Preparation and Biological Activity of D-Glucosamine Hydrochloride from the Waste Residues of <i>Pleurotus eryngii</i>

ZHANG Qianru; WU Qici; XUE Yu; LIN Zhichao; HUANG Jiafu; LÜ Haokun; PENG Wei; PAN Yutian; LIN Jinmei

doi:10.13386/j.issn1002-0306.2022110139

Volume 44 Issue 17

Aug. 2023

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Science and Technology of Food Industry > 2023 > 44(17): 263-271. > DOI: 10.13386/j.issn1002-0306.2022110139

ZHANG Qianru, WU Qici, XUE Yu, et al. Preparation and Biological Activity of D-Glucosamine Hydrochloride from the Waste Residues of Pleurotus eryngii[J]. Science and Technology of Food Industry, 2023, 44(17): 263−271. (in Chinese with English abstract). doi: 10.13386/j.issn1002-0306.2022110139.

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Preparation and Biological Activity of D-Glucosamine Hydrochloride from the Waste Residues of Pleurotus eryngii

1.
Fujian Universities Engineering Research Center of Fungus Industry, Minnan Normal University, Zhangzhou 363000, China
2.
College of Chemistry and Environment, Minnan Normal University, Zhangzhou 363000, China

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Received Date: November 13, 2022
Available Online: July 19, 2023

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Abstract

Abstract

In this paper, the preparation process of D-glucosamine hydrochloride (GAH) was investigated from the waste residues of Pleurotus eryngii (P. eryngii). Liquid chromatography-mass spectrometry (HPLC-MS), infrared spectroscopy (IR), and physicochemical indexes of GAH were also studied. Then the effect of GAH on the zebrafish embryonic development was evaluated. The experimental conditions for preparing GAH were optimized through single-factor experiments and response surface methodology. Under optimal conditions (HCl concentration of 31%, hydrolysis time of 4 h, hydrolysis temperature of 82 ℃, and the liquid-solid ratio of 5 mL/g), the yield of GAH reached 23.61%. HPLC-MS, IR, and physicochemical index analysis showed that the purity of the GAH-purified sample was 101.9% of the standard. The mass spectrometry and infrared spectroscopy were consistent with the standard. All indexes met or even outperformed the specifications of the United States Pharmacopeia 43-National Formulary 38 (USP 43-NF38), and the arsenic content was only 0.21 μg/g. In addition, the zebrafish experiment indicated that exposure to moderate and high concentrations (0.3%~0.5%) of GAH could induce more than 50% of the abnormal embryonic development of zebrafish. Moreover, 0.3% of GAH promotes the transforming growth factor-β (TGF-β) signal pathway. In conclusion, the results provide valuable insight into preparing and applying the industrial residue of P. eryngii.
- D-glucosamine hydrochloride,
- Pleurotus eryngii,
- waste residues,
- response surface optimization,
- zebrafish embryonic development

