A New Diketopiperazine from the Marine Sponge Callyspongia Species
Chemical investigation of the sponge Callyspongia sp . from the South China Sea afforded one new diketopiperazine , cyclo-(R-Pro-6-hydroxyl-S -Ile) (1), along with six known d iketopiperazines : staphyloamide A (2), cyclo- (S-Pro-S-Phe) (3), cyclo-(R-Pro-R-Phe) (4), cyclo- (S-Pro-R-Leu) (5 ) , cyclo...
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| Veröffentlicht in: | Records of natural products 2016-01, Vol.10 (1), p.117 |
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| creator | Yang, Bin Huang, Jingxia Lin, Xiu ping Yanying Zhang Huaming Tao Yong hong Liu |
| description | Chemical investigation of the sponge Callyspongia sp . from the South China Sea afforded one new diketopiperazine , cyclo-(R-Pro-6-hydroxyl-S -Ile) (1), along with six known d iketopiperazines : staphyloamide A (2), cyclo- (S-Pro-S-Phe) (3), cyclo-(R-Pro-R-Phe) (4), cyclo- (S-Pro-R-Leu) (5 ) , cyclo-(S-Pro-R-Ala) (6), cyclo-(R-Tyr-R-Phe) (7), and three known tryptophan-derived alkaloids: C 2-α-D-mannosylpyranosyl-tryptophan (8), (1 R , 3 S )-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid (9), and (1R,3R)-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid (10) . The structures were determined on the basis of NMR and MS analysis , and the absolute configuration was determined by comparison of the optical rotation with the known compounds. This is the first report of compounds 1, 2 , 8-10 from the sponge Callyspongia . Cyclo- (S-Pro-R-Leu) (5 ) , and cyclo-(S-Pro-R-Ala) (6) exhibited antifouling activity against cyprid larvae of the barnacle with the LC 50 values of 3.5 μg/cm 2 and 6.0 μg/cm 2, respectively . |
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The structures were determined on the basis of NMR and MS analysis , and the absolute configuration was determined by comparison of the optical rotation with the known compounds. This is the first report of compounds 1, 2 , 8-10 from the sponge Callyspongia . Cyclo- (S-Pro-R-Leu) (5 ) , and cyclo-(S-Pro-R-Ala) (6) exhibited antifouling activity against cyprid larvae of the barnacle with the LC 50 values of 3.5 μg/cm 2 and 6.0 μg/cm 2, respectively .</description><identifier>EISSN: 1307-6167</identifier><language>eng</language><publisher>Gebze: ACG Publications</publisher><subject>Acids ; Antimicrobial agents ; Bacteria ; E coli ; Laboratories ; R&D ; Research & development ; Settlements & damages</subject><ispartof>Records of natural products, 2016-01, Vol.10 (1), p.117</ispartof><rights>Copyright ACG Publications 2016</rights><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784</link.rule.ids></links><search><creatorcontrib>Yang, Bin</creatorcontrib><creatorcontrib>Huang, Jingxia</creatorcontrib><creatorcontrib>Lin, Xiu ping</creatorcontrib><creatorcontrib>Yanying Zhang Huaming Tao</creatorcontrib><creatorcontrib>Yong hong Liu</creatorcontrib><title>A New Diketopiperazine from the Marine Sponge Callyspongia Species</title><title>Records of natural products</title><description>Chemical investigation of the sponge Callyspongia sp . from the South China Sea afforded one new diketopiperazine , cyclo-(R-Pro-6-hydroxyl-S -Ile) (1), along with six known d iketopiperazines : staphyloamide A (2), cyclo- (S-Pro-S-Phe) (3), cyclo-(R-Pro-R-Phe) (4), cyclo- (S-Pro-R-Leu) (5 ) , cyclo-(S-Pro-R-Ala) (6), cyclo-(R-Tyr-R-Phe) (7), and three known tryptophan-derived alkaloids: C 2-α-D-mannosylpyranosyl-tryptophan (8), (1 R , 3 S )-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid (9), and (1R,3R)-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid (10) . The structures were determined on the basis of NMR and MS analysis , and the absolute configuration was determined by comparison of the optical rotation with the known compounds. This is the first report of compounds 1, 2 , 8-10 from the sponge Callyspongia . Cyclo- (S-Pro-R-Leu) (5 ) , and cyclo-(S-Pro-R-Ala) (6) exhibited antifouling activity against cyprid larvae of the barnacle with the LC 50 values of 3.5 μg/cm 2 and 6.0 μg/cm 2, respectively .</description><subject>Acids</subject><subject>Antimicrobial agents</subject><subject>Bacteria</subject><subject>E coli</subject><subject>Laboratories</subject><subject>R&D</subject><subject>Research & development</subject><subject>Settlements & damages</subject><issn>1307-6167</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>AZQEC</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><recordid>eNotjctOwzAURC0kJErLP1hiHcmOn1mW8JQKLArr6tq5BpcQmzgVgq9vK1jNnFmcOSEzLpipNNfmjJyXsmVMC2vkjFwt6RN-0-v4gVPKMeMIv3FAGsb0Sad3pI8wHnmd0_CGtIW-_ynHHuGwoY9YFuQ0QF_w4j_n5PX25qW9r1bPdw_tclVlzsVUgW0kE84Dd41TnXFBBgXMOC18rWztUbMOOmMZr7X2UnLQDnTg1ofgXSPm5PLPm8f0tcMybbZpNw6Hyw23TChWC8XFHr2aRW4</recordid><startdate>20160101</startdate><enddate>20160101</enddate><creator>Yang, Bin</creator><creator>Huang, Jingxia</creator><creator>Lin, Xiu ping</creator><creator>Yanying Zhang Huaming Tao</creator><creator>Yong hong Liu</creator><general>ACG Publications</general><scope>3V.</scope><scope>7WY</scope><scope>7XB</scope><scope>883</scope><scope>8FK</scope><scope>8FL</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>BEZIV</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FRNLG</scope><scope>K60</scope><scope>K6~</scope><scope>M0F</scope><scope>PIMPY</scope><scope>PQBIZ</scope><scope>PQBZA</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>Q9U</scope></search><sort><creationdate>20160101</creationdate><title>A New Diketopiperazine from the Marine Sponge Callyspongia Species</title><author>Yang, Bin ; 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The structures were determined on the basis of NMR and MS analysis , and the absolute configuration was determined by comparison of the optical rotation with the known compounds. This is the first report of compounds 1, 2 , 8-10 from the sponge Callyspongia . Cyclo- (S-Pro-R-Leu) (5 ) , and cyclo-(S-Pro-R-Ala) (6) exhibited antifouling activity against cyprid larvae of the barnacle with the LC 50 values of 3.5 μg/cm 2 and 6.0 μg/cm 2, respectively .</abstract><cop>Gebze</cop><pub>ACG Publications</pub><oa>free_for_read</oa></addata></record> |
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| subjects | Acids Antimicrobial agents Bacteria E coli Laboratories R&D Research & development Settlements & damages |
| title | A New Diketopiperazine from the Marine Sponge Callyspongia Species |
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