Citation: Shuying Li, Weiwei ZhuGe, Xuan Sun, Chongzhen Sun, Zhaojun Liu, Chenghe Xiong, Min Xiao, Guofeng Gu. Convergent synthesis and immunological study of oligosaccharide derivatives related to galactomannan from Antrodia cinnamomea[J]. Chinese Chemical Letters, ;2024, 35(5): 109089. doi: 10.1016/j.cclet.2023.109089 shu

Convergent synthesis and immunological study of oligosaccharide derivatives related to galactomannan from Antrodia cinnamomea

Shuying Li ^{a, 1} ,
Weiwei ZhuGe ^{a, 1} ,
Xuan Sun ^{a, 1} ,
Chongzhen Sun ^a ,
Zhaojun Liu ^a ,
Chenghe Xiong ^a ,
Min Xiao ^{a, b} ,
Guofeng Gu ^{a, b, *,}

a.
National Glycoengineering Research Center and Shandong Key Laboratory of Carbohydrate Chemistry and Glycobiology, Shandong University, Qingdao 266237, China
b.
NMPA Key Laboratory for Quality Research and Evaluation of Carbohydrate-based Medicine, Shandong University, Qingdao 266237, China

guofenggu@sdu.edu.edu

Received Date: 7 July 2023
Revised Date: 7 September 2023
Accepted Date: 11 September 2023
Available Online: 17 September 2023

Figures(6)

