Characterization of a membrane-bound C-glucosyltransferase responsible for carminic acid biosynthesis in Dactylopius coccus Costa

Kannangara, Rubini; Siukstaite, Lina; Borch-Jensen, Jonas; Madsen, Bjørn Stæhr; Kongstad, Kenneth T.; Bennedsen, Mads; Okkels, Finn T.; Rasmussen, Silas Anselm; Larsen, Thomas Ostenfeld; Frandsen, Rasmus John Normand; Møller, Birger Lindberg

doi:10.1038/s41467-017-02031-z

Cited by 20 publications

(31 citation statements)

References 35 publications

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“…Carminic acid is a famous red dye from beetles, with a similar structure to echinochrome, except that it is C-linked to glucose. Although the putative PKS is unknown as of this writing, recently, the glucosyltransferase was characterized and shown to be insect in origin (35), adding new evidence that aromatic polyketides might be biosynthesized by animals.…”

Section: Polyketide/fatty Acid Metabolismmentioning

confidence: 98%

The biosynthetic diversity of the animal world

Torres

Schmidt

2019

Journal of Biological Chemistry

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Secondary metabolites are often considered within the remit of bacterial or plant research, but animals also contain a plethora of these molecules with important functional roles. Classical feeding studies demonstrate that, whereas some are derived from diet, many of these compounds are made within the animals. In the past 15 years, the genetic and biochemical origin of several animal natural products has been traced to partnerships with symbiotic bacteria. More recently, a number of animal genome-encoded pathways to microbe-like natural products have come to light. These pathways are sometimes horizontally acquired from bacteria, but more commonly they unveil a new and diverse animal biochemistry. In this review, we highlight recent examples of characterized animal biosynthetic enzymes that reveal an unanticipated breadth and intricacy in animal secondary metabolism. The results so far suggest that there may be an immense diversity of animal small molecules and biosynthetic enzymes awaiting discovery. This biosynthetic dark matter is just beginning to be understood, providing a relatively untapped frontier for discovery.

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Section: Polyketide/fatty Acid Metabolismmentioning

confidence: 98%

The biosynthetic diversity of the animal world

Torres

Schmidt

2019

Journal of Biological Chemistry

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“…In the biosynthesis of cannabinoids, these two pathways are linked by the action of aromatic prenyl transferases. Aromatic prenyltransferases are ubiquitous in animals [130], plants [131], fungi [132], and bacteria [133] and their different reaction spectra serve to diversify the production of aromatic metabolites such as the phenylpropanoids, flavonoids, and coumarins in plants [134]. In combination with modules involved in phytocannabinoid synthesis in different species of higher plants, liverworts, and fungi, the option arises to use an aromatic prenyltransferase-based approach for the production of new-to-nature phytocannabinoids in heterologous hosts based on combinatorial uses of the modules across species.…”

