Isolation, characterization and antiproliferative activity of new metabolites from the South African endemic red algal species Laurencia alfredensis
- Dziwornu, Godwin A, Caira, Mino R, de la Mare, Jo-Anne, Edkins, Adrienne L, Bolton, John J, Beukes, Denzil R, Sunassee, Suthananda N
- Authors: Dziwornu, Godwin A , Caira, Mino R , de la Mare, Jo-Anne , Edkins, Adrienne L , Bolton, John J , Beukes, Denzil R , Sunassee, Suthananda N
- Date: 2017
- Language: English
- Type: article , text
- Identifier: http://hdl.handle.net/10962/59963 , vital:27715 , https://doi:10.3390/molecules22040513
- Description: The marine red algae of the genus Laurencia have been widely studied for their structurally diverse and biologically active secondary metabolites. We report here the natural product investigation of the organic extract of a newly identified South African endemic species, Laurencia alfredensis. A sequence of column chromatography, preparative TLC and normal phase HPLC resulted in the isolation of eleven compounds comprising three labdane-type diterpenes (1-3), four polyether triterpenes (4-7), three cholestane-type ecdysteroids (8-10) and a glycolipid (11). Compounds 1-3, 5-8 and 10 have not previously been reported, while compound 9 is reported here for the first time from a natural source and the known compound 11 isolated for the first time from the genus Laurencia. The structural elucidation and the relative configuration assignments of the compounds were accomplished by extensive use of ID- and 2D-NMR, HR-ESI-MS, UV and IR spectroscopic techniques, while the absolute configuration of compound 1 was determined by single-crystal X-ray diffraction analysis. All compounds were evaluated against the MDA-MB-231 breast and HeLa cervical cancer cell lines. Compound 2 exhibited low micromolar antiproliferative activity (IC50 = 9.3 gM) against the triple negative breast carcinoma and compound 7 was similarly active (IC50 = 8.8 gM) against the cervical cancer cell line.
- Full Text:
- Date Issued: 2017
- Authors: Dziwornu, Godwin A , Caira, Mino R , de la Mare, Jo-Anne , Edkins, Adrienne L , Bolton, John J , Beukes, Denzil R , Sunassee, Suthananda N
- Date: 2017
- Language: English
- Type: article , text
- Identifier: http://hdl.handle.net/10962/59963 , vital:27715 , https://doi:10.3390/molecules22040513
- Description: The marine red algae of the genus Laurencia have been widely studied for their structurally diverse and biologically active secondary metabolites. We report here the natural product investigation of the organic extract of a newly identified South African endemic species, Laurencia alfredensis. A sequence of column chromatography, preparative TLC and normal phase HPLC resulted in the isolation of eleven compounds comprising three labdane-type diterpenes (1-3), four polyether triterpenes (4-7), three cholestane-type ecdysteroids (8-10) and a glycolipid (11). Compounds 1-3, 5-8 and 10 have not previously been reported, while compound 9 is reported here for the first time from a natural source and the known compound 11 isolated for the first time from the genus Laurencia. The structural elucidation and the relative configuration assignments of the compounds were accomplished by extensive use of ID- and 2D-NMR, HR-ESI-MS, UV and IR spectroscopic techniques, while the absolute configuration of compound 1 was determined by single-crystal X-ray diffraction analysis. All compounds were evaluated against the MDA-MB-231 breast and HeLa cervical cancer cell lines. Compound 2 exhibited low micromolar antiproliferative activity (IC50 = 9.3 gM) against the triple negative breast carcinoma and compound 7 was similarly active (IC50 = 8.8 gM) against the cervical cancer cell line.
- Full Text:
- Date Issued: 2017
Cytotoxicity of lapachol, β-lapachone and related synthetic 1, 4-naphthoquinones against oesophageal cancer cells:
- Sunassee, Suthananda N, Veale, Clinton G L, Shunmoogam-Gounden, Nelusha, Osoniyi, Omalaja, Hendricks, Denver T, Caira, Mino R, De la Mare, Jo-Anne, Edkins, Adrienne L, Pinto, Antônio V, Da Silva Junior, Eufrânio N, Davies-Coleman, Michael T
- Authors: Sunassee, Suthananda N , Veale, Clinton G L , Shunmoogam-Gounden, Nelusha , Osoniyi, Omalaja , Hendricks, Denver T , Caira, Mino R , De la Mare, Jo-Anne , Edkins, Adrienne L , Pinto, Antônio V , Da Silva Junior, Eufrânio N , Davies-Coleman, Michael T
- Date: 2013
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/165207 , vital:41218 , DOI: 10.1016/j.ejmech.2012.12.048
- Description: Naphthoquinones have been found to have a wide range of biological activities, including cytotoxicity to cancer cells. The secondary metabolites lapachol, α- and β-lapachone and a series of 25 related synthetic 1,4-naphthoquinones were screened against the oesophageal cancer cell line (WHCO1). Most of the compounds exhibited enhanced cytotoxicity (IC50 1.6–11.7 μM) compared to the current drug of choice cisplatin (IC50 = 16.5 μM).
- Full Text:
- Date Issued: 2013
- Authors: Sunassee, Suthananda N , Veale, Clinton G L , Shunmoogam-Gounden, Nelusha , Osoniyi, Omalaja , Hendricks, Denver T , Caira, Mino R , De la Mare, Jo-Anne , Edkins, Adrienne L , Pinto, Antônio V , Da Silva Junior, Eufrânio N , Davies-Coleman, Michael T
- Date: 2013
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/165207 , vital:41218 , DOI: 10.1016/j.ejmech.2012.12.048
- Description: Naphthoquinones have been found to have a wide range of biological activities, including cytotoxicity to cancer cells. The secondary metabolites lapachol, α- and β-lapachone and a series of 25 related synthetic 1,4-naphthoquinones were screened against the oesophageal cancer cell line (WHCO1). Most of the compounds exhibited enhanced cytotoxicity (IC50 1.6–11.7 μM) compared to the current drug of choice cisplatin (IC50 = 16.5 μM).
- Full Text:
- Date Issued: 2013
Synthesis and structure determination of 8-and 9-iodocamphorquinone bis (ethylene ketal)
- Magqi, Nceba, Lobb, Kevin A, Kaye, Perry T, Caira, Mino R
- Authors: Magqi, Nceba , Lobb, Kevin A , Kaye, Perry T , Caira, Mino R
- Date: 2007
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/449399 , vital:74817 , xlink:href="https://doi.org/10.3184/030823407X209"
- Description: The structures of 8- and 9-iodocamphorquinone bis(ethylene ketal) have been confirmed by spectroscopic and single crystal X-ray analysis. The unexpected formation of the latter isomer is attributed to intramolecular rearrangement of the camphor skeleton, the mechanistic details of which have been explored using coset analysis.
- Full Text:
- Date Issued: 2007
- Authors: Magqi, Nceba , Lobb, Kevin A , Kaye, Perry T , Caira, Mino R
- Date: 2007
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/449399 , vital:74817 , xlink:href="https://doi.org/10.3184/030823407X209"
- Description: The structures of 8- and 9-iodocamphorquinone bis(ethylene ketal) have been confirmed by spectroscopic and single crystal X-ray analysis. The unexpected formation of the latter isomer is attributed to intramolecular rearrangement of the camphor skeleton, the mechanistic details of which have been explored using coset analysis.
- Full Text:
- Date Issued: 2007
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