Potent Antifouling Resorcylic Acid Lactones from the Gorgonian-Derived Fungus Cochliobolus lunatus
Three new 14-membered resorcylic acid lactones, two with a rare natural acetonide group and one with a 5-chloro-substituted lactone, named cochliomycins A−C (1−3), together with four known analogues, zeaenol (4), LL-Z1640-1 (5), LL-Z1640-2 (6), and paecilomycin F (7), were isolated from the culture...
Saved in:
| Published in | Journal of natural products (Washington, D.C.) Vol. 74; no. 4; pp. 629 - 633 |
|---|---|
| Main Authors | , , , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society and American Society of Pharmacognosy
25.04.2011
Amer Chemical Soc American Society of Pharmacognosy |
| Subjects | |
| Online Access | Get full text |
| ISSN | 0163-3864 1520-6025 1520-6025 |
| DOI | 10.1021/np100641b |
Cover
Loading…
| Abstract | Three new 14-membered resorcylic acid lactones, two with a rare natural acetonide group and one with a 5-chloro-substituted lactone, named cochliomycins A−C (1−3), together with four known analogues, zeaenol (4), LL-Z1640-1 (5), LL-Z1640-2 (6), and paecilomycin F (7), were isolated from the culture broth of Cochliobolus lunatus, a fungus obtained from the gorgonian Dichotella gemmacea collected in the South China Sea. Their structures and the relative configurations of 1−3 were elucidated using comprehensive spectroscopic methods including NOESY spectra and chemical conversions. A transetherification reaction was also observed in which cochliomycin B (2) in a solution of CDCl3 slowly rearranged to give cochliomycin A (1) at room temperature. These resorcylic acid lactones were evaluated against the larval settlement of barnacle Balanus amphitrite, and antifouling activity was detected for the first time for this class of metabolites. The antibacterial and cytotoxic activities of these compounds were also examined. |
|---|---|
| AbstractList | Three new 14 membered resorcylic acid lactones, two with a rare natural acetonide group and one with a 5-chloro-substituted lactone, named cochliomycins A-C (1-3), together with four known analogues, zeaenol (4), LL-Z1640-1 (5), LL-Z1640-2 (6), and paeciloniycin F (7), were isolated from the culture broth of Cochliobolius lunatus, a fungus obtained from the gorgonian. Dichotella gemmmacea collected in the South China Sea Their structures and the relative configurations of 1-3 were elucidated using comprehensive spectroscopic methods including NOESY spectra and chemical conversions. A transetherification reaction was also observed in which cochliomycin:B (2) in a, solution of CDCl3 slowly rearranged to give cochliomycin A (4) at room temperature. These resorcylic acid lactones were evaluated against the larval settlement of barnacle Balanus amphitrite and antifouling activity was detected for the first time for this class of metabolites. The antibacterial and cytotoxfc activities of these. compounds were alsoexamined. Three new 14-membered resorcylic acid lactones, two with a rare natural acetonide group and one with a 5-chloro-substituted lactone, named cochliomycins A-C (1-3), together with four known analogues, zeaenol (4), LL-Z1640-1 (5), LL-Z1640-2 (6), and paecilomycin F (7), were isolated from the culture broth of Cochliobolus lunatus, a fungus obtained from the gorgonian Dichotella gemmacea collected in the South China Sea. Their structures and the relative configurations of 1-3 were elucidated using comprehensive spectroscopic methods including NOESY spectra and chemical conversions. A