Anticancer activity of 3-O-acylated betulinic acid derivative obtained by enzymatic synthesis
An easy and efficient strategy to prepare betulinic acid esters with various anhydrides was used by the enzymatic synthesis method. It involves lipase-catalyzed acylation of betulinic acid with anhydrides as acylating agents in organic solvent. Lipase from Candida antarctica immobilized on an acryli...
| Main Authors: | , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Japan Society for Bioscience, Biotechnology, and Agrochemistry
2010
|
| Online Access: | http://psasir.upm.edu.my/id/eprint/13137/ http://psasir.upm.edu.my/id/eprint/13137/1/Anticancer%20activity%20of%203.pdf |
| _version_ | 1848842029617905664 |
|---|---|
| author | Ahmad @ Amat, Faujan Moghaddam, Mansour Ghaffari Basri, Mahiran Abdul Rahman, Mohd Basyaruddin |
| author_facet | Ahmad @ Amat, Faujan Moghaddam, Mansour Ghaffari Basri, Mahiran Abdul Rahman, Mohd Basyaruddin |
| author_sort | Ahmad @ Amat, Faujan |
| building | UPM Institutional Repository |
| collection | Online Access |
| description | An easy and efficient strategy to prepare betulinic acid esters with various anhydrides was used by the enzymatic synthesis method. It involves lipase-catalyzed acylation of betulinic acid with anhydrides as acylating agents in organic solvent. Lipase from Candida antarctica immobilized on an acrylic resin (Novozym 435) was employed as a biocatalyst. Several 3-O-acyl-betulinic acid derivatives were successfully obtained by this procedure. The anticancer activity of betulinic acid and its 3-O-acylated derivatives were then evaluated in vitro against human lung carcinoma (A549) and human ovarian (CAOV3) cancer cell lines. 3-O-glutaryl-betulinic acid, 3-O-acetyl-betulinic acid, and 3-O-succinyl-betulinic acid showed IC(50)<10 microg/ml against A549 cancer cell line tested and showed better cytotoxicity than betulinic acid. In an ovarian cancer cell line, all betulinic acid derivatives prepared showed weaker cytotoxicity than betulinic acid. |
| first_indexed | 2025-11-15T07:52:38Z |
| format | Article |
| id | upm-13137 |
| institution | Universiti Putra Malaysia |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-15T07:52:38Z |
| publishDate | 2010 |
| publisher | Japan Society for Bioscience, Biotechnology, and Agrochemistry |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | upm-131372018-10-09T03:17:45Z http://psasir.upm.edu.my/id/eprint/13137/ Anticancer activity of 3-O-acylated betulinic acid derivative obtained by enzymatic synthesis Ahmad @ Amat, Faujan Moghaddam, Mansour Ghaffari Basri, Mahiran Abdul Rahman, Mohd Basyaruddin An easy and efficient strategy to prepare betulinic acid esters with various anhydrides was used by the enzymatic synthesis method. It involves lipase-catalyzed acylation of betulinic acid with anhydrides as acylating agents in organic solvent. Lipase from Candida antarctica immobilized on an acrylic resin (Novozym 435) was employed as a biocatalyst. Several 3-O-acyl-betulinic acid derivatives were successfully obtained by this procedure. The anticancer activity of betulinic acid and its 3-O-acylated derivatives were then evaluated in vitro against human lung carcinoma (A549) and human ovarian (CAOV3) cancer cell lines. 3-O-glutaryl-betulinic acid, 3-O-acetyl-betulinic acid, and 3-O-succinyl-betulinic acid showed IC(50)<10 microg/ml against A549 cancer cell line tested and showed better cytotoxicity than betulinic acid. In an ovarian cancer cell line, all betulinic acid derivatives prepared showed weaker cytotoxicity than betulinic acid. Japan Society for Bioscience, Biotechnology, and Agrochemistry 2010 Article PeerReviewed application/pdf en http://psasir.upm.edu.my/id/eprint/13137/1/Anticancer%20activity%20of%203.pdf Ahmad @ Amat, Faujan and Moghaddam, Mansour Ghaffari and Basri, Mahiran and Abdul Rahman, Mohd Basyaruddin (2010) Anticancer activity of 3-O-acylated betulinic acid derivative obtained by enzymatic synthesis. Bioscience, Biotechnology, and Biochemistry, 74 (5). pp. 1025-1029. ISSN 0916-8451 https://www.tandfonline.com/doi/abs/10.1271/bbb.90917 10.1271/bbb.90917 |
| spellingShingle | Ahmad @ Amat, Faujan Moghaddam, Mansour Ghaffari Basri, Mahiran Abdul Rahman, Mohd Basyaruddin Anticancer activity of 3-O-acylated betulinic acid derivative obtained by enzymatic synthesis |
| title | Anticancer activity of 3-O-acylated betulinic acid derivative obtained by enzymatic synthesis |
| title_full | Anticancer activity of 3-O-acylated betulinic acid derivative obtained by enzymatic synthesis |
| title_fullStr | Anticancer activity of 3-O-acylated betulinic acid derivative obtained by enzymatic synthesis |
| title_full_unstemmed | Anticancer activity of 3-O-acylated betulinic acid derivative obtained by enzymatic synthesis |
| title_short | Anticancer activity of 3-O-acylated betulinic acid derivative obtained by enzymatic synthesis |
| title_sort | anticancer activity of 3-o-acylated betulinic acid derivative obtained by enzymatic synthesis |
| url | http://psasir.upm.edu.my/id/eprint/13137/ http://psasir.upm.edu.my/id/eprint/13137/ http://psasir.upm.edu.my/id/eprint/13137/ http://psasir.upm.edu.my/id/eprint/13137/1/Anticancer%20activity%20of%203.pdf |