Phenolic compounds in hemp

FLAVONIDS – OTHER COMPOUNDS IN HEMP

Many different organic compounds are synthesized in hemp. Among these molecules, the most important group is phytocannabinoids, to which many pharmacological effects are attributed, but too often the importance of other compounds such as falvonoids and terpenes is also neglected.

Phenolic compounds or phenylpropanoids are one of the most abundant secondary metabolites found in plants. This group of compounds includes phenolic acids (benzoic and hydroxycinnamic acids), flavonoids (flavonols and flavones), stilbenoids and lignans. (1)

FLAVONOIDS

Flavonoids are secondary metabolites that are composed of a group of polyphenolic compounds and are formed in various plants. There are more than 5,000 different flavonoids in plants. They give the plants pigment, protect the plant from UV radiation, microbes and help in the symbiotic binding of nitrogen. In addition, in the plant they perform the function of signaling molecules, physiological regulators and inhibitors of the cell cycle. (2)

Flavonoids, in addition to terpenes, are also responsible for the aroma and taste of cannabis. Those cannabis that turn their flowers purple are due to flavonoids such as anthoxanthins or anthocyanins. They are also responsible for coloring other plants. (3)

Most of the flavonoids found in cannabis belong to the subclasses of falvones and flavonols. These include the O-glycosidic version of aglycone apigenin, luteolin, kaempferol, quercetin, silymarin and orientin, as well as flavonoids that are unique to cannabis, namely cannaflavin A, B and C. (1)

The flavonoids and flavonols found in cannabis have a very wide range of bioavailability as they act as anti-inflammatory, anticancer and neuro-protective, and also show apigenin anxiotic and estrogenic properties. Specific canflavin A and B have a very strong anti-inflammatory effect. (1)

Table I: Flavonoid species and their biological activity (3) (4) (5)

LIGNANI

The second group are lignans. This class includes lignanamides, which are cannabisin-like compounds (types A-, B-, C-, D-, F-, and G-) and grossamide. Lignans are also found in hemp seeds. (1)

Lignans also have many properties that improve our health, as they act as antioxidants, antivirals, antidiabetics, antitumors and help reduce weight. Interestingly, certain lignans are converted to enterolignanes by the anaerobic intestinal microflora, which are phyto-estrogens and are therefore potential compounds to combat hormone-dependent cancers (1)

STILBENOIDS

Stilbenoids are phenolic compounds found in various plants. In plants, they are important primarily for plant protection. They are often found in stems and roots and have antifungal and antibacterial activity or are insect repellent substances. 19 stilbenoids were found in cannabis. (6)

Stilbenoids have been shown to exhibit anti-inflammatory, antineoplastic (anti-neoplastic), neuroprotective, cardiovascular, and antioxidant activity. (6)

Representatives of stilbeneids in cannabis are washed, phenanthrene, and bibenzyl. These include molecules such as cannabistilben I, IIa and IIb and dihydroresveratrol. (1)

1. Andre, C. M.; Hausman J.-F.; Guerriero, G.; 2016, »Cannabis sativa: The Plant of the Thousand and One Molecules.« Front. Plant Sci., Vol: 7:19, 1-17
2. https://en.wikipedia.org/wiki/Flavonoid
3. https://www.leafly.com/news/cannabis-101/what-are-marijuana-flavonoids
4. Russo, E. B.,; Grotenhermen, F., 2006, »Flavonoids«, V: Russo, E., B.,; Grotenhermen, F. (ur.), »Handbook of Cannabis Therapeutics, From Bench to Bedside.« 2006, The Haworth Press, Inc., 10 Alice Street, Binghamton, New York, str.: 187-191
5. https://www.fundacion-canna.es/en/flavonoids
6. Flores-Sanchez, I. J.; Verpoorte R.; 2008, »Secondary metabolism in cannabis.« Phytochem Rev, Vol.: 7, Str.: 615-639