Isolation and biological evaluation of prenylated flavonoids from Maclura pomifera

Abstract

Phytochemical analysis of the ethanolic extract of Maclura pomifera fruits yielded four new compounds (I-IV) along with eleven known compounds (V-XV). The crude extract exhibited significant activity towards cannabinoid receptors (CB1: 103.4% displacement; CB2: 68.8% displacement) and possibly allosteric interaction with and opioid receptors (−49.7 and −53.8% displacement, resp.). Compound I was found to be possibly allosteric for and opioid receptors (−88.4 and −27.2% displacement, resp.) and showed moderate activity (60.5% displacement) towards CB1 receptor. Compound II exhibited moderate activity towards cannabinoid receptors CB1 and CB2 (47.9 and 42.3% displacement, resp.). The known compounds (V-VIII) exhibited prominent activity towards cannabinoid receptors: pomiferin (V) (IC 50 of 2.110 and 1.318 M for CB1 and CB2, resp.), auriculasin (VI) (IC 50 of 8.923 M for CB1), warangalone (VII) (IC 50 of 1.670 and 4.438 M for CB1 and CB2, resp.), and osajin (VIII) (IC 50 of 3.859 and 7.646 M for CB1 and CB2, resp.). The isolated compounds were also tested for inhibition of human monoamine oxidase-A and monoamine oxidase-B enzymes activities, where all the tested compounds showed fewer inhibitory effects on MAO-A compared to MAO-B activities: auriculasin (VI) (IC 50 of 1.91 and 45.98 M for MAO-B and MAO-A, resp.).

Isolation and Biological Evaluation of Prenylated Flavonoids from Maclura pomifera

“…The Maclura pomifera total extract of the fruits showed significant activity towards cannabinoid receptors and possibly allosteric interactions with δ and μ opioid receptors [ 25 ]. Four new compounds ( I – IV ) along with eleven known compounds ( V – XV ) were isolated and identified from the extract.…”

“…The content is solely the responsibility of the authors and does not necessarily represent the official views of the National Institute of General Medical Sciences or the National Institutes of Health, USA. This work has been presented at GA 2017 Conference, Basel, Switzerland [ 25 ].…”

TRPV1-Dependent Antiproliferative Activity of Dioecious Maclura pomifera Extracts in Estrogen Receptor-Positive Breast Cancer Cell Lines Involves Multiple Apoptotic Pathways

“…M. pomifera (Moraceae), commonly known as Osage orange or hedge apple, is a dioecious (having separate male and female individuals) tree native to the south-central USA [12]. Several biological activities of M. pomifera have been reported, such as anti-inflammatory, antinociceptive, and antiproliferative [13][14][15][16][17]. Although M. pomifera has not been extensively studied for its anti-cancer properties, some research suggests that certain of its compounds, 2 of 21 such as pomiferin, a prenylated isoflavone, have potential as anti-cancer agents [16].…”