Limonoids from the fruits of Melia azedarach and their cytotoxic activities

Phytochemistry

Volumn 89, Issue , 2013, Pages 59-70

  Akihisa, Toshihiro ^a   Pan, Xin ^a   Nakamura, Yasuhiro ^a   Kikuchi, Takashi ^a   Takahashi, Nami ^a   Matsumoto, Masahiro ^a   Ogihara, Eri ^a   Fukatsu, Makoto ^a   Koike, Kazuo ^b   Tokuda, Harukuni ^c  

^a NIHON UNIVERSITY   (Japan)

^b TOHO UNIVERSITY   (Japan)

^c KANAZAWA UNIVERSITY   (Japan)

Author keywords

Cytotoxic activities; Epstein Barr virus early antigen (EBV EA); Fruits; Limonoids; Melia azedarach; Meliaceae

Indexed keywords

ANTINEOPLASTIC AGENT; LIMONOID; VIRUS ANTIGEN;

APOPTOSIS; ARTICLE; CHEMISTRY; CYTOLOGY; DRUG EFFECT; EPSTEIN BARR VIRUS; FRUIT; HUMAN; IC 50; IMMUNOLOGY; ISOLATION AND PURIFICATION; LYMPHOCYTE; MELIA AZEDARACH; METABOLISM; TUMOR CELL LINE;

ANTIGENS, VIRAL; ANTINEOPLASTIC AGENTS; APOPTOSIS; CELL LINE, TUMOR; FRUIT; HERPESVIRUS 4, HUMAN; HUMANS; INHIBITORY CONCENTRATION 50; LIMONINS; LYMPHOCYTES; MELIA AZEDARACH;

HUMAN HERPESVIRUS 4; MELIA AZEDARACH; MELIACEAE;

EID: 84875708791     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2013.01.015     Document Type: Article

References (42)

