Flavonoids in Cannabis

, 10/09/2021

By Uwe Blesching

Surprising Benefits from an Unexpected Source

Have you ever wondered what contributes to nature’s abundance of colors and scents that makes being around lush, aromatic plants so delightful? By the same token do you know what natural ingredients contribute to making one of the most basic pleasure of life, the taste of foods, so enjoyable? The answer to both is Flavonoids. Also known as bioflavonoids these natural substances are produced by plants such as citrus fruits, berries, vegetables, tea, cocoa, red wine and cannabis.

Flavonoids are a biologically diverse family of natural substances that help realize a number of beneficial effects to the plants that make them and those who consume them. Named after the Latin word for yellow (flavus) presumably chosen to describe the compounds that influence color schemes in plants but also help to generate their unique flavors and scents. Flavonoids are considered secondary metabolites that function to facilitate biological interactions within the same organism, between other organisms, and the environment. As such, flavonoids are not primary life-sustaining building blocks like sugars, proteins, or lipids but rather plant constituents that realize secondary benefits. In plants they function to attract pollinators, detract pests, protect against shifts in salinity, safeguard against UV light or establish freezing tolerances.

Chronic Conditions and Flavonoids

In people (or any other mammal) who consume them, flavonoids can mitigate some of  the shared underlying pathologies of numerous chronic conditions and in doing so  increase an organisms ability to generate and maintain health and wellness. More specifically, flavonoids help to make the process of managing chronic internal and environmental stressors such as the aging process,1 oxidative stress or inflammation,2 more efficient. Furthermore, if we take into consideration flavonoid’s very low adverse effects potential and its potential protective effects against environmental threats such as various viral diseases including COVID,3 for example it becomes easy to understand why flavonoids are found in a great number of pharmaceutical, nutraceutical, as well as cosmetic products generated across the globe. Indeed, most every Health Agency tasked with educating people about dietary health recommend fruits and vegetables abundant in flavonoids for these very reasons. However, due to their relatively low bioavailability, rapid metabolism, and elimination most people could benefit from an increase intake of flavonoids.

Chemical Structure of Flavonoids

Chemically, flavonoids present with variable phenolic structures (organic aromatic building blocks) that include thousands of individual members. Those that are of dietary importance are typically divided into six major sub-groups (in alphabetical order with food examples): anthocyanidins (blue berries, wine), flavan-3-ols (green teacocoa, various spices), flavanones (fresh lemon, fresh oranges), flavones (fresh parsley, fresh thyme, cannabis), flavonols (tea, fresh, raw kale, cannabis), and isoflavones (mature raw soybean seeds, firm, cooked tofu).4 For those readers interested in a bit more technical information flavonoids have a typical molecular structure containing a 15-carbon structure (abr. C6-C3-C6) comprised of three rings (i.e. two phenyl rings each made up of six carbon atoms (A, B) and one heterocyclic ring characterized by 2 atoms of at least 2 elements in this case carbon and oxygen (C).

                                                                                                                                                                          Cannaflavins

Cannaflavins

Cannabis-based flavonoids primarily belong two sub-classes i.e., flavones and flavonols. The earliest paper describing three cannabis-based flavonoids was published by Canadian researchers in 1979.5 By 2021 a team from the US described a total of 34 flavonoids (for a complete list in order of discovery scroll down to the end of article).6

And, while the scientific literature reporting on cannaflavins in the context of health, healing and well-being is relatively small, emerging data is beginning to describe cannflavin-induced effects with potential clinical relevance most notably anti-inflammatory,7 anti-oxidant8 and potential analgesic effects.9 Specific treatment examples include the potential mitigation of neurodegenerative processes with potential relevance to patients with Alzheimer’s disease.10 Also of note, the unnatural isomer of Cannflavin B (i.e. FBL-03G) has demonstrated therapeutic potential in preclinical models of metastatic pancreatic cancer notorious for extremely poor survival rates and orthodox treatment responses.11

Consider these emerging facts with potential practical relevance:

  • Flavonoids are not present in cannabis roots, stem or barks.12
  • Flavonoids are present in smaller amounts in cannabis flower (i.e., 0.07–0.14%).13
  • Flavonoids occurred in the highest concentrations in the leaves of cannabis (0.34–0.44%).14
  • Total flavonoid content in cannabis flowers was significantly higher in a cannabis chemotype III than Chemotype I and Chemotype II.15
  • Total flavonoid content in leaves was higher in Chemotype II and Chemotype III than in Chemotype I.16
  • Flavonoid content drops as cannabis ages.17
  • Sprouting hemp seeds (rich in Omega-3 Fatty Acid) induces the production of cannflavins A and B.18

The Takeaway:

Cannabis keeps on surprising us. The evidence-based underpinnings of flavonoids are but one example. Scientists continuously discover novel plant constituents, novel therapeutic effects, and novel complexities, which taken together allows us to make more informed and discerning decisions to amplify the health and wellness generating effects of cannabis-based therapeutics.

When exploring flavonoid profiles consider choosing a cannabis chemotype III (more CBD than THC), consider leaf-based cannabis products (e.g., leaf-based shake/kief), sprout hemp seeds, and/or juice fresh cannabis leaves. Alternatively, to maximize flavonoid content you can utilize fresh cannabis flower. The cannabinoids in fresh flower have not yet decarboxylated (i.e., do not produce cognitive changes) and as such exist in their acid forms with relatively high amounts of flavonoids and terpenes. If the taste is too unpleasant due its bitterness you may want to mix them with carrot juice or chop them up and fill a few gelatin capsules for easier consumption.

Cannabis-Based Flavonoids by Year of Discovery (Radwan et. al. 2021):19

1979
(Clark M.N. and Bohm B.A.):20 Vitexin • cytisoside • cytisoside glucoside

1980
(Turner CE, Elsohly MA, Boeren EG):21

Orientin • orientin-O-glucoside • orientin-7-O-glucoside • orientin-7-O-rhamnoglucoside ••

Vitexin-O-glucoside • vitexin-7-O-glucoside • vitexin-7-O- rhamnoglucoside ••

Isovitexin • isovitexin-O-glucoside • isovitexin-7-O-glucoarbinoside • isovitexin-7-O- rhamnoglucoside • apigenin-7-O-glucoside • apigenin-7-O-glucoronoid • apigenin-7-O-p-coumaroylglucoside ••

Luteolin-C-glucuronid • luteolin-7-0-glucuronid • kaempferol-3-0-diglucoside • quercetin-3-0-glucoside • quercetin-3-0-diglucoside

1982
(Crombie L. and Crombie W.M.L):22 Canniflavone 1 • Canniflavone 2

1986
(Barrett ML, Scutt AM, and Evans FJ):23 Cannflavin A • Cannflavin B (same compounds as above)

2005
(Ross SA, ElSohly MA. et. al.):24 Kaempferol-3-O-sophoroside • quercetin-3-O-sophoroside

2008
(Radwan et. al.):25 Cannflavin C • 6-prenylapigenin • chrysoeriol

2008
(Cheng L., Kong D., and Hu G.):26 Apigenin-6,8-di-C-β-D-glucopyranoside

2012
(Chen B., Cai G. et. al.):27 Rutin

2020
(Ingallina C. et. al.):28 Quercetin • Naringenin • Naringin

Source Article:
https://cannakeys.com/flavonoids-in-cannabis/

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