Research Progress on Extraction, Separation, Purification and Detection Technology of Limonins in Citrus

WANG Yemei; LI Jiangnan; YIN Huiping; ZHANG Yaohai; CHEN Aihua; SU Xuesu; JIAO Bining

doi:10.13386/j.issn1002-0306.2022070069

Volume 44 Issue 12

Jun. 2023

Turn off MathJax

Article Contents

Abstract

References

Science and Technology of Food Industry > 2023 > 44(12): 470-479. > DOI: 10.13386/j.issn1002-0306.2022070069

WANG Yemei, LI Jiangnan, YIN Huiping, et al. Research Progress on Extraction, Separation, Purification and Detection Technology of Limonins in Citrus[J]. Science and Technology of Food Industry, 2023, 44(12): 470−479. (in Chinese with English abstract). doi: 10.13386/j.issn1002-0306.2022070069.

Citation:

PDF (1279 KB)

Research Progress on Extraction, Separation, Purification and Detection Technology of Limonins in Citrus

1.
Citrus Research Institute of Southwest University, Citrus Product Quality and Safety Risk Assessment Laboratory of Ministry of Agriculture and Rural Affairs (Chongqing), Citrus and Seedling Quality Supervision, Inspection and Testing Center of Ministry of Agriculture and Rural Affairs, Key Laboratory of Quality and Safety Control of Citrus Fruits in Ministry of Agriculture and Rural Affairs, Chongqing 400712, China
2.
College of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, China

More Information

Received Date: July 07, 2022
Available Online: April 19, 2023

Graphical Abstract

Abstract

Abstract

Citrus is the largest fruit in the world, and a large number of citrus processing by-products are produced every year. These by-products are rich in limonoids, which have many physiological functions such as anti-tumor, anti-inflammatory and anti-virus, and have been used in food, medicine and agriculture. It is of great theoretical and practical value to develop efficient extraction, separation and purification technology of limonoids, and to develop rapid analysis and detection methods of limonoids. In this article, the structural characteristics and content of limonoids in citrus are introduced, and the extraction, separation, purification and detection techniques of limonoids are emphatically summarized. It is found that emerging technologies such as ultrasonic-assisted and supercritical fluid extraction has better extraction efficiency, and the combination of macroporous resin adsorption, high-speed countercurrent chromatography and preparative high-performance liquid chromatography has better separation effect. In terms of detection technology, liquid chromatography is the most widely used analytical method for limonoids in citrus, which can accurately detect the types and contents of limonoids in citrus. However, efficient, green and rapid pretreatment technology and convenient and high-throughput detection technology need to be developed. This paper would provide a reference for the in-depth research and comprehensive development and utilization of limonoids in citrus, and provide a basis for promoting the utilization of citrus by-product resources.
- citrus,
- limonoids,
- extraction,
- separation and purification,
- detection

FullText(HTML)

References (70)