1. T. Akihisa, K. Yasukawa, M. Yamaura, M. Ukiya, Y. Kimura, N. Shimizu, and K. Arai Triterpene alcohol and sterol ferulates from rice bran and their anti-inflammatory effects J. Agric. Food Chem. 48 2000 2313 2319
2. T. Akihisa, K. Yasukawa, and H. Tokuda Potentially cancer chemopreventive and anti-inflammatory terpenoids from natural sources Atta-ur-Rahman Studies in Natural Products Chemistry, vol. 29: Bioactive Natural Products (Part J) 2003 Elsevier Science Amsterdam 73 126
3. T. Akihisa, H. Tokuda, D. Hasegawa, M. Ukiya, Y. Kimura, E. Enjo, T. Suzuki, and H. Nishino Chalcones and other compounds from the exudates of Angelica keiskei and their cancer chemopreventive effects J. Nat. Prod. 69 2006 38 42
4. T. Akihisa, T. Noto, A. Takahashi, Y. Fujita, N. Banno, H. Tokuda, K. Koike, T. Suzuki, K. Yasukawa, and Y. Kimura Melanogenesis inhibitory, anti-inflammatory, and chemopreventive effects of limonoids from the seeds of Azadirachta indica A. Juss. (neem) J. Oleo Sci. 58 2009 581 594
5. T. Akihisa, A. Takahashi, T. Kikuchi, M. Takagi, K. Watanabe, M. Fukatsu, Y. Fujita, N. Banno, H. Tokuda, and K. Yasukawa The melanogenesis-inhibitory, anti-inflammatory, and chemopreventive effects of limonoids in n-hexane extract of Azadirachta indica A. Juss. (neem) seeds J. Oleo Sci. 60 2011 53 59
6. M. Bokel, R. Cramer, H. Gutzeit, S. Reeb, and W. Kraus Tetranortriterpenoids related to nimbin and nimbolide from Azadirachta indica A. Juss (Meliaceae) Tetrahedron 46 1990 775 782
7. S.B. Bratton, M. MacFarlane, K. Cain, and G.M. Cohen Protein complexes activate distinct caspase cascades in death receptor- and stress-induced apoptosis Exp. Cell Res. 256 2000 27 33
8. M.C. Carpinella, M.T. Defago, G. Valladares, and S.M. Palacios Antifeedant and insecticide properties of a limonoid from Melia azedarach (Meliaceae) with potential use for pest management J. Agric. Food Chem. 51 2003 369 374
9. S.-H. Dong, C.-R. Zhang, X.-F. He, H.-B. Liu, Y. Wu, and J.-M. Yue Mesendanins A-J, limonoids from the leaves and twigs of Melia toosendan J. Nat. Prod. 73 2010 1344 1349
10. Y. Fukuyama, I. Miura, and M. Ochi Bitter limonoids from the fruit of Melia azedarach L. var. japonica Makino Bull. Chem. Soc. Jpn. 56 1983 1139 1142
11. R.C. Huang, H. Okamura, T. Iwagawa, and M. Nakatani The structures of azedarachins, limonoid antifeedants from Chinese Melia azedarach Linn Bull. Chem. Soc. Jpn. 67 1994 2468 2472
12. S. Johnson, and E.D. Morgan Comparison of chromatographic systems for triterpenoids from Neem (Azadirachta indica) seeds J. Chromatogr. A 761 1997 53 63
13. T. Kikuchi, M. Nihei, H. Nagai, H. Fukushi, K. Tabata, T. Suzuki, and T. Akihisa Albanol A from the root bark of Morus alba L. induces apoptotic cell death in HL60 human leukemia cell line Chem. Pharm. Bull. 58 2010 568 571
14. T. Kikuchi, K. Ishii, T. Noto, A. Takahashi, K. Tabata, T. Suzuki, and T. Akihisa Cytotoxic and apoptosis-inducing activities of limonoids from the seeds of Azadirachta indica (neem) J. Nat. Prod. 74 2011 866 870
15. M. Kim, S.K. Kim, B.N. Park, K.H. Lee, G.H. Min, J.Y. Seoh, C.G. Park, E.S. Hwang, C.Y. Cha, and Y.H. Kook Antiviral effects of 28-deacetylsendanin on herpes simplex virus-1 replication Antiviral Res. 43 1999 103 112
16. H.-B. Liu, C.-R. Zhang, S.-H. Dong, L. Dong, Y. Wu, and J.-M. Yue Limonoids and triterpenoids from the seeds of Melia azedarach Chem. Pharm. Bull. 59 2011 1003 1007
17. K.M. Madyastha, and K. Venkatakrishnan Structural flexibility in the biocatalyst-mediated functionalization of ring 'A' in salannin, a tetranortriterpene from Azadirachta indica J. Chem. Soc Perkin Trans. 1 2000 3055 3062
18. S.J. Martin, C.P. Reutelingsperger, A.J. McGahon, J.A. Rader, R.C.A.A. van Schie, D.M. LaFace, and D.R. Green Early redistribution of plasma membrane phosphatidylserine is a general feature of apoptosis regardless of the initiating stimulus: inhibition by overexpression of Bcl-2 and Abl J. Exp. Med. 182 1995 1545 1556
