ZI Yuxiang,LU Zhaoxin,Lü Fengxia,et al.The study of antioxidant activities of glycoglycerolipids in leaves of Perilla frutescens[J].Journal of Nanjing Agricultural University,2021,44(3):561-567.[doi:10.7685/jnau.202007033]





The study of antioxidant activities of glycoglycerolipids in leaves of Perilla frutescens
訾玉祥 陆兆新 吕风霞 别小妹 张充 赵海珍
南京农业大学食品科学技术学院, 江苏 南京 210095
ZI Yuxiang LU Zhaoxin Lü Fengxia BIE Xiaomei ZHANG Chong ZHAO Haizhen
College of Food Science and Technology, Nanjing Agricultural University, Nanjing 210095, China
Perilla frutescensglycoglycerolipidsantioxidant activitystructure-activity relationship
[目的] 本文旨在研究紫苏叶中3种不同分子结构甘油糖脂的抗氧化活性并初步探讨其活性构效关系。[方法] 通过化学评价法评价甘油糖脂的2,2’-联氮-双-3-乙基苯并噻唑啉-6-磺酸(ABTS)、1,1-二苯基-2-三硝基苯肼(DPPH)、羟自由基(·OH)及超氧阴离子(O2·-)清除能力并测定其还原力,采用细胞氧化损伤模型研究甘油糖脂对抗氧化酶活性的影响。[结果] 从紫苏叶中分离纯化获得了3种甘油糖脂单体,即MGDG(C18:3/C18:3)、DGDG(C18:3/C18:3)和DGDG(C18:3/C16:0)。MGDG(C18:3/C18:3)和DGDG(C18:3/C18:3)的抗氧化能力强于DGDG(C18:3/C16:0)。3种甘油糖脂均可抑制ABTS自由基、DPPH自由基、·OH、O2·-的产生及提高超氧化物歧化酶(SOD)、过氧化氢酶(CAT)、谷胱甘肽过氧化物酶(GSH-Px)的活性,且具有较强的还原力。[结论] 3种甘油糖脂均具有抗氧化能力,但脂肪酰基组成不同的甘油糖脂具有不同的抗氧化能力,其中,脂酰基及糖基数量对甘油糖脂类化合物的抗氧化活性影响较大。
[Objectives] This article aimed to study the antioxidant activities of three different molecular structures of glycoglycerolipids in leaves of Perilla frutescens and the structure-activity relationship was preliminarily discussed. [Methods] The scavenging abilities of 2,2’-azino-bis-3-ethylbenzthiazoline-6-sulfonic acid(ABTS),1,1-diphenyl-2-picrylhydrazyl(DPPH),hydroxyl radicals(·OH) and superoxide anion radicals(O2·-) were measured by chemical evaluation method,and the cell oxidative damage model was used to study the effects of glycoglycerolipids on the activities of antioxidant enzymes. [Results] Three glycoglycerolipids monomers were separated and purified from leaves of P. frutescens,including MGDG(C18:3/C18:3),DGDG(C18:3/C18:3) and DGDG(C18:3/C16:0). The antioxidant activities of MGDG(C18:3/C18:3) and DGDG(C18:3/C18:3) were higher than that of DGDG(C18:3/C16:0). All glycoglycerolipids presented strong reducing power,and they could not only inhibit the production of ABTS,DPPH,·OH and O2·-,but also significantly enhance the activities of superoxide dismutase(SOD),catalase(CAT) and glutathione peroxidase(GSH-Px). [Conclusions] Glycoglycerolipids with different fatty acyl composition presented different antioxidant activity,and the preliminary study of structure-activity relationship showed that the saturation degree of fatty acyl group and the number of sugar groups greatly affected the antioxidant activities of glycoglycerolipids.


