Synthesis of betulin derivatives and their protective effects against the cytotoxicity of cadmium

被引:39
作者
Hiroya, K [1 ]
Takahashi, T [1 ]
Miura, N [1 ]
Naganuma, A [1 ]
Sakamoto, T [1 ]
机构
[1] Tohoku Univ, Grad Sch Pharmaceut Sci, Aoba Ku, Sendai, Miyagi 9808578, Japan
关键词
D O I
10.1016/S0968-0896(02)00172-4
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
The protecting effect of betulin against cadmium toxicity was investigated using 11 kinds of analogues. It was elucidated by analyzing the analogue activities that both hydroxyl groups on C-3 and C-28 and the isopropenyl group on C-19 played important roles for expressing efficient activities. In addition, the cytotoxicity of betulin was also reduced by being functionalized using the above functional group. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3229 / 3236
页数:8
相关论文
共 18 条
[1]   CONSTITUENTS OF BYRSONIMA-CRASSIFOLIA AND THEIR SPASMOGENIC ACTIVITY [J].
BEJAR, E ;
AMARQUAYE, A ;
CHE, CT ;
MALONE, MH ;
FONG, HHS .
INTERNATIONAL JOURNAL OF PHARMACOGNOSY, 1995, 33 (01) :25-32
[2]   ANTI-AIDS AGENTS .11. BETULINIC ACID AND PLATANIC ACID AS ANTI-HIV PRINCIPLES FROM SYZIGIUM-CLAVIFLORUM, AND THE ANTI-HIV ACTIVITY OF STRUCTURALLY RELATED TRITERPENOIDS [J].
FUJIOKA, T ;
KASHIWADA, Y ;
KILKUSKIE, RE ;
COSENTINO, LM ;
BALLAS, LM ;
JIANG, JB ;
JANZEN, WP ;
CHEN, IS ;
LEE, KH .
JOURNAL OF NATURAL PRODUCTS, 1994, 57 (02) :243-247
[3]   SELECTIVE REDUCTION OF ALIPHATIC KETONES AND ALDEHYDES TO HYDROCARBONS WITH SODIUM CYANOBOROHYDRIDE AND PARA TOLUENESULFONYL HYDRAZIDE IN DIMETHYLFORMAMIDE-SULFOLANE [J].
HUTCHINS, RO ;
MARYANOF.BE ;
MILEWSKI, CA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (07) :1793-&
[4]   Synthesis of betulinic acid derivatives with activity against human melanoma [J].
Kim, DSHL ;
Pezzuto, JM ;
Pisha, E .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (13) :1707-1712
[5]   Development of C-20 modified betulinic acid derivatives as antitumor agents [J].
Kim, JY ;
Koo, HM ;
Kim, DSHL .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (17) :2405-2408
[6]   Protective effects of soyasapogenol A on liver injury mediated by immune response in a concanavalin A-induced hepatitis model [J].
Kuzuhara, H ;
Nishiyama, S ;
Minowa, N ;
Sasaki, K ;
Omoto, S .
EUROPEAN JOURNAL OF PHARMACOLOGY, 2000, 391 (1-2) :175-181
[7]  
LIU J, 1994, J ETHNOPHARMACOL, V42, P183, DOI 10.1016/0378-8741(94)90084-1
[8]   THE EFFECTS OF 10 TRITERPENOID COMPOUNDS ON EXPERIMENTAL LIVER-INJURY IN MICE [J].
LIU, J ;
LIU, YP ;
MAO, Q ;
KLAASSEN, CD .
FUNDAMENTAL AND APPLIED TOXICOLOGY, 1994, 22 (01) :34-40
[9]  
LIU YP, 1993, J PHARMACOL EXP THER, V266, P400
[10]   Protective effects of triterpene compounds against the cytotoxicity of cadmium in HepG2 cells [J].
Miura, N ;
Matsumoto, Y ;
Miyairi, S ;
Nishiyama, S ;
Naganuma, A .
MOLECULAR PHARMACOLOGY, 1999, 56 (06) :1324-1328