Pachydictyols B and C: New Diterpenes from Dictyota dichotoma Hudson
Two new diterpenoids, pachydictyol B (1a/1b) and C (2), were isolated from the dichloromethane extract of the marine brown alga, Dictyota dichotoma, collected from the Red Sea coast of Egypt, along with the known metabolites, pachydictyol A (3a), dictyol E (4), cis-africanan-1α-ol (5a), fucosterol (...
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| Format: | Article |
| Language: | English |
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MDPI AG
2013-08-01
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| Series: | Marine Drugs |
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| Online Access: | http://www.mdpi.com/1660-3397/11/9/3109 |
| _version_ | 1817996641312964608 |
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| author | Hartmut Laatsch Armin Maier Heinz H. Fiebig Khaled A. Shaaban Mohamed E. E. El-Naggar Mohamed Shaaban Ghada S. E. Abou-El-Wafa |
| author_facet | Hartmut Laatsch Armin Maier Heinz H. Fiebig Khaled A. Shaaban Mohamed E. E. El-Naggar Mohamed Shaaban Ghada S. E. Abou-El-Wafa |
| author_sort | Hartmut Laatsch |
| collection | DOAJ |
| description | Two new diterpenoids, pachydictyol B (1a/1b) and C (2), were isolated from the dichloromethane extract of the marine brown alga, Dictyota dichotoma, collected from the Red Sea coast of Egypt, along with the known metabolites, pachydictyol A (3a), dictyol E (4), cis-africanan-1α-ol (5a), fucosterol (6), tetrahydrothiophen-1,1-dioxide and poly-β-hydroxybutyric acid. GC-MS analysis of the nonpolar fractions also indicated the presence of β-bourbonene and nonanal, along with three hydrocarbons and five fatty acids or their simple derivatives, respectively. GC-MS analysis of the unsaponifiable algal petroleum ether extract revealed the presence of a further eight compounds, among them 2,2,6,7-tetramethyl-10-oxatricyclo[4.3.0.1(1,7)]decan-5-one (7), N-(4-bromo-n-butyl)-pipe ridin-2-one (8) and tert-hexadecanethiol. Structures 1–6 were assigned by 1D and 2D NMR, mass spectra (EI, CI, HREI and HRESI) and by comparison with data from related structures. The crude algal extract was potently active against the breast carcinoma tumor cell line, MCF7 (IC50 = 0.6 µg mL−1); pachydictyol B (1a) and dictyol E (4) showed weak antimicrobial properties, and the other compounds were inactive. Pachydictyols B (1a) and C (2) demonstrated a weak and unselective cytotoxicity against twelve human tumor cell lines with a mean IC50 of >30.0 µM. |
| first_indexed | 2024-04-14T02:25:19Z |
| format | Article |
| id | doaj.art-53b9a98ed30f4de491468431db69a7b4 |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-04-14T02:25:19Z |
| publishDate | 2013-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-53b9a98ed30f4de491468431db69a7b42022-12-22T02:17:54ZengMDPI AGMarine Drugs1660-33972013-08-011193109312310.3390/md11093109Pachydictyols B and C: New Diterpenes from Dictyota dichotoma HudsonHartmut LaatschArmin MaierHeinz H. FiebigKhaled A. ShaabanMohamed E. E. El-NaggarMohamed ShaabanGhada S. E. Abou-El-WafaTwo new diterpenoids, pachydictyol B (1a/1b) and C (2), were isolated from the dichloromethane extract of the marine brown alga, Dictyota dichotoma, collected from the Red Sea coast of Egypt, along with the known metabolites, pachydictyol A (3a), dictyol E (4), cis-africanan-1α-ol (5a), fucosterol (6), tetrahydrothiophen-1,1-dioxide and poly-β-hydroxybutyric acid. GC-MS analysis of the nonpolar fractions also indicated the presence of β-bourbonene and nonanal, along with three hydrocarbons and five fatty acids or their simple derivatives, respectively. GC-MS analysis of the unsaponifiable algal petroleum ether extract revealed the presence of a further eight compounds, among them 2,2,6,7-tetramethyl-10-oxatricyclo[4.3.0.1(1,7)]decan-5-one (7), N-(4-bromo-n-butyl)-pipe ridin-2-one (8) and tert-hexadecanethiol. Structures 1–6 were assigned by 1D and 2D NMR, mass spectra (EI, CI, HREI and HRESI) and by comparison with data from related structures. The crude algal extract was potently active against the breast carcinoma tumor cell line, MCF7 (IC50 = 0.6 µg mL−1); pachydictyol B (1a) and dictyol E (4) showed weak antimicrobial properties, and the other compounds were inactive. Pachydictyols B (1a) and C (2) demonstrated a weak and unselective cytotoxicity against twelve human tumor cell lines with a mean IC50 of >30.0 µM.http://www.mdpi.com/1660-3397/11/9/3109marine brown algaDictyota dichotomapachydictyolsditerpenesbioactivity |
| spellingShingle | Hartmut Laatsch Armin Maier Heinz H. Fiebig Khaled A. Shaaban Mohamed E. E. El-Naggar Mohamed Shaaban Ghada S. E. Abou-El-Wafa Pachydictyols B and C: New Diterpenes from Dictyota dichotoma Hudson Marine Drugs marine brown alga Dictyota dichotoma pachydictyols diterpenes bioactivity |
| title | Pachydictyols B and C: New Diterpenes from Dictyota dichotoma Hudson |
| title_full | Pachydictyols B and C: New Diterpenes from Dictyota dichotoma Hudson |
| title_fullStr | Pachydictyols B and C: New Diterpenes from Dictyota dichotoma Hudson |
| title_full_unstemmed | Pachydictyols B and C: New Diterpenes from Dictyota dichotoma Hudson |
| title_short | Pachydictyols B and C: New Diterpenes from Dictyota dichotoma Hudson |
| title_sort | pachydictyols b and c new diterpenes from dictyota dichotoma hudson |
| topic | marine brown alga Dictyota dichotoma pachydictyols diterpenes bioactivity |
| url | http://www.mdpi.com/1660-3397/11/9/3109 |
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