The "Cannabinoid Spectrum" found in Cannabis


In my previous posts we had a preliminary look into informative datasets relating to the cannabinoids and terpenes found in cannabis as described by Certificates of Analysis (COAs) derived from third party cannabis testing labs.

Though a review of these datasets we were able to glean some global trends in cannabinoids and gain insight into terpene profiles of popular cannabis strains named the same.

Here, we take an academic approach to flush out and address what is often referred to as the "full spectrum of cannabinoids" or "cannabinoid spectrum". Two terms which get frequent mention but are often addressed with details lacking.

We are fortunate to stand on the shoulders of giants. Dr. ElSohly has compiled the spectrum of cannabinoids and terpenes found in cannabis in a chapter called Chemistry and Analysis of Phytocannabinoids and Other Cannabis Constituents in a publication we will return to often named Marijuana and the Cannabinoids [referenced in detail below].

Since a large number of compounds are listed (forty seven in fact) in this chapter it is a perfect opportunity for us to use cheminformatics tools and open source software to organize and display the compound relationships based on atomic similarities and differences (a topic that will be detailed in later posts). This was accomplished using the simlarity metrics from the fmcsR package available for the R programming language which uses a fragment based or Multiple Common Substructure (MCS) approach.

You may consider the cheminformatics method excessive or even pedantic for a meagre forty seven compounds that are classified and grouped nicely in the aforementioned publication.

Nonetheless, you will find that with cheminformatics will empower us to increase the scope of compounds we consider and the depth whereby we compare them.

If you don't believe me you will soon see how similarity metrics come in handy when we discuss phytocannabinoids derived from plants other than cannabis, endocannabinoids, and venture down the deep dark alley of synthetic cannabinoids.

The image you see in header of this article above is an fan cladogram derived from a distance matrix calculated using fmcsR. The relationship between the compounds shown, terpenes and cannabinoids, is based on a computational similarity algorithm that groups compounds that "fit" within each other or share a common substructure.

I will do a clade by clade analysis of these similarity trends in the next post, but merely want to introduce you to the global view first. Below is a cladogram from the same distance matrix shoing the relationships as a rooted cladogram.

In this rooted cladogram the length of the branches joining a clade visualize how similar compounds are to each other as computed by the fmcsR algorithm.

For those of you who are not satisfied with just the names of the compounds I have included a table for you to click out and view structural and detailed annotation of each compound. If you are a real keener you may have noticed I replaced the names of two compounds with "A" and "B" just to force you to click out and find out the identity.

Cladogram derived by using fmcsR to calculate a distance matrix based on common substructure matching
# Common name Pubchem
1 cis-beta-farnesene 5317319
2 myrcene 31253
3 ipsdienol 85734
4 humulene 5281520
5 (E)-beta-ocimene 5281553
6 alpha-farnesene 5281516
7 (Z)-beta-ocimene 5320250
8 z-gamma-bisabolene 3033866
9 terpinolene 11463
10 linalool 6549
11 cannabichromene (CBC) 30219
12 d-limonene 440917
13 alpha-cadinene 12306048
14 gamma-muurolene 12313020
15 alpha-guaiene 5317844
16 beta-caryophyllene 5281515
17 caryophyllene epoxide 14350
18 gamma-curcumene 12304273
19 (+)-epi-alpha-bisabolol 1201551
20 (+)-3-carene 443156
21 alpha-bergamotene 86608
22 (-)-endo-alpha-bergamotene 6429303
23 (-)-beta-fenchyl alcohol 61123
24 fenchone 14525
25 camphene 6616
26 (+)-borneol 6552009
27 alpha-pinene 6654
28 alpha-ylangene 442409
29 alpha-longipinene 520957
30 A 12444322
31 beta-selinene 442393
32 alpha-selinene 10856614
33 beta-elemene 6918391
34 beta-phellandrene 11142
35 beta-pinene 14896
36 cis-sabinene 25086832
37 alpha-eudesmol 92762
38 beta-eudesmol 91457
39 B 5317072
40 delta-9-tetrahydrocannabinolic acid (THCA) 98523
41 delta-9-tetrahydrocannabinol (d9THC) 16078
42 cannabidiol (CBD) 644019
43 cannabidiolic acid (CBDA) 160570
44 cannabigerol (CBG) 5315659
45 cannabinol (CBN) 2543
46 guaiacol 460
47 vitamin E 14985

If you are left with a feeling and want for more chemical minutia on this topic rest assured we will delve into the specific similarities and differences of each chemical grouping or clade in a future article, so stay tuned and be sure to subscribe.

References


  1. ElSohly, M. A. (Ed.). (2007). Marijuana and the Cannabinoids. Springer Science & Business Media.