Manoalide derivatives from a marine sponge Luffariella sp. collected in Palau
Two diastereomers of 24‐O‐methylmanoalide (1 and 2) and (6Z)‐neomanoalide‐24,25‐diacetate (3) were isolated together with manoalide (4), seco‐manoalide (5), (4E,6E)‐dehydromanoalide (6) and manoalide‐25‐acetate (7) from a marine sponge Luffariella sp. collected in Palau. Two methyl ethers of manoali...
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| Veröffentlicht in: | Fisheries science 2004-02, Vol.70 (1), p.152-158 |
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| creator | Namikoshi, M. (Tokyo Univ. or Marine Science and Technology (Japan)) Suzuki, S Meguro, S Nagai, H Koike, Y Kitazawa, A Kobayashi, H Oda, T Yamada, J |
| description | Two diastereomers of 24‐O‐methylmanoalide (1 and 2) and (6Z)‐neomanoalide‐24,25‐diacetate (3) were isolated together with manoalide (4), seco‐manoalide (5), (4E,6E)‐dehydromanoalide (6) and manoalide‐25‐acetate (7) from a marine sponge Luffariella sp. collected in Palau. Two methyl ethers of manoalide (1 and 2) were revealed to be derived from manoalide, the main component of the extract, during the separation procedure. The stereochemistries of 1 (24R) and 2 (24S) were assigned based on the NOESY data for 2 and two 24,25‐di‐O‐methylmanoalides (8 and 9), synthesized from 1 and 2. Although 3 has been chemically transformed from (6Z)‐neomanoalide, this is the first report of the isolation of this compound from a marine sponge. Compounds 1, 2, 4, 5 and 7 showed an antibacterial activity against Staphylococcus aureus at 5–10 µg, while 3, 8 and 9 were not active at 50 µg. |
| doi_str_mv | 10.1111/j.1444-2906.2003.00783.x |
| format | Article |
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(Tokyo Univ. or Marine Science and Technology (Japan)) ; Suzuki, S ; Meguro, S ; Nagai, H ; Koike, Y ; Kitazawa, A ; Kobayashi, H ; Oda, T ; Yamada, J</creator><creatorcontrib>Namikoshi, M. (Tokyo Univ. or Marine Science and Technology (Japan)) ; Suzuki, S ; Meguro, S ; Nagai, H ; Koike, Y ; Kitazawa, A ; Kobayashi, H ; Oda, T ; Yamada, J</creatorcontrib><description>Two diastereomers of 24‐O‐methylmanoalide (1 and 2) and (6Z)‐neomanoalide‐24,25‐diacetate (3) were isolated together with manoalide (4), seco‐manoalide (5), (4E,6E)‐dehydromanoalide (6) and manoalide‐25‐acetate (7) from a marine sponge Luffariella sp. collected in Palau. Two methyl ethers of manoalide (1 and 2) were revealed to be derived from manoalide, the main component of the extract, during the separation procedure. The stereochemistries of 1 (24R) and 2 (24S) were assigned based on the NOESY data for 2 and two 24,25‐di‐O‐methylmanoalides (8 and 9), synthesized from 1 and 2. Although 3 has been chemically transformed from (6Z)‐neomanoalide, this is the first report of the isolation of this compound from a marine sponge. Compounds 1, 2, 4, 5 and 7 showed an antibacterial activity against Staphylococcus aureus at 5–10 µg, while 3, 8 and 9 were not active at 50 µg.</description><identifier>ISSN: 0919-9268</identifier><identifier>EISSN: 1444-2906</identifier><identifier>DOI: 10.1111/j.1444-2906.2003.00783.x</identifier><language>eng</language><publisher>Melbourne, Australia: Blackwell Science Pty</publisher><subject>(6Z)‐neomanoalide‐24 ; 24‐O‐methylmanoalide ; 25‐diacetate ; ANTIMICROBIAL PROPERTIES ; ISOLATION ; Luffariella ; Luffariella sp ; manoalide ; MARINE ENVIRONMENT ; marine sponge ; PARAZOA ; Staphylococcus aureus ; TERPENOIDS</subject><ispartof>Fisheries science, 2004-02, Vol.70 (1), p.152-158</ispartof><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c6363-95dab175c9668dd5fdf8bfcac7774dfe699407535e60e5b47118f9a4ecba65733</citedby><cites>FETCH-LOGICAL-c6363-95dab175c9668dd5fdf8bfcac7774dfe699407535e60e5b47118f9a4ecba65733</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1111%2Fj.1444-2906.2003.00783.x$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1111%2Fj.1444-2906.2003.00783.x$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27903,27904,45553,45554</link.rule.ids></links><search><creatorcontrib>Namikoshi, M. 