Synthesis and Cytotoxic Activity of New Betulin and Betulinic Acid Esters with Conjugated Linoleic Acid (CLA)

The synthesis of new ester derivatives of betulin (3a-c) and betulinic acid (4) with conjugated linoleic acid isomers (CLA; in a mixture of 43.4% 9c, 11t; 49.5% 10t, 12c; 7.1% other isomers) is presented. Esterification was carried out with N,N’-dicyclohexylcarbodiimide (DCC) as the coupling agent i...

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Published in:Natural product communications 2013-04, Vol.8 (4), p.435-438
Main Authors: Tubek, Barbara, Mituła, Paweł, Niezgoda, Natalia, Kempińska, Katarzyna, Wietrzyk, Joanna, Wawrzeńczyk, Czesław
Format: Article
Language:English
Subjects:
Animals
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
Cell Line, Tumor
Humans
Linoleic Acids, Conjugated - chemical synthesis
Linoleic Acids, Conjugated - chemistry
Linoleic Acids, Conjugated - pharmacology
Mice
Triterpenes - chemical synthesis
Triterpenes - chemistry
Triterpenes - pharmacology
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Summary:The synthesis of new ester derivatives of betulin (3a-c) and betulinic acid (4) with conjugated linoleic acid isomers (CLA; in a mixture of 43.4% 9c, 11t; 49.5% 10t, 12c; 7.1% other isomers) is presented. Esterification was carried out with N,N’-dicyclohexylcarbodiimide (DCC) as the coupling agent in the presence of 4-dimethylamino-pyridine (DMAP) in dichloromethane (or pyridine). The in vitro cytotoxic effect of betulin (1), betulinic acid (2), a mixture of CLA isomers and their derivatives (3a-c, 4) was examined using the MTT assay against four cancer cell lines (P388, CEM/C2, CCRF/CEM and HL-60) and the SRB assay on the HT-29 cell line. Ester 4 was the most active among the esters synthesized against the CEM/C2 cell line with an ID50 value 16.9 ± 6.5 μg/mL. Betulin (1), betulinic acid (2) and CLA were the most active agents against the cancer cell lines studied.
ISSN:1934-578X
1555-9475
DOI:10.1177/1934578X1300800405