# Non-Cannabinoid Metabolites of _Cannabis sativa_ L. with Therapeutic Potential
## 2 Non-Cannabinoid Compounds
### Stilbenes and Stilbenoids  
Stilbenes (and their derivatives) are naturally occurring polyphenic phytochemicals that, aside from being a form of herbivore and disease resistance mechanisms for many lower and higher plants in the plant kingdom [71], have a wide range of biological activity and medicinal value to humans [72]. Stilbenoids are stilbene derivates that have been hydroxylated [73].  
A 2004 study by [PERSON] isolated, characterized and synthesized dihydro-resveratrol (3,5,4\({}^{\prime}\)-trihydroxybibenzyl), a metabolite derivative of the antioxidant, resveratrol, a dihydro-rostilbenoid from _Cannabis sativa_ (Figure 10 above) [74]. A 2019 study by [PERSON] and colleagues reported that dihydro-resveratrol and other metabolite derivatives of resveratrol induced senescence in breast cancer cells [75]. Studies on the antioxidant activity of dihydro-resveratrol are limited. A 2016 study by [PERSON] and colleagues report that dihydro-resveratrol demonstrated the ability to attenuate pancreatic oxidative damage and could possibly have therapeutic potential in the management of acute pancreatitis [3].  
Nineteen stilbenoids unique to the cannabis plant were identified in a 1995 study by [PERSON] and [PERSON] [5]. These can be divided into three main structural classes: eleven spiroindans, eight dihydrorostilbenes/bibenzyls, five phenanthrenes and prenylated, geranylated and glycosylated derivates [76]. Table 8 below is a list of these compounds.  
\begin{table}
\begin{tabular}{l l l l} \hline \hline  & **Spiroindans** & **Eight Dihydrorestilbenes/bibenzyls** & **Phenanthrenes and Derivatives** \\ \hline
1. & Cannabispirone & a. & **Prenylated** & \\
2. & Cannabispirenone-A & i. & 3,4\({}^{\prime}\)-dihydroxy-5,3\({}^{\prime}\)- & \\
3. & Isocannabispirenone & &dimethoxy-5\({}^{\prime}\) & 1. & 9,10-dihydrophenanthrene \\
4. & Isocannabispiradienone & & isoprenyl & i. & cannithrene-1 \\
5. & Cannabispirenone-B & ii. & Canniprene & ii. & cannithrene-2 \\
6. & \(\beta\)-cannabispirand & & iii. & Cannabistilbene I, \\
7. & \(\alpha\)-cannabispirand & & iv. & Cannabistilbene IIa \\
8. & Acetyl cannabispirol & & v. & Cannabistilbene IIb \\
**Cyclohexane Spirans** & b. & **Non-Prenylated** & \\
9. & 5,7-dihydroxyradn-1-spiro-cyclohexane & i. & 3,4\({}^{\prime}\)-dihydroxy-5-methoxy & 4. & 4-hydroxy-2,3,6,7-tetramethyl-9,10-dihydrophenanthrene \\
10. & 7-hydroxy-5-methoxylandan-1-spiro-cyclohexane & ii. & 3,3\({}^{\prime}\)-dihydroxy-5,4\({}^{\prime}\)- & 5. & Denbinbinbin \\
11. & 5-hydroxy-7-methoxylandan-1-spiro-cyclohexane & & dibenyl & (5-hydroxy-3,7-dimethoxy-1,4-phenylanthrenequinone) \\
12. & 13. & Dihydroresveratrol & \\ \hline \hline \end{tabular}
\end{table}
Table 8: Some stilbenes and their derivatives found in _C. sativa_ L.  
Figure 10: The chemical structure of dihydoresveratrol, a hydroxylated stilbene derivative.  
Denbinobin, first isolated in a 2008 study by [PERSON], is reported to have beneficial bioactive properties to human health as an anti-HIV, antioxidant, antitumor, and inhibitor of platelet aggregation [77]. The structure of denbinobin is shown in Figure 11 below.