Abstract
Betulinic acid amide was synthesized from the enzymatic reaction of betulinic acid and butylamine catalysed by Novozym 435. The effects of different reaction parameters, such as effect of reaction time, reaction temperature, amount of enzyme, and substrate molar ratio (betulinic acid : butylamine), were studied and conventionally optimised. Based on this study, the enzymatic synthesis of betulinic acid amide was found to be 64.6% at the optimum conditions of 24 h, 40°C, 100 mg enzyme, and 1 : 1 substrate molar ratio in 9 : 1 mixture of chloroform and hexane as solvent. The identification of final product was carried out using TLC, melting point, and FTIR and NMR showed the presence of betulinic acid amide.
Highlights
Betulinic acid (BA), 3β-hydroxy-lup-20(29)-en-28-oic acid (Figure 1), is a natural product that exhibits potent antitumor activities by triggering the mitochondrial path to apoptosis
It has been reported that the betulinic acid has three active sites, C-3 hydroxyl group, C-20 alkene, and C-28 carboxyl group which are suitable for derivatization
The betulinic acid amide (BAA) product obtained after purification appeared to be yellowish crystal with melting point in the range of 308–310∘C
Summary
Betulinic acid (BA), 3β-hydroxy-lup-20(29)-en-28-oic acid (Figure 1), is a natural product that exhibits potent antitumor activities by triggering the mitochondrial path to apoptosis. Betulinic acid is a naturally occurring pentacyclic triterpenoid which has broad range of biological properties such as anticancer, anti-inflammatory, anti-HIV, antimicrobial, and antimalarial activities [1]. It was shown that betulinic acid possesses a high toxicity towards cancer cells and a weak toxicity to healthy cells allowing a selective destruction of melanoma cells by apoptosis [2]. It has been reported that the betulinic acid has three active sites, C-3 hydroxyl group, C-20 alkene, and C-28 carboxyl group which are suitable for derivatization. The modification or introduction of polar groups such as phthalates, amino acids, or sugar moieties at the C-3 and C-28 positions of betulinic acid in certain cases may increase its hydrosolubility and its anticancer activities [3]. Derivatization at C-20 position is not an advantageous site to derivatize due to the loss of its cytotoxicity activity [4]
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