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RESEARCH ARTICLE
Contents Vol 75(4)

Research progress on hydroxyl protection of iridoid glycosides

Yuanfang Kong https://orcid.org/0000-0002-9220-4275 A * , Bin Yang A , Jingyu Zhang A and Chunhong Dong B C D *
+ Author Affiliations
- Author Affiliations

A College of Pharmacy, Henan University of Chinese Medicine, Zhengzhou, Henan 450046, China.

B Henan Polysaccharide Research Center, Zhengzhou, Henan 450046, China.

C Henan Key Laboratory of Chinese Medicine for Polysaccharides and Drugs Research, Zhengzhou, Henan 450046, China.

D Academy of Chinese Medical Science, Henan University of Chinese Medicine, Zhengzhou, Henan 450046, China.




Yuanfang Kong received her master’s degree from Lanzhou University. In 2018, she graduated from Nankai University with a doctorate degree in organic chemistry. She now teaches at Henan University of Chinese Medicine and her research direction is drug design, synthesis and development and application. In recent years, she has contributed towards more than 20 research papers that have been published in academic journals, such as Organic Letters, Advanced Synthesis & Catalysis and European Journal of Organic Chemistry. She has received approval for two invention patents.


Bin Yang is from Handan in Hebei, China. She studied medicinal chemistry at Henan University of Chinese Medicine, completing her undergraduate degree in 2019. She is pursuing her master’s degree at Henan Key Laboratory of Chinese Medicine for Polysaccharides and Drugs in Henan University of Chinese Medicine. Her research focuses on the structural modification and biological activity evaluation of iridoid glycosides.


Jingyu Zhang, PhD, professor of Henan University of Chinese Medicine. His research direction is drug design, synthesis and development and application. Zhang Jingyu has presided over the China Postdoctoral Science Fund, Henan Province Science and Technology Research Project, Zhengzhou City Science and Technology Research Project, University Basic Research Business Fee Project and the Henan University of Traditional Chinese Medicine Innovation Talents Program. In recent years, he has contributed towards 30 research papers published in academic journals, such as Journal of Advanced Research, Analytica Chimica Acta, Tetrahedron Letters and European Journal of Medicinal Chemistry. He has received approval for three invention patents.


Chunhong Dong, PhD, professor of Henan University of Chinese Medicine. Her research direction is drug design, synthesis and development and application. Chunhong Dong has published more than 50 academic papers and presided over six key scientific and technological projects of the National Natural Science Foundation of China and Henan Province. She has received approval for five invention patents.
* Correspondence to: kongyf@hactcm.edu.cn

Handling Editor: Manabu Abe

Australian Journal of Chemistry 75(4) 249-264 https://doi.org/10.1071/CH21260
Submitted: 5 October 2021  Accepted: 31 January 2022   Published: 13 April 2022

© 2022 The Author(s) (or their employer(s)). Published by CSIRO Publishing.

Abstract

Iridoids, an important active ingredient, are widely distributed in varieties of Chinese herbal medicines and have varieties of pharmacological activities, such as anti-tumor, hypoglycemic, anti-inflammatory and so on, most of which exist in the form of glycosides in nature. However, its clinical application is limited by poor lipid solubility, low bioavailability and short half-life. It is necessary to optimize the structure of iridoids. It is hard to modify the hydroxyl groups at specific sites because iridoid glycosides are polyhydroxy compounds and very complex. In this paper, the words of ‘Iridoid glycosides’ and ‘Hydroxyl protection’ were used as the keywords, more than 200 articles from 1965 to 2021 were obtained from databases, such as CNKI, PubMed, Scifinder and so on. Finally, 60 articles were selected to summarize the hydroxyl protection of iridoid glycosides, which will provide a theoretical basis for their structural modification and stimulate their application potential in the field of drug research and development.

Keywords: hydroxyl deprotection, hydroxyl protection, iridoid glycosides, natural product, polyhydroxy compounds, progress, research, structural modifications.


