Δ⁹-cis-Tetrahydrocannabinol: Natural Occurrence, Chirality, and Pharmacology

Calculated and experimental 1H and 13C NMR assignments for cannabicitran

“…This structural phenomenon is supported in recent work by Schafroth, et al identifying Δ 9 -cis-THC in Cannabis sativa, which is presumably produced from (À)-cis-cannabidiol ((À)-cis-CBD, 4), a rational biosynthetic intermediate for CBT-C (3). [9] This counters Iwata and Kitanaka's findings from electronic circular dichroism (ECD) studies on the side chain truncated structure of CBT-C (3), which suggested that it is a derivative of cannabichromene and possesses the 1S,3S,4R configuration. [10] Further work to unequivocally confirm the absolute configuration of naturally occurring CBT-C ( 3) is currently underway in our lab.…”

“…[1] Development of novel synthetic cannabinoids has also recently sparked heightened interest in the pharmaceutical industry. [2] The Cannabis plant produces more than 112 known secondary metabolites; the most prominent compounds include (À)-Δ 9 -trans-tetrahydrocannabinol ((À)-Δ 9 -trans-THC, 1) and (À)-trans-cannabidiol ((À)-trans-CBD, 2), along with their congeners (Figure 1). [3] Cannabicitran (CBT-C, 3), typically present in levels ranging from $1% to 10% (see Data S1) in purified CBD extracts, is another cannabinoid that is attracting increased attention (Figure 1).…”

Scalemic myrionsumamide A, tetracyclic skeleton alkaloids from Myrioneuron effusum

“…Both racemic and enantiomeric enrichment were observed in alkaloids from Myrioneuron faberi , 3 so we suppose that primary polycyclic structures could be formed spontaneously as biomimetic access to C 5 -lysine-derived nitraramine 11 and other scalemic natural products, 12,13 while the optical pure species should be resulted from late stage enzymatic modification(s). A proposed biosynthetic pathway for 1 starting from l -lysine was shown in Scheme 1.…”

“…An antibacterial experiment showed both (+)-1 and (−)-1 were active against Staphylococcus aureus with MIC at 7.81 mg ml −1 . 13 C NMR data (Table 1) revealed the presence of two quaternary carbons (d C 174.0 and d C 70.7), four methines, and nine methylenes. The IR absorption bands around 3555, 2932 and 1614 cm −1 showed the presence of hydroxyl, secondary amine, and carbonyl functionality, respectively.…”

Cannabidiol (CBD) From Non-Cannabis Plants: Myth or Reality?

“…A final issue worth attention is the absolute configuration of a hypothetical non-Cannabis CBD. Thus, CBD from Cannabis has a very high enantiomeric purity with a 3 R ,4 R configuration ( p -menthane numbering), 33 but cis -Δ 9 -THC ( 5 ) from Cannabis 34 and its phenethyl analogue perottetinene ( 6 ) from various Radula species 35, 36 have an opposite configuration at C-6a (corresponding to C-4 in the p -menthane numbering system). This suggests that, in the search for non-Cannabis sources of CBD, the relative configuration of the 2 stereogenic centers, as well as the absolute configuration and the optical purity need to be critically evaluated.…”