evaluated on a third in vivo model at the same dose. The in vitro anti-inflammatory activity was also recorded where all compounds showed the ability to scavenge nitric oxide (NO) radical in a dose-dependent manner. However, eight compounds (1, 4, 5, 6, 10, 13, 16, and 22) out of the fifteen tested compounds exhibited considerable in vivo anti-inflammatory activity which reached 64.91% for compound 10 at a dose of 10 mg/kg. Moreover, the tested compounds exhibited an antipyretic effect in a yeast-induced hyperthermia in mice. The activity was found to be highly pronounced with compounds 1, 5, 6, 10, 13, and 16 which decreased the rectal temperature to about 37 °C after 2 h of the induced hyperthermia (~39 °C) at a dose of 10 mg/kg. This study could provide scientific evidence for the traditional use of J. pelargoniifolia as an anti-inflammatory, analgesic, and antipyretic.

ACS Style

Hanan Y. Aati; Ali A. El-Gamal; Oliver Kayser; Atallah F. Ahmed. The Phytochemical and Biological Investigation of Jatropha pelargoniifolia Root Native to the Kingdom of Saudi Arabia. Molecules 2018, 23, 1892 .

AMA Style

Hanan Y. Aati, Ali A. El-Gamal, Oliver Kayser, Atallah F. Ahmed. The Phytochemical and Biological Investigation of Jatropha pelargoniifolia Root Native to the Kingdom of Saudi Arabia. Molecules. 2018; 23 (8):1892.

Chicago/Turabian Style

Hanan Y. Aati; Ali A. El-Gamal; Oliver Kayser; Atallah F. Ahmed. 2018. "The Phytochemical and Biological Investigation of Jatropha pelargoniifolia Root Native to the Kingdom of Saudi Arabia." Molecules 23, no. 8: 1892.

Journal article
Published: 24 July 2018 in Journal of Biotechnology
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Cannabinoids are secondary natural products from the plant Cannabis sativa L. Therapeutic indications of cannabinoids currently comprise a significant area of medicinal research. We have expressed the Δ9-tetrahydrocannabinolic acid synthase (THCAS) and cannabidiolic acid synthase (CBDAS) recombinantly in Komagataella phaffii and could detect eight different products with a cannabinoid scaffold after conversion of the precursor cannabigerolic acid (CBGA). Besides five products remaining to be identified, both enzymes were forming three major cannabinoids of C. sativa - Δ9-tetrahydrocannabinolic acid (THCA), cannabidiolic acid (CBDA) and cannabichromenic acid (CBCA). In pursuit of improved enzyme properties for a biotechnological cannabinoid production, we performed site-directed mutagenesis to investigate the glycosylation pattern, the C-terminal berberine-bridge-enzyme (BBE) domain, the active site and the product specificity of both enzymes. The THCAS variant T_N89Q + N499Q (lacking two glycosylation sites) exerted about two-fold increased activity compared to wild-type enzyme. Variant T_H494C + R532C (additional disulfide bridge) exerted about 1.7-fold increased activity compared to wild-type enzyme and a shifted temperature optimum from 52 °C to 57 °C. We generated two CBDAS variants, C_S116 A and C_A414 V, with 2.8 and 3.3-fold increased catalytic activities for CBDA production. C_A414 V additionally showed a broadened pH spectrum and a 19-fold increased catalytic activity for THCA production. These studies lay the groundwork for further research as well as biotechnological cannabinoid production.

ACS Style

Bastian Zirpel; Oliver Kayser; Felix Stehle. Elucidation of structure-function relationship of THCA and CBDA synthase from Cannabis sativa L. Journal of Biotechnology 2018, 284, 17 -26.

AMA Style

Bastian Zirpel, Oliver Kayser, Felix Stehle. Elucidation of structure-function relationship of THCA and CBDA synthase from Cannabis sativa L. Journal of Biotechnology. 2018; 284 ():17-26.