19. K. Mohamad, Y. Hirasawa, M. Litaudon, K. Awang, A.H.A. Hadi, K. Takeya, W. Ekasari, A. Widyawaruyanti, N.C. Zaini, and H. Morita Ceramicines B-D, new antiplasmodial limonoids from Chisocheton ceramicus Bioorg. Med. Chem. 17 2009 727 730
20. M. Nakatani, R.-C. Huang, H. Okamura, T. Iwagawa, K. Tadera, and H. Naoki Three new antifeeding meliacarpinins from chinese Melia azedarach Linn Tetrahedron 51 1995 11731 11736
21. M. Nakatani, M. Shimokoro, J.B. Zhou, H. Okamura, T. Iwagawa, K. Tadera, N. Nakayama, and H. Naoki Limonoids from Melia toosendan Phytochemistry 52 1999 709 714
22. M. Nakatani, Y. Fukuman, T. Sakumoto, N. Yamashita, H. Okamura, and H. Iwagawa Nimbolinins, C-seco limonoids from the fruits of Melia toosendan Heterocycles 53 2000 689 695
23. T. Namba The Encyclopedia of Wakan-Yaku (Traditional Sino-Japanese Medicines) with Color Pictures', revised ed. vol. I 1994 Hoikusya Osaka p. 247
24. N.G. Ntalli, F. Cottiglia, C.A. Bueno, L.E. Alche, M. Leonti, S. Vargiu, E. Bifulco, U. Menkissoglu-Spiroudi, and P. Caboni Cytotoxic tirucallane triterpenoids from Melia azedarach fruits Molecules 15 2010 5866 6877
25. M. Ochi, H. Kotsuki, H. Ishida, and T. Tokoroyama Limonoids from Melia azedarach Linn. var. japonica Makino. II. The natural hydroxyl precursor of sendanin Chem. Lett. 1978 99 102
26. M. Ochi, H. Kotsuki, T. Kataoka, and T. Tada Limonoids from Melia azedarach Linn. var. japonica Makino. III. The structures of ohchinal and ohchinin acetate Chem. Lett. 1978 331 334
27. M. Okada Newly Revised Illustrated Medicinal Plants of World 2002 Hokuryukan Publishing Co., Ltd. Tokyo p. 262
28. H.N. Pati, U. Das, M. Kawase, H. Sakagami, J. Balzaarini, E.De. Clercq, and J.R. Dimmock 1-Aryl-2-dimethylaminomethyl-2-propen-1-one hydrochlorides and related adducts: a quest for selective cytotoxicity for malignant cells Bioorg. Med. Chem. 16 2008 5747 5753
29. M.S. Rajab, and M.D. Bentley Tetranortriterpenes from Melia volkensii J. Nat. Prod. 51 1988 840 844
30. G.S. Salvesen, and V.M. Dixit Caspases: intracellular signaling by proteolysis Cell 91 1997 443 446
31. S. Siddiqui, T. Mahmood, B.S. Siddiqui, and S. Faizi Two new tetranortriterpenoids from Azadirachta indica J. Nat. Prod. 49 1986 1068 1073
32. S. Siddiqui, S. Faizi, T. Mahmood, and B.S. Siddiqui Margosinolide and isomargosinolide, two new tetranortriteprenoids from Azadirachta indica A. Juss. (Meliaceae) Tetrahedron 42 1986 4849 4856
33. Z.-S. Su, S.-P. Yang, S. Zhang, L. Dong, and J.-M. Yue Meliarachins A-K: eleven limonoids from the twigs and leaves of Melia azedarach Helv. Chim. Acta 94 2011 1515 1526
34. Y. Takaishi, K. Ujita, H. Tokuda, H. Nishino, A. Iwashima, and T. Fujita Inhibitory effects of dihydroagarofuran sesquiterpenes on Epstein-Barr virus activation Cancer Lett. 65 1992 19 26
35. Q.-G. Tan, and X.-D. Luo Meliaceous limonoids: chemistry and biological activities Chem. Rev. 111 2011 7437 7522
36. N.A. Thornberry, and Y. Lazebnik Caspases: enemies within Science 281 1998 1312 1316
37. S.-B. Wu, Q.-Y. Bao, W.-X. Wang, Y. Zhao, G. Xia, Z. Zhao, H. Zeng, and J.-F. Hu Cytotoxic triterpenoids and steroids from the bark of Melia azedarach Planta Med. 77 2011 922 928
38. B. Zhang, Z.-F. Wang, M.-Z. Tang, and Y.-L. Shi Growth inhibition and apoptosis-induced effect on human cancer cells of toosendanin, a triterpenoid derivative from Chinese traditional medicine Invest. New Drugs 23 2005 547 553
39. Y. Zhang, C.P. Tang, C.Q. Ke, S. Yao, and Y. Ye Limonoids and triterpenoids from the stem bark of Melia toosendan J. Nat. Prod. 73 2010 664 668
40. L. Zhao, C.-H. Huo, L.-R. Shen, Y. Yang, Q. Zhang, and Q.-W. Shi Chemical constituents of plants from the genus Melia Chem. Biodivers. 7 2010 839 859
41. H. Zhou, A. Hamazaki, J.D. Fontana, H. Takahashi, T. Esumi, C.B. Wandscheer, H. Tsujimoto, and Y. Fukuyama New ring C-seco limonoids from Brazilian Melia azedarach and their cytotoxic activity J. Nat. Prod. 67 2004 1544 1547
42. H. Zhou, A. Hamazaki, J.D. Fontana, H. Takahashi, C.B. Wandscheer, and Y. Fukuyama Cytotoxic limonoids from Brazilian Melia azedarach Chem. Pharm. Bull. 53 2005 1362 1365