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The stereochemistries of 1 (24R) and 2 (24S) were assigned based on the NOESY data for 2 and two 24,25‐di‐O‐methylmanoalides (8 and 9), synthesized from 1 and 2. Although 3 has been chemically transformed from (6Z)‐neomanoalide, this is the first report of the isolation of this compound from a marine sponge. Compounds 1, 2, 4, 5 and 7 showed an antibacterial activity against Staphylococcus aureus at 5–10 µg, while 3, 8 and 9 were not active at 50 µg.</description><subject>(6Z)‐neomanoalide‐24</subject><subject>24‐O‐methylmanoalide</subject><subject>25‐diacetate</subject><subject>ANTIMICROBIAL PROPERTIES</subject><subject>ISOLATION</subject><subject>Luffariella</subject><subject>Luffariella sp</subject><subject>manoalide</subject><subject>MARINE ENVIRONMENT</subject><subject>marine sponge</subject><subject>PARAZOA</subject><subject>Staphylococcus aureus</subject><subject>TERPENOIDS</subject><issn>0919-9268</issn><issn>1444-2906</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><recordid>eNqNkc1KAzEURoMoWKuPIGTlbsakmfyBGylWKy0W1HVIMzclZTpTJ21t396MFbeaTcK93wm5JwhhSnKa1u0yp0VRZANNRD4ghOWESMXy_Qnq_TZOUY9oqjM9EOocXcS4JIQITlQPTae2bmwVSsAltGFnN2EHEfu2WWGLV7YNNeC4buoF4MnW-1SAqrKplGPXVBW4DZQ41HhmK7u9RGfeVhGufvY-eh89vA2fssnL43h4P8mcYIJlmpd2TiV3WghVltyXXs29s05KWZQehNYFkZxxEAT4vJCUKq9tAW5uBZeM9dHN8d5123xsIW7MKkTXPayGZhsN1VIUA0H_DkqpKKMiBdUx6Nomxha8WbchjX8wlJhOtFmazqfpfJpOtPkWbfYJvTuin6GCw785Mxq_pkPCr4-4t42xizZE8zxLQZ7-SGnOvgDf6Ix4</recordid><startdate>200402</startdate><enddate>200402</enddate><creator>Namikoshi, M. 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(Tokyo Univ. or Marine Science and Technology (Japan))</au><au>Suzuki, S</au><au>Meguro, S</au><au>Nagai, H</au><au>Koike, Y</au><au>Kitazawa, A</au><au>Kobayashi, H</au><au>Oda, T</au><au>Yamada, J</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Manoalide derivatives from a marine sponge Luffariella sp. collected in Palau</atitle><jtitle>Fisheries science</jtitle><date>2004-02</date><risdate>2004</risdate><volume>70</volume><issue>1</issue><spage>152</spage><epage>158</epage><pages>152-158</pages><issn>0919-9268</issn><eissn>1444-2906</eissn><abstract>Two diastereomers of 24‐O‐methylmanoalide (1 and 2) and (6Z)‐neomanoalide‐24,25‐diacetate (3) were isolated together with manoalide (4), seco‐manoalide (5), (4E,6E)‐dehydromanoalide (6) and manoalide‐25‐acetate (7) from a marine sponge Luffariella sp. collected in Palau. Two methyl ethers of manoalide (1 and 2) were revealed to be derived from manoalide, the main component of the extract, during the separation procedure. The stereochemistries of 1 (24R) and 2 (24S) were assigned based on the NOESY data for 2 and two 24,25‐di‐O‐methylmanoalides (8 and 9), synthesized from 1 and 2. Although 3 has been chemically transformed from (6Z)‐neomanoalide, this is the first report of the isolation of this compound from a marine sponge. Compounds 1, 2, 4, 5 and 7 showed an antibacterial activity against Staphylococcus aureus at 5–10 µg, while 3, 8 and 9 were not active at 50 µg.</abstract><cop>Melbourne, Australia</cop><pub>Blackwell Science Pty</pub><doi>10.1111/j.1444-2906.2003.00783.x</doi><tpages>7</tpages><oa>free_for_read</oa></addata></record> |
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| identifier | ISSN: 0919-9268 |
| ispartof | Fisheries science, 2004-02, Vol.70 (1), p.152-158 |
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| language | eng |
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| source | J-STAGE (Free - Japanese); Wiley Online Library; EZB Electronic Journals Library |
| subjects | (6Z)‐neomanoalide‐24 24‐O‐methylmanoalide 25‐diacetate ANTIMICROBIAL PROPERTIES ISOLATION Luffariella Luffariella sp manoalide MARINE ENVIRONMENT marine sponge PARAZOA Staphylococcus aureus TERPENOIDS |
| title | Manoalide derivatives from a marine sponge Luffariella sp. collected in Palau |
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