References

[1]	NEELIMA M, KAVITA S, MUKTY S, et al. Bio-sorbents, industrially important chemicals and novel materials from citrus processing waste as a sustainable and renewable bioresource: A review[J]. Journal of Advanced Research,2020,23:61−82. doi: 10.1016/j.jare.2020.01.007
[2]	MONTOYA C, GONZÁLEZ L, PULIDO S, et al. Identification and quantification of limonoid aglycones content of citrus seeds[J]. Revista Brasileira de Farmacognosia,2019,29(6):710−714. doi: 10.1016/j.bjp.2019.07.006
[3]	MANNERS G D. Citrus limonoids: Analysis, bioactivity, and biomedical prospects[J]. Journal of Agricultural and Food Chemistry,2007,55(21):8285−8294. doi: 10.1021/jf071797h
[4]	SHI Y, ZHANG Y, LI H, et al. Limonoids from citrus: Chemistry, anti-tumor potential, and other bioactivities[J]. Journal of Functional Foods,2020,75:104213. doi: 10.1016/j.jff.2020.104213
[5]	GUALDANI R, CAVALLUZZI M, LENTINI G, et al. The chemistry and pharmacology of citrus limonoids[J]. Molecules,2016,21(11):1530. doi: 10.3390/molecules21111530
[6]	DONALD E C, OPENDER K, MURRAY B I, et al. Biological activity of limonoids from the rutales[J]. Phytochemistry,1992,31(2):377−394. doi: 10.1016/0031-9422(92)90003-9
[7]	张群琳, 何雅静, 李甜, 等. 柠檬苦素类化合物抗病原体作用及机制研究进展[J]. 天然产物研究与开发,2020,32(6):1078−1085. [ZHANG Qunlin, HE Yajing, LI Tian, et al. Research progress of anti-pathogen effect and mechanism of limonin compounds[J]. Research and Development of Natural Products,2020,32(6):1078−1085. ZHANG Qunlin, HE Yajing, LI Tian, et al. Research progress of anti-pathogen effect and mechanism of limonin compounds[J]. Research and Development of Natural Products, 2020, 32(6): 1078-1085.
[8]	ROSA T, MONICA ROSA L, FRANCESCO M. An overview on chemical aspects and potential health benefits of limonoids and their derivatives[J]. Critical Reviews in Food Science and Nutrition,2013,54(2):225−250.
[9]	LU X, ZHAO C, SHI H, et al. Nutrients and bioactives in citrus fruits: Different citrus varieties, fruit parts, and growth stages[J]. Critical Reviews in Food Science and Nutrition,2021,63(14):2018−2041.
[10]	RUSSO M, ARIGÒ A, CALABRÒ M L, et al. Bergamot (Citrus bergamia Risso) as a source of nutraceuticals: Limonoids and flavonoids[J]. Journal of Functional Foods,2016,20:10−19. doi: 10.1016/j.jff.2015.10.005
[11]	HUANG S, LIU X, XIONG B, et al. Variation in limonin and nomilin content in citrus fruits of eight varieties determined by modified HPLC[J]. Food Science and Biotechnology,2019,28(3):641−647. doi: 10.1007/s10068-018-0509-8
[12]	HUANG S, DONG T, XIONG B, et al. Variation in the content and composition of limonoids in fruits of four pomelo varieties during fruit development: The natural debittering process in pomelo fruits[J]. Journal of Food Composition and Analysis,2021,100:103928. doi: 10.1016/j.jfca.2021.103928
[13]	DREYER D L. Citrus bitter principles-II: Application of NMR to structural and stereochemical problems[J]. Tetrahedron,1965,21(1):75. doi: 10.1016/S0040-4020(01)82204-3
[14]	ISHII T, OHTA H, NOGATA Y, et al. Limonoids in seeds of Iyo tangor (Citrus iyo Hort. ex Tanaka)[J]. Food Science and Technology Research,2003,9(2):162−164. doi: 10.3136/fstr.9.162
[15]	KIM J, JAYAPRAKASHA G K, PATIL B S. Obacunone exhibits anti-proliferative and anti-aromatase activity in vitro by inhibiting the p38 MAPK signaling pathway in MCF-7 human breast adenocarcinoma cells.[J]. Biochimie,2014,105:36−44. doi: 10.1016/j.biochi.2014.06.002
[16]	OZAKI Y, FONG C H, HERMAN Z, et al. Limonoid glucosides in citrus seeds[J]. Agricultural and Biological Chemistry,1991,55(1):137−141.
[17]	BENNETT R D, HASEGAWA S, HERMAN Z. Glucosides of acidic limonoids in citrus[J]. Phytochemistry,1989,28(10):2777−2781. doi: 10.1016/S0031-9422(00)98087-7
[18]	HAMDAN D, EL-READI M Z, TAHRANI A, et al. Secondary metabolites of ponderosa lemon (Citrus pyriformis) and their antioxidant, anti-Inflammatory, and cytotoxic activities[J]. Zeitschrift Fur Naturforschung Section C-A Journal of Biosciences,2011,66(7−8):385−393. doi: 10.1515/znc-2011-7-810
[19]	MAKITA T, OHTA K, NAKABAYASHI T. New limonoid from the seeds of citrus-natsudaidai[J]. Agricultural and Biological Chemistry,1980,44(3):693−694.
[20]	CHAN Y Y, LI C H, SHEN Y C, et al. Anti-inflammatory principles from the stem and root barks of citrus medica[J]. Chemical& Pharmaceutical Bulletin,2010,58(1):61−65.
[21]	BENNETT R D, HASEGAWA S. 7α-Oxygenated limonoids from the rutaceae[J]. Phytochemistry, 1982: 2235-2349.