transetherification reaction was also observed in which cochliomycin B (2) in a solution of CDCl(3) slowly rearranged to give cochliomycin A (1) at room temperature. These resorcylic acid lactones were evaluated against the larval settlement of barnacle Balanus amphitrite, and antifouling activity was detected for the first time for this class of metabolites. The antibacterial and cytotoxic activities of these compounds were also examined. Three new 14-membered resorcylic acid lactones, two with a rare natural acetonide group and one with a 5-chloro-substituted lactone, named cochliomycins A−C (1−3), together with four known analogues, zeaenol (4), LL-Z1640-1 (5), LL-Z1640-2 (6), and paecilomycin F (7), were isolated from the culture broth of Cochliobolus lunatus, a fungus obtained from the gorgonian Dichotella gemmacea collected in the South China Sea. Their structures and the relative configurations of 1−3 were elucidated using comprehensive spectroscopic methods including NOESY spectra and chemical conversions. A transetherification reaction was also observed in which cochliomycin B (2) in a solution of CDCl3 slowly rearranged to give cochliomycin A (1) at room temperature. These resorcylic acid lactones were evaluated against the larval settlement of barnacle Balanus amphitrite, and antifouling activity was detected for the first time for this class of metabolites. The antibacterial and cytotoxic activities of these compounds were also examined. Three new 14-membered resorcylic acid lactones, two with a rare natural acetonide group and one with a 5-chloro-substituted lactone, named cochliomycins A-C (1-3), together with four known analogues, zeaenol (4), LL-Z1640-1 (5), LL-Z1640-2 (6), and paecilomycin F (7), were isolated from the culture broth of Cochliobolus lunatus, a fungus obtained from the gorgonian Dichotella gemmacea collected in the South China Sea. Their structures and the relative configurations of 1-3 were elucidated using comprehensive spectroscopic methods including NOESY spectra and chemical conversions. A transetherification reaction was also observed in which cochliomycin B (2) in a solution of CDCl(3) slowly rearranged to give cochliomycin A (1) at room temperature. These resorcylic acid lactones were evaluated against the larval settlement of barnacle Balanus amphitrite, and antifouling activity was detected for the first time for this class of metabolites. The antibacterial and cytotoxic activities of these compounds were also examined.Three new 14-membered resorcylic acid lactones, two with a rare natural acetonide group and one with a 5-chloro-substituted lactone, named cochliomycins A-C (1-3), together with four known analogues, zeaenol (4), LL-Z1640-1 (5), LL-Z1640-2 (6), and paecilomycin F (7), were isolated from the culture broth of Cochliobolus lunatus, a fungus obtained from the gorgonian Dichotella gemmacea collected in the South China Sea. Their structures and the relative configurations of 1-3 were elucidated using comprehensive spectroscopic methods including NOESY spectra and chemical conversions. A transetherification reaction was also observed in which cochliomycin B (2) in a solution of CDCl(3) slowly rearranged to give cochliomycin A (1) at room temperature. These resorcylic acid lactones were evaluated against the larval settlement of barnacle Balanus amphitrite, and antifouling activity was detected for the first time for this class of metabolites. The antibacterial and cytotoxic activities of these compounds were also examined. Three