Flavonoids: The colored compounds in cannabis

Flavonoids of purple cannabis

Have you ever wondered why some cannabis buds have such exotic have such exotic colors like red or purple? Today we talk about the flavonoids of the cannabis plant, the compounds responsible for the striking colors that this plant can adopt.

In addition to the known cannabinoids, such as cannabidiol (CBD) and cannabidiol (CBD) Cannabis also contains other lesser known but equally important compounds: flavonoids. These powerful bioactives not only add beauty to the plant, but can also synergize with other cannabis compounds to influence our cannabis experience.

Introduction to cannabis flavonoids

What are cannabis flavonoids?

Flavonoids are a class of phenolic compounds that are widely distributed in the plant kingdom. They are known for their wide range of colors and in addition to cannabis, these compounds are also found in various plant foods. They are also considered to be one of the most important phenols in the diet and are one of the largest groups of compounds in plants [1].

What coloration do flavonoids give to cannabis?

Etiomologically, the term “flavonoids” comes from the Latin “flavus”, meaning “yellow”, in reference to the coloration that many of these compounds give to the plants that contain them. Flavonoids can confer a wide range of colors, ranging from yellow to purple and red.

It is worth mentioning that in cannabis, as with other plants, the yellow coloration of some flavonoids may be overshadowed by the green color of chlorophyll (which is not a flavonoid). Therefore, the presence of these compounds is often not evident to the naked eye, but is hidden under the different shades of green. Other times, on the other hand, the purple or red color of the marijuana gives away its presence.

Functions of flavonoids in plants

Flavonoids are found in a great many plants and can serve several purposes, but one of their main functions is their role as pigments, particularly the coloration of flowers [3]. More than 4,000 types of natural flavonoids have been found [1]. Some also suggest that these compounds may play an important role in protecting the plant against ultraviolet light and disease [3].

Therefore, flavonoids are essential compounds for the survival of the plant and also give a distinctive character to many varieties of marijuana, such as the strains CBD Purple Haze y CBD Purple Tangie whose striking colors are due to these polyphenolic compounds.

Ranking

Flavonoids are usually found bound to carbohydrate molecules and can be divided into 13 classes according to their chemical characteristics. Some of these classes are [1]:

  • Flavonols: includes compounds such as quercetin and kaempferol.
  • Flavones: include compounds such as apigenin, luteolin and the canflavins A, B and C present in cannabis, which we will discuss below.
  • Flavanones: include compounds such as naringenin and hesperetin, which are abundant in citrus fruits.
  • Isoflavones: includes compounds such as genistein and daidzein, very present in fermented soybean products.
  • Anthocyanidins: include red, blue and purple pigments in plants (such as cyanidin, delphinidin…). They are the antioxidant pigments in blueberries and blackberries.

Where are flavonoids found?

Flavonoids are very common compounds in plants, including cannabis. On another occasion we talked about anthocyanins, a type of flavonoid responsible for the violet color in purple marijuana plants. purple marijuana plants .

These compounds can also be found in a variety of plant foods that make up our diet, mainly in fruits and vegetables.

Chemical structure

To understand the chemical structure of flavonoids, it is important to start with phenol, an aromatic organic compound consisting of a benzene ring with a hydroxyl (OH) group forming the basis of its structure [1]. Flavonoids are organic compounds containing a chain of 15 carbon atoms and two phenyl rings [2]. These compounds are closely related to phenol and are described as benzene rings in which a hydrogen has been replaced by another element or compound.

Cannabis flavonoids

Types of cannabis flavonoids

The marijuana plant has many flavonoids.Several flavonoids have been identified in the Cannabis sativa plant, some of the most prominent being flavones, such as vitexin, orientin, luteolin, and apigenin, and flavonols, such as kaempferol and quercetin [4].

Cannflavins A, B and C from cannabis

One of the first flavonoids described in Cannabis sativa is cannflavin [5] (also called cannaflavin or canflavin). It was later discovered that it can be divided into several compounds, the cannflavins A, B, and C [6, 7].

Cannflavins A and B have been found in young hemp plants with few cannabinoids [8] and also in homemade cannabis tinctures [9].

Cannflavins are flavonoids found only in the marijuana plant.

These two cannflavins are specific to the Cannabis sativa plant [6] and belong to the group of flavonoids called flavones, which serve many functions in plants including regulation, transport and mediation in the interaction with pathogens [5-7].

These two cannflavins are prenylated flavones [9], i.e., they have hydrophobic molecules added to them. Cannflavins A and B are produced from luteolin, which is a flavonoid common in many plants, including dietary vegetables and fruits [6].

In addition, the presence and concentration of flavonoids may vary between different cannabis strains and cultivation methods.

Properties of flavonoids and their effects on cannabis

Effects of flavonoids in cannabis

In cannabis, flavonoids can contribute to the cannabis experience through the entourage effect which is the synergistic interaction between various compounds present in the plant, including cannabinoids, terpenes and flavonoids.

Cannabis flavonoids can interact with receptors of the endocannabinoid system and other systems in the body, which can modulate the effect of cannabinoids and terpenes, enhancing or modifying their effects. This opens up new possibilities for the development of medical cannabis strains.

Although the flavonoid group has been extensively studied as they are present in numerous foods and medicinal plants, there is still much research to be done on the possible interactions between flavonoids and the other components of cannabis and little can be said about them.

Flavonoid properties

In general, flavonoids are antioxidant agents and have gained much attention for the possibility of preventing and treating a number of diseases and may also interrupt carcinogenesis [1]. Flavonoids also appear to have antiviral properties against viruses such as HIV, herpes, respiratory viruses, and polio among others [1].