[22]	HASEGAWA S, BENNETT R D, HERMAN Z, et al. Limonoid glucosides in citrus[J]. Phytochemistry, 1989: 1717-1720.
[23]	CHAVES J O, de SOUZA M C, DA SILVA L C, et al. Extraction of flavonoids from natural sources using modern techniques[J]. Frontiers in Chemistry, 2020, 8:507887.
[24]	尤文挺, 江天, 王洒, 等. 高橙皮中柠檬苦素超声提取工艺的优化[J]. 中成药,2020,42(5):1301−1303. [YOU W T, JIANG T, WANG S, et al. Optimization of ultrasonic extraction technology of limonin from high orange peel[J]. Chinese Patent Medicine,2020,42(5):1301−1303. YOU W T, JIANG T, WANG S, et al. Optimization of ultrasonic extraction technology of limonin from high orange peel [J]. Chinese Patent Medicine, 2020, 42(5): 1301-1303.
[25]	HONG Y, CHAO W, SHITING D, et al. Optimization of ultrasonic-assisted extraction and UPLC-TOF/MS analysis of limonoids from lemon seed[J]. LWT-Food Science and Technology,2017,84:135−142. doi: 10.1016/j.lwt.2017.05.059
[26]	YU J, DEEPAK V D, ROMEO T T, et al. Supercritical fluid extraction of limonoid glucosides from grapefruit molasses[J]. Journal of Agricultural and Food Chemistry,2006,54(16):6041−6045. doi: 10.1021/jf060382d
[27]	孟鹏. 金柑柠檬苦素类化合物的提取纯化、结构鉴定及生物活性研究[D]. 福州: 福建农林大学, 2013. MENG Peng. Extraction, purification, structure identification and biological activity of limonoids from kumquat[D]. Fuzhou: Fujian Agriculture and Forestry University, 2013.
[28]	CASTILLO-HERRERA G A, FARÍAS-ÁLVAREZ L J, GARCÍA-FAJARDO J A, et al. Bioactive extracts of Citrus aurantifolia swingle seeds obtained by supercritical CO₂ and organic solvents comparing its cytotoxic activity against L5178Y leukemia lymphoblasts[J]. The Journal of Supercritical Fluids,2015,101:81−86. doi: 10.1016/j.supflu.2015.02.026
[29]	汪建红, 廖立敏, 匡玉兰. 柠檬籽中柠檬苦素的双水相提取方法研究及工艺改进[J]. 食品工业,2016,37(11):111−113. [WANG Jianhong, LIAO Limin, KUANG Yulan. Study on aqueous two-phase extraction method of limonin from lemon seeds and process improvement[J]. Food Industry,2016,37(11):111−113. WANG Jianhong, LIAO Limin, KUANG Yulan. Study on aqueous two-phase extraction method of limonin from lemon seeds and process improvement [J]. Food Industry, 2016, 37(11): 111-113.
[30]	汪开拓, 蒋永波, 王富敏, 等. 柠檬籽粒中柠檬苦素离子液体双水相提取体系的优化与抗氧化活性分析[J]. 核农学报,2020,34(11):2507−2518. [WANG Kaituo, JIANG Yongbo, WANG Fumin, et al. Optimization of aqueous two-phase extraction system of limonin in lemon seeds and analysis of antioxidant activity[J]. Journal of Nuclear Agriculture,2020,34(11):2507−2518. WANG Kaituo, JIANG Yongbo, WANG Fumin, et al. Optimization of aqueous two-phase extraction system of limonin in lemon seeds and analysis of antioxidant activity[J]. Journal of Nuclear Agriculture, 2020, 34(11): 2507-2518.
[31]	NI H, ZHANG S F, GAO Q F, et al. Development and evaluation of simultaneous quantification of naringin, prunin, naringenin, and limonin in citrus juice[J]. Food Science and Biotechnology,2015,24(4):1239−1247. doi: 10.1007/s10068-015-0159-z
[32]	LIU S, ZHANG J, ZHOU L, et al. Quantification of limonin in human urine using solid-phase extraction by LC-MS/MS[J]. Journal of Chromatography B,2012,907:163−167. doi: 10.1016/j.jchromb.2012.08.038
[33]	ZHANG J W, TAN L, ZHANG Y Z, et al. Debittering of lemon juice using surface molecularly imprinted polymers and the utilization of limonin[J]. Journal of Chromatography B,2018,1104:205−211.
[34]	钟世欢, 陈青俊, 王京, 等. QuEChERS-HPLC测定柚类果实中柠檬苦素类化合物[J]. 食品与发酵工业,2022,48(4):261−265. [ZHONG Shihuan, CHEN Qingjun, JING Wang, et al. Determination of limonoids in pomelo fruits by QuEChERS-HPLC[J]. Food and Fermentation Industry,2022,48(4):261−265. ZHONG Shihuan, CHEN Qingjun, JING Wang, et al. Determination of limonoids in pomelo fruits by QuEChERS-HPLC [J]. Food and Fermentation Industry, 2022, 48(4): 261-265.
[35]	郁林娜, 程盛勇, 付洋, 等. 响应面法优化橘核中3种柠檬苦素类成分的超声辅助提取工艺[J]. 食品研究与开发,2019,40(5):133−137. [YU Linna, CHENG Shengyong, FU Yang, et al. Response surface methodology (RSM) was used to optimize the ultrasonic-assisted extraction process of three limonoids from orange kernels[J]. Food Research and Development,2019,40(5):133−137. YU Linna, CHENG Shengyong, FU Yang, et al. Response surface methodology (RSM) was used to optimize the ultrasonic-assisted extraction process of three limonoids from orange kernels[J]. Food Research and Development, 2019, 40(5): 133-137.