References

[1]  Z Liu, Y Niu, L Zhou, L Meng, S Chen, M Wang, J Hu, W Kang, Front Chem 2021, 9, 657028.
         | Crossref | GoogleScholarGoogle Scholar | 33855012PubMed |

[2]  JH Guo, CW Tian, X Liu, TJ Zhang, Drug Eval Res 2011, 34, 293. [In Chinese]

[3]  LN Ma, CW Tian, TJ Zhang, LJ Zhang, XH Xu, Chin Tradit Herb Drugs 2008, 39, 790. [In Chinese]

[4]  J Xing, WR Xu, P Liu, BN Liu, HX Fu, W Liu, YL Wang, LD Tang, Chin Tradit Herb Drugs 2009, 40, 930. [In Chinese]

[5]  XZ Yin, HX Hui, AH Jin, X Wang, JS Quan, Chin J Exp Tradit Med Formulae 2010, 16, 134. [In Chinese]

[6]  AH Jin, L Piao, XZ Yin, JS Quan, Chin Tradit Herb Drugs 2012, 43, 332. [In Chinese]

[7]  B Shukla, PK Visen, GK Patnaik, BN Dhawan, Planta Med 1991, 57, 29.
         | Crossref | GoogleScholarGoogle Scholar | 2062954PubMed |

[8]  B Ahmed, AJ Al-Rehaily, TA Al-Howiriny, KA El-Sayed, MS Ahmad, Biol Pharm Bull 2003, 26, 462.
         | Crossref | GoogleScholarGoogle Scholar | 12673026PubMed |

[9]  X Li, Z Xu, Z Jiang, L Sun, J Ji, J Miao, X Zhang, X Li, S Huang, T Wang, L Zhang, Acta Biochim Biophys Sin 2014, 46, 738.
         | Crossref | GoogleScholarGoogle Scholar | 25178463PubMed |

[10]  H Stuppner, H Wagner, Planta Med 1989, 55, 467.
         | Crossref | GoogleScholarGoogle Scholar | 17262460PubMed |

[11]  Y Dwivedi, R Rastogi, R Mehrotra, NK Garg, BN Dhawan, Pharmacol Res 1993, 27, 189.
         | Crossref | GoogleScholarGoogle Scholar | 8474962PubMed |

[12]  B Saraswat, P Visen, G Patnaik, Indian J Exp Biol 1993, 31, 316.
         | 8359830PubMed |

[13]  ZJ Zhu, ZY Qian, LH Lu, XM Ren, Chin Tradit Herb Drugs 1999, 30, 841.

[14]  W Qiao, Foreign Medicine (Botanical Medicine) 2002, 251. [In Chinese]

[15]  G Blatter, JM Beau, JC Jacquinet, Carbohydr Res 1994, 260, 189.
         | Crossref | GoogleScholarGoogle Scholar | 8069873PubMed |

[16]  N Kasuya, K Iiyama, G Meshitsuka, A Ishizu, Carbohydr Res 1994, 260, 251.
         | Crossref | GoogleScholarGoogle Scholar |

[17]  JG Moffatt, ID Jenkins, JPH Verheyden, J Am Chem Soc 1971, 93, 4323.
         | Crossref | GoogleScholarGoogle Scholar | 5131149PubMed |

[18]  A Sharma, I Ramos-Tomillero, A El-Faham, H Rodríguez, BG de la Torre, F Albericio, ChemistryOpen 2017, 6, 206.
         | Crossref | GoogleScholarGoogle Scholar | 28413752PubMed |

[19]  MA Ashraf, ZL Liu, C Li, DQ Zhang, Appl Organomet Chem 2021, 35, 6131.