Chicago/Turabian Style

Bastian Zirpel; Oliver Kayser; Felix Stehle. 2018. "Elucidation of structure-function relationship of THCA and CBDA synthase from Cannabis sativa L." Journal of Biotechnology 284, no. : 17-26.

Original research article
Published: 09 May 2018 in Frontiers in Plant Science
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The liverwort Radula marginata belongs to the bryophyte division of land plants and is a prospective alternate source of cannabinoid-like compounds. However, mechanistic insights into the molecular pathways directing the synthesis of these cannabinoid-like compounds have been hindered due to the lack of genetic information. This prompted us to do deep sequencing, de novo assembly and annotation of R. marginata transcriptome, which resulted in the identification and validation of the genes for cannabinoid biosynthetic pathway. In total, we have identified 11,421 putative genes encoding 1,554 enzymes from 145 biosynthetic pathways. Interestingly, we have identified all the upstream genes of the central precursor of cannabinoid biosynthesis, cannabigerolic acid (CBGA), including its two first intermediates, stilbene acid (SA) and geranyl diphosphate (GPP). Expression of all these genes was validated using quantitative real-time PCR. We have characterized the protein structure of stilbene synthase (STS), which is considered as a homolog of olivetolic acid in R. marginata. Moreover, the metabolomics approach enabled us to identify CBGA-analogous compounds using electrospray ionization mass spectrometry (ESI-MS/MS) and gas chromatography mass spectrometry (GC-MS). Transcriptomic analysis revealed 1085 transcription factors (TF) from 39 families. Comparative analysis showed that six TF families have been uniquely predicted in R. marginata. In addition, the bioinformatics analysis predicted a large number of simple sequence repeats (SSRs) and non-coding RNAs (ncRNAs). Our results collectively provide mechanistic insights into the putative precursor genes for the biosynthesis of cannabinoid-like compounds and a novel transcriptomic resource for R. marginata. The large-scale transcriptomic resource generated in this study would further serve as a reference transcriptome to explore the Radulaceae family.

ACS Style

Tajammul Hussain; Blue Plunkett; Mahwish Ejaz; Richard Espley; Oliver Kayser. Identification of Putative Precursor Genes for the Biosynthesis of Cannabinoid-Like Compound in Radula marginata. Frontiers in Plant Science 2018, 9, 537 .

AMA Style

Tajammul Hussain, Blue Plunkett, Mahwish Ejaz, Richard Espley, Oliver Kayser. Identification of Putative Precursor Genes for the Biosynthesis of Cannabinoid-Like Compound in Radula marginata. Frontiers in Plant Science. 2018; 9 ():537.

Chicago/Turabian Style

Tajammul Hussain; Blue Plunkett; Mahwish Ejaz; Richard Espley; Oliver Kayser. 2018. "Identification of Putative Precursor Genes for the Biosynthesis of Cannabinoid-Like Compound in Radula marginata." Frontiers in Plant Science 9, no. : 537.

Journal article
Published: 01 April 2018 in Journal of Biotechnology
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Δ-tetrahydrocannabinolic acid (THCA) is a secondary natural product from the plant Cannabis sativa L. with therapeutic indications like analgesics for cancer pain or reducing spasticity associated with multiple sclerosis. Here, we investigated the influence of the co-expression of 12 helper protein genes from Komagataella phaffii (formerly Pichia pastoris) on the functional expression of the Δ-tetrahydrocannabinolic acid synthase (THCAS) heterologously expressed in K. phaffii by screening 21 clones of each transformation. Our findings substantiate the necessity of a suitable screening system when interfering with the secretory network of K. phaffii. We found that co-production of the chaperones CNE1p and Kar2p, the foldase PDI1p, the UPR-activator Hac1p as well as the FAD synthetase FAD1p enhanced THCAS activity levels within the K. phaffii cells. The strongest influence showed co-expression of Hac1s - increasing the volumetric THCAS activities 4.1-fold on average. We also combined co-production of Hac1p with the other beneficial helper proteins to further enhance THCAS activity levels. An optimized strain overexpressing Hac1s, FAD1 and CNE1 was isolated that showed 20-fold increased volumetric, intracellular THCAS activity compared to the starting strain. We used this strain for a whole cell bioconversion of cannabigerolic acid (CBGA) to THCA. After 8 h of incubation at 37 °C, the cells produced 3.05 g L THCA corresponding to 12.5 % g g.

