Preparation of Hyaluronic Acid Oligosaccharides by Enzymatic Method and Its Transdermal Absorption Activity

LI Huining; ZHANG Jingliang; YANG Gen; JIANG Xiaolu

doi:10.13386/j.issn1002-0306.2021080002

Volume 43 Issue 6

Mar. 2022

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Science and Technology of Food Industry > 2022 > 43(6): 77-82. > DOI: 10.13386/j.issn1002-0306.2021080002

LI Huining, ZHANG Jingliang, YANG Gen, et al. Preparation of Hyaluronic Acid Oligosaccharides by Enzymatic Method and Its Transdermal Absorption Activity[J]. Science and Technology of Food Industry, 2022, 43(6): 77−82. (in Chinese with English abstract). doi: 10.13386/j.issn1002-0306.2021080002.

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Preparation of Hyaluronic Acid Oligosaccharides by Enzymatic Method and Its Transdermal Absorption Activity

LI Huining^1,,
ZHANG Jingliang^{2, 3},
YANG Gen⁴,
JIANG Xiaolu^{1, 4, ,}

1.
College of Food Science and Engineering, Ocean University of China, Qingdao 266003, China
2.
School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China
3.
Marine Biomedical Research Institute of Qingdao, Qingdao 266007, China
4.
Shandong Galaxy Bio-Tech Co., Ltd., Jining 273200, China

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Received Date: August 02, 2021
Available Online: January 10, 2022

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Abstract

Abstract

To investigate the transdermal absorption activity of hyaluronic acid oligosaccharides, hyaluronic acid oligosaccharides were prepared by enzymatic degradation of hyaluronic acid using hyaluronic acid lyase, and the hyaluronic acid oligosaccharides were analyzed by infrared spectroscopy and mass spectrometry, and their hygroscopic properties, body surface moisturizing properties and transdermal absorption properties were evaluated. The results showed that the optimum substrate concentration for the enzymatic preparation of hyaluronan oligosaccharides by hyaluronan lysis enzyme was 1%, and the optimum enzyme addition was 3.0 U/mg. The enzymatic preparation of hyaluronan oligosaccharides was free of moieties, and the enzymatic products were mainly unsaturated hyaluronan disaccharides. The enzymatically prepared hyaluronan oligosaccharide had excellent surface moisturizing and transdermal absorption properties, and would have a broad application prospect in the field of biochemicals.
- hyaluronan oligosaccharide,
- hyaluronic acid lyase,
- structural analysis,
- transdermal absorption activity