new 14-membered resorcylic acid lactones, two with a rare natural acetonide group and one with a 3-chloro-substituted lactone, named cochliomycins A-C (1-3), together with four known analogues, zeaenol (4), LL- Z1640-1 (5), LL-Z1640-2 (6), and paecilomycin F (7), were isolated from the culture broth of Cochliobolus lunatus, a fungus obtained from the gorgonian Dichotella gemmacea collected in the South China Sea. Their structures and the relative configurations of 1-3 were elucidated using comprehensive spectroscopic methods including NOESY spectra and chemical conversions. A transetherification reaction was also observed in which cochliomycin B (2) in a solution of CDCI3 slowly rearranged to give cochliomycin A (1) at room temperature. These resorcylic acid lactones were evaluated against the larval settlement of barnacle Balanus amphitrite, and antifouling activity was detected for the first time for this class of metabolites. The antibacterial and cytotoxic activities of these compounds were also examined. |
| Author | Wang, Chang-Yun Wu, Hui-Xian She, Zhi-Gang Wei, Mei-Yan Zheng, Cai-Juan Xu, Ying Lin, Yong-Cheng Shao, Chang-Lun Qian, Pei-Yuan Gu, Yu-Cheng Liu, Qing-Ai |
| Author_xml | – sequence: 1 givenname: Chang-Lun surname: Shao fullname: Shao, Chang-Lun – sequence: 2 givenname: Hui-Xian surname: Wu fullname: Wu, Hui-Xian – sequence: 3 givenname: Chang-Yun surname: Wang fullname: Wang, Chang-Yun email: changyun@ouc.edu.cn, cesshzhg@mail.sysu.edu.cn – sequence: 4 givenname: Qing-Ai surname: Liu fullname: Liu, Qing-Ai – sequence: 5 givenname: Ying surname: Xu fullname: Xu, Ying – sequence: 6 givenname: Mei-Yan surname: Wei fullname: Wei, Mei-Yan – sequence: 7 givenname: Pei-Yuan surname: Qian fullname: Qian, Pei-Yuan – sequence: 8 givenname: Yu-Cheng surname: Gu fullname: Gu, Yu-Cheng – sequence: 9 givenname: Cai-Juan surname: Zheng fullname: Zheng, Cai-Juan – sequence: 10 givenname: Zhi-Gang surname: She fullname: She, Zhi-Gang email: changyun@ouc.edu.cn, cesshzhg@mail.sysu.edu.cn – sequence: 11 givenname: Yong-Cheng surname: Lin fullname: Lin, Yong-Cheng |
| BackLink | http://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=24128391$$DView record in Pascal Francis https://www.ncbi.nlm.nih.gov/pubmed/21348465$$D View this record in MEDLINE/PubMed |
| BookMark | eNqN0ltrFDEUAOAgLXZbffAPyLyIiEyb22Qyj8toq7BQEX0OSSazTckmay5K_72RnVaQgn1KQr6Twzknp-DIB28AeIXgOYIYXfg9gpBRpJ6BFeowbBnE3RFYQcRISzijJ-A0pVsIIYFD9xycYEQop6xbAfUlZONzs_bZzqE467fNV5NC1HfO6mat7dRspM41YWrmGHZNvjHNVYjb4K307QcT7U8zNZfFb0tqxqBvnA0quHpwxctc0gtwPEuXzMtlPQPfLz9-Gz-1m-urz-N600pKcW45MmoeJFKQqJ5O0wTxTDmWRA5K9p3qTD-zYVAdJ0xBiimZUIe4rkWyqWeQnIG3h3f3MfwoJmWxs0kb56Q3oSTBB8Y7MtSe_FcyQgmiGFf5epFF7cwk9tHuZLwT9w2s4M0CZNLSzVF6bdNfRxHmNWd17w_ul1FhTtoar80Dq5PBfOgpJnWHSNX86Xq0WWYb_BiKzzX04hCqY0gpmlno5T5HaZ1AUPz5M-Lhz9SId_9E3Cd6zC7lSp3EbSjR14k-4n4DOc7JzA |
| CODEN | JNPRDF |
| CitedBy_id | crossref_primary_10_1007_s42995_022_00157_8 crossref_primary_10_1021_jf500248z crossref_primary_10_1039_C5NP00156K crossref_primary_10_1021_acs_jnatprod_7b00838 crossref_primary_10_1021_acs_jnatprod_0c00804 crossref_primary_10_1038_s41598_017_12336_0 crossref_primary_10_1007_s10600_015_1497_z crossref_primary_10_1016_j_jorganchem_2018_05_018 crossref_primary_10_1016_j_steroids_2014_12_001 crossref_primary_10_1080_14786419_2014_923423 crossref_primary_10_1016_j_tet_2013_10_042 crossref_primary_10_3390_molecules26020458 crossref_primary_10_1016_j_phytol_2017_09_013 crossref_primary_10_3390_md11062054 crossref_primary_10_1007_s11998_018_0110_3 