Quebrachitol: Global Status and Basic Research

doi:10.1007/s13659-017-0120-3

Natural Products and Bioprospecting ›› 2017, Vol. 7 ›› Issue (1): 113-122.DOI: 10.1007/s13659-017-0120-3

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Quebrachitol: Global Status and Basic Research

Dong Wang¹, Shu-Qun Zhang¹, Zhe Chang¹, De-Xin Kong², Zhi-Li Zuo^1,3

1. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China;
2. State Key Laboratory of Agricultural Microbiology, Huazhong Agricultural University, Wuhan 430070, China;
3. Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming 650201, China

Received:2016-11-23 Revised:2017-01-02 Online:2018-02-06 Published:2017-02-24
About author:10.1007/s13659-017-0120-3
Supported by:
We gratefully thank financial assistance from the State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences (Grant Number P2013-ZZ05), Fund of Basic Research Plan of Yunnan Provincial Science and Technology Department (Grant Number 2014FA042). We also appreciate the support of Western Light Talent Culture Project[2014]91(to Z. Z.).

Quebrachitol: Global Status and Basic Research

Dong Wang¹, Shu-Qun Zhang¹, Zhe Chang¹, De-Xin Kong², Zhi-Li Zuo^1,3

1. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China;
2. State Key Laboratory of Agricultural Microbiology, Huazhong Agricultural University, Wuhan 430070, China;
3. Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming 650201, China

通讯作者: De-Xin Kong,e-mail:dxkong@mail.hzau.edu.cn;Zhi-Li Zuo,e-mail:zuozhili@mail.kib.ac.cn
作者简介:Mohd Shabbir,e-mail:shabbirmeo@gmail.com;Faqeer Mohammad,e-mail:faqeermohammad@rediffmail.com
基金资助:
We gratefully thank financial assistance from the State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences (Grant Number P2013-ZZ05), Fund of Basic Research Plan of Yunnan Provincial Science and Technology Department (Grant Number 2014FA042). We also appreciate the support of Western Light Talent Culture Project[2014]91(to Z. Z.).

Abstract

Abstract: Recently, there has been a renewed interest in the natural-products-inspired drugs. Quebrachitol (QCT) is one of naturally occurring optically active cyclitols that has now received considerable attention. Until the last decade, it came to be a starting point for the lead discovery. In this review, we had a discussion on the basic research of QCT, including its source, structure, properties, and the recent advances on its application. The biological activities and QCT-inspired leads that are potentially effective for treating human diseases were also discussed.

Key words: Quebrachitol (QCT), Structure, Biological activity, Application

摘要： Recently, there has been a renewed interest in the natural-products-inspired drugs. Quebrachitol (QCT) is one of naturally occurring optically active cyclitols that has now received considerable attention. Until the last decade, it came to be a starting point for the lead discovery. In this review, we had a discussion on the basic research of QCT, including its source, structure, properties, and the recent advances on its application. The biological activities and QCT-inspired leads that are potentially effective for treating human diseases were also discussed.

关键词: Quebrachitol (QCT), Structure, Biological activity, Application

Dong Wang, Shu-Qun Zhang, Zhe Chang, De-Xin Kong, Zhi-Li Zuo. Quebrachitol: Global Status and Basic Research[J]. Natural Products and Bioprospecting, 2017, 7(1): 113-122.

Dong Wang, Shu-Qun Zhang, Zhe Chang, De-Xin Kong, Zhi-Li Zuo. Quebrachitol: Global Status and Basic Research[J]. 应用天然产物, 2017, 7(1): 113-122.