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References

[1]	KIM, SE-KWON. Chitin, chitosan, oligosaccharides and their derivatives: Biological activities and applications[M]. New York: CRC Press, 2010: 3-9.
[2]	ARTAMONOVA S D, SHARNINA F F. Isolation of D-glucosamine from chitin-glucan complexes[J]. Applied Biochemistry and Microbiology,2013,49(4):426−431. doi: 10.1134/S0003683813030046
[3]	张明川, 臧洪俊, 余松柏, 等. 甲壳素生物质转化为高附加值化合物研究进展[J]. 化工进展,2017,36(3):863−872. [ZHANG M C, ZANG H J, YU S B, et al. Advances in conversion of chitin biomass into high-value chemicals[J]. Chemical Industry and Engineering Progress,2017,36(3):863−872. doi: 10.16085/j.issn.1000-6613.2017.03.013 ZHANG M C, ZANG H J, YU S B, et al. Advances in conversion of chitin biomass into high-value chemicals [J]. Chemical Industry and Engineering Progress, 2017, 36（3）: 863-872. doi: 10.16085/j.issn.1000-6613.2017.03.013
[4]	江敏. 氨基葡萄糖的药理学研究进展[J]. 中国药房,2010,21(17):1622−1624. [JIANG M. Advances in pharmacological research of glucosamine[J]. China Pharmacy,2010,21(17):1622−1624. JIANG M. Advances in pharmacological research of glucosamine [J]. China Pharmacy, 2010, 21(17): 1622-1624.
[5]	ZHU X Y, SANG L L, WU D D, et al. Effectiveness and safety of glucosamine and chondroitin for the treatment of osteoarthritis: A meta-analysis of randomized controlled trials[J]. Journal of Orthopaedic Surgery and Research,2018,13(1):170. doi: 10.1186/s13018-018-0871-5
[6]	ZAHEDIPOUR F, DALIRFARDOUEI R, KARIMI G, et al. Molecular mechanisms of anticancer effects of glucosamine[J]. Biomedicine & Pharmacotherapy,2017,95:1051−1058.
[7]	DALIRFARDOUEI R, KARIMI G, JAMIALAHMADI K. Molecular mechanisms and biomedical applications of glucosamine as a potential multifunctional therapeutic agent[J]. Life Sciences,2013,152:21−29.
[8]	苏喆, 黄哲甦. D-氨基葡萄糖抗肿瘤作用机制的研究进展[J]. 现代药物与临床,2020,35(6):1268−1274. [SU Z, HUANG Z S. Research progress on antitumor mechanisms of D-glucosamine[J]. Drugs & Clinic,2020,35(6):1268−1274. SU Z, HUANG Z S. Research progress on antitumor mechanisms of D-glucosamine [J]. Drugs & Clinic, 2020, 35(6): 1268-1274.
[9]	DOSTROVSKY N R, TOWHEED T E, HUDSON R W, et al. The effect of glucosamine on glucose metabolism in humans: A systematic review of the literature[J]. Osteoarthritis and Cartilage,2011,19(4):375−380. doi: 10.1016/j.joca.2011.01.007
[10]	迟海林, 李菲菲, 张李伟, 等. 氨基葡萄糖类物质在保健食品中的应用及研究进展[J/OL]. 食品工业科技: 1−10. [2022-11-08]. DOI: 10.13386/j. issn1002-0306.2022050211. CHI H L, LI F F, ZHANG L W, et al. Application and research progress of glucosamine in health food[J/OL]. Science and Technology of Food Industry: 1−10 [2022-11-08]. DOI: 10.13386/j.issn1002-0306.2022050211.
[11]	黄金城, 杨其蒀, 梁诗飔. 蝉蜕制备盐酸氨基葡萄糖的研究[J]. 天然产物研究与开发,1993(3):28−29. [HUANG J C, YANG Q W, LIANG S S. Study on preparation of D-glucosamine hydrochloride from Periostracum cicadae[J]. Natural Product Research and Development,1993(3):28−29. doi: 10.16333/j.1001-6880.1993.03.004 HUANG J C, YANG Q W, LIANG S S. Study on preparation of D-glucosamine hydrochloride from Periostracum cicadae [J]. Natural Product Research and Development, 1993(3): 28-29. doi: 10.16333/j.1001-6880.1993.03.004
[12]	沈荣明. D-氨基葡萄糖盐酸盐的制备研究[J]. 湖州职业技术学院学报,2004(4):85−88. [SHEN R M. The study of preparation of D-glucosamine hydrochloride with chrysalis[J]. Journal of Huzhou Vocational and Technological College,2004(4):85−88. doi: 10.3969/j.issn.1672-2388.2004.04.024 SHEN R M. The study of preparation of D-glucosamine hydrochloride with chrysalis [J]. Journal of Huzhou Vocational and Technological College, 2004（4）: 85-88. doi: 10.3969/j.issn.1672-2388.2004.04.024