[36]	李珍柱, 苏学素, 焦必宁, 等. 柑橘中类黄酮的前处理及检测技术研究进展[J]. 食品工业科技,2018,39(4):329−336. [LI Zhenzhu, SU Xuesu, JIAO Bining, et al. Research progress of pretreatment and detection technology of flavonoids in citrus[J]. Food Industry Science and Technology,2018,39(4):329−336. LI Zhenzhu, SU Xuesu, JIAO Bining, et al. Research progress of pretreatment and detection technology of flavonoids in citrus[J]. Food Industry Science and Technology, 2018, 39(4): 329-336.
[37]	李俊超, 秦学磊, 吴圣江, 等. QuEChERS前处理方法在食品检测中的应用进展[J]. 食品研究与开发,2021,42(24):206−212. [LI Junchao, QIN Xuelei, WU Shengjiang, et al. Application progress of QuEChERS pretreatment method in food detection[J]. Food Research and Development,2021,42(24):206−212. LI Junchao, QIN Xuelei, WU Shengjiang, et al. Application progress of QuEChERS pretreatment method in food detection[J]. Food Research and Development, 2021, 42(24): 206-212.
[38]	邹连生. 柑桔类柠檬苦素的提取、纯化和体外抗肿瘤的研究[D]. 重庆: 西南农业大学, 2001. ZOU Liansheng. Study on extraction, purification and anti-tumor in vitro of citrus limonin[D]. Chongqing: Southwest Agricultural University, 2001.
[39]	庞立, 邓子牛, 刘吉凯, 等. 柑橘柠檬苦素大孔树脂分离纯化方法[J]. 食品科学,2015,36(14):24−28. [PANG Li, DENG Ziniu, LIU Jikai, et al. Separation and purification method of citrus limonin by macroporous resin[J]. Food Science,2015,36(14):24−28. PANG Li, DENG Ziniu, LIU Jikai, et al. Separation and purification method of citrus limonin by macroporous resin [J]. Food Science, 2015, 36(14): 24-28.
[40]	DANDEKAR D V, JAYAPRAKASHA G K, PATIL B S. Simultaneous extraction of bioactive limonoid aglycones and glucoside from Citrus aurantium L. using hydrotropy[J]. Z Naturforsch C J Biosci,2008,63(3−4):176−180. doi: 10.1515/znc-2008-3-403
[41]	XIANG Y, CAO J, LUO F, et al. Simultaneous purification of limonin, nomilin and isoobacunoic acid from pomelo fruit (Citrus grandis) segment membrane[J]. Journal of Food Science,2014,79(10):C1956−C1963. doi: 10.1111/1750-3841.12581
[42]	ZHANG P, ZHU K, ZHANG J, et al. Purification of flavonoids from mulberry leaves via high-speed counter-current chromatography[J]. Processes,2019,7(2):91. doi: 10.3390/pr7020091
[43]	GAO D, QUAN C, ZHANG W, et al. Purification of folic acid candidate reference material by preparative high-performance liquid chromatography[J]. Journal of Liquid Chromatography & Related Technologies,2017,40(8):419−427.
[44]	NANA O, MOMENI J, BOYOM F F, et al. Microwave-assisted extraction as an advanced technique for optimisation of limonoid yields and antioxidant potential from Trichilia roka (Meliaceae)[J]. Current Research in Green and Sustainable Chemistry,2021,4:100147. doi: 10.1016/j.crgsc.2021.100147
[45]	ABBASI S, ZANDI P, MIRBAGHERI E. Quantitation of limonin in Iranian orange juice concentrates using high-performance liquid chromatography and spectrophotometric methods[J]. European Food Research and Technology,2005,221(1−2):202−207. doi: 10.1007/s00217-005-1136-1
[46]	FISHER J F. Fluorometric determination of limonin in grapefruit and orange juice[J]. Journal of Agricultural and Food Chemistry,1973,21(6):1109−1110. doi: 10.1021/jf60190a020
[47]	LAN Z, ZHANG Y, CHEN X, et al. Efficient detection of limonoid from citrus seeds by handheld NIR: Compared with benchtop NIR[J]. Food Analytical Methods,2022,15(7):1909−1921. doi: 10.1007/s12161-022-02245-y
[48]	TONTSA A T, MKOUNGA P, NJAYOU F N, et al. Rubescins A, B and C: New havanensin type limonoids from root bark of Trichilia rubescens (Meliaceae)[J]. Chemical & Pharmaceutical Bulletin,2013,61(11):1178−1183.
[49]	VIKRAM A, JAYAPRAKASHA G K, PATIL B S. Simultaneous determination of citrus limonoid aglycones and glucosides by high performance liquid chromatography[J]. Analytica Chimica Acta,2007,590(2):180−186. doi: 10.1016/j.aca.2007.03.029
[50]	BREKSA A, KING D, VILCHES A. Determination of citrus limonoid glucosides by high performance liquid chromatography coupled to post-column reaction with ehrlich’s reagent[J]. Beverages,2015,1(2):70−81. doi: 10.3390/beverages1020070
[51]	WANG F, YU X, LIU X, et al. Temporal and spatial variations on accumulation of nomilin and limonin in the pummelos[J]. Plant Physiology and Biochemistry,2016,106:23−29. doi: 10.1016/j.plaphy.2016.04.039
[52]	孟鹏, 郑宝东. 超高效液相色谱法快速并同时检测金柑中柠檬苦素和诺米林[J]. 中国食品学报,2013,13(2):177−181. [MENG Peng, ZHENG Baodong. Rapid and simultaneous determination of limonin and nomilin in kumquat by ultra-high performance liquid chromatography[J]. China Journal of Food Science,2013,13(2):177−181. MENG Peng, ZHENG Baodong. Rapid and simultaneous determination of limonin and nomilin in kumquat by ultra-high performance liquid chromatography [J]. China Journal of Food Science, 2013, 13(2): 177-181.