The galactomannan from Antrodia cinnamomea (AC) is characterized as one of the important bioactive components that exhibits potential immunostimulatory propriety. The biological function of its corresponding oligosaccharide fragments has not been revealed yet. In this study, we reported the first chemical synthesis of the series of oligosaccharide fragments related to AC galactomannan via the convergent glycosylation strategy. The preliminary immunological evaluation of these synthesized AC oligosaccharides disclosed that the backbone tetrasaccharide 1d showed the best immunomodulatory ability on enhancing proliferation, phagocytosis and cytokines secretion of Raw264.7 macrophages in vitro, indicating its immense potential as an immunostimulant candidate.
- Antrodia cinnamomea,
- Galactomannan,
- Oligosaccharide,
- Immunostimulatory propriety,
- Chemical synthesis
1. [1]
  A. Bhambri, M. Srivastava, V.G. Mahale, et al., Front. Microbiol. 13 (2022) 837266. doi: 10.3389/fmicb.2022.837266
2. [2]
  V. Bell, C.R.P.G. Silva, J. Guina, T.H. Fernandes, Front. Nutr. 9 (2022) 1050099. doi: 10.3389/fnut.2022.1050099
3. [3]
  J. Xu, R. Shen, Z. Jiao, et al., Nutrients 14 (2022) 2622. doi: 10.3390/nu14132622
4. [4]
  S.H. Tu, C.H. Wu, L.C. Chen, et al., Agric. Food Chem. 60 (2012) 3612–3618. doi: 10.1021/jf300221g
5. [5]
  N. Perera, F.L. Yang, C.M. Chang, et al., Org. Lett. 19 (2017) 3486–3489. doi: 10.1021/acs.orglett.7b01468
6. [6]
  N. Perera, F.L. Yang, Y.T. Lu, et al., Int. J. Biol. Sci. 14 (2018) 1378–1388. doi: 10.7150/ijbs.24564
7. [7]
  C.S. Chao, C.Y. Lin, S. Mulani, W.C. Hung, K.K.T. Mong, Chem. Eur. J. 17 (2011) 12193–12202. doi: 10.1002/chem.201100732
8. [8]
  A. Kafle, J. Liu, L. Cui, Can. J. Chem. 94 (2016) 894–901. doi: 10.1139/cjc-2016-0417
9. [9]
  F. Yamazaki, S. Sato, T. Nukada, Y. Ito, T. Ogawa, Carbohydr. Res. 201 (1990) 31–50. doi: 10.1016/0008-6215(90)84223-H
10. [10]
  K. Chayajarus, D.J. Chambers, M.J. Chughtai, A.J. Fairbanks, Org. Lett. 6 (2004) 3797–3800. doi: 10.1021/ol048427o
11. [11]
  D. Wang, D.C. Xiong, X.S. Ye, Chin. Chem. Lett. 29 (2018) 1340–1342. doi: 10.1016/j.cclet.2017.12.014
12. [12]
  K.K.T. Mong, K.S. Shiau, Y.H. Lin, K.C. Cheng, C.H. Lin, Org. Biomol. Chem. 13 (2015) 11550–11560. doi: 10.1039/C5OB01786F
13. [13]
  C. Li, Y. Sun, J. Zhang, et al., Carbohydr. Res. 376 (2013) 15–23. doi: 10.1016/j.carres.2013.02.008
14. [14]
  C.H. Wang, S.T. Li, T.L. Lin, et al., Angew. Chem. Int. Ed. 52 (2013) 9157–9161. doi: 10.1002/anie.201302540
15. [15]
  D. Wang, W. Zhuge, Z. Guo, G. Gu, Carbohydr. Res. 442 (2017) 41–51. doi: 10.1016/j.carres.2017.03.004
16. [16]
  R.R. Schmidt, J. Michel, Angew. Chem. Int. Ed. 19 (1980) 731–732. doi: 10.1002/anie.198007311
17. [17]
  K. Ruda, J. Lindberg, P.J. Garegg, S. Oscarson, P. Konradsson, J. Am. Chem. Soc. 122 (2000) 11067–11072. doi: 10.1021/ja001515t
18. [18]
  M. Bertolini, C.P.J. Glaudemans, Carbohydr. Res. 15 (1970) 263–270. doi: 10.1016/S0008-6215(00)88010-6
19. [19]
  K. Bock, C. Pedersen, J. Chem. Soc., Perkin Trans. 2 (1974) 293–297.
20. [20]
  J. Duus, C.H. Gotfredsen, K. Bock, Chem. Rev. 100 (2000) 4589–4614. doi: 10.1021/cr990302n
21. [21]
  Y. Li, M. Liu, K. Yang, J. Tian, Chin. Herb. Med. 14 (2022) 254–262.
22. [22]
  Q.M. Liu, S.S. Xu, L. Li, et al., Carbohydr. Polym. 165 (2017) 189–196. doi: 10.1016/j.carbpol.2017.02.032
23. [23]
  Z. Liu, Z. Liu, L. Li, et al., Food Sci. Nutr. 10 (2022) 1093–1102. doi: 10.1002/fsn3.2735
24. [24]
  H. Sun, J. Zhang, F. Chen, et al., Carbohydr. Polym. 121 (2015) 388–402. doi: 10.1016/j.carbpol.2014.12.023
25. [25]
  Y. Chen, P. Li, Y. Peng, et al., Free Radic. Biol. Med. 172 (2021) 590–603. doi: 10.1016/j.freeradbiomed.2021.07.005
26. [26]
  N.G. Geum, H.J. Eo, H.J. Kim, et al., J. Funct. Foods 73 (2020) 104139. doi: 10.1016/j.jff.2020.104139
1. [1]
  Lingxin Li , Jing Hu , Chunjun Qin , Juntao Cai , Xiaopeng Zou , Guangzong Tian , Peter H. Seeberger , Jian Yin . Immunological evaluation of the autism-related bacterium Enterocloster bolteae capsular polysaccharide driven by chemical synthesis. Chinese Chemical Letters, 2025, 36(9): 110797-. doi: 10.1016/j.cclet.2024.110797
2. [2]
  Kai Zhou , Ao Sun , Yuchao Wang , Hang Dong , Chenkai Bai , Yidian Mo , Xuyang Ding , Xiangbao Meng , Zhongtang Li , Zhongjun Li . Semisynthesis of rare chondroitin sulfate B and T oligosaccharides. Chinese Chemical Letters, 2025, 36(9): 110783-. doi: 10.1016/j.cclet.2024.110783
3. [3]
  Yuheng Zhou . 大学课堂的色彩——探索过渡元素的美. University Chemistry, 2025, 40(6): 303-309. doi: 10.12461/PKU.DXHX202407110
4. [4]
  Xu-Hui Yue , Xiang-Wen Zhang , Hui-Min He , Lei Qiao , Zhong-Ming Sun . Synthesis, chemical bonding and reactivity of new medium-sized polyarsenides. Chinese Chemical Letters, 2024, 35(7): 108907-. doi: 10.1016/j.cclet.2023.108907