[1] Ganesan K,Xu B J. A critical review on polyphenols and health benefits of black soybeans[J]. Nutrients,2017,9(5):E455.
[2] Xu M H,Liang R,Li Y,et al. Anti-fatigue effects of dietary nucleotides in mice[J]. Food & Nutrition Research,2017,61(1):1334485.
[3] Lassoued I,Mora L,Nasri R,et al. Characterization and comparative assessment of antioxidant and ACE inhibitory activities of thornback ray gelatin hydrolysates[J]. Journal of Functional Foods,2015,13:225-238.
[4] Galano A,León-Carmona J R,Alvarez-Idaboy J R. Influence of the environment on the protective effects of guaiacol derivatives against oxidative stress:mechanisms,kinetics,and relative antioxidant activity[J]. The Journal of Physical Chemistry B,2012,116(24):7129-7137.
[5] Buonocore G,Perrone S,Tataranno M L. Oxygen toxicity:chemistry and biology of reactive oxygen species[J]. Seminars in Fetal and Neonatal Medicine,2010,15(4):186-190.
[6] 谭美莲,严明芳,汪磊,等. 国内外紫苏研究进展概述[J]. 中国油料作物学报,2012,34(2):225-231. Tan M L,Yan M F,Wang L,et al. Research progress on Perilla frutescens[J]. Chinese Journal of Oil Crop Sciences,2012,34(2):225-231(in Chinese with English abstract).
[7] Arya E,Saha S,Saraf S A,et al. Effect of Perilla frutescens fixed oil on experimental esophagitis in albino Wistar rats[J]. BioMed Research International,2013,2013:1-6.
[8] Sugawara T,Miyazawa T. Separation and determination of glycolipids from edible plant sources by high-performance liquid chromatography and evaporative light-scattering detection[J]. Lipids,1999,34(11):1231-1237.
[9] Matsufuji M,Taguchi K,Inagaki M,et al. Glyceroglycolipids preventing tert-butylhydroperoxide-induced cell death from Microbacterium sp. and Corynebacterium aquaticum strains[J]. Journal of Bioscience and Bioengineering,2000,89(2):170-175.
[10] Matsufuji M,Nagamatsu Y,Yoshimoto A. Protective effects of bacterial glyceroglycolipid M874B against cell death caused by exposure to heat and hydrogen peroxide[J]. Journal of Bioscience and Bioengineering,2000,89(4):345-349.
[11] Nakata K. High resistance to oxygen radicals and heat is caused by a galactoglycerolipid in Microbacterium sp. M874[J]. Journal of Biochemistry,2000,127(5):731-737.
[12] Matsufuji M,Nagamatsu Y,Yoshimoto A. Effects of bacterial glyceroglycolipid M874B on growth and TPA-induced differentiation of HL60 cells[J]. Bioscience,Biotechnology,and Biochemistry,2000,64(6):1302-1304.
[13] Zi Y X,Yao M J,Lu Z X,et al. Glycoglycerolipids from the leaves of Perilla frutescens(L.) Britton(Labiatae) and their anti-inflammatory activities in lipopolysaccharide-stimulated RAW264.7 cells[J]. Phytochemistry,2021,184(10):112679.
[14] Hanashima S,Mizushina Y,Ohta K,et al. Structure-activity relationship of a novel group of mammalian DNA polymerase inhibitors,synthetic sulfoquinovosylacylglycerols[J]. Japanese Journal of Cancer Research,2000,91(10):1073-1083.
[15] Hanashima S,Mizushina Y,Yamazaki T,et al. Synthesis of sulfoquinovosylacylglycerols,inhibitors of eukaryotic DNA polymerase α and B[J]. Bioorganic & Medicinal Chemistry,2001,9(2):367-376.
[16] Loya S,Reshef V,Mizrachi E,et al. The inhibition of the reverse transcriptase of HIV-1 by the natural sulfoglycolipids from cyanobacteria:contribution of different moieties to their high potency[J]. Journal of Natural Products,1998,61(7):891-895.
[17] Nagatsu A,Watanabe M,Ikemoto K,et al. Synthesis and structure-anti-tumor-promoting activity relationship of monogalactosyl diacylglycerols[J]. Bioorganic & Medicinal Chemistry Letters,1994,4(13):1619-1622.
[18] Colombo D,Compostella F,Ronchetti F,et al. Inhibitory effects of monoacylated 2-O-β-galactosylglycerols on Epstein-Barr virus activation:the significant role of the hexanoyl chain[J]. Cancer Letters,1999,143(1):1-4.
[19] Colombo D,Compostella F,Ronchetti F,et al. Anti-tumor-promoting effects of glycoglycerolipid analogues on two-stage mouse skin carcinogenesis[J]. Cancer Letters,2000,161(2):201-205.
[20] Oliveira Neto J R,de Oliveira T S,Ghedini P C,et al. Antioxidant and vasodilatory activity of commercial beers[J]. Journal of Functional Foods,2017,34:130-138.
[21] Zheng L,Zhao Y J,Dong H Z,et al. Structure-activity relationship of antioxidant dipeptides:dominant role of Tyr,Trp,Cys and Met residues[J]. Journal of Functional Foods,2016,21:485-496.
[22] 李慧. 基于NF-κB信号通路调控的黄酮类化合物抗炎活性及抗炎/抗氧化联运机制[D]. 武汉:华中农业大学,2019:22-23. Li H. Anti-inflammation and anti-inflammatory/antioxidant linkage mechanism of flavonoids based on NF-κB signaling pathway[D]. Wuhan:Huazhong Agricultural University,2019:22-23(in Chinese with English abstract).
[23] Li X C. 2-phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl 3-oxide(PTIO·) radical scavenging:a new and simple antioxidant assay in vitro[J]. Journal of Agricultural and Food Chemistry,2017,65(30):6288-6297.
[24] 蒋志国. 甘油糖脂的分离制备及生物活性研究[D]. 杭州:浙江工商大学,2010:119-120. Jiang Z G. The separation,preparation and biological activity of glyceroglycolipids[D]. Hangzhou:Zhejiang Gongshang University,2010:119-120(in Chinese with English abstract).
[25] Pongmuangmul S,Phumiamorn S,Sanguansermsri P,et al. Anti-herpes simplex virus activities of monogalactosyl diglyceride and digalactosyl diglyceride from Clinacanthus nutans,a traditional Thai herbal medicine[J]. Asian Pacific Journal of Tropical Biomedicine,2016,6(3):192-197.
[26] Dai J Q,Zhu Q X,Zhao C Y,et al. Glyceroglycolipids from Serratula strangulata[J]. Phytochemistry,2001,58(8):1305-1309.


更新日期/Last Update: 1900-01-01