[13]	朱晓萍, 颜毛毛, 权海峰, 等. 柠檬酸发酵废渣中氨基葡萄糖盐酸盐提取工艺优化[J]. 科技视界,2019(8):17−19,3. [ZHU X P, YAN M M, QUAN H F, et al. Study on extracting glucosamine hydrochloride from the waste Aspergillus niger of citric acid production plant[J]. Science & Technology Vision,2019(8):17−19,3. doi: 10.19694/j.cnki.issn2095-2457.2019.08.006 ZHU X P, YAN M M, QUAN H F, et al. Study on extracting glucosamine hydrochloride from the waste Aspergillus niger of citric acid production plant [J]. Science & Technology Vision, 2019（8): 17-19, 3. doi: 10.19694/j.cnki.issn2095-2457.2019.08.006
[14]	林进妹, 潘裕添, 庄远红, 等. 微波辐射快速制备氨基葡萄糖盐酸盐的研究[J]. 漳州师范学院学报(自然科学版),2006(4):87−92. [LIN J M, PAN Y T, ZHUANG Y H, et al. Study on the rapid preparation of glucosamine hydrochloride under microwave radiation[J]. Journal of Zhangzhou Teachers College (Natural Science),2006(4):87−92. LIN J M, PAN Y T, ZHUANG Y H, et al. Study on the rapid preparation of glucosamine hydrochloride under microwave radiation [J]. Journal of Zhangzhou Teachers College (Natural Science), 2006（4）: 87-92.
[15]	邹何, 夏雪, 王粟萍, 等. 杏鲍菇相关研究进展及其产业开发现状[J]. 食品工业,2019,40(2):276−283. [ZOU H, XIA X, WANG S P, et al. Research progress and industry development status of Pleurotus eryngi[J]. Food Industry,2019,40(2):276−283. ZOU H, XIA X, WANG S P, et al. Research progress and industry development status of Pleurotus eryngi [J]. Food Industry, 2019, 40（2）: 276-283.
[16]	林娇芬. 杏鲍菇胞壁β-葡聚糖的分离纯化、结构分析及生物活性研究[D]. 福州: 福建农林大学, 2013 LIN J F. Purification, structure analysis and bioactivity of β-glucan from cell-wall of Pleurotus eryngii[D]. Fuzhou: Fujian Agriculture and Forestry University, 2013.
[17]	李晓贝, 杨焱, 周峰, 等. 杏鲍菇子实体及其下脚料的营养成分和呈味物质研究[J]. 现代食品科技,2015,31(6):272−278. [LI X B, YANG Y, ZHOU F, et al. Nutritional contents and flavor substances in fruit bodies and leftovers of Pleurotus eryngii[J]. Modern Food Science and Technology,2015,31(6):272−278. doi: 10.13982/j.mfst.1673-9078.2015.6.043 LI X B, YANG Y, ZHOU F, et al. Nutritional contents and flavor substances in fruit bodies and leftovers of Pleurotus eryngii [J]. Modern Food Science and Technology, 2015, 31（6）: 272-278. doi: 10.13982/j.mfst.1673-9078.2015.6.043
[18]	苏畅, 夏文水, 姚惠源. 氨基葡萄糖和乙酰氨基葡萄糖的测定方法[J]. 食品工业科技,2003(6):74−75,77. [SU C, XIA W S, YAO H Y. The determination method of glucosamine and N-acetylglucosamine[J]. Science and Technology of Food Industry,2003(6):74−75,77. doi: 10.3969/j.issn.1002-0306.2003.06.031 SU C, XIA W S, YAO H Y. The determination method of glucosamine and N-acetylglucosamine [J]. Science and Technology of Food Industry, 2003（6）: 74-75, 77. doi: 10.3969/j.issn.1002-0306.2003.06.031
[19]	US PHARMACOPEIA CONVENTION. U. S. Pharmacopeia 43-national formulary 38[M]. Roehville MD: the United States Pharmacopeial Convention Inc, 2020: 5045.
[20]	LI Y, QIN G, CHENG C, et al. Purification, characterization and anti-tumor activities of polysaccharides from Ecklonia kurome obtained by three different extraction methods[J]. International Journal of Biological Macromolecules,2020,150:1000−1010. doi: 10.1016/j.ijbiomac.2019.10.216
[21]	KIMMEL C B, BALLARD W W, KIMMEL S R, et al. Stages of embryonic development of the zebrafish[J]. Developmental Dynamics,1995,203(3):253−310. doi: 10.1002/aja.1002030302
[22]	XUE Y, ZHENG X D, HUANG L, et al. Organizer-derived Bmp2 is required for the formation of a correct Bmp activity gradient during embryonic development[J]. Nature Communications,2014(5):3766.
[23]	崔玮, 丁玲强, 李佩佩, 等. 利用杏鲍菇残渣制备D-氨基葡萄糖盐酸盐的研究[J]. 中国食用菌,2022,41(6):70−74,81. [CUI W, DING L Q, LI P P, et al. Study on the preparation of D-glucosamine hydrochloride using the residue of Pleurotus eryngii[J]. Edible Fungi of China,2022,41(6):70−74,81. doi: 10.13629/j.cnki.53-1054.2022.06.012 CUI W, DING L Q, LI P P, et al. Study on the preparation of D-glucosamine hydrochloride using the residue of Pleurotus eryngii [J]. Edible Fungi of China, 2022, 41（6）: 70-74, 81. doi: 10.13629/j.cnki.53-1054.2022.06.012
