A Great Barrier Reef <em>Sinularia</em> sp. Yields Two New Cytotoxic Diterpenes
The methanol extract of a <em>Sinularia </em>sp., collected from Bowden Reef, Queensland, Australia, yielded ten natural products. These included the new nitrogenous diterpene (4<em>R</em>*,5<em>R</em>*,9<em&a...
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MDPI AG
2012-07-01
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| Series: | Marine Drugs |
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| Online Access: | http://www.mdpi.com/1660-3397/10/8/1619 |
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| author | Cherie A. Motti Catherine H. Liptrot Anthony D. Wright Jonathan L. Nielson Dianne M. Tapiolas |
| author_facet | Cherie A. Motti Catherine H. Liptrot Anthony D. Wright Jonathan L. Nielson Dianne M. Tapiolas |
| author_sort | Cherie A. Motti |
| collection | DOAJ |
| description | The methanol extract of a <em>Sinularia </em>sp., collected from Bowden Reef, Queensland, Australia, yielded ten natural products. These included the new nitrogenous diterpene (4<em>R</em>*,5<em>R</em>*,9<em>S</em>*,10<em>R</em>*,11<em>Z</em>)-4-methoxy-9-((dimethylamino)-methyl)-12,15-epoxy-11(13)-en-decahydronaphthalen-16-ol (<strong>1</strong>), and the new lobane, (1<em>R*</em>,2<em>R*</em>,4<em>S*</em>,15<em>E</em>)-loba-8,10,13(14),15(16)-tetraen-17,18-diol-17-acetate (<strong>2</strong>). Also isolated were two known cembranes, sarcophytol-B and (1<em>E</em>,3<em>E</em>,7<em>E</em>)-11,12-epoxycembratrien-15-ol, and six known lobanes, loba-8,10,13(15)-triene-16,17,18-triol, 14,18-epoxyloba-8,10,13(15)-trien-17-ol, lobatrientriol, lobatrienolide, 14,17-epoxyloba-8,10,13(15)-trien-18-ol-18-acetate and (17<em>R</em>)-loba-8,10,13(15)-trien-17,18-diol. Structures of the new compounds were elucidated through interpretation of spectra obtained after extensive NMR and MS investigations and comparison with literature values. The tumour cell growth inhibition potential of <strong>1</strong> and <strong>2</strong> along with loba-8,10,13(15)-triene-16,17,18-triol, 14,17-epoxyloba-8,10,13(15)-trien-18-ol-18-acetate, lobatrienolide, (1<em>E</em>,3<em>E</em>,7<em>E</em>)-11,12-epoxycembratrien-15-ol and sarcophytol-B were assessed against three human tumour cell lines (SF-268, MCF-7 and H460). The lobanes and cembranes tested demonstrated 50% growth inhibition in the range 6.8–18.5 µM, with no selectivity, whilst <strong>1</strong> was less active (GI<sub>50</sub> 70–175 µM). |
| first_indexed | 2024-04-11T22:03:44Z |
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| language | English |
| last_indexed | 2024-04-11T22:03:44Z |
| publishDate | 2012-07-01 |
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| spelling | doaj.art-f81fb3c6692a421ebe682feea098792b2022-12-22T04:00:48ZengMDPI AGMarine Drugs1660-33972012-07-011081619163010.3390/md10081619A Great Barrier Reef <em>Sinularia</em> sp. Yields Two New Cytotoxic DiterpenesCherie A. MottiCatherine H. LiptrotAnthony D. WrightJonathan L. NielsonDianne M. TapiolasThe methanol extract of a <em>Sinularia </em>sp., collected from Bowden Reef, Queensland, Australia, yielded ten natural products. These included the new nitrogenous diterpene (4<em>R</em>*,5<em>R</em>*,9<em>S</em>*,10<em>R</em>*,11<em>Z</em>)-4-methoxy-9-((dimethylamino)-methyl)-12,15-epoxy-11(13)-en-decahydronaphthalen-16-ol (<strong>1</strong>), and the new lobane, (1<em>R*</em>,2<em>R*</em>,4<em>S*</em>,15<em>E</em>)-loba-8,10,13(14),15(16)-tetraen-17,18-diol-17-acetate (<strong>2</strong>). Also isolated were two known cembranes, sarcophytol-B and (1<em>E</em>,3<em>E</em>,7<em>E</em>)-11,12-epoxycembratrien-15-ol, and six known lobanes, loba-8,10,13(15)-triene-16,17,18-triol, 14,18-epoxyloba-8,10,13(15)-trien-17-ol, lobatrientriol, lobatrienolide, 14,17-epoxyloba-8,10,13(15)-trien-18-ol-18-acetate and (17<em>R</em>)-loba-8,10,13(15)-trien-17,18-diol. Structures of the new compounds were elucidated through interpretation of spectra obtained after extensive NMR and MS investigations and comparison with literature values. The tumour cell growth inhibition potential of <strong>1</strong> and <strong>2</strong> along with loba-8,10,13(15)-triene-16,17,18-triol, 14,17-epoxyloba-8,10,13(15)-trien-18-ol-18-acetate, lobatrienolide, (1<em>E</em>,3<em>E</em>,7<em>E</em>)-11,12-epoxycembratrien-15-ol and sarcophytol-B were assessed against three human tumour cell lines (SF-268, MCF-7 and H460). The lobanes and cembranes tested demonstrated 50% growth inhibition in the range 6.8–18.5 µM, with no selectivity, whilst <strong>1</strong> was less active (GI<sub>50</sub> 70–175 µM).http://www.mdpi.com/1660-3397/10/8/1619<em>Sinularia</em><em> </em>Alcyoniidae<em> </em>anticancer activitylobanecembranediterpene |
| spellingShingle | Cherie A. Motti Catherine H. Liptrot Anthony D. Wright Jonathan L. Nielson Dianne M. Tapiolas A Great Barrier Reef <em>Sinularia</em> sp. Yields Two New Cytotoxic Diterpenes Marine Drugs <em>Sinularia</em> <em> </em>Alcyoniidae <em> </em>anticancer activity lobane cembrane diterpene |
| title | A Great Barrier Reef <em>Sinularia</em> sp. Yields Two New Cytotoxic Diterpenes |
| title_full | A Great Barrier Reef <em>Sinularia</em> sp. Yields Two New Cytotoxic Diterpenes |
| title_fullStr | A Great Barrier Reef <em>Sinularia</em> sp. Yields Two New Cytotoxic Diterpenes |
| title_full_unstemmed | A Great Barrier Reef <em>Sinularia</em> sp. Yields Two New Cytotoxic Diterpenes |
| title_short | A Great Barrier Reef <em>Sinularia</em> sp. Yields Two New Cytotoxic Diterpenes |
| title_sort | great barrier reef lt em gt sinularia lt em gt sp yields two new cytotoxic diterpenes |
| topic | <em>Sinularia</em> <em> </em>Alcyoniidae <em> </em>anticancer activity lobane cembrane diterpene |
| url | http://www.mdpi.com/1660-3397/10/8/1619 |
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