crossref_primary_10_1016_j_bioorg_2025_108389 crossref_primary_10_1007_s10600_020_03023_0 crossref_primary_10_1016_j_tet_2013_01_021 crossref_primary_10_1021_np300707x crossref_primary_10_1007_s10600_016_1849_3 crossref_primary_10_1007_s11802_020_4489_y crossref_primary_10_3390_md19040180 crossref_primary_10_1039_C2NP20112G crossref_primary_10_1177_1934578X211048652 crossref_primary_10_1038_ja_2017_21 crossref_primary_10_1021_acs_jnatprod_9b00735 crossref_primary_10_1039_C7NJ02799K crossref_primary_10_3390_md10010234 crossref_primary_10_1039_D2NP00025C crossref_primary_10_1016_j_tetasy_2012_05_017 crossref_primary_10_1016_j_tet_2014_06_055 crossref_primary_10_1007_s10600_017_1921_7 crossref_primary_10_3390_molecules25215077 crossref_primary_10_1016_j_ejmech_2014_11_067 crossref_primary_10_1016_S1875_5364_13_60036_9 crossref_primary_10_1021_acs_orglett_5b01995 crossref_primary_10_1016_j_biotechadv_2015_01_013 crossref_primary_10_1039_C4OB01400F crossref_primary_10_1080_08927014_2013_776042 crossref_primary_10_3390_jof8101043 crossref_primary_10_1016_j_fitote_2021_104884 crossref_primary_10_1039_C6NP00124F crossref_primary_10_1021_np200766d crossref_primary_10_1007_s11802_024_5975_4 crossref_primary_10_1016_j_tet_2014_08_055 crossref_primary_10_1038_aps_2013_155 crossref_primary_10_1021_np5001686 crossref_primary_10_1039_C4NP00144C crossref_primary_10_1177_1934578X1300801204 crossref_primary_10_1080_14786419_2019_1633646 crossref_primary_10_1002_ejoc_201500395 crossref_primary_10_1007_s42995_021_00103_0 crossref_primary_10_1021_np300103w crossref_primary_10_1007_s10600_020_03040_z crossref_primary_10_1016_j_tetlet_2016_05_046 crossref_primary_10_1021_np3007556 crossref_primary_10_1021_acs_jnatprod_9b01167 crossref_primary_10_1007_s10126_015_9634_z crossref_primary_10_1007_s12272_020_01275_6 crossref_primary_10_1177_1934578X1300800808 crossref_primary_10_1002_cbdv_201400267 crossref_primary_10_1016_j_tetlet_2021_153410 crossref_primary_10_1007_s10600_017_2230_x crossref_primary_10_1016_j_tetlet_2018_08_030 crossref_primary_10_1002_ejoc_201301613 crossref_primary_10_1016_j_tetasy_2017_07_004 crossref_primary_10_1002_ejoc_201701272 crossref_primary_10_1080_08927014_2014_997226 crossref_primary_10_1080_10286020_2024_2335254 crossref_primary_10_1016_j_ibiod_2014_01_009 crossref_primary_10_1007_s12272_012_0309_2 crossref_primary_10_1080_08927014_2015_1121245 crossref_primary_10_3390_md21020063 crossref_primary_10_1055_a_1326_2600 crossref_primary_10_1002_ejoc_201402133 crossref_primary_10_1016_j_bioorg_2019_102973 crossref_primary_10_3390_md15090266 crossref_primary_10_1016_j_ejbt_2016_02_002 crossref_primary_10_1016_j_tetlet_2017_08_021 crossref_primary_10_1016_j_tetlet_2014_06_096 crossref_primary_10_1016_S2095_3119_15_61145_5 crossref_primary_10_3390_md22100431 crossref_primary_10_7717_peerj_5049 crossref_primary_10_1016_j_tet_2022_132723 crossref_primary_10_3390_md13074044 crossref_primary_10_1039_C8NJ02534G crossref_primary_10_3390_md16120485 crossref_primary_10_3390_md22030135 crossref_primary_10_3390_md20020082 crossref_primary_10_1080_14786419_2023_2272022 crossref_primary_10_3389_fchem_2019_00763 crossref_primary_10_1002_cbdv_201400321 crossref_primary_10_3390_md20020090 crossref_primary_10_1007_s10126_015_9628_x crossref_primary_10_1007_s10126_014_9598_4 crossref_primary_10_1016_j_tetlet_2022_153777 crossref_primary_10_1002_aoc_4210 crossref_primary_10_1007_s10126_017_9760_x crossref_primary_10_3390_md11041050 crossref_primary_10_1002_ejoc_201800535 