[24]	游庆红, 尹秀莲. 正交设计优化甲壳素制备D-氨基葡萄糖盐酸盐工艺[J]. 广州化工,2013,41(10):71−72,88. [YOU Q H, YIN X L. Preparation of D-glucosamine hydrochloride from chitin by orthogonal experimental design[J]. Guangzhou Chemical Industry,2013,41(10):71−72,88. doi: 10.3969/j.issn.1001-9677.2013.10.028 YOU Q H, YIN X L. Preparation of D-glucosamine hydrochloride from chitin by orthogonal experimental design [J]. Guangzhou Chemical Industry, 2013, 41(10): 71-72, 88. doi: 10.3969/j.issn.1001-9677.2013.10.028
[25]	盛洁, 田欢, 刘原野, 等. 响应面法优化红枣益生菌发酵饮料工艺[J]. 中国酿造,2021,40(2):203−209. [SHENG J, TIAN H, LIU Y Y, et al. Optimization of fermentation process of probiotics jujube beverage by response surface methodology[J]. China Brewing,2021,40(2):203−209. doi: 10.11882/j.issn.0254-5071.2021.02.040 SHENG J, TIAN H, LIU Y Y, et al. Optimization of fermentation process of probiotics jujube beverage by response surface methodology [J]. China Brewing, 2021, 40（2）: 203-209. doi: 10.11882/j.issn.0254-5071.2021.02.040
[26]	HUANG J F, HUANG A X, LU L M, et al. Improving the yield of Anoectochilus roxburghii by Bacillus licheniformis cultured in Agaricus bisporus industrial wastewater[J]. Electronic Journal of Biotechnology,2020,48:13−22. doi: 10.1016/j.ejbt.2020.08.002
[27]	薛山, 巩子童, 林靖娟, 等. 芽球菊苣根粗多糖提取工艺优化及其体外抗氧化活性和相对分子量分析[J]. 食品工业科技,2021,42(10):138−145. [XUE S, GONG Z T, LIN J J, et al. Optimization of extraction process of crude polysaccharide from chicory root of Cichorium intybus L. var. foliosum Hegi, and analysis of antioxidant activity in vitro and relative molecular weight[J]. Science and Technology of Food Industry,2021,42(10):138−145. doi: 10.13386/j.issn1002-0306.2020060337 XUE S, GONG Z T, LIN J J, et al. Optimization of extraction process of crude polysaccharide from chicory root of Cichorium intybus L. var. foliosum Hegi, and analysis of antioxidant activity in vitro and relative molecular weight [J]. Science and Technology of Food Industry, 2021, 42(10): 138-145. doi: 10.13386/j.issn1002-0306.2020060337
[28]	尚锐峰, 刘华, 吴静, 等. 响应面法优化亚临界丁烷萃取崖柏油及其成分分析[J]. 粮食与油脂,2022,35(9):96−99,144. [SHANG R F, LIU H, WU J, et al. Optimization of subcritical butane extraction and component analysis of Thuja sutchuenensis Franch. oil by response surface methodology[J]. Cereals & Oils,2022,35(9):96−99,144. doi: 10.3969/j.issn.1008-9578.2022.09.025 SHANG R F, LIU H, WU J, et al. Optimization of subcritical butane extraction and component analysis of Thuja sutchuenensis Franch. oil by response surface methodology [J]. Cereals & Oils, 2022, 35(9): 96-99, 144. doi: 10.3969/j.issn.1008-9578.2022.09.025
[29]	HUANG J F, ZHANG G G, ZHENG L H, et al. Plackett-Burman design and response surface optimization of conditions for culturing Saccharomyces cerevisiae in Agaricus bisporus industrial wastewater[J]. Acta Scientiarum Polonorum Technologia Alimentaria,2019,18(1):65−74.
[30]	黄捷. 氨基葡萄糖盐酸盐离子交换萃取及反萃工艺研究[D]. 杭州: 浙江大学, 2012 HUANG J. Ion-exchange extraction and back extraction of glucosamine hydrochloride[D]. Hangzhou: Zhejiang University, 2012.
[31]	张文娟, 许璟瑾, 姚丽云, 等. 氨基葡萄糖盐酸盐及其衍生物对斑马鱼骨骼损伤修复的比较研究[J]. 中国比较医学杂志,2018,28(12):9−13,31. [ZHANG W J, XU J J, YAO L Y, et al. Comparison of the effect of glucosamine hydrochloride and its derivatives on the skeletal repair in zebrafish[J]. Chinese Journal of Comparative Medicine,2018,28(12):9−13,31. doi: 10.3969/j.issn.1671-7856.2018.12.002 ZHANG W J, XU J J, YAO L Y, et al. Comparison of the effect of glucosamine hydrochloride and its derivatives on the skeletal repair in zebrafish [J]. Chinese Journal of Comparative Medicine, 2018, 28(12): 9-13, 31. doi: 10.3969/j.issn.1671-7856.2018.12.002
[32]	PENG W, ZHANG W J, WU Q C, et al. Agaricus bisporus-derived glucosamine hydrochloride facilitates skeletal injury repair through Bmp signaling in Zebrafish Osteoporosis model[J]. Journal of Natural Products,2021,84(4):1294−1305. doi: 10.1021/acs.jnatprod.1c00002

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