Pinobanksin was isolated from a peony seed shell using macroporous resin and C18 reversed bonded silica gel column (C18 column) with a recovery of (98.33±0.64)%.The maximum yield of MDKF from peony seed shell was (10.54±0.13)% with 70% ethanol (volume fraction).The adsorption and analytical rates of six macroporous resins (AB-8, S-8, DM301, HPD600, HPD100, and D101) were compared, and the adsorption and analytical rates of S-8 macroporous resins were the best, which were 83.47% and 84.46%, respectively.The optimal conditions for the separation of MDKF by S-8 macroporous resin were that the mass concentration of loading liquid was 1.6 mg/mL, the flow rate of loading liquid was 2.0 mL/min, the volume fraction of elution agent ethanol was 60%, the flow rate of eluent was 1.5 mL/min, and the eluent volume was 100 mL.The fractions separated by the C18 column were analyzed by LC-MS and the recovery was (98.33±0.64)%.Comparing antioxidant activities before and after separation, results showed that C18 purified substance> S-8 macroporous resin purified substance >MDKF crude extract.Molecular docking experiments showed that pinobanksin had a binding ability with super oxide dimutese, catalase from Micrococcus lysodeiktic, peroxidase, and glutathione peroxidase enzymes, and the binding ability of catalase was -9.1 kcal/mol. Results showed that pinobanksin had a good antioxidant capacity and could be used as an antioxidant supplement for food, medicine, or cosmetics.It has a very broad application prospect and provides theoretical support for further development and utilization of peony seed shells.
[1] 王高潮, 刘仲健. 中国牡丹: 培育与鉴赏及文化渊源[M]. 北京: 中国林业出版社, 2000.
WANG G C, LIU Z J. Chinese Peony: Cultivation and Appreciation and Cultural Origins[M]. Beijing: China Forestry Publishing House, 2000.
[2] 周逢旭, 闫小满. 油用牡丹的应用和研究现状及发展对策[J]. 山东农业工程学院学报, 2018, 35(6):3-4.
ZHOU F X, YAN X M. Application and research status and development countermeasures of oil peony[J]. The Journal of Shandong Agriculture and Engineering University, 2018, 35(6):3-4.
[3] 张海丽, 毕珂, 陈长坤, 等. 牡丹籽壳黑色素应用研究[J]. 菏泽学院学报, 2021, 43(5):89-93.
ZHANG H L, BI K, CHEN C K, et al. On the application of melanin in peony seed shell[J]. Journal of Heze University, 2021, 43(5):89-93.
[4] 吴永玲, 王静怡, 李俊伟, 等 响应面法优化牡丹籽壳黄酮提取及抑菌活性[J]. 陕西农业科学, 2021, 67(11): 57-62.
WU Y L, WANG J Y, LI J W, et al. Optimal extraction of flavonoids from peony seed husk and its antifungal activity by response surface methodology[J]. Shaanxi Journal of Agricultural Sciences, 2021, 67(11): 57-62.
[5] 刘丹丹, 郑旭煦, 殷钟意, 等. 响应面法优化超声提取牡丹籽壳低聚茋类化合物的工艺研究[J]. 中国油脂, 2017, 42(12):108-112.
LIU D D, ZHENG X X, YIN Z Y, et al. Optimization of ultrasound-assisted extraction of oligomeric stilbene compound from peony seed shell by response surface methodology[J]. China Oils and Fats, 2017, 42(12):108-112.
[6] 李婉仪, 吉文丽, 李蕊, 等. 响应面优化牡丹籽壳总黄酮超声波提取工艺及抗氧化活性研究[J]. 中国油脂, 2018, 43(4):114-118.
LI W Y, JI W L, LI R, et al. Optimization of ultrasound extraction of total flavonoids from peony seed shell by response surface methodology and its antioxidant activity[J]. China Oils and Fats, 2018, 43(4):114-118.
[7] BANG H J, AHN M R. Antiangiogenic effect of pinobanksin on human umbilical vein endothelial cells[J]. Journal of Functional Foods, 2021, 79:104408.
[8] JIA X C, XIE H H, JIANG Y M, et al. Flavonoids isolated from the fresh sweet fruit of Averrhoa carambola, commonly known as star fruit[J]. Phytochemistry, 2018, 153:156-162.
[9] TRAN T N T, TRUONG T M H, NGUYEN T D P, et al. Enrichment of soy isoflavone extracts through macroporous resin for characterization of toxicity and estrogenic activities[J]. Journal of Food Science and Technology, 2023, 60(3):1097-1106.
