Phytochemical Analysis of the Methanolic Extract and Essential Oil from Leaves of Industrial Hemp Futura 75 Cultivar: Isolation of a New Cannabinoid Derivative and Biological Profile Using Computational Approaches

Abstract

Cannabis sativa L. is a plant belonging to the Cannabaceae family, cultivated for its psychoactive cannabinoid (Δ⁹-THC) concentration or for its fiber and nutrient content in industrial use. Industrial hemp shows a low Δ⁹-THC level and is a valuable source of phytochemicals, mainly represented by cannabinoids, flavones, terpenes, and alkaloids, with health-promoting effects. In the present study, we investigated the phytochemical composition of leaves of the industrial hemp cultivar Futura 75, a monoecious cultivar commercially used for food preparations or cosmetic purposes. Leaves are generally discarded, and represent waste products. We analyzed the methanol extract of Futura 75 leaves by HPLC and NMR spectroscopy and the essential oil by GC-MS. In addition, in order to compare the chemical constituents, we prepared the water infusion. One new cannabinoid derivative (1) and seven known components, namely, cannabidiol (2), cannabidiolic acid (3), β-cannabispirol (4), β-cannabispirol (5), canniprene (6), cannabiripsol (7), and cannflavin B (8) were identified. The content of CBD was highest in all preparations. In addition, we present the outcomes of a computational study focused on elucidating the role of 2α-hydroxy-Δ^3,7-cannabitriol (1), CBD (2), and CBDA (3) in inflammation and thrombogenesis.

Keywords: Cannabis sativa L. vr. Futura 75; biological profile; cannabinoids; essential oil; inverse virtual screening; phytochemicals.

Figure 1

Natural compounds isolated from the leaves of Cannabis sativa L. vr. Futura 75.

Figure 2

Binding poses of 1 (A), 2 (B), and 3 (C) inside the pocket of TNFα (PDB 6X83 for 1 and PDB 7KPA for 2 and 3), with different ribbon colors for each monomer The hydrogen bonds are depicted as yellow dotted lines and π-π stacking interactions as cyan dotted lines. Interacting residues and other important binding site amino acids are labeled (chain name + residue).

Figure 3

Binding poses of 1 (A), 2 (B), and 3 (C) in the catalytic domain of thrombin (PDBs 6ZUX, 6ZV8, and 1RD3, respectively) are represented with red ribbons. The hydrogen bonds are depicted as yellow dotted lines and π-π stacking interactions as cyan dotted lines. Interacting residues and catalytic triad amino acids are labeled.

Figure 4

Binding poses of 1 (A), 2 (B), and 3 (C) in the catalytic domain of PPARγ (PDB 2ZK6 for 1 and 4PRG for 2 and 3) depicted with lime green ribbons. The hydrogen bonds are depicted as yellow dotted lines, the salt bridges with magenta dotted lines, and π-π stacking interactions as cyan dotted lines. Interacting residues are labeled.