Naringin (NR, 4′,5,7 trihydrocyflavanone-7-O-rhamnoglucoside) is a flavanone found in citrus fruit that is composed of a phenolic compound, naringenin, and a disaccharide, neohesperidose. Poly(NR) [p(NR)] particles in the size range of few micrometers to few hundred nanometers were prepared from highly purified NR and subsequently characterized using UV/visible spectroscopy, Fourier transform infrared spectroscopy, nuclear magnetic resonance spectroscopy, scanning electron microscopy, thermogravimetric analysis, and zeta potential measurements. The hydrolytic degradation of p(NR) particles at 37.5 °C was investigated at pHs 5.4, 7.4, and 9.0. The particles degraded most rapidly at pH 7.4, with >90% degradation after 5 h. The cytotoxicity was assessed by growing COS-1 fibroblasts for 5 days in the presence of increasing concentrations of NR or eluates from the p(NR) particles. Both NR and p(NR) particles were nontoxic for these mammalian fibroblasts; at the highest concentration tested (571 μg/mL), the percentages of surviving cells after 5 days in culture were 96.7 ± 0.93 and 91 ± 11% for NR and p(NR), respectively. The effect of p(NR) on red blood cell hemolysis was also negligible (<2%) at concentrations up to 100 μg/mL; unpolymerized NR showed slightly higher levels of hemolysis than the p(NR) particles, but values never exceeded 5% at 50 and 100 μg/mL. Both NR and p(NR) stimulated blood coagulation in a dose-dependent manner; the hemostatic effect was greater for p(NR), which, at 100 μg/mL, stimulated in vitro blood clotting by ∼50%. Neither NR nor eluates from p(NR) particles inhibited α-glucosidase activity; in fact, both provided a modest (10–30%) stimulation at concentrations from 0.67 to 1.67 mg/mL. p(NR) particles are easily synthesized, break down readily at physiological pH, and have excellent blood and biocompatibility. As such, they will be a useful carrier for drug delivery and as an oral antioxidant supplement.

中文翻译：

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具有抗氧化活性和低毒性的可生物降解聚柚皮苷颗粒的制备

柚皮苷（NR，4'，5,7 trihydrocyflavanvanone-7- O-鼠李糖苷）是一种在柑桔类水果中发现的黄烷酮，由酚类化合物柚皮苷和二糖新橙皮苷组成。由高度纯化的NR制备了几微米至几百纳米大小的聚（NR）[p（NR）]颗粒，然后使用UV /可见光谱，傅里叶变换红外光谱，核磁共振光谱，扫描电子显微镜对它们进行了表征，热重分析和Zeta电位测量。在pH值为5.4、7.4和9.0的条件下研究了p（NR）颗粒在37.5°C下的水解降解。颗粒在pH 7.4时降解最快，在5 h后降解> 90％。通过在浓度不断增加的NR或来自p（NR）颗粒的洗脱液中生长COS-1成纤维细胞5天来评估细胞毒性。NR和p（NR）颗粒均对这些哺乳动物成纤维细胞无毒。在最高测试浓度（571μg/ mL）下，培养5天后NR和p（NR）存活细胞的百分比分别为96.7±0.93和91±11％。当浓度高达100μg/ mL时，p（NR）对红细胞溶血的影响也可以忽略不计（<2％）；未聚合的NR的溶血水平略高于p（NR）颗粒，但在50和100μg/ mL时，溶血值从未超过5％。NR和p（NR）均以剂量依赖性方式刺激血液凝结。p（NR）的止血作用更大，其以100μg/ mL的浓度刺激体外血液凝结约50％。NR和来自p（NR）颗粒的洗脱液均不能抑制α-葡萄糖苷酶的活性。实际上，两者在0.67至1.67 mg / mL的浓度下均提供了适度（10-30％）的刺激。p（NR）颗粒易于合成，在生理pH值下容易分解，并且具有出色的血液和生物相容性。这样，它们将是用于药物递送和作为口服抗氧化剂补充剂的有用载体。