[53]	MANNERS G D, BREKSA A P, SCHOCH T K, et al. Analysis of bitter limonoids in citrus juices by atmospheric pressure chemical ionization and electrospray ionization liquid chromatography-mass spectrometry[J]. Journal of Agricultural and Food Chemistry,2003,51(13):3709−3714. doi: 10.1021/jf021124t
[54]	PURI R, MALIK M, GHOSH M. An amperometric biosensor developed for detection of limonin levels in kinnow mandarin juices[J]. Annals of Microbiology,2012,62(3):1301−1309. doi: 10.1007/s13213-011-0376-5
[55]	ZOCCALI M, ARIGÒ A, RUSSO M, et al. Characterization of limonoids in citrus essential oils by means of supercritical fluid chromatography tandem mass spectrometry[J]. Food Analytical Methods,2018,11(11):3257−3266. doi: 10.1007/s12161-018-1303-1
[56]	邵金良, 刘兴勇, 王丽, 等. 高效液相色谱法同时测定柠檬中柠檬苦素和诺米林含量[J]. 食品安全质量检测学报,2018,9(13):3309−3314. [SHAO Jinliang, LIU Xingyong, WANG Li, et al. Simultaneous determination of limonin and nomilin in lemon by high performance liquid chromatography[J]. Journal of Food Safety and Quality Inspection,2018,9(13):3309−3314. SHAO Jinliang, LIU Xingyong, WANG Li, et al. Simultaneous determination of limonin and nomilin in lemon by high performance liquid chromatography [J]. Journal of Food Safety and Quality Inspection, 2018, 9(13): 3309-3314.
[57]	CHEN J, GAO Y, WU W, et al. Determination of bitter components in citrus juice by high performance liquid chromatography[J]. Se Pu Chinese Journal of Chromatography,2006,24(2):157−160.
[58]	LIU S, CHEN P, ZHANG N, et al. Comprehensive characterization of the in vitro and in vivo metabolites of limonin in human samples using LC-Q-TOF/MS[J]. Journal of Chromatography B,2017,1068:226−232.
[59]	BRECHT D, UTESCHIL F, SCHMITZ O J. Development of a fast-switching dual (ESI/APCI) ionization source for liquid chromatography/mass spectrometry[J]. Rapid Communications in Mass Spectrometry,2020,34(17).
[60]	TIAN Q, SCHWARTZ S J. Mass spectrometry and tandem mass spectrometry of citrus limonoids[J]. Analytical Chemistry (Washington),2003,75(20):5451−5460. doi: 10.1021/ac030115w
[61]	ANDREW P B, MARLENE B H, MICHELLE L Y. Liquid chromatography-electrospray ionisation mass spectrometry method for the rapid identification of citrus limonoid glucosides in citrus juices and extracts[J]. Food Chemistry,2009,117(4):739−744. doi: 10.1016/j.foodchem.2009.04.050
[62]	ERICA Z, OLLE I. Active materials for organic electrochemical transistors[J]. Advanced Materials,2018,30(44):1800941. doi: 10.1002/adma.201800941
[63]	SARAF N, BARKAM S, PEPPLER M, et al. Microsensor for limonin detection: An indicator of citrus greening disease[J]. Sensors and Actuators B:Chemical,2019,283:724−730. doi: 10.1016/j.snb.2018.12.067
[64]	DAS S, SAHU P P. A novel electrochemical interdigitated electrodes sensor for limonin quantification and reduction in Citrus limetta juice[J]. Food Chemistry,2022,381:132248. doi: 10.1016/j.foodchem.2022.132248
[65]	BRADDOCK R J, BRYAN C R. Extraction parameters and capillary electrophoresis analysis of limonin glucoside and phlorin in citrus byproducts[J]. Journal of Agricultural and Food Chemistry,2001,49(12):5982−5988. doi: 10.1021/jf010737n
[66]	BREKSA A P, MANNERS G D. Determination of limonin D-Ring lactone hydrolase activity by solid phase extraction with indirect fluorescence detection[J]. Journal of Agricultural and Food Chemistry,2004,52(12):3772−3775. doi: 10.1021/jf049928r
[67]	PARK S, NHIEM N X, SUBEDI L, et al. Isolation of bioactive limonoids from the fruits of Melia azedarach[J]. Journal of Asian Natural Products Research,2020,22(9):830−838. doi: 10.1080/10286020.2019.1666826
[68]	QIN S, LÜ C H, WANG Q S, et al. Extraction, identification, and antioxidant property evaluation of limonin from pummelo seeds[J]. Animal Nutrition (Zhongguo xu mu shou yi xue hui),2018,4(3):281−287.
[69]	PANAWAN S, VACHIRA C. Microwave-assisted improved extraction and purification of anticancer nimbolide from Azadirachta indica (Neem) leaves[J]. Molecules,2020,25(12):2913. doi: 10.3390/molecules25122913
[70]	SHI X, WU Y, LÜ T, et al. A chemometric-assisted LC-MS/MS method for the simultaneous determination of 17 limonoids from different parts of Xylocarpus granatum fruit[J]. Analytical and Bioanalytical Chemistry,2017,409(19):4669−4679. doi: 10.1007/s00216-017-0413-8

