The chemical and biological potential of C ring modified triterpenoids

被引：50

作者：

Siewert, Bianka ^{[1
]}

Wiemann, Jana ^{[1
]}

Koewitsch, Alexander ^{[1
]}

Csuk, Rene ^{[1
]}

机构：

[1] Univ Halle Wittenberg, Bereich Organ Chem, D-06120 Halle, Saale, Germany

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2014年 / 72卷

关键词：

Oleanolic acid acid; Ursolic acid; Triterpenoids; Antitumor activity; Apoptosis; Structure-activity relationships; OLEANOLIC ACID-DERIVATIVES; URSOLIC ACID; ZUR KENNTNIS; CONSTITUENTS; INHIBITORS; SEPARATION; APOPTOSIS; ASSAY; FLOW; INDUCTION;

D O I：

10.1016/j.ejmech.2013.11.025

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A convenient and elegant route has been developed to separate the natural regioisomers triterpenoids ursolic acid (UA) and oleanolic acid (OA) as well as derivatives thereof. Eleven unknown derivatives of OA were designed, synthesized, and their cytotoxicity was investigated. Further sixteen compounds were prepared to correlate all compounds in a SAR study. It could be shown that C-ring modifications of OA and UA have only a moderate influence onto the cytotoxic activity of the compounds but a significant impact onto the ability to trigger apoptosis in ovarian cancer cells (cell line A2780). (C) 2013 Elsevier Masson SAS. All rights reserved.

引用

页码：84 / 101

页数：18

共 50 条

[11] NATURALLY-OCCURRING SECO-RING-A-TRITERPENOIDS AND THEIR POSSIBLE BIOLOGICAL SIGNIFICANCE
BAAS, WJ
PHYTOCHEMISTRY, 1985, 24 (09) : 1875 - 1889
[12] A-Ring-Modified Triterpenoids and Their Spermidine-Aldimines with Strong Antibacterial Activity
Kazakova, Oxana B.
Brunel, Jean Michel
Khusnutdinova, Elmira F.
Negrel, Sophie
Giniyatullina, Gulnara V.
Lopatina, Tatyana V.
Petrova, Anastasiya V.
MOLBANK, 2019, 2019 (03)
[13] TRITERPENOIDS .5. SOME RELATIVE CONFIGURATIONS IN RING-C, RING-D, AND RING-E OF THE BETA-AMYRIN AND THE LUPEOL GROUP OF TRITERPENOIDS
BARTON, DHR
HOLNESS, NJ
JOURNAL OF THE CHEMICAL SOCIETY, 1952, (JAN): : 78 - 92
[14] BIOLOGICAL SIGNIFICANCE OF TRITERPENOIDS
KAPOOR, VK
CHAWLA, AS
JOURNAL OF SCIENTIFIC & INDUSTRIAL RESEARCH, 1986, 45 (11): : 503 - 511
[15] Semisynthesis, Biological Activity, and Molecular Modeling Studies of C-Ring-Modified Camptothecins
Samori, Cristian
Guerrini, Andrea
Varchi, Greta
Fontana, Gabriele
Bombardelli, Ezio
Tinelli, Stella
Beretta, Giovanni Luca
Basili, Serena
Moro, Stefano
Zunino, Franco
Battaglia, Arturo
JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (04) : 1029 - 1039
[16] CHEMICAL, BIOCHEMICAL, AND BIOLOGICAL STUDIES ON SELECT C(1) TRIOL MODIFIED BICYCLOMYCINS
ZHANG, ZM
KOHN, H
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (22) : 9815 - 9826
[17] Chemical, biochemical, and biological studies on select C(I) triol modified bicyclomycins
1600, ACS, Washington, DC, USA (116):
[18] CHEMICAL AND BIOLOGICAL OXIDATION OF THE DIMETHOXYPHENOL RING OF ETOPOSIDE
VANMAANEN, JMS
DERUITER, C
VANDESTRAAT, R
BROERSEN, J
DEVRIES, J
PINEDO, HM
BRITISH JOURNAL OF CANCER, 1985, 52 (03) : 463 - 463
[19] SAR Analysis and Bioactive Potential of C(3) Alkylated Triterpenoids
Konysheva, Anastasia, V
Grishko, Victoria V.
MODERN SYNTHETIC METHODOLOGIES FOR CREATING DRUGS AND FUNCTIONAL MATERIALS (MOSM2019), 2020, 2280
[20] Triterpenoids with a Five-Membered a-Ring: Distribution in Nature, Transformations, Synthesis, and Biological Activity
Grishko, V. V.
Tolmacheva, I. A.
Pereslavtseva, A. V.
CHEMISTRY OF NATURAL COMPOUNDS, 2015, 51 (01) : 1 - 21

← 1 2 3 4 5 →