LI Chuantian, GAO Peng, ZHU Jinfang, et al. Preparation of Lycopene Micelles with Different Block Ratios of mPEG-PLA as Carriers and the Solubilization and Controlled Release of Lycopene Isomers[J]. Science and Technology of Food Industry, 2023, 44(17): 18−26. (in Chinese with English abstract). doi: 10.13386/j.issn1002-0306.2022090018.
Citation: LI Chuantian, GAO Peng, ZHU Jinfang, et al. Preparation of Lycopene Micelles with Different Block Ratios of mPEG-PLA as Carriers and the Solubilization and Controlled Release of Lycopene Isomers[J]. Science and Technology of Food Industry, 2023, 44(17): 18−26. (in Chinese with English abstract). doi: 10.13386/j.issn1002-0306.2022090018.

Preparation of Lycopene Micelles with Different Block Ratios of mPEG-PLA as Carriers and the Solubilization and Controlled Release of Lycopene Isomers

More Information
  • Received Date: September 04, 2022
  • Available Online: July 04, 2023
  • By applying three different block ratios of polyethylene glycol monomethyl ether-polylactic acid (mPEG-PLA) copolymers as carriers, the lycopene micelles (M-LYC) were created by emulsification-solvent evaporation method. The content of each isomer of lycopene (LYC) in M-LYC was determined by high performance liquid chromatography (HPLC), and the encapsulation rate (EE) and drug loading capacity (DL) of micelles were calculated. To screen the mPEG-PLA copolymers for the ideal block ratio of encapsulating LYC, the particle size and zeta potential were evaluated using a dynamic light scattering nano-particle size analyzer, and the in vitro release of M-LYC in different release media was assessed using dialysis method. The results showed that the EE of Total LYC in mPEG45-PLA36-M-LYC, mPEG114-PLA90-M-LYC, and mPEG114-PLA180-M-LYC were 65.04%, 71.73% and 23.62%, respectively, with DL of 3.96%, 4.43% and 1.39%, particle sizes of 164.6, 190.1 and 210.3 nm, and zeta potential of −15.38, −9.43 and −10.96 mV, respectively. The EE of each isomer and Total-LYC in mPEG114-PLA90-M-LYC was the highest, followed by mPEG45-PLA36-M-LYC. The order of encapsulation rate of each cis-isomer in the three micelles was 5Z>9Z>13Z. The mPEG45-PLA36-M-LYC had the smallest particle size and the largest absolute value of zeta potential among the three micelles, indicating that it had the best stability. The release of LYC in LYC feedstock was not detected in different release media. Among the three micelles, the mPEG45-PLA36-M-LYC had the highest cumulative release percentage of Total LYC within 72 h in different release media, with 42.35% (pH6.8) and 60.82% (pH7.4), respectively. The cumulative release percentages of all three micelles in the pH7.4 release medium were higher than those in the pH6.8 condition, and the cumulative release percentages of all-trans lycopene (All-E) were slightly higher than those of Total LYC within 72 h. 5Z had the higher cumulative release percentages than All-E after 72 h, with no initial release. In conclusion, the mPEG45-PLA36 has a better effect on the encapsulation of LYC than other copolymers. The M-LYC prepared with its carrier has the smallest particle size, the largest absolute zeta potential, the best stability and the highest cumulative release percentage of 72 h Total LYC among the three micelles, which is a promising polymeric carrier material for encapsulating LYC and is expected to improve the in vivo bioavailability of fat-soluble nutrients.
  • [1]
    龙海涛, 薛利新, 张志霞, 等. 固定化混合酶提取番茄红素的工艺研究[J]. 食品工业科技,2014,35(4):189−193. [LONG H T, XUE L X, ZHANG Z X, et al. Extraction of lycopene from tomato paste with immobilized pectinase and cellulase[J]. Science and Technology of Food Industry,2014,35(4):189−193. doi: 10.13386/j.issn1002-0306.2014.04.064