[10] YAO H L, LI H H. Extraction and purification process optimization and antioxidant activity in vitro of flavonoids in Amaranthus caudatus L[J]. Medicinal Plant, 2020, 11(4): 48-53.
[11] 让凤菊, 刘伟, 欧阳艳. 大孔树脂分离纯化伊犁野核桃叶总黄酮的工艺研究[J]. 伊犁师范学院学报(自然科学版), 2017, 11(4):62-67.
RANG F J, LIU W, OUYANG Y. Separation and purification of flavonoids from Yili hickory leaves by macroporous adsorption resin[J]. Journal of Yili Normal University (Natural Science Edition), 2017, 11(4):62-67.
[12] 李金祥, 于雪, 王梦阳. 硅胶颗粒担载的C18毛细管液相色谱整体柱的评价[J]. 鲁东大学学报(自然科学版), 2016, 32(1):61-65.
LI J X, YU X, WANG M Y. Silica-particle-supported C18 polymeric monolithic column forcapillary liquid chromatography[J]. Journal of Ludong University (Natural Science Edition), 2016, 32(1):61-65.
[13] JANJIC T J, VUCKOVIC G, CELAP M B. Application of the C18 column chromatography mobile phase polarity parameter PmN to thin layer chromatography[J]. Journal of the Serbian Chemical Society, 1997, 62(8): 683-686.
[14] 张岩, 曹国杰, 张燕, 等. 黄酮类化合物的提取以及检测方法的研究进展[J]. 食品研究与开发, 2008, 29(1):154-158.
ZHANG Y, CAO G J, ZHANG Y, et al. Research on the extraction and identification of flavonoids[J]. Food Research and Development, 2008, 29(1):154-158.
[15] ZHANG Y, WANG B Y, JIA Z, et al. Adsorption/desorption characteristics and enrichment of quercetin, luteolin and apigenin from Flos populi using macroporous resin[J]. Revista Brasileira De Farmacognosia, 2019, 29(1):69-76.
[16] LIU H A, WANG B C, DAI C Y, et al. Optimization of preparative separation and purification of total flavonoids from Radix puerariae by macroporous resin method[J]. Journal of Chinese Pharmaceutical Sciences, 2006, 15(2):121-126.
[17] 于智峰, 王敏, 张家峰. 大孔树脂精制苦荞总黄酮工艺条件的优化研究[J]. 农业工程学报, 2007, 23(4):253-257.
YU Z F, WANG M, ZHANG J F. Optimization of purifying technology of tartary buckwheat total flavonoids with macroporous resin[J]. Transactions of the Chinese Society of Agricultural Engineering, 2007, 23(4):253-257.
[18] BRAND-WILLIAMS W, CUVELIER M E, BERSET C. Use of a free radical method to evaluate antioxidant activity[J]. LWT-Food Science and Technology, 1995, 28(1):25-30.
[19] BANGAR S P, SANDHU K S, TRIF M, et al. The effect of mild and strong heat treatments on in vitro antioxidant properties of barley (Hordeum vulgare) cultivars[J]. Food Analytical Methods, 2022, 15(8):2193-2201.
[20] YANG M H, CHE T, LI Z X, et al. Identification, taste properties and molecular docking of novel umami peptides from Butyriboletus roseoflavus[J]. European Food Research and Technology, 2022, 248(11):2665-2677.
[21] 吴金义, 李兴杰, 陈雪松, 等. 大孔树脂纯化苦碟子总黄酮的工艺条件和参数[J]. 吉林大学学报(医学版), 2011, 37(5):792-796.
WU J Y, LI X J, CHEN X S, et al. Process conditions and parameters of purification of total flavonoid of China ixeris by macroporous resin[J]. Journal of Jilin University (Medicine Edition), 2011, 37(5):792-796.
[22] 钱慧碧, 辛秀兰, 兰蓉, 等. 大孔吸附树脂分离纯化越橘果渣总黄酮的研究[J]. 吉林农业大学学报, 2009, 31(5):611-615.
QIAN H B, XIN X L, LAN R, et al. Studies on purification of total flavonoids from the Marc of blueberry by macroporous resins[J]. Journal of Jilin Agricultural University, 2009, 31(5):611-615.
[23] 林燕如, 曹迁永. 大孔树脂纯化金毛狗脊叶黄酮的工艺研究[J]. 湖北农业科学, 2011, 50(3):583-586.
LIN Y R, CAO Q Y. Study on the purification of flavonoid from the leaves of Cibotium barometz(L)J.Sm.by macroporous resin[J]. Hubei Agricultural Sciences, 2011, 50(3):583-586.