References

1. D.J. Newman, G.M. Cragg, J. Nat. Prod. 79, 629-661 (2016)
2. H. Caner, E. Groner, L. Levy, I. Agranat, Drug Discov. Today 9, 105-110 (2004)
3. F.E. Koehn, G.T. Carter, Nat. Rev. Drug Discov. 4, 206-220 (2005)
4. A.L. Harvey, Drug Discov. Today 13, 894-901 (2008)
5. T. Rodrigues, D. Reker, P. Schneider, G. Schneider, Nat. Chem. 8, 531-541 (2016)
6. J. Vanalphen, Ind. Eng. Chem. 43, 141-145 (1951)
7. R. Adams, D.C. Pease, J.H. Clark, J. Am. Chem. Soc. 62, 2194-2196 (1940)
8. M. Diaz, A. Gonzalez, I. Castro-Gamboa, D. Gonzalez, C. Rossini, Carbohydr. Res. 343, 2699-2700 (2008)
9. M.G. de Carvalho, D.C. Cranchi, D.G. Kingston, A.A. Werle, Phytother. Res. 15, 715-717 (2001)
10. M.S. Chung, N.C. Kim, L. Long, L. Shamon, W.Y. Ahmad, S.N. Lorenzo, L.B.S. Kardono, E.J. Kennelly, J.M. Pezzuto, D.D. Soejarto, A.D. Kinghorn, Phytochem. Anal. 8, 49-54 (1997)
11. H. Kallio, M. Lassila, E. Jarvenpaa, G.G. Haraldsson, S. Jonsdottir, B. Yang, J. Chromatogr. B 877, 1426-1432 (2009)
12. Z.C. Wu, Z.Y. Yang, J.G. Li, H.B. Chen, X.M. Huang, H.C. Wang, Int. J. Food Sci. Nutr. 67, 762-772 (2016)
13. A.L. Patterson, T.N. White, Z. Kristallogr. 78, 86-90 (1931)
14. K.F. Huang, W.L. Luo, J. Chin. Chem. Soc. 41, 115-117 (1994)
15. M. Dowd, E. Stevens, J. Carbohydr. Chem. 21, 373-383 (2002)
16. R.H. Michell, Nat. Rev. Mol. Cell Biol. 9, 151-161 (2008)
17. R.A. Mccance, R.D. Lawrence, Biochem. J. 27, 986-989 (1933)
18. A. Dusotoit-Coucaud, B. Porcheron, N. Brunel, P. Kongsawadworakul, J. Franchel, U. Viboonjun, H. Chrestin, R. Lemoine, S. Sakr, Plant Cell Physiol. 51, 1878-1888 (2010)
19. P. Zimmet, K.G. Alberti, D.J. Magliano, P.H. Bennett, Nat. Rev. Endocrinol. 12, 616-622 (2016)
20. Y. Xue, Q. Miao, A. Zhao, Y. Zheng, Y. Zhang, P. Wang, H. Kallio, B. Yang, J. Funct. Foods 16, 223-233 (2015)
21. A.K. Rines, K. Sharabi, C.D. Tavares, P. Puigserver, Nat. Rev. Drug Discov. 15, 786-804 (2016)
22. B. Bussolati, L. Biancone, P. Cassoni, S. Russo, M. RolaPleszczynski, G. Montrucchio, G. Camussi, Am. J. Pathol. 157, 1713-1725 (2000)
23. L.S. Wang, K.C. Chow, Y.C. Wu, Scand. J. Gastroenterol. 37, 467-475 (2002)
24. S.M. Sato, J.A. Johansen, C.L. Jordan, R.I. Wood, Psychoneuroendocrinology 35, 1063-1073 (2010)
25. J. Yu, M. Akishita, M. Eto, H. Koizumi, R. Hashimoto, S. Ogawa, K. Tanaka, Y. Ouchi, T. Okabe, Biochem. Biophys. Res. Commun. 424, 538-543 (2012)
26. B. Xu, L. Gao, L. Wang, G. Tang, M. He, Y. Yu, X. Ni, Y. Sun, Br. J. Cancer 109, 1279-1286 (2013)
27. B.A. Moharam, I. Jantan, J. Jalil, K. Shaari, Molecules 15, 7840-7848 (2010)
28. R.L. Auten, J.M. Davis, Pediatr. Res. 66, 121-127 (2009)
29. A.R. Kim, Y.N. Zou, T.H. Park, K.H. Shim, M.S. Kim, N.D. Kim, J.D. Kim, S.J. Bae, J.S. Choi, H.Y. Chung, Phytother. Res. 18, 1-7 (2004)
30. S.S. Kim, C.K. Lee, S.S. Kang, H.A. Jung, J.S. Choi, Arch. Pharmacal Res. 20, 148-154 (1997)
31. H.V. Nobre Junior, G.M. Cunha, M.O. Moraes, M.F. Luciana, R.A. Oliveira, F.D. Maia, M.A. Nogueira, T.L. Lemos, V.S. Rao, Food Chem. Toxicol. 44, 1544-1551 (2006)
32. A. Lanas, M.A. Perez-Aisa, F. Feu, J. Ponce, E. Saperas, S. Santolaria, L. Rodrigo, J. Balanzo, E. Bajador, P. Almela, J.M. Navarro, F. Carballo, M. Castro, E. Quintero, G. Investigators of the Asociacion Espanola de, Am. J. Gastroenterol. 100, 1685-1693 (2005)
33. A. Lanas, Am. J. Gastroenterol. 103, 1104-1105 (2008)
34. T.M. de Olinda, T.L. Lemos, L.L. Machado, V.S. Rao, F.A. Santos, Phytomedicine 15, 327-333 (2008)