    LONG H T, XUE L X, ZHANG Z X, et al. Extraction of lycopene from tomato paste with immobilized pectinase and cellulase [J]. Science and Technology of Food Industry, 2014, 35(4): 189-193. doi: 10.13386/j.issn1002-0306.2014.04.064
    [2]
    SHI J, LE MAGUER M, BRYAN M. Lycopene from tomatoes[J]. Functional Foods: Biochemical and Processing Aspects,2002(2):135−167.
    [3]
    ONO M, TAKESHIMA M, NAKANO S. Mechanism of the anticancer effect of lycopene (Tetraterpenoids)[J]. The Enzymes,2015,37:139−166.
    [4]
    UGWOR E I, UGBAJA R N, JAMES A S, et al. Inhibition of fat accumulation, lipid dysmetabolism, cardiac inflammation, and improved NO signalling mediate the protective effects of lycopene against cardio-metabolic disorder in obese female rats[J]. Nutrition Research,2022,104:140−153. doi: 10.1016/j.nutres.2022.05.009
    [5]
    SONG X Y, LUO Y H, MA L J, et al. Recent trends and advances in the epidemiology, synergism, and delivery system of lycopene as an anti-cancer agent[J]. Seminars in Cancer Biology,2021,73:331−346. doi: 10.1016/j.semcancer.2021.03.028
    [6]
    LUO C, WU X G. Lycopene enhances antioxidant enzyme activities and immunity function in N-Methyl-N′-nitro-N-nitrosoguanidine-induced gastric cancer rats[J]. International Journal of Molecular Sciences,2011,12(5):3340−3351. doi: 10.3390/ijms12053340
    [7]
    SAINI R K, RENGASAMY K R R, MAHOMOODALLY F M, et al. Protective effects of lycopene in cancer, cardiovascular, and neurodegenerative diseases: An update on epidemiological and mechanistic perspectives[J]. Pharmacological Research,2020,155:104730. doi: 10.1016/j.phrs.2020.104730
    [8]
    NOBRE B P, PALAVRA A F, PESSOA F, et al. Supercritical CO2 extraction of trans-lycopene from Portuguese tomato industrial waste[J]. Food Chemistry,2009,116(3):680−685. doi: 10.1016/j.foodchem.2009.03.011
    [9]
    HONDA M, KAGEYAMA H, HIBINO T, et al. Efficient and environmentally friendly method for carotenoid extraction from Paracoccus carotinifaciens utilizing naturally occurring Z-isomerization-accelerating catalysts[J]. Process Biochemistry,2020,89:146−154. doi: 10.1016/j.procbio.2019.10.005
    [10]
    朱金芳, 王莹, 胡强, 等. 番茄红素胶束与番茄红素原料稳定性对比研究[J]. 新疆医科大学学报,2017,40(4):503−508. [ZHU J F, WANG Y, HU Q, et al. Contrastive study on stabilities of lycopene micelles and lycopene[J]. Journal of Xinjiang Medical University,2017,40(4):503−508. doi: 10.3969/j.issn.1009-5551.2017.04.022

    ZHU J F, WANG Y, HU Q, et al. Contrastive study on stabilities of lycopene micelles and lycopene[J]. Journal of Xinjiang Medical University, 2017, 40(4): 503-508. doi: 10.3969/j.issn.1009-5551.2017.04.022
    [11]
    MURAKAMI K, HONDA M, TAKEMURA R, et al. Effect of thermal treatment and light irradiationon the stability of lycopene with high Z-isomers content[J]. Food Chemistry,2018,250:253−258. doi: 10.1016/j.foodchem.2018.01.062
    [12]
    PEER D, KARP J M, HONG S, et al. Nanocarriers as an emerging platform for cancer therapy[J]. Nano-Enabled Medical Applications,2007,2(12):751.
    [13]
    TURECEK P L, BOSSARD M J, SCHOETENS F, et al. PEGylation of biopharmaceuticals: A review of chemistry and nonclinical safety information of approved drugs[J]. Journal of Pharmaceutical Sciences,2016,105(2):460−475. doi: 10.1016/j.xphs.2015.11.015
    [14]
    TYLER B, GULLOTTI D, MANGRAVITI A, et al. Polylactic acid (PLA) controlled delivery carriers for biomedical applications[J]. Advanced Drug Delivery Reviews,2016,107:163−175. doi: 10.1016/j.addr.2016.06.018
    [15]
    王丽, 黄一聆, 房伟. 柚皮素-mPEG-PLA聚合物胶束的制备及其体内药动学研究[J]. 中成药,2022,44(4):1052−1057. [WANG L, HUANG Y L, FANG W. Preparation and in vivo pharmacokinetics of naringenin-loaded mPEG-PLA polymeric micelles[J]. Chinese Traditional Patent Medicine,2022,44(4):1052−1057. doi: 10.3969/j.issn.1001-1528.2022.04.003

