Planta Med 2011; 77(16): 1844-1847
DOI: 10.1055/s-0030-1271197
Natural Product Chemistry
Letters
© Georg Thieme Verlag KG Stuttgart · New York

Cytotoxic Triterpenoids from Azadirachta indica

JinXiong Chen1 , 2 , JianChao Chen1 , Yun Sun1 , 2 , YuXin Yan1 , 2 , LingMei Kong1 , 2 , Yan Li1 , MingHua Qiu1
  • 1Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, Yunnan, P. R. China
  • 2Graduate School of the Chinese Academy of Sciences, Beijing, P. R. China
Further Information

Publication History

received April 11, 2011 revised May 13, 2011

accepted May 13, 2011

Publication Date:
14 June 2011 (online)

Abstract

Two new tirucallane triterpenoids, 24,25-epoxy-3β-hydroxy-20-oxo-7-tirucallene (1) and 22,23;24,25-diepoxy-3β-hydroxy-7-tirucallene (2), and a new tetranortriterpenoid, 4α-hydroperoxy-6-O-acetylnimbandiol (3), along with eight known compounds, were isolated from the branches and leaves of Azadirachta indica. Their structures were elucidated through spectroscopic and chemical methods. The cytotoxic assay showed that the abundant constituent nimbolide (8) had obvious cytotoxic activities against HL-60, SMMC7721, A549, MCF-7, and SW-480 cell lines, with IC50 values of 0.8 ± 0.1, 2.2 ± 0.2, 1.9 ± 1.3, 4.5 ± 1.1, and 2.3 ± 0.1 µM, respectively.

Supporting Information

References

  • 1 Vietmeyer N D. Neem – a tree for solving global problems. Washington: National Academy Press; 1992: 25
  • 2 Pandhawa N S, Parmar B S. Neem. New Delhi: India and New Age International (P) Limited; 1996: 6
  • 3 Garcia E S, Rembold H. Effects of azadirachtin on ecdysis of Rhodnius prolixus.  J Insect Physiol. 1984;  30 934-941
  • 4 Biswas K, Chattopadhyay I, Banerjee R K, Bandyopadhyay U. Biological activities and medicinal properties of neem (Azadirachta indica).  Curr Sci. 2002;  82 1336-1345
  • 5 Brahmachari G. Neem – an omnipotent plant: a retrospection.  ChemBioChem. 2004;  5 408-421
  • 6 Roy K M, Kobori M, Takenaka M, Nakahara K, Shinmoto H, Tsushida T. Inhibition of colon cancer (HT-29) cell proliferation by a triterpenoid isolated from Azadirachta indica is accompanied by cell cycle arrest and up-regulation of p 21.  Planta Med. 2006;  72 917-923
  • 7 Kumar S, Suresh P K, Vijayababu M R, Arunkumar A, Arunakaran J. Anticancer effects of ethanolic neem leaf extract on prostate cancer cell line (PC-3).  J Ethnopharmacol. 2006;  105 246-250
  • 8 Manikandan P, Anandan R, Nagini S. Evaluation of Azadirachta indica leaf fractions for in vitro antioxidant potential and protective effects against H2O2-induced oxidative damage to pBR322 DNA and red blood cells.  J Agric Food Chem. 2009;  57 6990-6996
  • 9 Pongtip S, Roongtawan S, Wandee G. Antioxidant activity of Siamese neem tree (VP1209).  J Ethnopharmacol. 2005;  99 109-112
  • 10 Kraus W, Cramer R. Pentanortriterpenoide aus Azadirachta indica A. Juss (Meliaceae).  Chem Ber. 1981;  114 2375-2381
  • 11 Siddiqui S, Siddiqui B S, Faizi S, Mahmood T. Tetracyclic triterpenoids and their derivatives from Azadirachta indica.  J Nat Prod. 1988;  51 30-43
  • 12 Luo X D, Wu S H, Ma Y B, Wu D G. Tirucallane triterpenoids from Dysoxylum hainanense.  Phytochemistry. 2000;  54 801-805
  • 13 Akihisa T, Noto T, Takahashi A, Fujita Y, Banno N, Tokuda H, Koike K, Suzuki T, Yasukawa K, Kimura Y. Melanogenesis inhibitory, anti-inflammatory, and chemopreventive effects of limonoids from the seeds of Azadirachta indicia A. Juss. (neem).  J Oleo Sci. 2009;  58 581-594
  • 14 Luo X D, Wu S H, Ma Y B, Wu D G. A new triterpenoid from Azadirachta indica.  Fitoterapia. 2000;  71 668-672
  • 15 Cantrell C L, Rajab M S, Franzblau S G, Fischer N H. Antimycobacterial triterpenes from Melia volkensii.  J Nat Prod. 1999;  62 546-548
  • 16 Bokel M, Cramer R, Gutzeit H, Reeb S, Kraus W. Tetranortriterpenoids related to nimbin and nimbolide from Azadirachta indica A. Juss (Meliaceae).  Tetrahedron. 1990;  46 775-782
  • 17 Kraus W, Cramer R. Neue Tetranortriterpenoide mit insektenfraßhemmender Wirkung aus Neem-Öl.  Liebigs Ann Chem. 1981;  1981 181-189
  • 18 Haba H, Lavaud C, Harkat H, Magid A A, Marcourt L, Benkhaled M. Diterpenoids and triterpenoids from Euphorbia guyoniana.  Phytochemistry. 2007;  68 1255-1260
  • 19 Vassilikogiannakis G, Margaros I, Montagnon T. Biomimetic total synthesis of litseaverticillols B, E, I, and J and structural reassignment of litseaverticillol E.  Org Lett. 2004;  6 2039-2042

MingHua Qiu

State Key Laboratory of Phytochemistry and Plant Resources in West China
Kunming Institute of Botany, Chinese Academy of Sciences

132, LanHei Road

Kunming 650204, Yunnan

P. R. China

Phone: +86 871 5 22 33 27

Fax: +86 871 5 22 32 55

Email: mhchiu@mail.kib.ac.cn

>