5. [5]
  Ying Li , Long-Jie Wang , Yong-Kang Zhou , Jun Liang , Bin Xiao , Ji-Shen Zheng . An improved installation of 2-hydroxy-4-methoxybenzyl (iHmb) method for chemical protein synthesis. Chinese Chemical Letters, 2024, 35(5): 109033-. doi: 10.1016/j.cclet.2023.109033
6. [6]
  Xueling Yu , Lixing Fu , Tong Wang , Zhixin Liu , Na Niu , Ligang Chen . Multivariate chemical analysis: From sensors to sensor arrays. Chinese Chemical Letters, 2024, 35(7): 109167-. doi: 10.1016/j.cclet.2023.109167
7. [7]
  Tiantian Long , Hongmei Luo , Jingbo Sun , Fengniu Lu , Yi Chen , Dong Xu , Zhiqin Yuan . Carbonization-engineered ultrafast chemical reaction on nanointerface. Chinese Chemical Letters, 2025, 36(3): 109728-. doi: 10.1016/j.cclet.2024.109728
8. [8]
  Xi Xue , Kai Chen , Hanyu Sun , Xiangying Liu , Xue Liu , Shize Li , Jingjie Yan , Yu Peng , Mohammad S. Mubarak , Ahmed Al-Harrasi , Hai-Yu Hu , Yafeng Deng , Xiandao Pan , Xiaojian Wang . Bidirectional Chemical Intelligent Net: A unified deep learning–based framework for predicting chemical reaction. Chinese Chemical Letters, 2025, 36(11): 110968-. doi: 10.1016/j.cclet.2025.110968
9. [9]
  Min Fu , Pan He , Sen Zhou , Wenqiang Liu , Bo Ma , Shiying Shang , Yaohao Li , Ruihan Wang , Zhongping Tan . An unexpected stereochemical effect of thio-substituted Asp in native chemical ligation. Chinese Chemical Letters, 2024, 35(8): 109434-. doi: 10.1016/j.cclet.2023.109434
10. [10]
  Xianxu Chu , Lu Wang , Junru Li , Hui Xu . Surface chemical microenvironment engineering of catalysts by organic molecules for boosting electrocatalytic reaction. Chinese Chemical Letters, 2024, 35(8): 109105-. doi: 10.1016/j.cclet.2023.109105
11. [11]
  Ali Dai , Zhiguo Zheng , Liusheng Duan , Jian Wu , Weiming Tan . Small molecule chemical scaffolds in plant growth regulators for the development of agrochemicals. Chinese Chemical Letters, 2025, 36(4): 110462-. doi: 10.1016/j.cclet.2024.110462
12. [12]
  Hongen Cao , Xinrui Xiao , Xu Zhang , Yiyang Zhang , Lei Yu . Element Transfer Reaction theory: Scientific connotation and its applications in chemical industry. Chinese Chemical Letters, 2025, 36(9): 110924-. doi: 10.1016/j.cclet.2025.110924
13. [13]
  Huimin Luan , Qinming Wu , Jianping Wu , Xiangju Meng , Feng-Shou Xiao . Templates for the synthesis of zeolites. Chinese Journal of Structural Chemistry, 2024, 43(4): 100252-100252. doi: 10.1016/j.cjsc.2024.100252
14. [14]
  Hang Wang , Qi Wang , Chuan-De Wu . Continuous synthesis of ammonia. Chinese Journal of Structural Chemistry, 2025, 44(3): 100437-100437. doi: 10.1016/j.cjsc.2024.100437
15. [15]
  Min Huang , Ru Cheng , Shuai Wen , Liangtong Li , Jie Gao , Xiaohui Zhao , Chunmei Li , Hongyan Zou , Jian Wang . Ultrasensitive detection of microRNA-21 in human serum based on the confinement effect enhanced chemical etching of gold nanorods. Chinese Chemical Letters, 2024, 35(9): 109379-. doi: 10.1016/j.cclet.2023.109379
16. [16]
  Lian Sun , Honglei Wang , Ming Ma , Tingting Cao , Leilei Zhang , Xingui Zhou . Shape and composition evolution of Pt and Pt₃M nanocrystals under HCl chemical etching. Chinese Chemical Letters, 2024, 35(9): 109188-. doi: 10.1016/j.cclet.2023.109188
17. [17]
  Yongjian Li , Xinyu Zhu , Chenxi Wei , Youyou Fang , Xinyu Wang , Yizhi Zhai , Wenlong Kang , Lai Chen , Duanyun Cao , Meng Wang , Yun Lu , Qing Huang , Yuefeng Su , Hong Yuan , Ning Li , Feng Wu . Unraveling the chemical and structural evolution of novel Li-rich layered/rocksalt intergrown cathode for Li-ion batteries. Chinese Chemical Letters, 2024, 35(12): 109536-. doi: 10.1016/j.cclet.2024.109536
18. [18]
  Xue Zheng , Jizhen Xie , Xing Zhang , Weiting Sun , Heyang Zhao , Yantuan Li , Cheng Wang . Corrigendum to "An overview of polymeric nanomicelles in clinical trials and on the market" [Chinese Chemical Letters 32 (2021) 243-257]. Chinese Chemical Letters, 2025, 36(2): 110545-. doi: 10.1016/j.cclet.2024.110545
19. [19]
  Jingyu Shi , Xiaofeng Wu , Yutong Chen , Yi Zhang , Xiangyan Hou , Ruike Lv , Junwei Liu , Mengpei Jiang , Keke Huang , Shouhua Feng . Structure factors dictate the ionic conductivity and chemical stability for cubic garnet-based solid-state electrolyte. Chinese Chemical Letters, 2025, 36(5): 109938-. doi: 10.1016/j.cclet.2024.109938
20. [20]
  Jian Li , Jinjin Chen , Qi-Long Hu , Zhen Wang , Xiao-Feng Xiong . Recent progress of chemical methods for lysine site-selective modification of peptides and proteins. Chinese Chemical Letters, 2025, 36(5): 110126-. doi: 10.1016/j.cclet.2024.110126

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(1027)
HTML views(23)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142