Phenolics from the Fruits of Maclura pomifera

Abstract

Two new compounds, maclurin A (1) and maclurin B (2), and six known ones, ononin (3), pterofuran (4), osajin (5), pomiferin (6), 3,4-dihydroxybenzoic acid (7), and 2,3,4-trihydroxybenzoic acid (8) were isolated from the fruit of Maclura pomifera. Compounds 3 and 4 were isolated from the genus for the first time. Structure elucidation was achieved by spectroscopic measurements and by comparison with literature data. Compounds 2-4 exhibited activities against the cancer cell lines A549 and Panc-28 with GI 50 values from 18.1 to 32.2, and 20.6 to 43.5 µM, respectively. Compounds 2 and 4 also showed cytotoxicity against HCT 116 with GI 50 values of 47.2 and 24.4 µM, respectively.

Antioxidant Activity of Osage Orange Extract in Soybean Oil and Fish Oil during Storage

“…Table 1 summarizes comparisons of the extraction yields and the contents of osajin and pomiferin, when reported. Among the solvents, 95% ethanol had the highest extraction yields ranging between 13.3% and 14.8% (Mahmoud, 1981; Su et al, 2017). However, Su et al (2017) reported low contents of osajin and pomiferin (0.09% and 0.03%, respectively) in the extract while Mahmoud (1981) reported high contents of osajin (10.0%) and pomiferin (5.0%) in the extract.…”

“…Among the solvents, 95% ethanol had the highest extraction yields ranging between 13.3% and 14.8% (Mahmoud, 1981; Su et al, 2017). However, Su et al (2017) reported low contents of osajin and pomiferin (0.09% and 0.03%, respectively) in the extract while Mahmoud (1981) reported high contents of osajin (10.0%) and pomiferin (5.0%) in the extract. In another study using ethanol extraction of wet fruit, the extract (yield: 0.43%) contained 6.3% osajin and 6.3% pomiferin (Orazbekov et al, 2018).…”

Fluorometry of natural latex from Maclura pomifera

“…However, a little caution is required. Osage oranges have yielded many unusual chemical compounds and it is possible that some of these are contributing to Osage orange fluorescence [10][11][12][13][14]. Testing the fluorescence of newly identified chemical compounds from the Osage orange might help to resolve this doubt.…”

Chemical composition and antimicrobial activity of Osage orange (Maclura pomifera) leaf extracts

“…[5] The EtOH, H 2 O 2 , CHCl 3 extracts of the fruit contain two isoflavones linear isomers of osajin and pomiferin-scandenone and auriculasin. [12] In research reported by Orazbekov et al [6] and Su et al [9] in ethanolic extracts was isolated a few new isoflavones and flavones. From the root bark and heartwood was detected xanthones (macluraxanthone, osajaxanthone, alvaxanthone, etc.)…”

“…[5,6] The compounds isolated from various parts of Osage orange (fruit, bark, leaves, seeds, and roots) belong to different classes, such as flavonoids, xanthones, triterpenes, and stilbenes. [7][8][9] These secondary metabolites were reported to possess a number of biological activities, such as insect repellant, [10] antimicrobial, [11] anti-inflammatory/antinociceptive, [12] antitumor, [13,14] cardioprotective, [15] and cholinesterase inhibitory activities. [16] A wide range of bioactivities of these compounds is attributed to the prenylation of the flavonoids, which increases their lipophilicity and membrane permeability.…”