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References

[1]	唐泽严, 郭学平, 温喜明, 等. 不同相对分子质量透明质酸对还原型谷胱甘肽透皮吸收的影响[J]. 中国药科大学学报,2021,52(2):203−210. [TANG Zeyan, GUO Xueping, WEN Ximing, et al. Effects of hyaluronic acid with different molecular weight on the trans-dermal absorption of reduced glutathione[J]. J China Pharm Univ,2021,52(2):203−210. doi: 10.11665/j.issn.1000-5048.20210209
[2]	瞿晓梅, 国大亮, 刘洋, 等. 透明质酸制备方法的研究进展[J]. 药学研究,2020,39(4):233−235. [ZHAI Xiaomei, GUO Daliang, LIU Yang, et al. Research progress on preparation of hyaluronic acid[J]. Journal of Pharmacentical Research,2020,39(4):233−235.
[3]	CUI Y L, WANG F, VOORHEES J J, et al. Rejuvenation of aged human skin by injection of cross-linked hyaluronic acid[J]. Plastic and Reconstructive Surgery,2021,147(1S-2):43S−49S. doi: 10.1097/PRS.0000000000007620
[4]	刘硕, 王景召. 透明质酸的特性及其在食品中的应用[J]. 化工设计通讯,2018,44(8):62. [LIU Shuo, WANG Jingzhao. Characteristics of hyaluronic acid and its application in food[J]. Chenical Enginceering Design Communications,2018,44(8):62. doi: 10.3969/j.issn.1003-6490.2018.08.058
[5]	SAFDAR M H, HUSSAIN Z, ABOUREHAB Mohammed A S, et al. New developments and clinical transition of hyaluronic acid-based nanotherapeutics for treatment of cancer: Reversing multidrug resistance, tumour-specific targetability and improved anticancer efficacy[J]. Artificial Cells, Nanomedicine, and Biotechnology,2018,46(8):1967−1980.
[6]	LI J J, DU R, BIAN Q, et al. Topical application of HA-g-TEMPO accelerates the acute wound healing via reducing reactive oxygen species (ROS) and promoting angiogenesis[J]. International Journal of Pharmaceutics,2021,597:120328. doi: 10.1016/j.ijpharm.2021.120328
[7]	LIN Z F, WU T T, WANG W S, et al. Biofunctions of antimicrobial peptide-conjugated alginate/hyaluronic acid/collagen wound dressings promote wound healing of a mixed-bacteria-infected wound[J]. International Journal of Biological Macromolecules,2019:140.
[8]	CAI J, FU J R, LI R R, et al. A potential carrier for anti-tumor targeted delivery-hyaluronic acid nanoparticles[J]. Carbohydrate Polymers,2019,208:356−364. doi: 10.1016/j.carbpol.2018.12.074
[9]	赖永勤, 刘玉川, 周正东, 等. 低分子量透明质酸功能与制备研究进展[J]. 食品与发酵科技,2015,51(6):77−80,99. [LAI Yongqin, LIU Yuchuan, ZHOU Zhengdong, et al. Research progress in function and production of low molecular weights of hyaluronic acid[J]. Food and Fermentaion Technology,2015,51(6):77−80,99.
[10]	张文强, 黄岳山. 低相对分子质量透明质酸的超声降解制备[J]. 中国组织工程研究与临床康复,2009,13(25):4883−4885. [ZHANG Wenqiang, HUANG Yueshan. Preparation of low molecular weight hyaluronan using ultrasonic degradation[J]. Hournal of Clinical Rehabilitative Tissue Engineering Research,2009,13(25):4883−4885.
[11]	王鑫, 郭瑞琳, 王派丽, 等. 透明质酸降解工艺条件优化[J]. 食品与发酵工业,2014,40(1):130−135. [WANG Xin, GUO Ruilin, WANG Paili, et al. Optimization of the degradation conditions of hyaluronic acid by response surface methodology[J]. Food and Fermentation Industries,2014,40(1):130−135.
[12]	岑潇龙, 雷曦, 马诗云, 等. 金黄色葡萄球菌透明质酸裂解酶HylS的异源表达与特性研究[J/OL]. 生物技术通报: 1−12 [2021-08-01]. https://doi. org/10.13560/j. cnki. biotech. bull.1985.2021-0129. CEN Xiaolong, LEI Xi, MA Shiyun, et al. Heterologous expression and characterization of the hyaluronic acid lyase HylS from Staphy lococcus aureus[J]. Biotechnology Bulletin: 1−12 [2021-08-01].https://doi.org/10.13560/j.cnki.biotech.bull.1985.2021-0129.
[13]	卢方云, 吴瑀婕, 黄瑾, 等. 透明质酸的制备及其应用的研究进展[J/OL]. 食品工业科技: 1−13 [2021-08-25]. https: //doi. org/10.13386/j. issn1002-0306.2021030186. LU Fangyun, WU Yujie, HUANG Jin, et al. Research progress on preparation and application of hyaluronic acid[J/OL]. Science and Technology of Food Industry: 1−13[2021-08-25].https://doi.org/10.13386/j.issn1002-0306.2021030186.
[14]	李憬昱. 基于NIRS技术进行分子量监测的酶解法制备LMW-HA的工艺研究[D]. 济南: 山东大学, 2019. LI Jingyu. Study on preparation procedure of LMW-HA by enzymatic hydrolysis based on the molecular weight monitering with NIRS[D]. Jinan: Shandong University, 2019.
