Preparation of Betulinic Acid Derivatives in Organic Solvents

Betulinic acid has been identified as a potential natural product in medical field. The objectives of this research were to discover a new method for the modification of betulinic acid’s functional groups (C-3 and C-28 position) and to evaluate its activity against cancer cell. Modification at C-3 p...

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Main Author:	Issak, Anishah
Format:	Thesis
Language:	English English
Published:	2004
Subjects:	Organic solvents Antineoplastic agents
Online Access:	http://psasir.upm.edu.my/id/eprint/383/1/549696_FSAS_2004_41.pdf
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spelling	my-upm-ir.3832013-05-27T06:47:58Z Preparation of Betulinic Acid Derivatives in Organic Solvents 2004-05 Issak, Anishah Betulinic acid has been identified as a potential natural product in medical field. The objectives of this research were to discover a new method for the modification of betulinic acid’s functional groups (C-3 and C-28 position) and to evaluate its activity against cancer cell. Modification at C-3 position was firstly carried out using acetate anhydride/pyridine with chemical reaction of 79% yield and was successfully modified using enzymatic reaction using Novozyme 435 in 85% yield. The later reaction is a new method for the preparation of 3β-acetoxy-lup20(29)-ene-28-oic acid using enzymatic reaction. Further modification at C- 28 position was carried out through an enzymatic reaction to produce betulinic acetate ester (3β-acetoxy-lup20(29)-ene-28-decanoate). Immobilized lipase from Candida antartica and Mucor miehei (Novozyme 435 and Lipozyme) were used. Novozyme 435 gave better esterification product of 3β-acetoxy-lup20(29)-ene-28-decanoate. To our knowledge, the esterification of 3β-acetoxy-lup20(29)-ene-28-decanoate using enzymatic reaction has not been reported previously. The effect of various parameters such as reaction time (1-24 h), initial water activity aw (0.11 - 0.90), substrate molar ratio of 1-decanol to 3β-axetoxy-lup20(29)-ene-28-oic acid (1:1 to 1:30) and various organic solvents on the esterification reaction was studied. Novozyme 435 was observed performed well in this study and gave maximum percent conversions of esterification under the following condition: reaction time (24 h), initial water activity aw (0.33), substrate molar ratio (1:15) in chloroform. These betulinic acid derivatives were then evaluated for their inhibitory activity against human leukemia cell line (HL60). Our results suggested that betulinic acid derivatives reduce their cytotoxicity compared with betulinic acid itself. Organic solvents Antineoplastic agents 2004-05 Thesis http://psasir.upm.edu.my/id/eprint/383/ http://psasir.upm.edu.my/id/eprint/383/1/549696_FSAS_2004_41.pdf application/pdf en public masters Universiti Putra Malaysia Organic solvents Antineoplastic agents Faculty of Environmental Studies English
institution	Universiti Putra Malaysia
collection	PSAS Institutional Repository
language	English English
topic	Organic solvents Antineoplastic agents
spellingShingle	Organic solvents Antineoplastic agents Issak, Anishah Preparation of Betulinic Acid Derivatives in Organic Solvents
description	Betulinic acid has been identified as a potential natural product in medical field. The objectives of this research were to discover a new method for the modification of betulinic acid’s functional groups (C-3 and C-28 position) and to evaluate its activity against cancer cell. Modification at C-3 position was firstly carried out using acetate anhydride/pyridine with chemical reaction of 79% yield and was successfully modified using enzymatic reaction using Novozyme 435 in 85% yield. The later reaction is a new method for the preparation of 3β-acetoxy-lup20(29)-ene-28-oic acid using enzymatic reaction. Further modification at C- 28 position was carried out through an enzymatic reaction to produce betulinic acetate ester (3β-acetoxy-lup20(29)-ene-28-decanoate). Immobilized lipase from Candida antartica and Mucor miehei (Novozyme 435 and Lipozyme) were used. Novozyme 435 gave better esterification product of 3β-acetoxy-lup20(29)-ene-28-decanoate. To our knowledge, the esterification of 3β-acetoxy-lup20(29)-ene-28-decanoate using enzymatic reaction has not been reported previously. The effect of various parameters such as reaction time (1-24 h), initial water activity aw (0.11 - 0.90), substrate molar ratio of 1-decanol to 3β-axetoxy-lup20(29)-ene-28-oic acid (1:1 to 1:30) and various organic solvents on the esterification reaction was studied. Novozyme 435 was observed performed well in this study and gave maximum percent conversions of esterification under the following condition: reaction time (24 h), initial water activity aw (0.33), substrate molar ratio (1:15) in chloroform. These betulinic acid derivatives were then evaluated for their inhibitory activity against human leukemia cell line (HL60). Our results suggested that betulinic acid derivatives reduce their cytotoxicity compared with betulinic acid itself.
format	Thesis
qualification_level	Master's degree
author	Issak, Anishah
author_facet	Issak, Anishah
author_sort	Issak, Anishah
title	Preparation of Betulinic Acid Derivatives in Organic Solvents
title_short	Preparation of Betulinic Acid Derivatives in Organic Solvents
title_full	Preparation of Betulinic Acid Derivatives in Organic Solvents
title_fullStr	Preparation of Betulinic Acid Derivatives in Organic Solvents
title_full_unstemmed	Preparation of Betulinic Acid Derivatives in Organic Solvents
title_sort	preparation of betulinic acid derivatives in organic solvents
granting_institution	Universiti Putra Malaysia
granting_department	Faculty of Environmental Studies
publishDate	2004
url	http://psasir.upm.edu.my/id/eprint/383/1/549696_FSAS_2004_41.pdf
_version_	1747810208995868672

Preparation of Betulinic Acid Derivatives in Organic Solvents

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