Delta9technologies
Terpenes
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Introduction
In addition to the four major metabolites (proteins, carbohydrates, nucleic acids, and lipids) produced in plants in animals, plants produce a unique secondary class of metabolites referred to as terpenoids. [1] The wide variety of aromas emitted from essential oils isolated from plants are attributable to terpenoids and other compounds known as shikimates (flavanoids, lignans, and coumarins) and polyketides. Animals use volatile plant compounds to find food and suitable sites for their offspring; however, plant volatiles can also be unfavorable and act deterrents. As shown in Figure 1, terpenoids, polyketides, and shikimates are all produced through a common convergent pathway beginning with glucose (1). Phosphoenolpyruvate (2) is produced through glycolysis and can undergo conversion to shikimic acid (3), which leads to the flavanoids, lignans, and coumarins. Alternatively, 2 can undergo conversion to acetylcoenzymeA (4), which is the common intermediate for polyketides, lipids, and terpenoids. In this section we will focus on predominately on the terpenoids since they are most relevant to the smell of cannabis. Terpenoids are produced in the plant from mevalonic acid (5), which is made from acetyl coenzyme A (4).
Figure 1. Biosynthetic pathway for the production molecules of smells and flavours in plants.
From melavonic acid (5), geranyl phosphate (8) is produced in plants according to the pathway illustrated in Figure 2. [1] Geranyl phosphate is the precursor to terpenoids and the cannabinoids such as THC and CBD. The first step in the formation of geranyl phosphate (8) involves the elimation of mevalonic acid (5) to form compounds 6 and 7, which undergo a base catalyzed polymeric head-to-tail coupling that can lead to rather large terpenoids and cannabagiberol (CBG), which is the precursor to the cannabinoids.
Figure 2. Biosynthetic pathway for the production of geranyl phosphate (8) from mevalonic. Geranyl phosphate is the precursor to terpenoids, but is also the building block for the cannabinoids such as THC and CBD.
Figure 2. Biosynthetic pathway for the production of geranyl phosphate (8) from mevalonic. Geranyl phosphate is the precursor to terpenoids, but is also the building block for the cannabinoids such as THC and CBD.
Geranyl phosphate (8) is an intermediate for the synthesis of monoterpenoids and sesquiterpenoids produced by the biosynthetic pathway depicted in Figure 3. Monoterpenoids such as limonene (11) are produced by synthase enzymes such as limonene synthase. In contrast to the monoterpenoids, the sesquiterpenoids are generated from farnesyl pyrophosphate (12), which is generated in the plant from 8 and FPP synthase. Geranyl phosphate (8) is also the precursor to the building block of the cannabinoids, CBGA (10) via olivetolic acid (9) and the enzyme catalyst, olivetolate geranyltransferase. Therefore, the production of geranyl phosphate is critical in the cannabinoid content and flavor of cannabis plants. A list of monoterpenoids and sesquiterpenoids including structure are depicted below in Figure 4.
Figure 3. Biosynthetic pathway for the production of cannabinoids, monoterpenoids, and sesquiterpenoids from geranyl phosphate (8).
Common Terpenoids in Cannabis
Figure 4. Common terpenoids in cannabis that are believed to have synergistic effects with the cannabinoids. These terpenoids are found in various plants listed below the name.
Cannabis Flavor Wheel (credit: GreenhouseseedCo.)
There can be an overwhelming number of cannabis strains to choose from at a quality dispensary. The majority of plants provided at modern storefronts have a high THC content. Therefore, many patients are choosing their favorite strain based on the taste and smell as opposed to cannabinoid levels. The delicious aromatic properties associated with plants, including cannabis, result from terpenes and essential oils produced in plants. Lavender and eucalyptus produce abundant quantities of terpenes, and have been used in aromatherapy as an alternative medicine for millenia. Recently, GreenHouseSeedCo. contributed a Flavor Wheel to help patients make a decision by associating strain names with well known flavors. Thanks for this nice piece of work Greenhouseseed Co.!
Figure 5. The flavor and smell of cannabis is complex due to the variety strains cultivated. GreenhouseseedCo. put together a flavor wheel to help patients identify some the subtle undertones they can identify from various food sources. This graphical illustration is a great way to identify strains that you may find appealling.
References
Terpenes/Terpenoids
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