[15]	ZHU C L, ZHANG J L, LI L Y, et al. Purification and characterization of hyaluronate lyase from arthrobacter globiformis A152[J]. Applied Biochemistry and Biotechnology,2017,182(1):216−228. doi: 10.1007/s12010-016-2321-3
[16]	姜言晖, 张京良, 江晓路. 球形节杆菌A152产透明质酸酶的发酵优化及动力学模型的建立[J]. 生物工程学报,2017,33(11):1883−1888. [JIANG Yanhui, ZHANG Jingliang, JIANG Xiaolu. Establishment of kinetics digital model for hyaluronate lyase production based on fermentation optimization of Arthrobacter globiformis A152[J]. Chin J Biotech,2017,33(11):1883−1888.
[17]	GAO Z, CHEN J, QIU S, et al. Optimization of selenylation modification for garlic polysaccharide based on immune-enhancing activity[J]. Carbohydr Polym,2016,136:560−569. doi: 10.1016/j.carbpol.2015.09.065
[18]	SILVIA R, GIOVANNA B, SARATH B N, et al. Advanced quantitative proteomics to evaluate molecular effects of low-molecular-weight hyaluronic acid in human dermal fibroblasts[J]. Journal of Pharmaceutical and Biomedical Analysis,2020,185(5):113199.
[19]	陈晓磊, 刘盼, 陈夫山. 麦麸多肽抗氧化及吸湿保湿性能的测定[J]. 齐鲁工业大学学报,2018,32(2):8−12. [CHEN Xiaolei, LIU Pan, CHEN Fushan. Determination of antioxidative and moisture absorption and moisture retention properties of wheat bran peptides[J]. Journal of Qilu University of Technology,2018,32(2):8−12.
[20]	屈义, 周斯仪, 冯陶, 等. 鱼鳔糖胺聚糖的提取及其吸湿保湿性能评价[J]. 食品工业科技,2017,38(16):118−125. [QU Yi, ZHOU Siyi, FENG Tao, et al. Extraction of glycosaminoglycans from swim bladder and evaluation of the capacities of its hygroscopicity and moisture retention[J]. Science and Technology of Food Industry,2017,38(16):118−125.
[21]	LUDOWIEHG J, VENNESLAND B, DORFMAN A. The mechanism of action of hyaluronidase[J]. The Journal of Biological Chemistry,1961,236:333−339. doi: 10.1016/S0021-9258(18)64363-7
[22]	SATISH L, SANTRA S, TSURKAN M V, et al. Conformational changes of GDNF-derived peptide induced by heparin, heparan sulfate, and sulfated hyaluronic acid–analysis by circular dichroism spectroscopy and molecular dynamics simulation[J]. International Journal of Biological Macromolecules,2021,182:2144−2150. doi: 10.1016/j.ijbiomac.2021.05.194
[23]	ZHA S, ZHAO Q, CHEN J, et al. Extraction, purification and antioxidant activities of the polysaccharides from maca (Lepidium meyenii)[J]. Carbohydr Polym,2014,111:584−587. doi: 10.1016/j.carbpol.2014.05.017
[24]	GUO S, MAO W, LI Y, et al. Preparation, structural characterization and antioxidant activity of an extracellular polysaccharide produced by the fungus Oidiodendron truncatum GW[J]. Process Biochem,2013,48:539−544. doi: 10.1016/j.procbio.2013.01.014
[25]	HAO L, SHENG Z, LU J, et al. Characterization and antioxidant activities of extracellular and intracellular polysaccharides from Fomitopsis pinicola[J]. Carbohydr Polym,2016,141:54−59. doi: 10.1016/j.carbpol.2015.11.048
[26]	JESUS V, MIRIAM R G, UXIA R V, et al. Hyaluronic acid of tailored molecular weight by enzymatic and acid depolymerization[J]. International Journal of Biological Macromolecules,2020,145:788−794. doi: 10.1016/j.ijbiomac.2019.12.221
[27]	GUO X, LIU F, ZHU X, et al. Expression of a novel hyaluronidase from Streptococcus zooepidemicus in Escherichia coli and its application for the preparation of HA oligosaccharides[J]. Carbohydr Polym,2009,77:254−260. doi: 10.1016/j.carbpol.2008.12.036
[28]	KAKIZAKI I, IBORI N, KOJIMA K, et al. Mechanism for the hydrolysis of hyaluronan oligosaccharides by bovine testicular hyaluronidase[J]. FEBS J,2010,277:1025−1033.
[29]	刘坤, 白阳, 杨靖, 等. 基于透明质酸构筑的药物递送载体及其应用[J]. 化学通报,2021,84(3):225−231. [LIU Kun, BAI Yang, YANG Jing, et al. Hyaluronic acid-based drug delivery carriers and their applications[J]. Chemistry Bulletin,2021,84(3):225−231.
[30]	郭丽, 胡欣月, 马松艳, 等. 透明质酸对胶原蛋白复合物抗氧化增效作用及应用[J]. 食品科技,2020,45(12):258−264. [GUO Li, HU Xinyue, MA Songyan, et al. Synergistic effect and application of hyaluronic acid on antioxidant activity of collagen complex[J]. Food Science and Technology,2020,45(12):258−264.

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