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Polyketide Synthases in Cannabis Sativa L Flores-Sanchez, I.J

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Polyketide Synthases in Cannabis Sativa L Flores-Sanchez, I.J Polyketide synthases in Cannabis sativa L Flores-Sanchez, I.J. Citation Flores-Sanchez, I. J. (2008, October 29). Polyketide synthases in Cannabis sativa L. Retrieved from https://hdl.handle.net/1887/13206 Version: Corrected Publisher’s Version Licence agreement concerning inclusion of doctoral thesis in the License: Institutional Repository of the University of Leiden Downloaded from: https://hdl.handle.net/1887/13206 Note: To cite this publication please use the final published version (if applicable). Polyketide synthases in Cannabis sativa L. Isvett Josefina Flores Sanchez Isvett Josefina Flores Sanchez Polyketide synthases in Cannabis sativa L. ISBN 978-90-9023446-5 Printed by PrintPartners Ipskamp B.V., Amsterdam, The Netherlands Cover photographs: Cannabis sativa, “Skunk” pistillate floral clusters (1, 4, 10, 14); “Skunk” leaf (2, 7); “Skunk” young leaves (9); “Skunk” seed and calyx (3, 18); “Kompolti” flowers (6, 11, 13, 16); “Skunk” seeded calyxes (8); “Kompolti” leaves (5, 12, 15); “Kompolti” staminate floral clusters (19); “Skunk” seeds (17); “Kompolti” seeds (21); “Skunk” and “Kompolti” seeds (20); “Kompolti” pistillate floral clusters (22). Photograph: Isvett J. Flores-Sanchez Polyketide Synthases in Cannabis sativa L. Proefschrift Ter verkrijging van de graad van Doctor aan de Universiteit Leiden, op gezag van Rector Magnificus prof. mr. P. F. van der Heijden, volgens besluit van het College voor Promoties te verdedigen op woensdag 29 october 2008 klokke 11.15 uur door Isvett Josefina Flores Sanchez Geboren te Pachuca de Soto, Hidalgo, Mexico in 1971 Promotiecommissie Promotor Prof. dr. R. Verpoorte Co-promotor Dr. H. J. M. Linthorst Referent Prof. dr. O. Kayser (University of Groningen) Overige leden Prof. dr. P. J. J. Hooykaas Prof. dr. C. A. M. J. J. van den Hondel Dr. Frank van der Kooy Contents Chapter I Introduction to secondary metabolism in cannabis 1 Chapter II Plant Polyketide Synthases 29 Chapter III Polyketide synthase activities and biosynthesis of cannabinoids and flavonoids in Cannabis sativa L. plants 43 Chapter IV In silicio expression analysis of a PKS gene isolated from Cannabis sativa L. 73 Chapter V Elicitation studies in cell suspension cultures of Cannabis sativa L. 93 Concluding remarks and perspectives 121 Summary 123 Samenvatting 125 References 127 Acknowledgements 167 Curriculum vitae 168 List of publications 169 Chapter I Introduction to secondary metabolism in cannabis Isvett J. Flores Sanchez • Robert Verpoorte Pharmacognosy Department, Institute of Biology, Gorlaeus Laboratories, Leiden University Leiden, The Netherlands Published in Phytochem Rev (2008) 7:615-639 Abstract: 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 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 discussed. 1 Introduction I.1 Cannabis plant Cannabis is an annual plant, which belongs to the family Cannabaceae. There are only 2 genera in this family: Cannabis and Humulus. While in Humulus only one species is recognized, namely lupulus, in Cannabis different opinions support the concepts for a mono or poly species genus. Linnaeus (1753) considered only one species, sativa, however, McPartland et al. (2002) described 4 species, sativa, indica, ruderalis and afghanica; and Hillig (2005) proposed 7 putative taxa, ruderalis, sativa ssp. sativa, sativa ssp. spontanea, indica ssp. kafiristanica, indica ssp. indica, indica ssp. afghanica and indica ssp. chinensis. Nevertheless, the tendency in literature is to refer to all types of cannabis as Cannabis sativa L. with a variety name indicating the characteristics of the plant. The cultivation of this plant, native from Central Asia, and its use has been spread all over the world by man since thousands of years as a source of food, energy, fiber and medicinal or narcotic preparations (Jiang et al., 2006; Russo, 2004; Wills, 1998). Cannabis is a dioecious plant, i.e. it bears male and female flowers on separate plants. The male plant bears staminate flowers and the female plant pistillate flowers which eventually develop into the fruit and achenes (seeds). The sole function of male plants is to pollinate the females. Generally, the male plants commence flowering slightly before the females. During a few weeks the males produce abundant anthers that split open, enabling passing air currents to transfer the released pollen to the pistillate flowers. Soon after pollination, male plants wither and die, leaving the females maximum space, nutrients and water to produce a healthy crop of viable seeds. As result of special breeding, monoecious plants bearing both male and female flowers arose frequently in varieties developed for fiber production. The pistillate flowers consist of an ovary surrounded by a calyx with 2 pistils which trap passing pollen (Clarke, 1981; Raman, 1998). Each calyx is covered with glandular hairs (glandular trichomes), a highly specialized secretory tissue (Werker, 2000). In cannabis, these glandular trichomes are also present on bracts, leaves and on the underside of the anther lobes from male flowers (Mahlberg et al., 1984). 