ACS Style

Bastian Zirpel; Friederike Degenhardt; Chantale Zammarelli; Daniel Wibberg; Jörn Kalinowski; Felix Stehle; Oliver Kayser. Optimization of Δ 9 -tetrahydrocannabinolic acid synthase production in Komagataella phaffii via post-translational bottleneck identification. Journal of Biotechnology 2018, 272-273, 40 -47.

AMA Style

Bastian Zirpel, Friederike Degenhardt, Chantale Zammarelli, Daniel Wibberg, Jörn Kalinowski, Felix Stehle, Oliver Kayser. Optimization of Δ 9 -tetrahydrocannabinolic acid synthase production in Komagataella phaffii via post-translational bottleneck identification. Journal of Biotechnology. 2018; 272-273 ():40-47.

Chicago/Turabian Style

Bastian Zirpel; Friederike Degenhardt; Chantale Zammarelli; Daniel Wibberg; Jörn Kalinowski; Felix Stehle; Oliver Kayser. 2018. "Optimization of Δ 9 -tetrahydrocannabinolic acid synthase production in Komagataella phaffii via post-translational bottleneck identification." Journal of Biotechnology 272-273, no. : 40-47.

Perspectives
Published: 04 January 2018 in Planta Medica
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The plant Cannabis sativa contains a number of psychoactive chemical compounds, the cannabinoids, which possess a significant pharmaceutical potential. Recently, the usage of Cannabis for medicinal purposes was legalized in many countries. Thus, the study on the influence of different cannabinoids in combination with other Cannabis-derived compounds with respect to the treatment of various diseases becomes increasingly important. Besides the production of distinct cannabinoids in a heterologous host, like tobacco or yeast, transgenic Cannabis plants would be a suitable alternative to modify and therefore optimize the cannabinoid profile. This perspective highlights the current efforts on Cannabis cell culture systems, in vitro propagation, and transformation of the plant and reveals the resulting opportunities concerning biotechnological production of cannabinoids. Furthermore, alternative platform organisms for the heterologous production of cannabinoids, like tobacco, are considered and evaluated.

ACS Style

Julia Schachtsiek; Heribert Warzecha; Oliver Kayser; Felix Stehle. Current Perspectives on Biotechnological Cannabinoid Production in Plants. Planta Medica 2018, 84, 214 -220.

AMA Style

Julia Schachtsiek, Heribert Warzecha, Oliver Kayser, Felix Stehle. Current Perspectives on Biotechnological Cannabinoid Production in Plants. Planta Medica. 2018; 84 (4):214-220.

Chicago/Turabian Style

Julia Schachtsiek; Heribert Warzecha; Oliver Kayser; Felix Stehle. 2018. "Current Perspectives on Biotechnological Cannabinoid Production in Plants." Planta Medica 84, no. 4: 214-220.

