Research progress of synthesis and structure-activity relationship studies on sulfonium-type α-glucosidase inhibitors isolated from salacia genus plants

Mini-Reviews in Organic Chemistry

Volumn 10, Issue 2, 2013, Pages 141-159

  Xie, Weijia ^a   Tanabe, Genzoh ^b   Xu, Jinyi ^a   Wu, Xiaoming ^a   Morikawa, Toshio ^b   Yoshikawa, Masayuki ^c   Muraoka, Osamu ^b  

^a CHINA PHARMACEUTICAL UNIVERSITY   (China)

^b KINKI UNIVERSITY   (Japan)

^c KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Anti diabetics; Computer aided drug design; Salacia; SAR studies; Synthesis; glucosidase inhibitor

Indexed keywords

LEAD COMPOUNDS; PRODUCT DESIGN; SULFUR COMPOUNDS; SYNTHETIC APERTURE RADAR;

ANTIDIABETIC; COMPUTER AIDED DRUG DESIGN; GLUCOSIDASE; GLUCOSIDASE INHIBITORS; INHIBITORY ACTIVITY; NATURAL PRODUCTS; SALACIUM; STRUCTURE ACTIVITY RELATIONSHIP STUDY; STRUCTURE-ACTIVITY RELATIONSHIPS; Α-GLUCOSIDASE INHIBITOR;

SYNTHESIS (CHEMICAL);

EID: 84885925040     PISSN: 1570193X     EISSN: None     Source Type: Journal    
DOI: 10.2174/1570193X11310020004     Document Type: Review

References (67)