crossref_primary_10_1016_j_tet_2015_06_035 crossref_primary_10_3390_md12031569 crossref_primary_10_1007_s10600_014_1189_0 crossref_primary_10_1016_j_fbr_2018_09_002 crossref_primary_10_2174_1570178619666220523094936 crossref_primary_10_1007_s10600_019_02732_5 crossref_primary_10_3987_REV_11_SR_P_5 crossref_primary_10_1021_acs_jnatprod_0c00144 crossref_primary_10_1016_j_tetlet_2015_11_066 crossref_primary_10_1007_s10600_016_1677_5 crossref_primary_10_1021_jo5024602 crossref_primary_10_1007_s42995_019_00021_2 crossref_primary_10_1021_acs_jnatprod_9b00164 crossref_primary_10_1016_j_tet_2014_03_001 crossref_primary_10_1021_np4002042 crossref_primary_10_1080_14786419_2019_1576041 crossref_primary_10_1002_aoc_4464 crossref_primary_10_1146_annurev_matsci_070511_155012 crossref_primary_10_1016_j_molstruc_2024_137763 crossref_primary_10_1002_ejoc_201200241 crossref_primary_10_1021_acs_orglett_6b01963 crossref_primary_10_1039_C6RA00374E crossref_primary_10_1016_j_scitotenv_2024_172824 crossref_primary_10_1016_j_tetlet_2011_10_137 crossref_primary_10_1080_08927014_2017_1391951 crossref_primary_10_1080_00397911_2018_1472282 crossref_primary_10_1080_14786419_2017_1359177 crossref_primary_10_2174_0929867326666190626153819 crossref_primary_10_3390_md11051718 crossref_primary_10_1080_14786419_2014_891114 crossref_primary_10_1016_j_tet_2016_03_054 crossref_primary_10_1016_j_bcab_2024_103385 crossref_primary_10_1016_j_bmcl_2011_12_083 crossref_primary_10_1186_s12936_019_3026_1 crossref_primary_10_1016_j_tetlet_2016_03_010 crossref_primary_10_1007_s10600_015_1445_y crossref_primary_10_1007_s13225_012_0191_8 crossref_primary_10_1039_C7RA04941B crossref_primary_10_1007_s10600_015_1406_5 crossref_primary_10_1007_s42995_024_00246_w crossref_primary_10_1186_s13568_016_0272_2 crossref_primary_10_1016_j_tet_2013_02_033 crossref_primary_10_1039_C6RA24009G |
| Cites_doi | 10.1016/0031-9422(92)80346-G 10.1007/s00227-003-1077-9 10.1021/np900853n 10.1021/np060248n 10.1016/S0041-0101(00)00259-2 10.1016/j.tet.2009.03.050 10.1016/S0040-4039(00)82292-3 10.1007/s10886-007-9256-7 10.1021/jo010930g 10.1246/cl.2001.172 10.1039/B610344H 10.1128/AAC.37.1.39 10.1016/S0040-4020(01)88900-6 10.1016/S0040-4039(00)71472-9 10.1021/jo00406a007 10.1021/np100146y 10.1039/b610344h |
| ContentType | Journal Article |
| Copyright | Copyright © 2011 American Chemical Society and American Society of Pharmacognosy and American Society of Pharmacognosy 2015 INIST-CNRS |
| Copyright_xml | – notice: Copyright © 2011 American Chemical Society and American Society of Pharmacognosy and American Society of Pharmacognosy – notice: 2015 INIST-CNRS |
| DBID | AAYXX CITATION 17B 1KM BLEPL DTL EGQ GIRYA IQODW CGR CUY CVF ECM EIF NPM 7X8 |
| DOI | 10.1021/np100641b |
| DatabaseName | CrossRef Web of Knowledge Index Chemicus Web of Science Core Collection Science Citation Index Expanded Web of Science Primary (SCIE, SSCI & AHCI) Web of Science - Science Citation Index Expanded - 2011 Pascal-Francis Medline MEDLINE MEDLINE (Ovid) MEDLINE MEDLINE PubMed MEDLINE - Academic |
| DatabaseTitle | CrossRef Web of Science MEDLINE Medline Complete MEDLINE with Full Text PubMed MEDLINE (Ovid) MEDLINE - Academic |
| DatabaseTitleList | Web of Science MEDLINE MEDLINE - Academic |
| Database_xml | – sequence: 1 dbid: NPM name: PubMed url: https://proxy.k.utb.cz/login?url=http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed sourceTypes: Index Database – sequence: 2 dbid: 1KM name: Index Chemicus url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/woscc/search-with-editions?editions=WOS.IC sourceTypes: Enrichment Source Index Database |
