Two New Triterpene Glycosides from Centella asiatica

Abstract

Phytochemical investigation of the leaves of Centella asiatica resulted in the isolation and characterization of eight triterpenes and/or saponins [which were characterized as 23-O-acetylmadecassoside (1), asiatic acid (2), madecassic acid (3), asiaticoside C (4), asiaticoside F (5), asiaticoside (6), madecassoside (7), and 23-O-acetylasiaticoside B (8)] together with sitosterol 3-O-β-glucoside (9), stigmasterol 3-O-β-glucoside (10), and querectin-3-O-β-D-glucuronide (11). A new ursane-derived saponin (23-O-acetylmadecassoside) and a new oleanane-derived saponin (23-O-acetylasiaticoside B) were found as well. Structure elucidation was done by using spectroscopic techniques (HR‐ESI‐MS, 1D and 2D NMR), chemical methods, and comparative literature studies.

Key words

Centella asiatica - Apiaceae - saponins - 23‐O‐acetylmadecassoside - 23‐O‐acetylasiaticoside B

References

• 1 Brinkhaus B, Linder M, Schuppan D, Hahn E G. Chemcial, pharmacological and clinical profile of the East Asian medical plant Centella asiatica.  Phytomedicine. 2000;  7 427-448
• 2 Siddiqui B S, Aslam H, Ali S T, Khan S, Begum S. Chemical constituents of Centella asiatica.  J Asian Nat Prod Res. 2007;  9 407-414
• 3 Subban R, Veerakumar A, Manimaran R, Hashim K M, Balachandran I. Two new flavonoids from Centella asiatica (Linn.).  Nat Med (Tokyo). 2008;  62 369-373
• 4 Zheng C J, Qin L P. Chemical components of Centella asiatica and their bioactivities.  J Chin Integr Med. 2007;  5 348-351
• 5 Yu Q, Gao W, Zhang Y, Teng J, Duan H. Studies on chemical constituents in herb of Centella asiatica.  Zhongguo Zhongyao Zazhi. 2007;  32 1182-1184
• 6 Liu Y, Zhao Y. Chemical studies on the saponin compounds of Centella asiatica.  Zhongguo Xiandai Zhongyao. 2008;  10 7-9
• 7 Jiang Z Y, Zhang X M, Zhou J, Chen J J. New triterpenoid glycosides from Centella asiatica.  Helv Chim Acta. 2005;  88 297-303
• 8 Kuroda M, Mimaki Y, Harada H, Sakagami H, Sashida Y. Five new triterpene glycoside from Centella asiaitica.  Natural Med. 2001;  55 134-138
• 9 Sahu N P, Roy S K, Mahato S B. Spectroscopic determination of structures of triterpenoid trisaccharides from Centella asiatica.  Phytochemistry. 1989;  28 2852-2854
• 10 Adnyana I K, Tezuka Y, Banskota A H, Xiong Q, Tran K Q, Kadota S. Quadranosides I–V, new triterpene glucosides from the seeds of Combretum quadrangulare.  J Nat Prod. 2000;  63 496-500
• 11 Collins D J, Pillotti C A, Wallis A F A. Triterpene acids from some Papua New Guinea Terminalia species.  Phytochemistry. 1992;  31 881-884
• 12 Goad L J, Akihisa Y. Analysis of sterols, 1st edition. Weinheim; Blackie Academic & Professional 1997: 378-380
• 13 Mahmoud I, Moharram F A, Marzouk M S, Linscheid M W, Saleh M I. Polyphenolic constituents of Callistemon lanceolatus leaves.  Pharmazie. 2002;  57 494-496
• 14 Castillo-Munoz N, Gomez-Alonso S, Garcia-Romero E, Gomez M V, Velders A H, Hermosin-Gutierrez I. Flavonol 3-O-glycosides series of Vitis vinifera Cv. Petit Verdot red wine grapes.  J Agric Food Chem. 2009;  57 209-219
• 15 Jain M, Khan S I, Tekwani B L, Jacob M R, Singh S, Singh P P, Jain R. Synthesis, antimalarial, antileishmanial, and antimicrobial activities of some 8-quinolinamine analogues.  Bioorg Med Chem. 2005;  13 4458-4466
• 16 Mustafa J, Khan S I, Ma G, Walker L A, Khan I A. Synthesis, spectroscopic, and biological studies of novel estolides derived from anticancer active 4-O-podophyllotoxinyl 12-hydroxyl-octadec-Z-9-enoate.  Lipids. 2004;  39 659-666