二苯乙烯C-糖苷和O-糖苷的合成研究进展
Research Progress in the Synthesis of C-Glycosides and O-Glycosides of Styrene
DOI: 10.12677/jocr.2026.143038, PDF,   
作者: 王丽丽, 袁嘉遥, 李文玲：兰州交通大学化学化工学院，甘肃 兰州
关键词: 二苯乙烯；C-糖苷；O-糖苷；溶解度；合成；Stilbenes； C-Glycosides； O-Glycosides； Solubility； Synthesis
摘要: 二苯乙烯类化合物具有丰富多样的生物活性，在人类生活中具有潜在的药用价值，它们的合成和应用已被广泛研究，然而，这些二苯乙烯类化合物在水中的不溶性极大限制了它们的生物利用度和药物开发。因此，在二苯乙烯单体上引入糖基有助于增加溶解度，降低毒性。本文归纳总结了近年来二苯乙烯0-糖苷和C-糖苷化合物的化学合成以及生物合成等方面的研究进展，并对未来该邻域的发展进行了展望。
Abstract: Stilbene compounds exhibit a wide range of biological activities and possess potential medicinal value for human applications, and their synthesis and application have been extensively investigated. Nevertheless, the poor water solubility of stilbenes severely restricts their bioavailability and pharmaceutical development. Accordingly, glycosylation modification on stilbene monomers can improve their aqueous solubility and reduce toxicity. This paper summarizes the recent advances in chemical synthesis and biosynthesis of stilbene O-glycosides and C-glycosides, and prospects the future development of this field.
文章引用：王丽丽, 袁嘉遥, 李文玲. 二苯乙烯C-糖苷和O-糖苷的合成研究进展[J]. 有机化学研究, 2026, 14(3): 440-450. https://doi.org/10.12677/jocr.2026.143038

