Cytotoxic triterpenoid saponins from the roots of Platycodon grandiflorum

Molecules

Volumn 12, Issue 4, 2007, Pages 832-841

  Zhang, Lin ^a   Liu, Zhen Huan ^a   Tian, Jing Kui ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

Cytotoxic activity; Platycodon grandiflorum; Triterpenoid saponins

Indexed keywords

LACTONE; PLANT EXTRACT; SAPONIN; TERPENE;

ARTICLE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; DRUG SCREENING; HUMAN; MASS SPECTROMETRY; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PLANT ROOT; PLATYCODON; TEMPERATURE; TUMOR CELL LINE;

CELL LINE, TUMOR; DRUG EVALUATION, PRECLINICAL; HUMANS; LACTONES; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PLANT EXTRACTS; PLANT ROOTS; PLATYCODON; SAPONINS; TEMPERATURE; TERPENES;

EID: 34247876145     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/12040832     Document Type: Article

References (35)

1. Pharmacopoeia of the People's Republic of China; Chemical Industry Press: Beijing, 2005; Vol. I, p. 196.
2. Akiyama, T.; Iitaka, Y.; Tanaka, O. Structure of platicodigenin, a saogenin of Platycodon grandiflorum A. De Candolle. Tetrahedron Lett. 1968, 53, 5577-5580.
3. Fu, W.W.; Dou, D.Q.; Shimizu, N.; Takeda, T.; Fu, R.; Pei, Y.H.; Chen, Y.J. Studies on the chemical constituents from the roots of Platycodon grandiflorum. J. Nat. Med. 2006, 60, 68-72.
4. Fu, W.W.; Hou, W.B.; Dou, D.Q.; Hua, H.M.; Gui, M.H.; Fu, R.; Chen, Y.J.; Pei, Y.H. Saponins of polygalacic acid type from Platycodon grandiflorum. Acta Pharm. Sin. 2006, 41, 358-360.
5. Fu, W.W.; Shimizu, N.; Dou, D.Q.; Takeda, T.; Fu, R.; Pei, Y.H.; Chen, Y.J. Five new triterpenoid saponins from the roots of Platycodon grandiflorum. Chem. Pharm. Bull. 2006, 54, 557-560.
6. Fu, W.W.; Shimizu, N.; Takeda, T.; Dou, D.Q.; Chen, B.H.; Pei, Y.H.; Chen, Y.J. New A-ring lactone triterpenoid saponins from the roots of Platycodon grandiflorum. Chem. Pharm. Bull. 2006, 54, 1285-1287.
7. He, Z.D.; Qiao, C.F.; Han, Q.B.; Wang, Y.; Ye, W.C.; Xu, H.X. New triterpenoid saponins from the roots of Platycodon grandiflorum. Tetrahedron 2005, 61, 2211-2215.
8. 2, and Their Monoacetates, Saponins isolated from Platycodon grandiflorum A. DC., determined by Carbon-13 Nuclear Magnetic Resonance Spectroscopy. Chem. Pharm. Bull. 1978, 26, 674-677.
9. 3, platyconic acid -A, and their derivatives, saponins isolated from roots of Platycodon grandiflorum A. De Candolle, determined by carbon-13 NMR spectroscopy. Chem. Lett. 1978, 719-722.
10. Ishii, H.; Tori, K.; Tozyo, T.; Yoshimura, Y. Saponins from roots of Platycodon grandiflorum. Part 1. Structure of prosapogenins. J. Chem. Soc. Perkin Trans. 1 1981, 1928-1933.
11. Ishii, H.; Tori, K.; Tozyo, T.; Yoshimura, Y. Saponins from roots of Platycodon grandiflorum. Part 2. Isolation and structure of new triterpene glycosides. J. Chem. Soc. Perkin Trans. 1984, 661-668.
12. Kim, Y.-S.; Kim, J.-S.; Choi, S.-U.; Kim, J.-S.; Lee, H.-S.; Roh, S.-H.; Jeong, Y.-C.; Kim, Y.-K.; Ryu, S.-Y. Isolation of a new saponin and cytotoxic effect of saponins from the root of Platycodon grandiflorum on human tumor cell lines. Planta Med. 2005, 71, 566-568.
13. Konishi, T.; Rada, A.; Shoji, J.; Kasai, R.; Tanaka, O. The Structures of Platcodin A and C, Monoacetylated Saponins of the Roots of Platycodon grandiflorum A. DC. Chem. Pharm. Bull. 1978, 26, 668-670.
14. Kubota, T.; Kitatani, H.; Hinoh, H. Structure of platycogenic acids A, B and C Further Trierpenoid Constituents of Platycodon grandiflorum. J. Chem. Soc. D. 1969, 22, 1313-1314.
15. Nikaido, T.; Koike, K.; Mitsunaga, K.; Saeki, T. Tirterpenoid saponins from root of Platycodon grandiflorum. Nat. Med. 1998, 52, 54-59.
16. Nikaido, T.; Koike, K.; Mitsunaga, K.; Saeki, T. Two New Triterpenoid Saponins from Platycodon grandflorum. Chem. Pharm. Bull. 1999, 47, 903-904.
