Chemical and Biological Studies of Cannabis sativa Roots

Mostafa A. Elhendawy, Amira S. Wanas, Mohamed M. Radwan, Nabil A. Azzaz, ElShahat S. Toson, Mahmoud A. ElSohly

Medical Cannabis and Cannabinoids, 2018, 1, 104–111

DOI: 10.1159/000495582

https://www.karger.com/Article/FullText/495582

Abstract :
The chemical study of Cannabis sativa roots led to the isolation and identification of 10 compounds. Their chemical structures were unambiguously established on the basis of 1D and 2D NMR spectroscopy and mass spectrometry as friedelan- 3-one (1), epifriedelanol (2), β-sitosterol (3), ergost-5- en-3-ol (4), methyl hexadecanoate (5), pentadecanoic acid (6), 10E-hexadecenoic acid (7), 4-hydroxy 3-methoxybenzaldehyde (8), β-sitosterol-β-D-glucoside (9) and p-coumaroyltyramine (10). Compounds 5–9 were reported for the first time from C. sativa roots. All the isolated compounds were tested for their antimicrobial activity. Compound 4 showed modest activity against Cryptococcus neoformans with an IC50 value of 13.7 μg/mL, while compound 10 displayed potent activity against Escherichia coli with an IC50 value of 0.8 μg/mL. A high-performance liquid chromatography method was developed and validated for the detection and quantification of p-coumaroyltyramine (10) in the extracts of different varieties of C. sativa roots.

Keywords :
Cannabis sativa · Secondary metabolites · High-performance liquid chromatography · Quantitative analysis · Cannabis roots

Introduction

Cannabis sativa L. is one of the most widely used plants for both recreational and medicinal purposes. To date, a total of 567 natural constituents covering several chemical classes have been identified from C. sativa [1, 2]. The most important classes are the cannabinoids, terpenoids, nitrogenous compounds, noncannabinoid phenols, flavonoids, and steroids [3]. The principal use of cannabis in medicine is for easing pain and in ameliorating nervous system disorders. It is reported to be useful in the treatment of gout, neuralgia, rheumatism, insanity, and insomnia among others, with actions almost entirely on the higher nerve centers [4].

The first reference to cannabis consumption dates as far back as 2,700 BC in China, with Shennong pên Ts’ao ching, one of the oldest Chinese medicine books, mentioning the use of cannabis roots as a remedy to sooth pain. Throughout history, cannabis roots were documented in ancient Greek medicine, and a medical article in how Indians boiled them together with other leaves to make poultices for the treatment of inflamed skin surfaces and skin rash [3, 5]. There are numerous reports on the traditional use of cannabis root for the treatment of fever, inflammation, gout, arthritis, and joint pain, as well as skin burns and hard tumors [3]. Also, they were used to treat postpartum hemorrhage, difficult child labor, sexually transmitted disease, and gastrointestinal activity and infection [6]. Despite a long history of therapeutic use, the roots of cannabis plants have been ignored in modern medical research and practice. Cannabis roots have been reported to have many different compounds, including triterpenoids, monoterpenes, alkaloids, sterols, amides, and choline [3].

On continuation of our search for bioactive compounds from C. sativa [7, 8], this article describes the isolation and structural elucidation as well as the antimicrobial activity of 10 compounds from C. sativa roots. A high-performance liquid chromatography (HPLC) method was also developed and validated for the quantification of p-coumaroyltyramine (10) in extracts of different varieties of C. sativa roots which could be used as a possible marker compound to distinguish between roots of different varieties of C. sativa.

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