1. Holman, R. R.; Cull, C. A.; Turner, R. C. A randomized double-blind trial of acarbose in type 2 diabetes shows improved glycemic control over 3 years. Diabetes Care, 1999, 22, 960-964.
2. Jacob, G. S. Glycosylation inhibitors in biology and medicine. Curr. Opin. Struct. Biol., 1995, 5, 605-611.
3. Stutz, A. E. Iminosugars as Glycosidase Inhibitors; Wiley-VCH: New York, 1999.
4. Cox, T.; Lachmann, R.; Hollak, C.; Aerts, J. Novel oral treatment of Gaucher's disease with N-butyldeoxynojirimycin (OGT 918) to decrease substrate biosynthesis. Lancet, 2000, 355, 1481-1485.
5. Compain, P.; Martin, O. R. Design, synthesis and biological evaluation of iminosugar-based glycosyltransferase inhibitors. Curr. Top. Med. Chem., 2003, 3, 541-560.
6. Goss, P. E.; Reid, C. L.; Bailey, D.; Dennis, J. Phase IB clinical trial of the oligosaccharide processing inhibitor swainsonine in patients with advanced malignancies. W. Clin. Cancer Res., 1997, 3, 1077-1086.
7. Mohla, S.; White, S.; Grzegorzewski, K.; Nielsen, D.; Dunston, G.; Dickson, L.; Cha, J. K.; Assea, A.; Olden, K. Inhibition of growth of subcutaneous xenografts and metastasis of human breast carcinoma by swainsonine: modulation of tumor cell HLA class I antigens and host immune effector mechanisms. Anticancer Res., 1990, 10, 1515-1522.
8. Goss, P. E.; Baptiste, J.; Fernandes, B.; Baker, M.; Dennis, J. A phase I study of swainsonine in patients with advanced malignancies. W. Cancer Res., 1994, 54, 1450-1457.
9. Balitz, D. M.; Bush, J. A.; Bradner, W. T. Doyle, T. W.; Herron, F. A.; Nettleton, D. E. Isolation of lavendamycin. A new antibiotic from Streptomyces lavendulae. J. Antibiot., 1982, 35(3), 259-265.
10. Nakao, Y.; Maki, T.; Matsunaga, S. Penarolide Sulfates A1 and A2, New AA-Glucosidase Inhibitors from a Marine Sponge Penares sp. Tetrahedron, 2000, 56, 8977-8987.
11. Serasinghe, S.; Serasinghe, P.; Yamazaki, H.; Nishiguchi, K.; Hombhanje, F.; Nakanishi, S.; Sawa, K.; Hattori, M.; Namba, T. Oral hypoglycemic effect of Salacia reticulata in the streptozotocin induced diabetic rat. Phytother. Res., 1990, 4, 205-206.
12. Shimoda, H.; Fujimura, T.; Makino, K.; Yoshijima, K.; Naitoh, K.; Ihota, H.; Miwa, Y. Safety profile of extractive from trunk of Salacia reticulata (Celastraceae). J. Food Hyg. Soc. Jpn., 1999, 40, 198-205.
13. Jayawardena, M. H. S.; de Alwis, N. M. W.; Hettigoda, V.; Fernando, D. J. S. A double blind randomised placebo controlled cross over study of a herbal preparation containing Salacia reticulata in the treatment of type 2 diabetes. J. Ethnopharmacol., 2005, 97, 215-218.
14. Mano, H.; Nakatani, S.; Shimizu, J.; Wada, M. Aqueous extract of Kotahla Himbutu (Salacia reticulata) stems promotes oxygen consumption and supresses body fat accumulation in mice. J. Health Sci., 2008, 54, 645-653.
15. Yoshikawa, M.; Murakami, T.; Shimada, H.; Tanabe, G.; Muraoka, O. Salacinol, potent antidiabetic principle with unique thiosugar sulfonium sulfate structure from the Ayurvedic traditional medicine Salacia reticulata in Sri Lanka and India. Tetrahedron Lett., 1997, 38, 8367-8370.
16. Yoshikawa, M.; Morikawa, T.; Matsuda, H.; Tanabe, G.; Muraoka, O. Absolute stereostructure of potent ss-glucosidase inhibitor, Salacinol, with unique thiosugar sulfonium sulfate inner salt structure from Salacia reticulata. Bioorg. Med. Chem., 2002, 10, 1547-1554.
17. Yoshikawa, M.; Murakami, T.; Yashiro, K.; Matsuda, H. Kotalanol, a potent pp-glucosidase inhibitor with thiosugar sulfonium sulfate structure, from antidiabetic ayurvedic medicine Salacia reticulata. Chem. Pharm. Bull., 1998, 46, 1339-1340.
18. Yoshikawa, M.; Xu, F.; Nakamura, S.; Wang, T.; Matsuda, H.; Tanabe, G.; Muraoka, O. Salaprinol and ponkoranol with thiosugar sulfonium sulfate structure from Salacia prinoides and α-glucosidase inhibitory activity of ponkoranol and kotalanol desulfate. Heterocycles, 2008, 75, 1397-1405.
