LDL-Antioxidant Pterocarpans from Roots of Glycine max (L.) Merr.

Abstract

The methanolic root extract of Glycine max (L.) Merr. was chromatographed, which yielded 10 flavonoids, including three isoflavones 1-3, five pterocarpans 4-8, one flavonol 9, and one anthocyanidin 10. All isolated compounds were examined for LDL-antioxidant activities using four different assay systems on the basis of Cu2+-mediated oxidation. Among them, seven compounds showed potent LDL-antioxidant activities in the thiobarbituric acid reactive substances (TBARS) assay, the lag time of conjugated diene formation, relative electrophoretic mobility (REM), and fragmentation of apoB-100 on copper-mediated LDL oxidation. Three pterocarpans 4, 6, and 7, never reported as LDL-antioxidant, showed potent activities with IC50 values of 19.8, 0.9, 45.0 microM, respectively, in comparison with probucol (IC50 = 5.6 microM) as positive control. Interestingly, coumestrol 6 (IC50 = 0.9 microM) showed 20 times more activity in the TBARS assay than genistein (IC50 = 30.1 microM) and daidzein (IC50 = 21.6 microM), representative antioxidants in soybean. Moreover, coumestrol 6 had an extended lag time of 190 min at 3.0 microM in measuring conjugated diene formation, while both genistein (120 min) and daidzein (93 min) lag times were extended to less than 120 min at the same concentration.

Beneficial Effects of Pterocarpan-High Soybean Leaf Extract on Metabolic Syndrome in Overweight and Obese Korean Subjects: Randomized Controlled Trial

“…A kaempferol glycoside (KG)-rich fraction from unripe soybean leaf attenuated blood glucose and hepatic lipid levels in KK-A y mice [19]. In particular, pterocarpans such as coumesterol, glyceofuran, glyceollin III suppressed the oxidation of low-density lipoprotein (LDL) [20], and have been reported to have cancer prevention and anti-inflammatory effects [21,22,23]. In addition, glyceollins (I–III), prenylated pterocarpan have known antiestrogenic effects in vivo [24,25].…”

Determination of Phytochemical Contents and Biological Activities from the Fruits of Elaeagnus multiflora

“…They possess various beneficial effects, including antitumor, anticancer, antioxidant, anti-inflammatory, anti-atherosclerotic, and anti-diabetic (3)(4)(5)(6). In particular, these components are of great interest in the food industry because of their nutritional values (7).…”

Effect of Soybean Coumestrol on Bradyrhizobium japonicum Nodulation Ability, Biofilm Formation, and Transcriptional Profile

“…For example, 20 l of the 100 mM stock solution was added into 200 ml culture to make a final concentration of 10 M. A corresponding volume of DMSO was also added to each control sample to ensure that the amounts of DMSO used did not affect bacterial growth. Coumestrol was obtained from soybean root exudates as described in our previous study (31), and DMSO, daidzein, and genistein were purchased from Sigma (St. Louis, MO).…”

“…Ten polyphenolic compounds (three isoflavones, five pterocarpans, one flavonol, one anthocyanidin) were isolated from soybean roots in our previous study (31). The antioxidant activity of the isolated compounds was evaluated by measuring their inhibitory activity in copper-induced low-density lipoprotein (LDL) oxidation.…”