    WANG L, HUANG Y L, FANG W. Preparation and in vivo pharmacokinetics of naringenin⁃loaded mPEG⁃PLA polymeric micelles [J]. Chinese Traditional Patent Medicine, 2022, 44(4): 1052-1057. doi: 10.3969/j.issn.1001-1528.2022.04.003
    [16]
    HUANG S, JIANG S. Structures and morphologies of biocompatible and biodegradable block copolymers[J]. Rsc Advances,2014,4(47):24566−24583. doi: 10.1039/C4RA03043E
    [17]
    朱金芳. DOX和CA4P共载mPEG-PLA聚合物囊泡的制备及其肿瘤抑制作用研究[D]. 杭州: 浙江大学, 2014.

    ZHU J F. Preparation and evaluation of mPEG-PLA polymersomes co-encapsulating DOX and CA4P to inhibit cancer growth[D]. Hangzhou: Zhejiang University, 2014.
    [18]
    MELÉNDEZ-MARTÍNEZ A J, PAULINO M, STINCO C M, et al. Study of the time-course of cis/trans (Z/E) isomerization of lycopene, phytoene, and phytofluene from tomato[J]. Journal of Agricultural and Food Chemistry,2014,62(51):12399−12406. doi: 10.1021/jf5041965
    [19]
    HONDA M, TAKAHASHI N, KUWA T, et al. Spectral characterisation of Z-isomers of lycopene formed during heat treatment and solvent effects on the E/Z isomerisation process[J]. Food Chemistry,2015,171:323−329. doi: 10.1016/j.foodchem.2014.09.004
    [20]
    TAKEHARA M, NISHIMURA M, KUWA T, et al. Characterization and thermal isomerization of (all-E)-lycopene[J]. Journal of Agricultural and Food Chemistry,2014,62(1):264−269. doi: 10.1021/jf404497k
    [21]
    国家药典委员会. 中华人民共和国药典[S]. 四部. 北京: 中国医药科技出版社, 2020: 475.

