综述与进展

尼亚那属二萜天然产物的全合成研究进展

  • 孟龙 ,
  • 乔金宝 ,
  • 赵玉明
展开
  • 陕西师范大学化学化工学院 应用表面与胶体化学教育部重点实验室 西安 710119

收稿日期: 2024-09-26

  修回日期: 2024-12-19

  网络出版日期: 2025-01-03

基金资助

国家自然科学基金(22371176); 国家自然科学基金(22201168)

Progress on the Total Synthesis of Ryania Diterpenoids

  • Long Meng ,
  • Jin-Bao Qiao ,
  • Yu-Ming Zhao
Expand
  • Key Laboratory of Applied Surface and Colloid Chemistry of Ministry of Education (MOE), School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an 710119

Received date: 2024-09-26

  Revised date: 2024-12-19

  Online published: 2025-01-03

Supported by

National Natural Science Foundation of China(22371176); National Natural Science Foundation of China(22201168)

摘要

尼亚那属二萜是从中/南美洲大枫子科灌木中分离得到的一类天然产物, 是一类具有五环笼状结构、多个连续立体中心及高度氧化态的二萜天然产物. 生物学研究发现, 其成员ryanodine对心肌钙离子通道(PyR)具有专一的亲和调节作用, 是迄今发现的少数几个具有此功能的有机小分子化合物之一, 对心血管疾病的治疗具有潜在药用价值, 然而, 复杂的化学结构使得这类天然产物的合成充满了极大挑战. 综述了目前有机合成化学家对该类天然产物的全合成研究进展.

本文引用格式

孟龙 , 乔金宝 , 赵玉明 . 尼亚那属二萜天然产物的全合成研究进展[J]. 有机化学, 2025 , 45(3) : 804 -813 . DOI: 10.6023/cjoc202409037

Abstract

Ryania diterpene natural products were isolated from Ryania speciosa in the Central/South American, structurally which have a cage-type pentacyclic core, multiple continuous stereocenters, and a high oxidation state. Biological studies have found that its member ryanodine has a specific regulatory effect on myocardial calcium ion channels (PyR). It is one of the few organic small molecule compounds with this function discovered so far and has potential medicinal value for treating cardiovascular diseases. However, the complex chemical structure makes the synthesis of these natural products full of challenges. Herein the current research progress of organic chemists on the total synthesis of these natural products is reviewed.

参考文献

[1]
Rogers, E. F.; Koniuszy, F. R.; Shavel, J., Jr.; Folkers, K. J. Am. Chem. Soc. 1948, 70, 3086.
[2]
(a) Kelly, R. B.; Whittingham, D. J.; iesner, K. Can. J. Chem. 1951, 29, 905.
[2]
(b) Wiesner, K.; Valenta, Z.; Findlay, J. A. Tetrahedron Lett. 1967, 8, 221.
[2]
(c) Srivastava, S. N.; Przybylska, M. Can. J. Chem. 1968, 46, 795.
[2]
(d) Wiesner, K. Collect. Czech. Chem. Commun. 1968, 33, 2656.
[2]
(e) Koshimizu, M.; Nagatomo, M.; Inoue, M. Angew. Chem., nt. Ed. 2016, 55, 2493.
[3]
Totini, C. H.; Umehara, E.; Reis, I. M. A.; Lago, J. H. G.; Branco, A. Chem. Biodiversity 2023, 20, e202300947.
[4]
Ruest, L.; Deslongchamps, P. Can. J. Chem. 1993, 71, 634.
[5]
For recent reviews on ryanodine receptors, see: (a) Wehrens, X. H. T.; Marks, A. R. Ryanodine Receptors: Structure, Function and Dysfunction in Clinical Disease. Springer, New York, 2005.
[5]
(b) Betzenhauser, M. J.; Marks, A. R. Pfluegers Arch. 2010, 460, 467.
[5]
(c) Mackrill, J. J. Biochem. Pharmacol. 2010, 79, 1535.
[5]
(d) Van Petegem, F. J. Biol. Chem. 2012, 287, 31624.
[6]
For selected reviews for drug discovery and natural products, see: (a) Li, J. W.-H.; Vederas, J. C. Science 2009, 325, 161.
[6]
(b) Newman, D. J.; Cragg, G. M. J. Nat. Prod. 2012, 75, 311.
[6]
(c) Butler, M. S.; Robertson, A. A. B.; Cooper, M. A. Nat. Prod. Rep. 2014, 31, 1612.
[7]
For a review on ryanodine, see: Sutko, J. L.; Airey, J. A.; Welch, W.; Ruest, L. Pharmacol. Rev. 1997, 49, 53.
[8]
Zeng, J. F.; Xue, Y. B.; Shu, P. H.; Qian, H. Q.; Sa, R. J.; Xiang, M.; Li, X.-N.; Luo, Z. W.; Yao, G. M.; Zhang, Y. H. J. Nat. Prod. 2014, 77, 1948.
[9]
(a) Be?langer, A.; Berney, D. J. F.; Borschberg, H.-J.; Brousseau, R.; Doutheau, A.; Durand, R.; Katayama, H.; Lapalme, R.; Leturc, D. M.; Liao, C.-C.; MacLachlan, F. N.; Maffrand, J.-P.; Marazza, F.; Martino, R.; Moreau, C.; Saint-Laurent, L.; Saintonge, R.; Soucy, P.; Ruest, L.; Deslongchamps, P. Can. J. Chem. 1979, 57, 3348.
[9]
(b) Deslongchamps, P.; Be?langer, A.; Berney, D. J. F.; Borschberg, H.-J.; Brousseau, R.; Doutheau, A.; Durand, R.; Katayama, H.; Lapalme, R.; Leturc, D. M.; Liao, C.-C.; MacLachlan, F. N.; Maffrand, J.-P.; Marazza, F.; Martino, R.; Moreau, C.; Ruest, L.; Saint-Laurent, L.; Saintonge, R.; Soucy, P. Can. J. Chem. 1990, 68, 186.
[10]
(a) Hagiwara, K.; Himuro, M.; Hirama, M.; Inoue, M. Tetrahedron Lett. 2009, 50, 1035.
[10]
(b) Urabe, D.; Nagatomo, M.; Hagiwara, K.; Masuda, K.; Inoue, M. Chem. Sci. 2013, 4, 1615.
[11]
Nagatomo, M.; Koshimizu, M.; Masuda, K.; Tabuchi, T.; Urabe, D.; Inoue, M. J. Am. Chem. Soc. 2014, 136, 5916.
[12]
Masuda, K.; Nagatomo, M.; Inoue, M. Chem. Pharm. Bull. 2016, 64, 874.
[13]
Nagatomo, M.; Hagiwara, K.; Masuda, K.; Koshimizu, M.; Kawamata, T.; Matsui, Y.; Urabe, D. Inoue, M. Chem.-Eur. J. 2016, 22, 222.
[14]
Chuang, K. V.; Xu, C.; Reisman, S. E. Science 2016, 353, 912.
[15]
Han, A.; Virgil, S. C.; Reisman, S. E. ACS Cent. Sci. 2017, 3, 278.
[16]
Du, K.; Kier, M. J.; Stempel, Z. D.; Jeso, V.; Rheingold, A. L.; Micalizio, G. C. J. Am. Chem. Soc. 2020, 142, 12937.
[17]
Qiao, J.-B.; Meng, L.; Pei, J. Y.; Shao, H.; Zhao, Y.-M. Angew. Chem.,Int. Ed. 2024, 63, e202417647.
文章导航

/