[20]  D Zheng, W Cao, H Ma, K Ding, Chin J Org Chem 2016, 36, 1122.
         | Crossref | GoogleScholarGoogle Scholar |

[21]  S Valverde, AM Gómez, A Hernández, B Herradón, JC López, J Chem Soc Chem Commun 1995, 2005.
         | Crossref | GoogleScholarGoogle Scholar |

[22]  CK Hill, JF Hartwig, Nat Chem 2017, 9, 1213.
         | Crossref | GoogleScholarGoogle Scholar | 29168493PubMed |

[23]  D Lee, MS Taylor, J Am Chem Soc 2011, 133, 3724.
         | Crossref | GoogleScholarGoogle Scholar | 21355584PubMed |

[24]  CC Wang, JC Lee, SY Luo, SS Kulkarni, YW Huang, CC Lee, KL Chang, SC Hung, Nature 2007, 446, 896.
         | Crossref | GoogleScholarGoogle Scholar | 17443183PubMed |

[25]  MA Witschi, J Gervay-Hague, Org Lett 2010, 12, 4312.
         | Crossref | GoogleScholarGoogle Scholar | 20799705PubMed |

[26]  Y Wang, YZ Xu, ZW Yang, XY Liu, QW Wang, Chin J Chem 1988, 6, 244.

[27]  F Björkling, SE Godtfredsen, l Kirk, J Chem Soc, Chem Commun 1989, 934.
         | Crossref | GoogleScholarGoogle Scholar |

[28]  T Kawabata, W Muramatsu, T Nishio, T Shibata, H Schedel, J Am Chem Soc 2007, 129, 12890.
         | Crossref | GoogleScholarGoogle Scholar | 17902666PubMed |

[29]  S Liu, X Cheng, XF Li, Y Kong, S Jiang, C Dong, G Wang, Sci Rep-Uk 2020, 10, 20415.
         | Crossref | GoogleScholarGoogle Scholar |

[30]  C Dong, S Liu, X Cheng, Q Wang, S Jiang, G Wang, BMC Chem 2019, 13, 109.
         | Crossref | GoogleScholarGoogle Scholar | 31453572PubMed |

[31]  X Cachet, B Deguin, F Tillequin, Y Rolland, M Koch, Helv Chim Acta 2000, 83, 2812.
         | Crossref | GoogleScholarGoogle Scholar |

[32]  VC Rakotondramasy, C Mouriès, X Cachet, A Neghra, M El Mourabet, Mou Chemistry 2010, 45, 2314.
         | Crossref | GoogleScholarGoogle Scholar |

[33]  H Lemoine, D Marković, B Deguin, J Org Chem 2014, 79, 4358.
         | Crossref | GoogleScholarGoogle Scholar | 24738692PubMed |

[34]  C Lemus, M Koch, S Michel, B Deguin, ARKIVOC 2014, 2014, 184.
         | Crossref | GoogleScholarGoogle Scholar |

[35]  C Mouriès, VC Rakotondramasy, F Libot, M Koch, F Tillequin, B Deguin, Chem Biodiversity 2005, 2, 695.
         | Crossref | GoogleScholarGoogle Scholar |

[36]  X Zheng, RD Gandour, KJ Edgar, Carbohydr Polym 2014, 111, 25.
         | Crossref | GoogleScholarGoogle Scholar | 25037325PubMed |

[37]  S Lei, D Zhang, Y Qi, SR Chowdhury, R Sun, J Wang, Y Du, L Fu, F Jiang, Eur J Med Chem 2020, 205, 112508.
         | 32738350PubMed |

[38]  X Cachet, B Deguin, M Koch, K Makhlouf, F Tillequin, J Nat Prod 1999, 62, 400.
         | Crossref | GoogleScholarGoogle Scholar | 10075802PubMed |

[39]  S Wu, L Yang, W Sun, L Si, S Xiao, Q Wang, L Dechoux, S Thorimbert, M Sollogoub, D Zhou, Y Zhang, Eur J Med Chem 2017, 130, 308.
         | Crossref | GoogleScholarGoogle Scholar | 28254701PubMed |

[40]  AK Mohammad-Ali, TH Chan, AW Thomas, et al. Can J Chem 1994, 72, 2137.
         | Crossref | GoogleScholarGoogle Scholar |