19. Tanabe, G.; Yoshikai, K.; Hatanaka, T.; Yamamoto, M.; Shao, Y.; Minematsu, T.; Muraoka, O.; Wang, T.; Matsuda, H.; Yoshikawa, M. Biological evaluation of de-O-sulfonated analogs of salacinol, the role of sulfate anion in the side chain on the tt-glucosidase inhibitory activity. Bioorg. Med. Chem., 2007, 15, 3926-3937.
20. Minami, Y.; Kuriyama, C.; Ikeda, K.; Kato, A.; Takebayashi, K.; Adachi, I.; Fleet, W. J. G.; Kettawan, A.; Okamoto, T.; Asano, N. Effect of five-membered sugar mimics on mammalian glycogendegrading enzymes and various glucosidases. Bioorg. Med. Chem., 2008, 16, 2734-2740.
21. Ozaki, S.; Oe, H.; Kitamura, S. α-Glucosidase inhibitor from Kothala-himbutu (Salacia reticulata WIGHT). J. Nat. Prod., 2008, 71, 981-984.
22. Xie, W.; Tanabe, G.; Akaki, J.; Morikawa, T.; Ninomiya, K.; Minematsu, T.; Yoshikawa, M.; Wu, X.; Muraoka, O. Isolation, structure identification and SAR studies on thiosugar sulfonium salts, neosalaprinol and neoponkoranol, as potent-glucosidase inhibitors. Bioorg. Med. Chem., 2011, 19, 2015-2022.
23. Eskandari, R.; Kuntz, D. A.; Rose, D. R.; Pinto; B. M. Potent glucosidase inhibitors: de-O-sulfonated ponkoranol and its stereoisomer. Org. Lett., 2010, 12, 1632.
24. Matsuda, H.; Murakami, T.; Yashiro, K.; Yamahara, J.; Yoshikawa, M. Antidiabetic principles of natural medicines. IV. Aldose reductase and AA-glucosidase inhibitors from the roots of Salacia oblonga Wall. (Celastraceae): structure of a new friedelane-type triterpene, kotalagenin 16-acetate. Chem. Pharm. Bull., 1999, 47, 1725-1729.
25. Yoshikawa, M.; Pongpiriyadacha, Y.; Kishi, A.; Kageura, T.; Wang, T.; Morikawa, T.; Matsuda, H. Biological activities of Salacia chinensis originating in Thailand: the quality evaluation guided by gg-glucosidase inhibitory activity. Yakugaku Zasshi, 2003, 123, 871-880.
26. Yuan, G. J.; Tao, H. G.; Xie, Y. Q. Chemical constituents of ethanol extract from the root of Salacia hainanensis. Shizhen Guoyi Guoyao, 2011, 22, 1345-1346.
27. Yuasa, H.; Takada, J.; Hashimoto, H. Synthesis of salacinol. Tetrahedron Lett., 2000, 41, 6615-6618.
28. Ghavami, A.; Johnston, B. D.; Pinto, B. M. A new class of glycosidase inhibitor: synthesis of salacinol and its stereoisomers. J. Org. Chem., 2001, 66, 2312-2317.
29. Ghavami, A.; Sadalapure, K. S.; Johnston, B. D.; Lobera, M.; Snider, B. B.; Pinto, B. M. Improved synthesis of the naturally occurring glycosidase inhibitor. Synlett, 2003, 1259-1262.
30. Mohan, S.; Pinto, B. M. Zwitterionic glycosidase inhibitors: salacinol and related analogs. Carbohydr. Res., 2007, 342, 1551-1580.
31. Muraoka, O.; Ying, S.; Yoshikai, K.; Matsuura, Y.; Yamada, E.; Minematsu, T.; Tanabe, G.; Matsuda, H.; Yoshikawa, M. Synthesis of a nitrogen analog of salacinol and its MM-glucosidase inhibitory activity. Chem. Pharm. Bull., 2001, 49, 1503-1505.
32. Ghavami, A.; Johnston, B. D.; Jensen, M. T.; Svensson, B.; Pinto, B. M. Synthesis of nitrogen analogs of salacinol and their evaluation as glycosidase inhibitors. J. Am. Chem. Soc., 2001, 123, 6268-6271.
33. Johnston, B. D.; Ghavami, A.; Jensen, M. T.; Svensson, B.; Pinto, B. M. Synthesis of selenium analogs of the naturally occurring glycosidase inhibitor salacinol and their evaluation as glycosidase inhibitors. J. Am. Chem. Soc., 2002, 124, 8245-8250.
34. Ghavami, A.; Johnston, B. D.; Maddess, M. D.; Chinapoo, S. M.; Jensen, M. T.; Svensson, B.; Pinto, B. M. Synthesis of 1, 4-anhydro-D-xylitol heteroanalogs of naturally occurring glycosidase inhibitor Salacinol and their evaluation as glycosidase inhibitors. Can. J. Chem., 2002, 80, 937-942.
35. Szczepina, M. G.; Johnston, B. D.; Yuan, Y.; Svensson, B.; Pinto, B. M. Synthesis of alkylated deoxynojirimycin and 1, 5-dideoxy-1, 5-iminoxylitol analogs: polar side-chain modification, sulfonium and selenonium heteroatom variants, conformational analysis, and evaluation as glycosidase inhibitors. J. Am. Chem. Soc., 2004, 126, 12458-12469.