Flavonoids are antioxidants and have gained much attention due to their possible anticarcinogenic properties.

The three cannflavins in cannabis have antioxidant, anti-inflammatory and apparently also anti-cancer properties [10]. Canflavins A and B have anti-inflammatory properties that can be up to 30 times higher than those of aspirin [5]. These two cannaflavins inhibit the production of two inflammatory mediators, prostaglandin E2 and leukotrienes [6, 8].

As I was saying, there are many flavonoids in plants. One of the best known is quercetin, which has been widely investigated for its anticarcinogenic properties, and is the most abundant flavonoid in fruits after kaempferol and myricetin. Kaempferol also has anticancer properties [1].

Another well-known flavonoid is apigenin, which is found in fruits and vegetables and may also be present in cannabis [1, 4]. Apparently, apigenin could reduce GABA receptor activity (as do cannabinoids such as THC, CBD, and possibly some terpenes), which could explain its sedative properties (11). It also has anticancer properties in breast, cervical, colon, leukemia, lung, ovarian, prostate, skin, thyroid, gastric, liver, among other forms of cancer [1].

In conclusion…

Cannabis flavonoids are fascinating compounds that not only bring striking colors to the buds of the plant, but can also influence the cannabis experience through the entourage effect. Their presence and concentration may vary among different cannabis strains and cultivation methods.

I hope you found it interesting to learn more about these compounds. As research progresses, it is expected that more information will be revealed about how they may influence the effects associated with cannabis use. See you next time!

Doubts and quick questions about cannabis flavonoids…

How many flavonoids does cannabis contain?

It is estimated that cannabis contains more than 20 different flavonoids, including flavones, flavonols and other related compounds. Some specific flavonoids found in cannabis are cannaflavin A, cannaflavin B, cannaflavin C, orientin, vitexin, apigenin, luteolin, kaempferol and quercetin, among others (4, 12).

What foods contain flavonoids?

In addition to cannabis, flavonoids can also be found in a variety of plant foods that make up our diet, such as fruits (especially citrus fruits, red fruits, apples, grapes…), vegetables (onions are especially rich in quercetin), legumes (soy is very rich in isoflavones) and spices (such as the gingerol in ginger or the curcumin in turmeric). In addition, they are also found in medicinal plants and in products made from plants, such as red wine, chocolate and green tea (all three rich in catechins).

Is chlorophyll a type of flavonoid?

Chemically, chlorophyll is not classified within the flavonoid group, but is a green photosynthetic pigment classified within the porphyrins. Another group of plant pigments are carotenoids. Like some flavonoids, carotenoids give yellow coloration to some fruits and foods, but they are not flavonoids either. In other words: not all plant pigments are flavonoids!

Referencias
  1. Bhuyan, D.J. and A. Basu, Phenolic compounds potential health benefits and toxicity, in Utilisation of bioactive compounds from agricultural and food waste. 2017, CRC Press. p. 27-59.
  2. Stalikas, C.D., Extraction, separation, and detection methods for phenolic acids and flavonoids. Journal of separation science, 2007. 30(18): p. 3268-3295.
  3. Falcone Ferreyra, M.L., S. Rius, and P. Casati, Flavonoids: biosynthesis, biological functions, and biotechnological applications. Frontiers in Plant Science, 2012. 3(222).
  4. Vanhoenacker, G., et al., Chemotaxonomic features associated with flavonoids of cannabinoid-free cannabis (Cannabis sativa subsp sativa L.) in relation to hops (Humulus lupulus L.). Natural Product Letters, 2002. 16(1): p. 57-63.
  5. Barrett, M., D. Gordon, and F. Evans, Isolation from Cannabis sativa L. of cannflavin-a novel inhibitor of prostaglandin production. Biochemical pharmacology, 1985. 34(11): p. 2019-2024.
  6. Rea, K.A., et al., Biosynthesis of cannflavins A and B from Cannabis sativa L. Phytochemistry, 2019. 164: p. 162-171.
  7. Barrett, M., A. Scutt, and F. Evans, Cannflavin A and B, prenylated flavones from Cannabis sativa L. Experientia, 1986. 42(4): p. 452-453.
  8. Werz, O., et al., Cannflavins from hemp sprouts, a novel cannabinoid-free hemp food product, target microsomal prostaglandin E2 synthase-1 and 5-lipoxygenase. PharmaNutrition, 2014. 2(3): p. 53-60.
  9. Peschel, W., Quality control of traditional cannabis tinctures: pattern, markers, and stability. Scientia pharmaceutica, 2016. 84(3): p. 567-584.
  10. Moreau, M., et al., Flavonoid derivative of cannabis demonstrates therapeutic potential in preclinical models of metastatic pancreatic cancer. Frontiers in oncology, 2019. 9: p. 660.
  11. Losi G, Puia G, Garzon G, de Vuono MC, Baraldi M. Apigenin modulates GABAergic and glutamatergic transmission in cultured cortical neurons. Eur J Pharmacol. 2004 Oct 11;502(1-2):41-6. doi: 10.1016/j.ejphar.2004.08.043. PMID: 15464088.
  12. Bautista JL, Yu S, Tian L. Flavonoids in Cannabis sativa: Biosynthesis, Bioactivities, and Biotechnology. ACS Omega. 2021 Feb 18;6(8):5119-5123. doi: 10.1021/acsomega.1c00318. PMID: 33681553; PMCID: PMC7931196.

Dra. Daniela Vergara
Investigadora y catedrática | Especialista en cultivos emergentes y consultora de cannabis

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