35. K. Gharzouli, A. Gharzouli, S. Amira, S. Khennouf, Exp. Toxicol. Pathol. 53, 175-180 (2001)
36. B.L. DeCorte, J. Med. Chem. 59, 9295-9304 (2016)
37. J.J. Kiddle, Chem. Rev. 95, 2189-2202 (1995)
38. N. Chida, T. Tobe, M. Suwama, M. Ohtsuka, S. Ogawa, J. Chem. Soc. Perkin Trans. 1, 2667-2673 (1992)
39. N. Chida, K. Yamada, S. Ogawa, J. Chem. Soc. Perkin Trans. 1, 1957-1962 (1993)
40. N. Chida, T. Tobe, K. Murai, K. Yamazaki, S. Ogawa, Heterocycles 38, 2383-2388 (1994)
41. N. Chida, S. Ogawa, Chem. Commun. 807-813 (1997)
42. N. Chida, M. Yoshinage, T. Tobe, S. Ogawa, Chem. Commun. 1043-1044 (1997)
43. N. Chida, N. Sakata, K. Murai, T. Tobe, T. Nagase, S. Ogawa, Bull. Chem. Soc. Jpn 71, 259-272 (1998)
44. T. Akiyama, M. Ohnari, H. Shima, S. Ozaki, Synlett 831-832 (1991)
45. A. Falshaw, J.B. Hart, P.C. Tyler, Carbohydr. Res. 329, 301-308 (2000)
46. D. Barton, S. Bath, D. Billington, S. Gero, B. Quicletsire, M. Samadi, J. Chem. Soc. Perkin Trans. 1, 1551-1558 (1995)
47. J.V. de Assis, M.R.C. Couri, R.S. Porto, W.B. de Almeida, L.H.R. dos Santos, R. Diniz, M.V. de Almeida, J. Heterocycl. Chem. 50, E142-E147 (2013)
48. C.S. Liu, S.R. Nahorski, B.V.L. Potter, J. Chem. Soc. Chem. Commun. 1014-1016 (1991)
49. C.S. Liu, S.T. Safrany, S.R. Nahorski, B.V.L. Potter, Bioorg. Med. Chem. Lett. 2, 1523-1528 (1992)
50. C.S. Liu, S.R. Nahorski, B.V.L. Potter, Carbohydr. Res. 234, 107-115 (1992)
51. C.S. Liu, J. Al-Hafidh, J. Westwick, B.V.L. Potter, Bioorg. Med. Chem. 2, 253-257 (1994)
52. X. Liu, E.C. Moody, S.S. Hecht, S.J. Sturla, Bioorg. Med. Chem. 16, 3419-3427 (2008)
53. S.C. Johnson, J. Dahl, T.L. Shih, D.J.A. Schedler, L. Anderson, T.L. Benjamin, D.C. Baker, J. Med. Chem. 36, 3628-3635 (1993)
54. L. Qiao, Y. Hu, F. Nan, G. Powis, A.P. Kozikowski, Org. Lett. 2, 115-117 (2000)
55. A.P. Kozikowski, H. Sun, J. Brognard, P.A. Dennis, J. Am. Chem. Soc. 125, 1144-1145 (2003)
56. A.P. Kozikowski, G. Powis, A. Gallegos, W. Tuckmantel, Bioorg. Med. Chem. Lett. 3, 1323-1326 (1993)
57. A.P. Kozikowski, V.I. Ognyanov, A.H. Fauq, R.A. Wilcox, S.R. Nahorski, J. Chem. Soc. Chem. Commun. 599-600 (1994)
58. M.V. De Almeida, R.M. Figueiredo, H.F. Dos Santos, A.D. Da Silva, W.B. De Almeida, Tetrahedron Lett. 42, 2767-2769 (2001)
59. S.M. Baars, J.O. Hoberg, Carbohydr. Res. 341, 1680-1684 (2006)
60. P.H. Hewitt, V.B. Whitehead, J.S. Read, J. Insect Physiol. 15, 1929-1933 (1969)
61. T. Akiyama, M. Hara, K. Fuchibe, S. Sakamoto, K. Yamaguchi, Chem. Commun. 1734 (2003)
62. B. Orthen, M. Popp, Environ. Exp. Bot. 44, 125-132 (2000)
63. M. Ortbauer, M. Popp, Plant Physiol. Biochem. 46, 428-434 (2008)
64. A. Kamb, S. Wee, C. Lengauer, Nat. Rev. Drug Discov. 6, 115-120 (2007)
65. D. Brown, G. Superti-Furga, Drug Discov. Today 8, 1067-1077 (2003)
66. J.B. Fitzgerald, B. Schoeberl, U.B. Nielsen, P.K. Sorger, Nat. Chem. Biol. 2, 458-466 (2006)
67. A.S. Perelson, P. Essunger, Y. Cao, M. Vesanen, A. Hurley, K. Saksela, M. Markowitz, D.D. Ho, Nature 387, 188-191 (1997)
68. A. Cavalli, M.L. Bolognesi, A. Minarini, M. Rosini, V. Tumiatti, M. Recanatini, C. Melchiorre, J. Med. Chem. 51, 347-372 (2008)
69. J.D. Feala, J. Cortes, P.M. Duxbury, C. Piermarocchi, A.D. McCulloch, G. Paternostro, Wiley Interdiscip. Rev. Syst. Biol. Med. 2, 181-193 (2010)

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Quebrachitol: Global Status and Basic Research

Quebrachitol: Global Status and Basic Research

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