Supplements (0)

Cited By

Cited by

Periodical cited type(5)

1.	张惠琪，陈晓，金雪玲，黎晶晶，袁娟丽，高金燕，陈红兵，武涌. 发芽粟米活性肽减轻铜诱导秀丽隐杆线虫氧化损伤及其分子机制. 食品工业科技. 2025(01): 384-393 . 本站查看
2.	陈思羽，李晓，杜文珍，耿月华，刘刚，谢宁. 丝状真菌Podospora anserina中光敏色素基因的鉴定及功能分析. 微生物学报. 2024(02): 443-460 .
3.	刘鸿基，曾琛悦，曾霞，黄钰婷，谢炜城，罗丹琪，马鸿雁，汤丹. 甜茶木姜叶柯及其主要活性成分三叶苷药理作用研究进展. 广东药科大学学报. 2024(03): 129-135 .
4.	赖玉萍，陈颖仪，魏婉娉，安苗青，邹泽斌，杜冰，黎攀. 美藤果叶醇提物对延缓秀丽隐杆线虫衰老的影响. 食品工业科技. 2023(21): 402-411 . 本站查看
5.	张余威，赵文俊，李伟杰，杜冰，黎攀. 灭活芽孢杆菌DU-106对秀丽隐杆线虫的抗衰老作用. 食品科学. 2023(23): 134-141 .