17. Tada, A.; Kaneiwa, Y.; Shoji, J.; Shibata, S. Studies on the saponins of the Roots of Platycodon grandiflorum A. De Candolle. I. Isolation and the Stricture of Platycodin-D. Chem. Pharm. Bull. 1975, 23, 2965-2972.
18. Fu, W.W.; Dou, D.Q.; Zhao, C.J.; Shimizu, N.; Pei, Y.P.; Pei, Y.H.; Takeda, T.; Chen, Y.J.; Takeda, T. Triterpenoid saponins from Platycodon grandiflurum. J. Asia Nat. Prod. Res. 2007, 9, 35-40.
19. Kim, Y.-P.; Lee, E.-B.; Kim, S.-Y.; Li, D.-W.; Ban, H.-S.; Lim, S.-S.; Shin, K.-H.; Ohuchi, K. Inhibition of Prostaglandin E2 Production by Platycodin D Isolated from the Root of Platycodon grandiflorum. Planta Med. 2001, 67, 362-364.
20. Kim, J.-Y.; Hwang, Y.-P.; Kim, D.-H.; Han, E.-H.; Chung, Y.-C.; Roh, S.-H.; Jeong, H.-G. Inhibitory effect of the saponins derived from roots of Platycodon grandiflorum on carrageenan-induced inflammation. Biosci. Biotech. Biochem. 2006, 70, 858-864.
21. Kim, J.-Y.; Kim, D.-H.; Kim, H.-G.; Song, G.-Y.; Chung, Y.-C.; Roh, S.-H.; Jeong, H.-G. Inhibition of tumor necrosis factor-alpha-induced expression of adhesion molecules in human endothelial cells by the saponins derived from roots of Platycodon grandiflorum. Toxicol. Appl. Pharmacol. 2006, 210, 150-156.
22. Kubo, A.; Sasada, M.; Yamamoto, K.; Nishiyama, H.; Nishimura, T.; Nakamura, T.; Uchino, H. Immune Pharmacological Studies on Platycodi Radii (I). Effect on the Phagocytosis in Mouse. Shoyakugaku Zasshi 1986, 40, 367-374.
23. Lee, K.-J.; Kim, J.-Y.; Choi, J.-H.; Kim, H.-G.; Chung, Y.-C.; Roh, S.-H.; Jeong, H.-G. Inhibition of tumor invasion and metastasis by aqueous extract of the radix of Platycodon grandiflorum. Food Chem. Toxico. 2006, 44, 1890-1896.
24. 3 Increase Airway Mucin Release in vivo and in vitro in Rats and Hamsters. Planta Med. 2002, 68, 221-225
25. Takagi, K.; Lee, E.-B. Pharmacological Studies on Platycodon grandiflorum A.DC. I. Acute Toxicity and Central Depressant Activity of Crude Platycodin. Yakugaku Zasshi 1972, 92, 951-960.
26. Yokoyama, H.; Hiai, S.; Oura, H. Rat Plasma Corticosterone Secretion- inducing Activities of Total Saponin and Prosapogenin Methyl Esters from the Roots of Platycodon grandiflorum A.DC. Yakugaku Zasshi 1982, 102, 1191-1194.
27. Xu, B.J.; Han, L.K.; Zheng, Y.N.; Lee, J.-H.; Sung, C.-K. In vitro inhibitory of triterpenoidal saponins from platycodi radix on pancreatic lipase. Arch. Pharm. Res. 2005, 28, 180-185.
28. Zhao, H.L.; Kim, Y.-S. Determination of kinetic properties of platycodin D for the inhibition of pancreatic lipase using a 1,2-diglyceride-based colorimetric assay. Arch. Pharm. Res. 2004, 27, 1048-1052.
29. Zhao, H.L.; Sim, J.-S.; Shim, S.H.; Ha, Y.W.; Kang, S.S.; Kim, Y.S. Antiobese and hypolipidemic effects of platicodin saponins in diet-induced obese rats: evidences for lipase inhibition and calorie intake restriction. Int. J. Obesity 2005, 29, 983-990.
30. Zhao, H.L.; Cho, K.-H.; Ha, Y.W.; Jeong, T.-S.; Lee, W.S.; Kim, Y.S. Cholesterol-lowering effect of platycodin D in hypercholesterolemic ICR mice. Eur. J. Pharmacol. 2006, 537, 166-173.
31. Ahn, K.S.; Hahn, B.-S.; Kwack, K.B.; Lee, E.B.; Kim, Y.S. Platycodin D-induced apoptosis through nuclear factor-κB activation in immortalized keratinocytes. Eur. J. Pharmacol. 2006, 537, 1-11.
32. Ahn, K.S.; Noh, E. J.; Zhao, H.L.; Jung, S.H.; Kang, S.S.; Kim, Y.S. Inhibition of inducible nitric oxide synthase and cyclooxygenase II by Platycodon grandiflorum saponins via suppression of nuclear factor-κB activation in RAW 264.7 Life Sci. 2005, 76, 2315-2328.
33. Hara, S.; Okabe, H.; Mihashi, K. Separation of aldose enantiomers by gas-liquid chromatography. Chem. Pharm. Bull. 1986, 34, 1843-1844.
34. Li, W.-F.; Zhang, S.-J.; Li, N.; Wang, M.-Z.; Sakai, J.; Hasegawa, T.; Mitsui, T.; Kataoka, T.; Oka, S.; Kiuchi, M.; Hirose, K.; Ando, M. Three new triterpenes from Nerium oleander and biological activity of the isolated compounds. J. Nat. Prod. 2005, 68, 198-206
35. Guido, F.; Pauli. The cardenolide of Speirantha convallarioides. Planta Med. 1995, 61,162-166.