Cancer Hospital of Dalian University of Technology, Dalian University of Technology, Shenyang 110042, People's Republic of China.
State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, People's Republic of China.
Langmuir. 2024 Jun 4;40(22):11610-11625. doi: 10.1021/acs.langmuir.4c00856. Epub 2024 May 17.
Low solubility and chemical instability are the main problems with insoluble bioactives. Lignin, with its exceptional biological properties and amphiphilicity, holds promise as a delivery system material. In this study, glycerol esters were incorporated into alkali lignin (AL) through ether and ester bonds, resulting in the successful synthesis of three hydrophobically modified alkali lignins (AL-OA, AL-OGL, and AL-SAN-OGL). Subsequently, lignin composite nanoparticles (LNPs@BC) encapsulating β-carotene were prepared using antisolvent and sonication techniques. The encapsulation rates were determined to be 37.69 ± 2.21%, 84.01 ± 5.55%, 83.82 ± 5.23%, and 83.11 ± 5.85% for LNP@BC-1, LNP@BC-2, LNP@BC-3, and LNP@BC-4, respectively, with AL, AL-OA, AL-OGL, and AL-SAN-OGL serving as the wall materials under optimized preparation conditions. The antioxidant properties and UV-absorbing capacity of the four lignins were characterized, demonstrating their efficacy in enhancing the oxygen and photostability of β-carotene. Following 6 h of UV irradiation, LNP@BC-4 exhibited a retention rate of 83.03 ± 2.85% for β-carotene, while storage under light-protected conditions at 25 °C for 7 days retained 73.33 ± 7.62% of β-carotene. Furthermore, the encapsulated β-carotene demonstrated enhanced thermal and storage stability. In vitro release experiments revealed superior stability of LNPs@BC in simulated gastric fluid (SGF), with β-carotene retention exceeding 77% in both LNP@BC-3 and LNP@BC-4. LNP@BC-4 exhibited the highest bioaccessibility in simulated intestinal fluid (SIF) at 46.96 ± 0.80%, that LNP@BC-1 only achieved 10.87 ± 0.90%. The enzymatic responsiveness of AL-OGL and AL-SAN-OGL was confirmed. Moreover, LNPs@BC exhibited no cytotoxicity toward L929 cells and demonstrated excellent hemocompatibility. In summary, this study introduces a novel enzyme-responsive modified lignin that has promising applications in the fields of food, biomedicine, and animal feed.
低溶解度和化学不稳定性是不溶性生物活性物质的主要问题。木质素具有特殊的生物学性质和两亲性，有望成为一种输送系统材料。在这项研究中，通过醚键和酯键将甘油酯掺入碱木质素（AL）中，成功合成了三种疏水性改性碱木质素（AL-OA、AL-OGL 和 AL-SAN-OGL）。随后，采用抗溶剂和超声技术制备了包埋β-胡萝卜素的木质素复合纳米粒子（LNPs@BC）。在优化的制备条件下，当壁材分别为 AL、AL-OA、AL-OGL 和 AL-SAN-OGL 时，包埋率分别为 37.69±2.21%、84.01±5.55%、83.82±5.23%和 83.11±5.85%，得到 LNP@BC-1、LNP@BC-2、LNP@BC-3 和 LNP@BC-4。四种木质素的抗氧化性能和紫外吸收能力得到了表征，证明它们能够提高β-胡萝卜素的氧稳定性和光稳定性。经过 6 小时的紫外线照射，LNP@BC-4 对β-胡萝卜素的保留率为 83.03±2.85%，而在 25°C 避光条件下储存 7 天，β-胡萝卜素的保留率为 73.33±7.62%。此外，包埋的β-胡萝卜素表现出增强的热稳定性和储存稳定性。体外释放实验表明，LNPs@BC 在模拟胃液（SGF）中具有优异的稳定性，LNP@BC-3 和 LNP@BC-4 中β-胡萝卜素的保留率均超过 77%。LNP@BC-4 在模拟肠液（SIF）中的生物利用度最高，为 46.96±0.80%，而 LNP@BC-1 仅为 10.87±0.90%。AL-OGL 和 AL-SAN-OGL 的酶响应性得到了证实。此外，LNPs@BC 对 L929 细胞无细胞毒性，表现出良好的血液相容性。总之，本研究介绍了一种新型酶响应性改性木质素，在食品、生物医学和动物饲料等领域具有广阔的应用前景。
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