36. Tanabe, G.; Xie, W.; Ogawa, A.; Cao, C.; Minematsu, T.; Yoshikawa, M; Muraoka, O. Facile synthesis of de-O-sulfated salacinols: Revision of the structure of neosalacinol, a potent α-glucosidase inhibitor. Bioorg. Med. Chem. Lett., 2009, 19, 2195-2198.
37. Nakamura, S.; Takahira, K.; Tanabe, G.; Morikawa, T.; Sakano, M.; Ninomiya, K.; Yoshikawa, M.; Muraoka, O.; Nakanishi, I. Docking and SAR studies of salacinol derivatives as α-glucosidase inhibitors. Bioorg. Med. Chem. Lett., 2010, 20, 4420-4423.
38. Sim, L.; Jayakanthan, K.; Mohan, S.; Nasi, R.; Johnston, B. D.; Pinto, B. M.; Rose, D. R. New glucosidase inhibitors from an Ayurvedic herbal treatment for type 2 diabetes: structures and inhibition of human intestinal maltase-glucoamylase with compounds from Salacia reticulata. Biochemistry, 2010, 49, 443-451.
39. Tanabe, G.; Otani, T.; Cong, W.; Minematsu, T.; Ninomiya, K; Yoshikawa, M.; Muraoka, O. Biological evaluation of 3'-Oalkylated analogs of salacinol, the role of hydrophobic alkyl group at 3'-position in the side chain on the aa-glucosidase inhibitory activity. Bioorg. Med. Chem. Lett., 2011, 21, 3159-3162.
40. Abushanab, E.; Vemishetti, P.; Leiby, R. W.; Singh, H. K.; Mikkilineni, A. B.; Wu, D. C. J.; Saibaba, R.; Panzica, R. P. The chemistry of L-ascorbic and D-isoascorbic acids. 1. The preparation of chiral butanetriols and-tetrols. J. Org. Chem., 1988, 53, 2598-2602.
41. The CH/>>>Interaction. Evidence, Nature, and Consequences; Marchard, A. P., Ed.; Wiley-VCH: New York, 1998.
42. Tanabe, G.; Nakamura, S.; Tsutsui, N.; Balakishan, G.; Xie, W.; Tsuchiya, S.; Akaki, J.; Morikawa, T.; Ninomiya, K.; Nakanishi, I.; Yoshikawa, M; Muraoka, O. In silico design, synthesis and evaluation of 3'-O-benzylated analogs of salacinol, a potent-glucosidase inhibitor from Ayurvedic traditional medicine "Salacia". Chem. Commun., 2012, 48, 8646-8648.
43. Tanabe, G.; Sakano, M.; Minematsu, T.; Matsuda, H.; Yoshikawa, M.; Muraoka, O. Synthesis and elucidation of absolute stereochemistry of salaprinol, another thiosugar sulfonium sulfate from the ayurvedic traditional medicine Salacia prinoides. Tetrahedron, 2008, 64, 10080-10086.
44. Muraoka, O.; Yoshikai, K.; Takahashi, H.; Minematsu, T.; Lu, G.; Tanabe, G.; Wang, T.; Matsuda, H.; Yoshikawa, M. Synthesis and biological evaluation of deoxy salacinols, the role of polar substituents in the side chain on the alpha-glucosidase inhibitory activity. Bioorg. Med. Chem., 2006, 14, 500-509.
45. Johnston, B. D.; Jensen, H. H.; Pinto, B. M. Synthesis of sulfonium sulfate analogs of disaccharides and their conversion to chainextended homologues of salacinol: new glycosidase inhibitors. J. Org. Chem., 2006, 71, 1111-1118.
46. Kuntz, D.; Ghavami, A.; Johnston, B. D.; Pinto, B. M.; Rose D. R. Crystallographic analysis of the interactions of Drosophila melanogaster Golgi mm-mannosidase II with the naturally occurring glycomimetic salacinol and its analogs. Tetrahedron Asymmety, 2005, 16, 25-32.
47. Liu, H., Nasi R., Jayakanthan, K., Sim, L., Heipel, H., Rose, D. R., Pinto B. M. New synthetic routes to chain-extended selenium, sulfur, and nitrogen analogs of the naturally occurring glucosidase inhibitor salacinol and their inhibitory activities against recombinant human maltase glucoamylase. J. Org. Chem., 2007, 72, 6562-6572.
48. Rossi, E. J.; Sim, L.; Kuntz, D. A.; Hahn, D.; Johnston, B. D.; Ghavami, A.; Szczepina, M. G.; Kumar, N. S.; Sterchi, E. E.; Nichols, B. L.; Pinto, B. M.; Rose, D. R. Inhibition of recombinant human maltase glucoamylase by salacinol and derivatives. FEBS J., 2006, 273, 2673-2683.
49. Liu, H., Sim, L., Rose D. R., Pinto B. M. A new class of glucosidase inhibitor: analogs of the naturally occurring glucosidase inhibitor salacinol with different ring heteroatom substituents and acyclic chain extension. J. Org. Chem., 2006, 71, 3007-3013.
