Semi-synthesis of Several Stigmasterol Saponins
Chun-Xia Li
Key Laboratory of Marine Drugs of the Ministry of Education of China, Institute of Marine Drug and Food, Ocean University of China, Qingdao, Shandong 266003, China
Search for more papers by this authorTian-Tian Guo
Key Laboratory of Marine Drugs of the Ministry of Education of China, Institute of Marine Drug and Food, Ocean University of China, Qingdao, Shandong 266003, China
Search for more papers by this authorPeng Wang
Key Laboratory of Marine Drugs of the Ministry of Education of China, Institute of Marine Drug and Food, Ocean University of China, Qingdao, Shandong 266003, China
Search for more papers by this authorHua-Shi Guan
Key Laboratory of Marine Drugs of the Ministry of Education of China, Institute of Marine Drug and Food, Ocean University of China, Qingdao, Shandong 266003, China
Search for more papers by this authorYing-Xia Li
Project supported by the National Natural Science Foundation of China (No. 30400564).
Search for more papers by this authorChun-Xia Li
Key Laboratory of Marine Drugs of the Ministry of Education of China, Institute of Marine Drug and Food, Ocean University of China, Qingdao, Shandong 266003, China
Search for more papers by this authorTian-Tian Guo
Key Laboratory of Marine Drugs of the Ministry of Education of China, Institute of Marine Drug and Food, Ocean University of China, Qingdao, Shandong 266003, China
Search for more papers by this authorPeng Wang
Key Laboratory of Marine Drugs of the Ministry of Education of China, Institute of Marine Drug and Food, Ocean University of China, Qingdao, Shandong 266003, China
Search for more papers by this authorHua-Shi Guan
Key Laboratory of Marine Drugs of the Ministry of Education of China, Institute of Marine Drug and Food, Ocean University of China, Qingdao, Shandong 266003, China
Search for more papers by this authorYing-Xia Li
Project supported by the National Natural Science Foundation of China (No. 30400564).
Search for more papers by this authorAbstract
Several stigamasterol saponins were concisely synthesized. Namely, four monosaccharide (glucopyranose, galactopyranose, xylopyranose, 2-acetamido-2-deoxy-α-D-glucopyranose), lactopyranose and chacotriose were coupled with 3-OH of stigmasterol. All the compounds were identified by NMR, IR and high resolusion MS.
REFERENCES
- 1
Hostettmann, K.;
Marston, A., In Saponins, Cambridge University Press, New York, 1995.
10.1017/CBO9780511565113 Google Scholar
- 2a Schopke, T.; Hiller, K.. Pharmazie, 1990, 45, 313.
- 2b Iorizzi, M.; De Marino, S.; Zollo, F.. Curr. Org. Chem., 2001, 5, 951.
- 2c Sparg, S. G.; Light, M. E.; Van Staden, J.. J. Ethnopharmacol., 2004, 94, 219.
- 3a Yokosuka, A.; Mimaki, Y.; Sashida, Y.. Phytochemistry, 2002, 61, 73.
- 3b Yu, W.; Jin, Z.. J. Am. Chem. Soc., 2002, 124, 6576.
- 3c Mimaki, Y.; Yokosuka, A.; Kuroda, M.; Sashida, Y.. Biol. Pharm. Bull., 2001, 24, 1286.
- 3d Dong, M.; Feng, X. Z.; Wu, L. J.; Wang, B. X.; Ikejima, T.. Planta Med., 2001, 67, 853.
- 3e Hufford, C. D.; Liu, S.; Clark, A. M.. J. Nat. Prod., 1988, 51, 94.
- 4a Saito, S.; Nagase, S.; Kawase, M.; Nagamura, Y.. Eur. J. Med. Chem., 1996, 31, 557.
- 4b Saito, S.; Sumita, S.; Kanda, Y.; Sasaki, Y.. Chem. Pharm. Bull., 1994, 42, 1016.
- 4c Baltina, L. A.; Flekhter, O. B.; Vasil'eva, E. V.. Russ. J. Bioorg. Chem., 1997, 23, 512.
- 4d Baltina, L. A.; Flekhter, O. B.; Davydova, V. A.. Russ. J. Bioorg. Chem., 1997, 23, 745.
- 5a Zhang, X.; Qi, J.; Ye, W.; Zhao, S.. J. Chin. Pharm. Univer., 2004, 35, 404.
- 5b Tang, H.; Yi, Y.; Yao, X.; Zhou, D.; Lü, T.; Jiang, Y.. Chin. Pharm. J., 2002, 37, 262.
- 6 Sheng, Y.; Hua, W.; Gu, W. Y.. Chin. Western Cereals Oils Technol., 2003, 2, 32 (in Chinese).
- 7 DeNinno, M. P.; McCarthy, P. A.; Duplantier, K. C.. J. Med. Chem, 1997, 40, 2547.
- 8a Roddick, J. G.; Weissenberg, M.; Leonard, A. L.. Phytochemistry, 2001, 56, 603.
- 8b Nakamura, T.; Komori, C.; Lee, Y.; Hashimoto, F.; Yahara, S.; Nohara, T.; Ejima, A.. Biol. Pharm. Bull., 1996, 19, 564.
- 8c Liu, M. J.; Wang, Z.; Ju, Y.. Biol. Pharm. Bull., 2004, 27, 1059.
- 9a Yu, B.; Tao, H.. J. Org. Chem., 2002, 67, 9099.
- 9b Gu, G. F.; Du, Y. G.; Linhardt, R. J.. J. Org. Chem., 2004, 69, 5497.
- 9c Toshima, K.; Tasuta, K.. Chem. Rev., 1993, 93, 1503.
- 9d Schmidt, R. R.; Kinzy, W.. Adv. Carbohydr. Chem. Biochem., 1994, 50, 21.
- 9e Garegg, P. J.. Adv. Carbohydr. Chem. Biochem., 1997, 52, 179.
- 10 Crich, D.; Dai, Z.; Gastaldi, S.. J. Org. Chem., 1999, 64, 5224.
- 11a Deng, S.; Yu, B.; Xie, J.; Hui, Y.. J. Org. Chem., 1999, 64, 7265.
- 11b Qu, F.; Li, Y. X.; Zhang, Y. C.; Zang, J.. Chin. J. Org. Chem., 2003, 23, 249 (in Chinese).
- 11c Gerhard, K.; Wilhelm, S.. Tetrahedron, 1998, 54, 6341.
- 12 Zhang, Y. C.; Li, Y. X.; Guo, T. T.; Guan, H. S.; Shi, J. W.; Yu, Q.; Yu, B.. Carbohydr. Res., 2005, 340, 1453.
- 13 Schmidt, R. R.; Toepfer, A.. Tetrahedron Lett., 1991, 32, 3353.