    Chinese Pharmacopoeia Commission. Pharmacopoeia of the People's Republic of China[S]. Four parts. Beijing: The Medicine Science and Technology Press of China, 2020: 475.
    [22]
    LIN C H, CHEN B H. Determination of carotenoids in tomato juice by liquid chromatography[J]. Journal of Chromatography A,2003,1012(1):103−109. doi: 10.1016/S0021-9673(03)01138-5
    [23]
    AVEYARD R, BINKS B P, ESQUENA J, et al. Flocculation transitions of weakly charged oil-in-water emulsions stabilized by different surfactants[J]. Langmuir,2002,18(9):3487−3494. doi: 10.1021/la011723e
    [24]
    MUSUMECI T, VENTURA C A, GIANNONE I, et al. PLA/PLGA nanoparticles for sustained release of docetaxel[J]. International journal of Pharmaceutics,2006,325(1-2):172−179. doi: 10.1016/j.ijpharm.2006.06.023
    [25]
    KNOCKAERT G, PULISSERY S K, LEMMENS L, et al. Carrot β-carotene degradation and isomerization kinetics during thermal processing in the presence of oil[J]. Journal of Agricultural and Food Chemistry,2012,60(41):10312−10319. doi: 10.1021/jf3025776
    [26]
    GUO W H, TU C Y, HU C H. Cis-trans isomerizations of β-carotene and lycopene: A theoretical study[J]. The Journal of Physical Chemistry B,2008,112(38):12158−12167. doi: 10.1021/jp8019705
    [27]
    YU J, GLEIZE B, ZHANG L, et al. Heating tomato puree in the presence of lipids and onion: The impact of onion on lycopene isomerization[J]. Food Chemistry,2019,296:9−16. doi: 10.1016/j.foodchem.2019.05.188
    [28]
    PHAM D T, CHOKAMONSIRIKUN A, PHATTARAVORAKARN V, et al. Polymeric micelles for pulmonary drug delivery: A comprehensive review[J]. Journal of Materials Science,2021,56(3):2016−2036. doi: 10.1007/s10853-020-05361-4
    [29]
    CHAUDHURI A, RAMESH K, KUMAR D N, et al. Polymeric micelles: A novel drug delivery system for the treatment of breast cancer[J]. Journal of Drug Delivery Science and Technology, 2022: 103886.
    [30]
    GUERRA A S, HOYOS C G, MOLINA-RAMÍREZ C, et al. Extraction and preservation of lycopene: A review of the advancements offered by the value chain of nanotechnology[J]. Trends in Food Science & Technology,2021,116:1120−1140.
    [31]
    KIM K S, PARK S J. Effect of porous silica on sustained release behaviors of pH sensitive pluronic F127/poly (acrylic acid) hydrogelscontaining tulobuterol[J]. Colloids and Surfaces B: Biointerfaces,2010,80(2):240−246. doi: 10.1016/j.colsurfb.2010.06.017
    [32]
    MORADKHANNEJHAD L, ABDOUSS M, NIKFARJAM N, et al. The effect of molecular weight and content of PEG on in vitro drug release of electrospun curcumin loaded PLA/PEG nanofibers[J]. Journal of Drug Delivery Science and Technology,2020,56:101554. doi: 10.1016/j.jddst.2020.101554
    [33]
    ZHANG K, TANG X, ZHANG J, et al. PEG-PLGA copolymers: Their structure and structure-influenced drug delivery applications[J]. Journal of Controlled Release,2014,183:77−86. doi: 10.1016/j.jconrel.2014.03.026
    [34]
    MAPELLI-BRAHM P, MARGIER M, DESMARCHELIER C, et al. Comparison of the bioavailability and intestinal absorption sites of phytoene, phytofluene, lycopene and β-carotene[J]. Food Chemistry,2019,300:125232. doi: 10.1016/j.foodchem.2019.125232
    [35]
    ZHAO W, SU L, YU Z, et al. Improved stability and controlled release of lycopene via self-assembled nanomicelles encapsulation[J]. LWT,2022,155:112878. doi: 10.1016/j.lwt.2021.112878
    [36]
    SUNOQROT S, ALSADI A, TARAWNEH O, et al. Polymer type and molecular weight dictate the encapsulation efficiency and release of quercetin from polymeric micelles[J]. Colloid and Polymer Science,2017,295(10):2051−2059. doi: 10.1007/s00396-017-4183-9
    [37]
    WEI Y, WANG Y X, WANG W, et al. Microcosmic mechanisms for protein incomplete release and stability of various amphiphilic mPEG-PLA microspheres[J]. Langmuir,2012,28(39):13984−13992. doi: 10.1021/la3017112
    [38]
    BU X, JI N, DAI L, et al. Self-assembled micelles based on amphiphilic biopolymers for delivery of functional ingredients[J]. Trends in Food Science & Technology,2021,114:386−398.
    [39]
    ALAI M S, LIN W J, PINGALE S S. Application of polymeric nanoparticles and micelles in insulin oral delivery[J]. Journal of Food and Drug Analysis,2015,23(3):351−358. doi: 10.1016/j.jfda.2015.01.007
  • Cited by

    Periodical cited type(2)

    1. 杨春霞,王芳焕. 贺兰山东麓产区酿酒葡萄中高氯酸盐暴露风险评估. 食品安全质量检测学报. 2024(08): 298-305 .
    2. 陈秋宇,梁江,王小丹,张磊,魏晟. 我国重点和非重点地区居民膳食中高氯酸盐暴露风险概率评估. 中国食品卫生杂志. 2023(12): 1740-1748 .

    Other cited types(3)

Catalog

    Article Metrics

    Article views (130) PDF downloads (29) Cited by(5)

    /

    DownLoad:  Full-Size Img  PowerPoint
    Return
    Return