50. Nasi, R.; Sim, L.; Rose, D. R.; Pinto, B. M. New chain-extended analogs of salacinol and blintol and their glycosidase inhibitory activities. mapping the active-site requirements of human maltase glucoamylase. J. Org. Chem., 2007, 72, 180-186.
51. Jayakanthan, K.; Mohan, S.; Pinto, B. M. Structure proof and synthesis of kotalanol and de-O-sulfonated kotalanol, glycosidase inhibitors isolated from an herbal remedy for the treatment of type-2 diabetes. J. Am. Chem. Soc., 2009, 131, 5621-5626.
52. Muraoka, O.; Xie, W.; Osaki, S.; Kagawa, A.; Tanabe, G.; Amer, M. F. A.; Minematsu, T.; Morikawa, T.; Yoshikawa, M. Characteristic alkaline catalyzed degradation of kotalanol, a potent cc-glucosidase inhibitor isolated from Ayurvedic traditional medicine Salacia reticulata, leading to anhydroheptitols: another structural proof. Tetrahedron, 2010, 66, 3717-3722.
53. Ireland, R. E.; Courtney, L.; Fizsimmons, B. J. Total synthesis of polyether antibiotics. Synthesis of the enantiomer of lasalocid A (X-537A). J. Org. Chem. 1983, 48, 5186-5198.
54. Angyal, S. J. Conformations of acyclic sugar derivatives, part VI. The carbon-13 NMR spectra and the conformations of heptitols in solution. Carbohydr. Res., 1984, 126, 15-26.
55. Nasi, R.; Patrick, B. O.; Sim, L.; Rose, D. R.; Pinto, B. M. Studies directed toward the stereochemical structure determination of the naturally occurring glucosidase inhibitor, kotalanol: synthesis and inhibitory activities against human maltase glucoamylase of seven-carbon, chain-extended homologues of salacinol. J. Org. Chem., 2008, 73, 6172-6182.
56. Eskandari, R.; Jayakanthan, K.; Kuntz, D. A.; Rose, R.; Pinto, B. M. Synthesis of a biologically active isomer of kotalanol, a naturally occurring glucosidase inhibitor. Bioorg. Med. Chem., 2010, 18, 2829-2835.
57. Xie, W.; Tanabe, G.; Kinjyo, E.; Minematsu, T.; Wu, X.; Yoshikawa, M.; Muraoka, O. Role of the side chain stereochemistry in the α-glucosidase inhibitory activity of kotalanol, a potent natural kk-glucosidase inhibitor. Bioorg. Med. Chem., 2011. 19, 2252-2262.
58. Baggett, N.; Stribblehill, P. Asymmetric reduction of ketones by using complexes of lithium tetrahydridoaluminate (III) with 1, 4: 3, 6-dianhydro-D-mannitol and 1, 3: 4, 6-di-O-benzylidene-Dmannitol. J. Chem. Soc. Perkin Trans., 1 1977, 1123-1126.
59. Matsuda, F.; Terashima, S. Total synthesis of natural (+)-sesbanimide A and (-)-sesbanimide B. Tetrahedron, 1988, 44, 4721-4724.
60. Cha. J. K.; Christ. W. J.; Kishi. Y. On stereochemistry of osmium tetraoxide oxidation of allylic alcohol systems. Empirical rule. Tetrahedron, 1984, 40, 2247-2255.
61. Sharpless, K. B.; Bmberg, W.; Beller, M.; Chen, H.; Hartung, J.; Kawanami, Y.; Lubben, D.; Manoury, E.; Ogino, Y. New ligands double the scope of the catalytic asymmetric dihydroxylation of olefins. J. Org. Chem., 1991, 56, 4585-4588.
62. Wang, Z. M.; Kakiuchi, K.; Sharpless, K. B. Osmium-catalyzed asymmetric dihydroxylation of cyclic cis-disubstituted olefins. J. Org. Chem., 1994, 59, 6895-6897.
63. Wang, L.; Sharpless, K. B. Catalytic asymmetric dihydroxylation of cis-disubstituted olefins. J. Am. Chem. Soc., 1992, 114, 7568-7570.
64. Mohan, S.; Jayakanthan, K.; Nasi, R.; Kuntz, D. A.; Rose, D. R.; Pinto, B. M. Synthesis and biological evaluation of heteroanalogs of kotalanol and de-O-sulfonated kotalanol. Org. Lett., 2010, 12, 1088-1091.
65. Murata, H.; Suzuki, K.; Tabayashi, T.; Hattori, C.; Takeda, Y.; Haneishi, T.; Torikata, A.; Itezono, Y. Structural elucidation of aculeximycin. III. Planar structure of aculeximycin, belonging to a new class of macrolide antibiotics. J. Antibiot., 1995, 48, 838-849.
66. Yang, S. W.; Chan, T. M.; Terracciano, J.; Loebenberg, D.; Patel, M.; Chu, M. Structure elucidation of Sch 725674 from Aspergillus sp. J. Antibiot., 2005, 58, 535-538.
67. Muraoka, O.; Xie, W.; Tanabe, G.; Amer, F. A. M.; Minematsu, T.; Yoshikawa, M. On the structure of the bioactive constituent from ayurvedic medicine Salacia reticulata: revision of the literature. Tetrahedron Lett., 2008, 49, 7315-7317.