Journal article
Published: 31 October 2017 in Plant and Cell Physiology
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Tropane alkaloids (TAs), especially hyoscyamine and scopolamine, are important precursors for anticholinergic and antispasmodic drugs. Hyoscyamine and scopolamine are currently obtained at commercial scale from hybrid crosses of Duboisia myoporoides × Duboisia leichhardtii plants. In this study, we present a global investigation of the localization and organization of TA biosynthesis in a Duboisia myoporoides R. Br. wild-type line. The tissue-specific spatial distribution of TAs within D. myoporoides is presented, including quantification of the TAs littorine, 6-hydroxy hyoscyamine, hyoscyamine, scopolamine and, additionally, hyoscyamine aldehyde as well as scopolamine glucoside. Scopolamine (14.77 ± 5.03 mg g–1), and to a lesser extent hyoscyamine (3.01 ± 1.54 mg g–1) as well as 6-hydroxy hyoscyamine (4.35 ± 1.18 mg g–1), are accumulated in leaves during plant development, with the highest concentration of total TAs detected in 6-month-old plants. Littorine, an early precursor in TA biosynthesis, was present only in the roots (0.46 ± 0.07 mg g–1). During development, the spatial distribution of all investigated alkaloids changed due to secondary growth in the roots. Transcripts of pmt, tr-I and cyp80f1 genes, involved in early stages of TA biosynthesis, were found to be most abundant in the roots. In contrast, the transcript encoding hyoscyamine 6β-hydroxylase (h6h) was highest in the leaves of 3-month-old plants. This investigation presents the spatial distribution of biochemical components as well as gene expression profiles of genetic factors known to participate in TA biosynthesis in D. myoporoides. The results of this investigation may aid in future breeding or genetic enhancement strategies aimed at increasing the yields of TAs in these medicinally valuable plant species.

ACS Style

Kathrin Laura Kohnen; Selahaddin Sezgin; Michael Spiteller; Hansj�Rg Hagels; Oliver Kayser. Localization and Organization of Scopolamine Biosynthesis in Duboisia myoporoides R. Br. Plant and Cell Physiology 2017, 59, 107 -118.

AMA Style

Kathrin Laura Kohnen, Selahaddin Sezgin, Michael Spiteller, Hansj�Rg Hagels, Oliver Kayser. Localization and Organization of Scopolamine Biosynthesis in Duboisia myoporoides R. Br. Plant and Cell Physiology. 2017; 59 (1):107-118.

Chicago/Turabian Style

Kathrin Laura Kohnen; Selahaddin Sezgin; Michael Spiteller; Hansj�Rg Hagels; Oliver Kayser. 2017. "Localization and Organization of Scopolamine Biosynthesis in Duboisia myoporoides R. Br." Plant and Cell Physiology 59, no. 1: 107-118.

Journal article
Published: 01 October 2017 in Chemosphere
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During production of active pharmaceutical ingredients, process waste water is generated at several stages of manufacturing. Whenever possible, the resulting waste water will be processed by conventional waste water treatment plants. Currently, incineration of the process waste water is the method to eliminate compounds with high biological activity. Thus, ozone treatment followed by biological waste water treatment was tested as an alternative method. Two prominent representatives of the large group of fluoroquinolone antibiotics (ciprofloxacin and moxifloxacin) were investigated, focussing on waste water of the bulk production. Elimination of the target compounds and generation of their main transformation products were determined by liquid chromatography - high resolution mass spectrometry (LC-HRMS). The obtained results demonstrated, that the concentration of moxifloxacin and its metabolites can be effectively reduced (>99.7%) prior entering the receiving water. On the contrary, the concentration of ciprofloxacin and its metabolites remained too high for safe discharge, necessitating application of prolonged ozonation for its further degradation. The required ozonation time can be estimated based on the determined kinetics. To assure a low biological activity the ecotoxicity of the ozonated waste water was investigated using three trophic levels. By means of multiple-stage mass spectrometry (MS(n)) experiments several new transformation products of the fluoroquinolones were identified. Thus, previously published proposed structures could be corrected or confirmed.

ACS Style

Fares Daoud; David Pelzer; Sebastian Zuehlke; Michael Spiteller; Oliver Kayser. Ozone pretreatment of process waste water generated in course of fluoroquinolone production. Chemosphere 2017, 185, 953 -963.

AMA Style

Fares Daoud, David Pelzer, Sebastian Zuehlke, Michael Spiteller, Oliver Kayser. Ozone pretreatment of process waste water generated in course of fluoroquinolone production. Chemosphere. 2017; 185 ():953-963.

Chicago/Turabian Style

Fares Daoud; David Pelzer; Sebastian Zuehlke; Michael Spiteller; Oliver Kayser. 2017. "Ozone pretreatment of process waste water generated in course of fluoroquinolone production." Chemosphere 185, no. : 953-963.