2 Introduction I.2 Secondary metabolites of Cannabis The phytochemistry in cannabis is very complex; more than 480 compounds have been identified (ElSohly and Slade, 2005) representing different chemical classes. Some belong to primary metabolism, e.g. amino acids, fatty acids and steroids, while cannabinoids, flavonoids, stilbenoids, terpenoids, lignans and alkaloids represent secondary metabolites. The concentrations of these compounds depend on tissue type, age, variety, growth conditions (nutrition, humidity and light levels), harvest time and storage conditions (Keller et al., 2001; Kushima et al., 1980; Roos et al., 1996). The production of cannabinoids increases in plants under stress (Pate, 1999). Ecological interactions have also been reported (McPartland et al., 2000). Feeding studies in grasshoppers indicated that minimum amounts of cannabinoids are stored in their exoskeletons, being excreted in their frass (Rothschild et al., 1977); although a neurotoxic activity was reported in midge larvaes using cannabis leaf extracts (Roy and Dutta, 2003). I.2.1 Cannabinoids This group represents the most studied compounds from cannabis. The term cannabinoid is given to the terpenophenolic compounds with 22 carbons (or 21 carbons for neutral form) of which 70 cannabinoids have been found so far and which can be divided into 10 main structural types (Figure 1). All other compounds that do not fit into the main types are grouped as miscellaneous (Figure 2). The neutral compounds are formed by decarboxylation of the unstable corresponding acids. Although decarboxylation occurs in the living plant, it increases during storage after harvesting, especially at elevated temperatures (Mechoulam and Ben-Shabat, 1999). Both forms are also further degraded into secondary products by the effects of temperature, light (Lewis and Turner, 1978) and auto-oxidation (Razdan et al., 1972). 3 Introduction OH R'O OH R" R2 OH R OH R2 R2 R O 5 R3 O R3 O R3 OR R3 5 Cannabigerol (CBG) type Cannabichromene (CBC) type Cannabitriol (CBT) type Cannabidiol (CBD) type R2: H or COOH R2: H or COOH R3: C3 or C5 side chain R2: H or COOH R3: C3 or C5 side chain R3: C3 or C5 R: H or OH R3: C1, C3, C4 or C5 side chain R5: H or CH3 R’: H or CBDA-C5 ester = , S-configuration R5: H or CH3 R”: H, OH or OEt = , R-configuration OH H H OH H H R2 O OH R2 H O R3 R3 OH R3 Cannabicyclol (CBL) type R4 OH R2: H or COOH Cannabielsoin (CBE) type Cannabinodiol (CBND) type R3: C3 or C5 side chain R2: H or COOH R3: C3 or C5 side chain R3: C3 or C5 R4: COOH or H H OH OR1 R2 R2 H H OH R2 O R3 O R3 H R4 Cannabinol (CBN) type O Δ9-Tetrahydrocannabinol (Δ9-THC) type R1: H or CH R2 or R4: H or COOH 3 Δ8-Tetrahydrocannabinol (Δ8-THC) type R2: H or COOH R3: C1, C3, C4 or C5 side chain R2: H or COOH R3: C1, C2, C3, C4 or C5 side chain R4: COOH or H Figure 1. Cannabinoid structural types. In cannabis, the most prevalent compounds are Δ9-THC acid, CBD acid and CBN acid, followed by CBG acid, CBC acid and CBND acid, while the others are minor compounds. Based on the absolute concentration of Δ9-THC (Δ9-THC+ Δ9-THC acid) and CBD (CBD + CBD acid) obtained via HPLC or GC analyses, the plants are classified as follows: Drug type (chemotype I), the concentration of Δ9-THC is more than 2% and CBD concentration is less 0.5%; Fiber type (chemotype III), the Δ9-THC concentration is less than 0.3% and the concentration of CBD is more than 0.5%; Intermediate type (chemotype II), the concentrations of both are similar, usually more than 0.5% for each; and Propyl isomer/C3 type (chemotype IV), which can be differentiated by the dominant key cannabinoids Δ9-tetrahydrocannabivarinic acid (Δ9-THCVA) and Δ9-tetrahydrocannabivarin (Δ9-THCV), while also containing considerable amounts of Δ9-THC (Brenneisen and ElSohly, 1988; Fournier et al., 1987; Lehmann and Brenneisen, 1995). 4 Introduction O O OH O O O R3 O Cannabichromanone Cannabicoumaronone R3: C3 or C5 side chain O O OH O O 10-oxo-Δ6a(10a)-Tetrahydrocannabinol (OTHC) Cannabicitran O OH OH OH O R3 Cannabiglendol Δ7-Isotetrahydrocannabinol R3: C3 or C5 Figure 2. Miscellaneous cannabinoids.
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