Section: Synthetic Biology Approaches In Phytocannabinoid Productionmentioning

confidence: 99%

Phytocannabinoids: Origins and Biosynthesis

Gülck

Møller

2020

Trends in Plant Science

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Phytocannabinoids are bioactive natural products found in some flowering plants, liverworts, and fungi that can be beneficial for the treatment of human ailments such as pain, anxiety, and cachexia. Targeted biosynthesis of cannabinoids with desirable properties requires identification of the underlying genes and their expression in a suitable heterologous host. We provide an overview of the structural classification of phytocannabinoids based on their decorated resorcinol core and the bioactivities of naturally occurring cannabinoids, and we review current knowledge of phytocannabinoid biosynthesis in Cannabis, Rhododendron, and Radula species. We also highlight the potential in planta roles of phytocannabinoids and the opportunity for synthetic biology approaches based on combinatorial biochemistry and protein engineering to produce cannabinoid derivatives with improved properties. Phytocannabinoids The term phytocannabinoid (see Glossary, also cannabinoid) defines meroterpenoids with a resorcinyl core typically decorated with a para-positioned isoprenyl, alkyl, or aralkyl side chain [1]. The alkyl side chain typically contains an odd number of carbon atoms, where orcinoids contain one carbon, varinoids three, and olivetoids five. Cannabinoids with an even number of carbon atoms in the side chain are known but rare. The term cannabinoid generally refers to molecules with a characteristic chemical structure; however, the term may also refer to pharmacological ligands of human endocannabinoid receptors [2]. In this review we use the chemical definition of cannabinoids. Phytocannabinoids occur in flowering plants, liverworts, and fungi (Figure 1, Key Figure). They were first isolated from Cannabis sativa L. (Cannabaceae), a plant with a long and controversial history of use and abuse [3]. The mammalian brain has receptors that respond to compounds found in C. sativa. Accordingly, these receptors were named cannabinoid receptors (CB x) and are the basis of the endocannabinoid system. Studies in human and animals demonstrated that the endocannabinoid system regulates a broad range of biological functions, including memory, mood, brain reward systems, and drug addiction, as well as metabolic processes such as lipolysis, glucose metabolism, and energy balance [2]. More than 113 different cannabinoids have been isolated from C. sativa and these are classified into distinct types: cannabigerols (CBGs), cannabichromenes (CBCs), cannabidiols (CBDs), (−)-Δ 9-trans-tetrahydrocannabinols (Δ 9-THCs), (−)-Δ 8-trans-tetrahydrocannabinols (Δ 8-THCs), cannabicyclols (CBLs), cannabielsoins (CBEs), cannabinols (CBNs), cannabinodiols (CBNDs), cannabitriols (CBTs), and the miscellaneous cannabinoids (Figure 2) [4]. C. sativa predominantly produces alkyl type cannabinoids that carry a monoterpene isoprenyl moiety (C10) and a pentyl side chain (C5) [1]. The most abundant constituents are trans-Δ 9-THC, CBD, CBC, and CBG, together with their respective acid forms (Δ 9-THCA, CBDA, CBCA, and CBGA) [5]. Cannabinoid biosynthetic pathways ty...

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“…2). Glyco‐conjugation of allele‐chemicals helps in the compartmentalized storage to increase their solubility and to reduce their autotoxicity (Kannangara et al ., 2018). Along with GTs, many other families of enzymes can be involved in detoxification, such as glutathione‐ S ‐transferases (GST), phosphotransferases, sulfotransferases, aminotransferases and glycosidases (Berenbaum and Johnson, 2015).…”

Section: The Indispensability Of Insect Gts For Detoxificationmentioning

confidence: 99%

“…This flavonoid acts as a chemical UV shield and protects the pre‐pupae from the harmful effect of UV radiation during metamorphosis (Daimon et al ., 2010). Another GT, isolated from Dactylopius coccus DcUGT2 is crucial for the biosynthesis of Carminic acid, a well‐known red colouring agent, used in food and pharmaceutical products as a dye and is also used as a microscopic stain (Kannangara et al ., 2018).…”

Section: Additional Physiological Processes and Specialized Functionsmentioning

confidence: 99%

Glycosyltransferases: the multifaceted enzymatic regulator in insects

Nagare

Ayachit

Agnihotri

et al. 2020

Insect Molecular Biology

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Glycosyltransferases (GTs) catalyse the reaction of glyco‐conjugation of various biomolecules by transferring the saccharide moieties from an activated nucleotide sugar to nucleophilic glycosyl acceptor. In insects, GTs show diverse temporal and site‐specific expression patterns and thus play significant roles in forming the complex biomolecular structures that are necessary for insect survival, growth and development. Several insects exhibit GT‐mediated detoxification as a key defence strategy against plant allelochemicals and xenobiotic compounds, as well as a mechanism for pesticide cross‐resistance. Also, these enzymes act as crucial effectors and modulators in various developmental processes of insects such as eye development, UV shielding, cuticle formation, epithelial development and other specialized functions. Furthermore, many of the known insect GTs have been shown to play a fundamental role in other physiological processes like body pigmentation, cuticular tanning, chemosensation and stress response. This review provides a detailed overview of the multifaceted functionality of insect GTs and summarizes numerous case studies associated with it.

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Characterization of a membrane-bound C-glucosyltransferase responsible for carminic acid biosynthesis in Dactylopius coccus Costa

Cited by 20 publications

References 35 publications

The biosynthetic diversity of the animal world

The biosynthetic diversity of the animal world

Phytocannabinoids: Origins and Biosynthesis

Glycosyltransferases: the multifaceted enzymatic regulator in insects

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