[41]  P Samara, N Christoforidou, C Lemus, A Argyropoulou, K Ioannou, K Vougogiannopoulou, N Aligiannis, E Paronis, N Gaboriaud-Kolar, O Tsitsilonis, AL Skaltsounis, Eur J Med Chem 2017, 137, 11.
         | Crossref | GoogleScholarGoogle Scholar | 28551177PubMed |

[42]  G Sarikaki, N Christoforidou, N Gaboriaud-Kolar, AB Smith III, IK Kostakis, A-L Skaltsounis, J Nat Prod 2020, 83, 1735.
         | Crossref | GoogleScholarGoogle Scholar | 32441936PubMed |

[43]  HA Garro, C García, VS Martín, CE Tonn, CR Pungitore, Bioorg Med Chem Lett 2015, 25, 914.
         | Crossref | GoogleScholarGoogle Scholar | 25582597PubMed |

[44]  S Pandeti, K Sharma, SR Bathula, N Tadigoppula, Phytomedicine 2014, 21, 333.
         | Crossref | GoogleScholarGoogle Scholar | 24075214PubMed |

[45]  W Muramatsu, K Mishiro, Y Ueda, T Furuta, T Kawabata, Eur J Org Chem 2010, 2010, 827.
         | Crossref | GoogleScholarGoogle Scholar |

[46]  VC Rakotondramasy, R Laschiazza, M Lecsö-Bornet, M Koch, F Tillequin, B Deguin, J Nat Prod 2007, 70, 19.
         | Crossref | GoogleScholarGoogle Scholar | 17253843PubMed |

[47]  Jiang FQ, Lei SW, Lv D, Zhang Y, Du Y. Chinese Patent, 113004356. 2021.

[48]  B Danieli, M Luisetti, G Sampognaro, G Carrea, S Riva, J Mol Catal B: Enzym 1997, 3, 193.
         | Crossref | GoogleScholarGoogle Scholar |

[49]  P Qin, NW Duncan, C Wiebking, et al. J Pharm Biomed Anal 2012, 70, 337.
         | Crossref | GoogleScholarGoogle Scholar |

[50]  HR Hao, Y Chu, W Li, L Ding, Drug Eval Res 2018, 41, 1147. [In Chinese]

[51]  Li YF, Yang B, Yan L, Gao W, Omer KM, Foong LK. Synthetic Communications 2020; 50: 2132–2155.
| Crossref |

[52]  MJ Martinelli, R Vaidyanathan, JM Pawlak, NK Nayyar, UP Dhokte, CW Doecke, LMH Zollars, ED Moher, VV Khau, B Košmrlj, J Am Chem Soc 2002, 124, 3578.
         | Crossref | GoogleScholarGoogle Scholar | 11929246PubMed |

[53]  W Muramatsu, J Org Chem 2012, 77, 8083.
         | Crossref | GoogleScholarGoogle Scholar | 22928768PubMed |

[54]  L Chan, MS Taylor, Org Lett 2011, 13, 3090.
         | Crossref | GoogleScholarGoogle Scholar | 21591630PubMed |

[55]  H Hsieh, MW Schombs, MA Witschi, HJ Gervay, ChemInform 2014, 45, 9677.

[56]  AA Joseph, VP Verma, XY Liu, CH Wu, VM Dhurandhare, CC Wang, Eur J Org Chem 2012, 2012, 744.
         | Crossref | GoogleScholarGoogle Scholar |

[57]  EV Evtushenko, J Carbohydr Chem 2010, 29, 369.
         | Crossref | GoogleScholarGoogle Scholar |

[58]  EV Evtushenko, Carbohydr Res 2012, 359, 111.
         | Crossref | GoogleScholarGoogle Scholar | 22925773PubMed |

[59]  IH Chen, KGM Kou, DN Le, CM Rathbun, VM Dong, Chem - Eur J 2014, 20, 5013.
         | Crossref | GoogleScholarGoogle Scholar | 24623522PubMed |