参考文献

[1] Ahuja, I., Kissen, R. and Bones, A.M. (2012) Phytoalexins in Defense against Pathogens. Trends in Plant Science, 17, 73-90. [Google Scholar] [CrossRef] [PubMed]
[2] Zhang, Z., Chen, N., Liu, J., Wu, J., Zhang, J., Zhang, Y., et al. (2014) Protective Effect of Resveratrol against Acute Lung Injury Induced by Lipopolysaccharide via Inhibiting the myd88-Dependent Toll-Like Receptor 4 Signaling Pathway. Molecular Medicine Reports, 10, 101-106. [Google Scholar] [CrossRef] [PubMed]
[3] Hung, L.M., Chen, J.K., Lee, R.S., Liang, H.C. and Su, M.J. (2001) Beneficial Effects of Astringinin, a Resveratrol Analogue, on the Ischemia and Reperfusion Damage in Rat Heart. Free Radical Biology and Medicine, 30, 877-883. [Google Scholar] [CrossRef] [PubMed]
[4] Xiao, J. and Högger, P. (2015) Stability of Dietary Polyphenols under the Cell Culture Conditions: Avoiding Erroneous Conclusions. Journal of Agricultural and Food Chemistry, 63, 1547-1557. [Google Scholar] [CrossRef] [PubMed]
[5] Langenhan, J.M., Griffith, B.R. and Thorson, J.S. (2005) Neoglycorandomization and Chemoenzymatic Glycorandomization: Two Complementary Tools for Natural Product Diversification. Journal of Natural Products, 68, 1696-1711. [Google Scholar] [CrossRef] [PubMed]
[6] Torres, P., Poveda, A., Jimenez‐Barbero, J., Parra, J.L., Comelles, F., Ballesteros, A.O., et al. (2011) Enzymatic Synthesis of α‐Glucosides of Resveratrol with Surfactant Activity. Advanced Synthesis & Catalysis, 353, 1077-1086. [Google Scholar] [CrossRef] 
[7] Sovak, M. (2001) Grape Extract, Resveratrol, and Its Analogs: A Review. Journal of Medicinal Food, 4, 93-105. [Google Scholar] [CrossRef] [PubMed]
[8] Lee, S., Kim, J.H., Kim, Y.S., et al. (2013) Resveratrol Suppresses LPS-Induced Inflammatory Responses in RAW264.7 Macrophages through Inhibition of NF‑κB and MAPK Pathways. International Immunopharmacology, 15, 292‑299.
[9] Şöhretoğlu, D., Baran, M.Y., Arroo, R. and Kuruüzüm-Uz, A. (2018) Recent Advances in Chemistry, Therapeutic Properties and Sources of Polydatin. Phytochemistry Reviews, 17, 973-1005. [Google Scholar] [CrossRef] 
[10] Regev-Shoshani, G., Shoseyov, O., Bilkis, I. and Kerem, Z. (2003) Glycosylation of Resveratrol Protects It from Enzymic Oxidation. Biochemical Journal, 374, 157-163. [Google Scholar] [CrossRef] [PubMed]
[11] 张晶晶, 姚明, 李丽, 等. 白藜芦醇、白皮杉醇和赤松素的合成[J]. 有机化学, 2020, 40(4): 1062‑1067.
[12] Huang, G., Lv, M., Hu, J., Huang, K. and Xu, H. (2016) Glycosylation and Activities of Natural Products. Mini-Reviews in Medicinal Chemistry, 16, 1013-1016. [Google Scholar] [CrossRef] [PubMed]
[13] Xiao, J.B., Capanoglu, E., Jassbi, A.R. and Miron, A. (2015) Advance on the Flavonoid c-Glycosides and Health Benefits. Critical Reviews in Food Science and Nutrition, 56, S29-S45. [Google Scholar] [CrossRef] [PubMed]
[14] Baderschneider, B. and Winterhalter, P. (2000) Isolation and Characterization of Novel Stilbene Derivatives from Riesling Wine. Journal of Agricultural and Food Chemistry, 48, 2681-2686. [Google Scholar] [CrossRef] [PubMed]
[15] Ito, T., Tanaka, T., Ido, Y., Nakaya, K., Iinuma, M. and Riswan, S. (2000) Stilbenoids Isolated from Stem Bark of Shorea Hemsleyana. Chemical and Pharmaceutical Bulletin, 48, 1001-1005. [Google Scholar] [CrossRef] [PubMed]
[16] Kiessling, L.L. and Splain, R.A. (2010) Chemical Approaches to Glycobiology. Annual Review of Biochemistry, 79, 619-653. [Google Scholar] [CrossRef] [PubMed]
[17] Bokor, É., Kun, S., Goyard, D., Tóth, M., Praly, J., Vidal, S., et al. (2017) c-Glycopyranosyl Arenes and Hetarenes: Synthetic Methods and Bioactivity Focused on Antidiabetic Potential. Chemical Reviews, 117, 1687-1764. [Google Scholar] [CrossRef] [PubMed]
[18] Dos Santos, R.G., Jesus, A.R., Caio, J.M., et al. (2011) Fries-Type Reactions for the c-Glycosylation of Phenols. Current Organic Chemistry, 15, 128-148. [Google Scholar] [CrossRef] 
[19] Lucas, R., Alcantara, D. and Morales, J.C. (2009) A Concise Synthesis of Glucuronide Metabolites of Urolithin-B, Resveratrol, and Hydroxytyrosol. Carbohydrate Research, 344, 1340-1346. [Google Scholar] [CrossRef] [PubMed]
[20] Qiu, H., Tang, Z., Ma, W., Yuan, J. and Li, W. (2025) Total Synthesis of Four Natural Trans-Stilbene O-Glucosides. Tetrahedron, 171, Article 134417. [Google Scholar] [CrossRef] 
[21] Yoshida, M., Takahashi, Y. and Hattori, T. (2004) Synthesis of Resveratrol O‑Glucosides via Glycosylation with Glycosyl Fluoride. Carbohydrate Research, 339, 1767‑1773.
[22] Zhang, Z., Yu, B. and Schmidt, R.R. (2006) Synthesis of Mono‑ and di‑O‑β‑Glucopyranoside Conjugates of (E)‑Resveratrol. Synthesis, 2006, 1301-1306. [Google Scholar] [CrossRef] 
[23] Poulsen, M.M., Jørgensen, J.O.L., Jessen, N., Richelsen, B. and Pedersen, S.B. (2013) Resveratrol in Metabolic Health: An Overview of the Current Evidence and Perspectives. Annals of the New York Academy of Sciences, 1290, 74-82. [Google Scholar] [CrossRef] [PubMed]
[24] Kraft, T.E., Parisotto, D., Schempp, C. and Efferth, T. (2009) Fighting Cancer with Red Wine? Molecular Mechanisms of Resveratrol. Critical Reviews in Food Science and Nutrition, 49, 782-799. [Google Scholar] [CrossRef] [PubMed]
[25] Xu, L., Qi, T., Xu, L., Lu, L. and Xiao, M. (2016) Recent Progress in the Enzymatic Glycosylation of Phenolic Compounds. Journal of Carbohydrate Chemistry, 35, 1-23. [Google Scholar] [CrossRef] 
[26] Dirks-Hofmeister, M.E., Verhaeghe, T., De Winter, K. and Desmet, T. (2015) Creating Space for Large Acceptors: Rational Biocatalyst Design for Resveratrol Glycosylation in an Aqueous System. Angewandte Chemie International Edition, 54, 9289-9292. [Google Scholar] [CrossRef] [PubMed]
[27] Kumar-Ponnapalli, K., Kumar Adak, A., Das, A., Song, J., Wu, S., Sun, C., et al. (2017) Trans-Stilbene c-Glycosides: Synthesis by a Microwave-Assisted Heck Reaction and Evaluation of the SGLT-2 Inhibitory Activity. Asian Journal of Organic Chemistry, 6, 1308-1321. [Google Scholar] [CrossRef] 
[28] Schmidt, R.R. and Michel, J. (1984) Glycosyl Imidates. 31. Syntheses of Aryl O-Glycosides by Use of Glycosyl Trichloroacetimidates. Carbohydrate Research, 128, 275‑287.
[29] Mavlan, M., Ng, K., Panesar, H., Yepremyan, A. and Minehan, T.G. (2014) Synthesis of 3,3’-Di-o-Methyl Ardimerin and Exploration of Its DNA Binding Properties. Organic Letters, 16, 2212-2215. [Google Scholar] [CrossRef] [PubMed]
[30] Ma, W., Liu, H., Lei, T., Qiu, H., Yuan, J. and Li, W. (2024) Stereoselective Synthesis of Stilbene C-Glucosides. Chinese Journal of Organic Chemistry, 44, Article 2943. [Google Scholar] [CrossRef] 
[31] Guleria, S.P.S. and Gupta, A.K. (2002) Phenolic Compounds in the Heartwood of Tectona Grandis. Journal of Wood Science, 48, 242‑246.

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