A new ursane-type triterpenoid glycoside from Centella asiatica leaves modulates the production of nitric oxide and secretion of TNF-α in activated RAW 264.7 cells

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 6, 2011, Pages 1777-1781

  Nhiem, Nguyen Xuan ^a,b   Tai, Bui Huu ^a,b   Quang, Tran Hong ^a,b   Kiem, Phan Van ^b   Minh, Chau Van ^b   Nam, Nguyen Hoai ^b   Kim, Jun Ho ^c   Im, Lee Rang ^c   Lee, Young Mi ^c   Kim, Young Ho ^a  

^a Chungnam National University   (South Korea)

^b GRADUATE UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Viet Nam)

^c Wonkwang University   (South Korea)

Author keywords

Anti inflammatory; Apiaceae; Asiaticoside G; Centella asiatica; IL 2; Nitric oxide; Tumor necrosis factor ; Ursane type triterpene glycoside

Indexed keywords

2ALPHA,3BETA,6BETA TRIHYDROXYOLEAN 12 EN 28 OIC ACID 28 O [ALPHA LEVO RHAMNOPYRANOSYL(1-4) BETA DEXTRO GLUCOPYRANOSYL(1-6) BETA DEXTRO GLUCOPYRANOSYL]ESTER; AGLYCONE; ANTIINFLAMMATORY AGENT; ASIATIC ACID; ASIATICOSIDE; ASIATICOSIDE F; ASIATICOSIDE G; ASTRAGALIN; CENTELLA ASIATICA EXTRACT; DEXAMETHASONE; FLAVONOID; ISOQUERCITRIN; KAEMPFEROL; NITRIC OXIDE; PLANT GLYCOSIDE; QUADRANOSIDE IV; QUERCETIN; TRITERPENE DERIVATIVE; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG;

ANTIINFLAMMATORY ACTIVITY; ARTICLE; CELL STIMULATION; CELL STRAIN; CELL STRAIN RAW 264.7; CENTELLA ASIATICA; CONCENTRATION RESPONSE; CYTOKINE RELEASE; DRUG ISOLATION; DRUG STRUCTURE; NONHUMAN; PLANT LEAF; PROTEIN SYNTHESIS INHIBITION;

ANIMALS; CELL LINE; CENTELLA; GLYCOSIDES; MICE; NITRIC OXIDE; PLANT LEAVES; TRITERPENES; TUMOR NECROSIS FACTOR-ALPHA;

APIACEAE; CENTELLA ASIATICA;

EID: 79952361538     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.01.066     Document Type: Article

References (27)

1. B. Sinha, A. Eigler, K.H. Baumann, T.F. Greten, J. Moeller, and S. Endres Res. Immunol. 149 1998 139
2. C. Wang, G.B.S. Levis, E.B. Lee, W.R. Levis, D.W. Lee, B.S. Kim, S.Y. Park, and E. Park Int. Immunopharmacol. 4 2004 1039
3. K. Ishibe, T. Yamanishi, Y. Wang, K. Osatomi, K. Hara, K. Kanai, K. Yamaguchi, and T. Oda Fish Shellfish Immunol. 27 2009 386
4. M.A. Palladino, F.R. Bahjat, E.A. Theodorakis, and L.L. Moldawer Nat. Rev. Drug Discovery 2 2003 736
5. D.H. Bich, D.Q. Chung, B.X. Chuong, N.T. Dong, D.T. Dam, P.V. Hien, V.N. Lo, P.D. Mai, P.K. Man, D.T. Nhu, N. Tap, and T. Toan The Medicinal Plants and Animals in Vietnam 2004 Hanoi Science and Technology Publishing House Hanoi
6. Z.Y. Jiang, X.M. Zhang, J. Zhou, and J. Chen Helv. Chim. Acta 88 2005 297
7. M. Kuroda, Y. Mimaki, H. Harada, H. Sakagami, and Y. Sashida Nat. Med. 55 2001 134
8. J.T. James, and I.A. Dubery Molecules 14 2009 3922
9. G. Govindan, T.G. Sambandan, M. Govindan, A. Sinskey, J. Vanessendelft, I. Adenan, and C.K. Rha Planta Med. 73 2007 597
10. T. Satake, K. Kamiya, Y. An, T. Oishi, and J. Yamamoto Biol. Pharm. Bull. 30 2007 935
11. J.H. Won, J.S. Shin, H.J. Park, H.J. Jung, D.J. Koh, B.G. Jo, J.Y. Lee, K. Yun, and K.T. Lee Planta Med. 76 2010 251
12. H. Li, X. Gong, L. Zhang, Z. Zhang, F. Luo, Q. Zhou, J. Chen, and J. Wan Phytomedicine 16 2009 538
13. R.G. Krishnamurthy, M.C. Senut, D. Zemke, J. Min, M.B. Frenkel, E.J. Greenberg, S.W. Yu, N. Ahn, J. Goudreau, M. Kassab, K.S. Panickar, and A. Majid J. Neurosci. Res. 87 2009 2541
14. K.J. Yun, J.Y. Kim, J.B. Kim, K.W. Lee, S.Y. Jeong, H.J. Park, H.J. Jung, Y.W. Cho, K. Yun, and K.T. Lee Int. Immunopharmacol. 8 2008 431
15. J.S. Guo, C.L. Cheng, and M.W.L. Koo Planta Med. 70 2004 1150
16. M.C. Aguirre, C. Delporte, N. Backhouse, S. Erazo, M.E. Letelier, B.K. Cassels, X. Silva, S. Alegria, and R. Negrete Bioorg. Med. Chem. 14 2006 5673
17. I.K. Adnyana, Y. Tezuka, A.H. Banskota, Q. Xiong, K.Q. Tran, and S. Kadota J. Nat. Prod. 63 2000 496
18. J.T. Han, M.H. Bang, O.K. Chun, D.O. Kim, C.Y. Lee, and N.I. Baek Arch. Pharmacol. Res. 27 2004 390
19. The sample of Centella asiatica (L.) was collected at Tam Dao National Park, Vinh Phuc, Vietnam, during June 2009 and identified by Dr. Ninh Khac Ban (Institute of Ecology and Biological Resources, VAST). A voucher specimen (IMBC CA-0609) was deposited at the Herbarium of Institute of Marine Biochemistry, VAST.
20. 2O (35:10:1, v/v/v), yielding compound 10 (7.0 mg).
21. V.U. Ahmad, S. Bano, and N. Bano Phytochemistry 25 1986 1487
22. H. Kojima, H. Tominaga, S. Sato, and H. Ogura Phytochemistry 26 1987 1107
23. C. Maeda, K. Ohtani, R. Kasai, K. Yamasaki, N.M. Duc, N.T. Nham, and N.K.Q. Cu Phytochemistry 37 1994 1131
24. 2O (0.1 mL, each), and the organic layer was analyzed by gas liquid chromatography (GC): Column: column SPB-1 (0.25 mm × 30 m); detector FID, column temp 210 °C, injector temp 270 °C, detector temp 300 °C, carrier gas He (2.0 mL/min). The retention times of persilylated glucose and rhamnose were founded to be 14.11 and 4.50 min, respectively, when compared with the standard solutions prepared by the same reaction from the standard monosaccharides. (The retention times of persilylated d-glucose, l-glucose, and l-rhamnose were 14.11, 14.26, and 4.50 min, respectively).
25. 20: 975.5165).
26. 2 serial dilution standard curve and the nitrite production was measured.
27. TNF-α production in the supernatant of RAW 264.7 cells was quantified using an OptEIA™ assay kits according to the manufacturer's instructions.