Limonoids from the fruits of Melia azedarach and their cytotoxic activities

被引:49
作者
Akihisa, Toshihiro [1 ]
Pan, Xin [1 ]
Nakamura, Yasuhiro [1 ]
Kikuchi, Takashi [1 ]
Takahashi, Nami [1 ]
Matsumoto, Masahiro [1 ]
Ogihara, Eri [1 ]
Fukatsu, Makoto [1 ]
Koike, Kazuo [2 ]
Tokuda, Harukuni [3 ]
机构
[1] Nihon Univ, Coll Sci & Technol, Chiyoda Ku, Tokyo 1018308, Japan
[2] Toho Univ, Sch Pharmaceut Sci, Funabashi, Chiba 2748510, Japan
[3] Kanazawa Univ, Grad Sch Med Sci, Kanazawa, Ishikawa 9208640, Japan
基金
日本学术振兴会;
关键词
Melia azedarach; Meliaceae; Fruits; Limonoids; Cytotoxic activities; Epstein-Barr virus early antigen (EBV-EA); VAR-JAPONICA-MAKINO; C-SECO LIMONOIDS; TRITERPENOIDS; TETRANORTRITERPENOIDS; INHIBITION; LEAVES; DEATH; TWIGS; SEEDS; RING;
D O I
10.1016/j.phytochem.2013.01.015
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Thirty-one limonoids and one tirucallane-type triterpenoid were isolated from the fruits of Melia azedarach (Meliaceae). The structures of 14 of these isolated compounds were elucidated on the basis of spectroscopic analyses and comparison with literature. All of these compounds were evaluated for. their cytotoxic activities against HL60, A549, AZ521, and SK-BR-3 human cancer cell lines. Meliarachin C (IC50 0.65 mu M) and 3-O-deacetyl-4'-demethyl-28-oxosalannin (IC50 2.8 mu M) exhibited potent cytotoxic activity against HL60 cells, and this was demonstrated mainly due to the induction of apoptosis by flow cytometry. Western blot analysis suggested that both compounds induced apoptosis via both the mitochondrial and death receptor-mediated pathways. In addition, 25 compounds were evaluated for their inhibitory effects against the Epstein-Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码:59 / 70
页数:12
相关论文
共 42 条
[11]   THE STRUCTURES OF AZEDARACHINS, LIMONOID ANTIFEEDANTS FROM CHINESE MELIA-AZEDARACH LINN [J].
HUANG, RC ;
OKAMURA, H ;
IWAGAWA, T ;
NAKATANI, M .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1994, 67 (09) :2468-2472
[12]   Comparison of chromatographic systems for triterpenoids from Neem (Azadirachta indica) seeds [J].
Johnson, S ;
Morgan, ED .
JOURNAL OF CHROMATOGRAPHY A, 1997, 761 (1-2) :53-63
[13]   Cytotoxic and Apoptosis-Inducing Activities of Limonoids from the Seeds of Azadirachta indica (Neem) [J].
Kikuchi, Takashi ;
Ishii, Koichi ;
Noto, Taisuke ;
Takahashi, Akitomo ;
Tabata, Keiichi ;
Suzuki, Takashi ;
Akihisa, Toshihiro .
JOURNAL OF NATURAL PRODUCTS, 2011, 74 (04) :866-870
[14]   Albanol A from the Root Bark of Morus alba L. Induces Apoptotic Cell Death in HL60 Human Leukemia Cell Line [J].
Kikuchi, Takashi ;
Nihei, Masatoshi ;
Nagai, Hisashi ;
Fukushi, Hidekuni ;
Tabata, Keiichi ;
Suzuki, Takashi ;
Akihisa, Toshihiro .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2010, 58 (04) :568-571
[15]   Antiviral effects of 28-deacetylsendanin on herpes simplex virus-1 replication [J].
Kim, M ;
Kim, SK ;
Park, BN ;
Lee, KH ;
Min, GH ;
Seoh, JY ;
Park, CG ;
Hwang, ES ;
Cha, CY ;
Kook, YH .
ANTIVIRAL RESEARCH, 1999, 43 (02) :103-112
[16]   Limonoids and Triterpenoids from the Seeds of Melia azedarach [J].
Liu, Hong-Bing ;
Zhang, Chuan-Rui ;
Dong, Shi-Hui ;
Dong, Lei ;
Wu, Yan ;
Yue, Jian-Min .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2011, 59 (08) :1003-1007
[17]   Structural flexibility in the biocatalyst-mediated functionalization of ring 'A' in salannin, a tetranortriterpene from Azadirachta indica [J].
Madyastha, KM ;
Venkatakrishnan, K .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (18) :3055-3062
[18]   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].
MARTIN, SJ ;
REUTELINGSPERGER, CPM ;
MCGAHON, AJ ;
RADER, JA ;
VANSCHIE, RCAA ;
LAFACE, DM ;
GREEN, DR .
JOURNAL OF EXPERIMENTAL MEDICINE, 1995, 182 (05) :1545-1556
[19]   Ceramicines B-D, new antiplasmodial limonoids from Chisocheton ceramicus [J].
Mohamad, Khalit ;
Hirasawa, Yusuke ;
Litaudon, Marc ;
Awang, Khalijah ;
Hadi, A. Hamid A. ;
Takeya, Koichi ;
Ekasari, Wiwied ;
Widyawaruyanti, Aty ;
Zaini, Noor Cholies ;
Morita, Hiroshi .
BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (02) :727-730
[20]   3 NEW ANTIFEEDING MELIACARPININS FROM CHINESE MELIA-AZEDARACH LINN [J].
NAKATANI, M ;
HUANG, RC ;
OKAMURA, H ;
IWAGAWA, T ;
TADERA, K ;
NAOKI, H .
TETRAHEDRON, 1995, 51 (43) :11731-11736