| DeliveryMethod | fulltext_linktorsrc |
| Discipline | Chemistry Biology Pharmacy, Therapeutics, & Pharmacology |
| EISSN | 1520-6025 |
| EndPage | 633 |
| ExternalDocumentID | 21348465 24128391 000289742300013 10_1021_np100641b a869374121 |
| Genre | Research Support, Non-U.S. Gov't Journal Article |
| GeographicLocations | South China Sea |
| GrantInformation_xml | – fundername: Ministry of Science and Technology of China; Ministry of Science and Technology, China grantid: 2007FY210500 – fundername: National Natural Science Foundation of China; National Natural Science Foundation of China (NSFC) grantid: 30901879; 40976077; 40776073 – fundername: Ministry of Education of China; Ministry of Education of the People's Republic of China grantid: 20090132110002 |
| GroupedDBID | - 4.4 53G 55A 5GY 5VS 7~N AABXI AAWTL ABFLS ABFSI ABMVS ABOCM ABUCX ACGFS ACJ ACNCT ACS AEESW AENEX AFEFF ALMA_UNASSIGNED_HOLDINGS AQSVZ BAANH CS3 DU5 EBS ED ED~ EJD F5P GNL IH9 IHE JG JG~ LG6 P2P ROL TN5 UI2 VF5 VG9 W1F X XKZ YZZ --- -~X AAHBH AAYOK AAYXX ABBLG ABJNI ABLBI ABQRX ADHLV AGXLV AHGAQ CITATION CUPRZ GGK 17B 1KM BLEPL DTL GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED GROUPED_WOS_WEB_OF_SCIENCE .GJ 1WB ABHMW ACRPL ADNMO AEYZD AFFNX AGQPQ ANPPW ANTXH H~9 IQODW RNS XOL ZXP CGR CUY CVF ECM EIF NPM 7X8 |
| ID | FETCH-LOGICAL-a442t-81ebf9a1b03b74ddd02f482a3a9ba75b5e7f699b5836b04243d1518c0166d7603 |
| IEDL.DBID | ACS |
| ISICitedReferencesCount | 152 |
| ISICitedReferencesURI | https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=000289742300013 |
| ISSN | 0163-3864 1520-6025 |
| IngestDate | Fri Jul 11 16:27:23 EDT 2025 Sun Aug 24 04:10:47 EDT 2025 Mon Jul 21 05:47:21 EDT 2025 Mon Jul 21 09:14:16 EDT 2025 Fri Aug 29 16:02:25 EDT 2025 Wed Aug 06 10:55:01 EDT 2025 Tue Jul 01 02:21:27 EDT 2025 Thu Apr 24 23:04:49 EDT 2025 Thu Aug 27 13:41:58 EDT 2020 |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 4 |
| Keywords | HYPOTHEMYCIN MACROLIDES METABOLITES Ascomycota Human Liver Lung Animal origin Cytotoxicity Lactone Tricyclic compound Biological activity Cochliobolus lunatus Macrocycle Fungi Marine environment Coelenterata Cell line Hepatocyte Antifouling protection Cnidaria Isolation Invertebrata Tumor cell Structural analysis |
| Language | English |
| License | CC BY 4.0 |
| LinkModel | DirectLink |
| LogoURL | https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg |
| MergedId | FETCHMERGED-LOGICAL-a442t-81ebf9a1b03b74ddd02f482a3a9ba75b5e7f699b5836b04243d1518c0166d7603 |
| Notes | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 ObjectType-Article-2 ObjectType-Feature-1 |
| ORCID | 0000-0002-6400-6167 0000-0003-4074-9078 |
| PMID | 21348465 |
| PQID | 863431422 |
| PQPubID | 23479 |
| PageCount | 5 |
| ParticipantIDs | pubmed_primary_21348465 webofscience_primary_000289742300013CitationCount webofscience_primary_000289742300013 pascalfrancis_primary_24128391 acs_journals_10_1021_np100641b proquest_miscellaneous_863431422 crossref_primary_10_1021_np100641b crossref_citationtrail_10_1021_np100641b proquest_miscellaneous_896853916 |
| ProviderPackageCode | JG~ 55A AABXI GNL VF5 XKZ 7~N ACJ VG9 W1F ACS AEESW AFEFF ABMVS ABUCX IH9 BAANH AQSVZ ED~ UI2 CITATION AAYXX |
| PublicationCentury | 2000 |
| PublicationDate | 2011-04-25 |
| PublicationDateYYYYMMDD | 2011-04-25 |
| PublicationDate_xml | – month: 04 year: 2011 text: 2011-04-25 day: 25 |
| PublicationDecade | 2010 |
| PublicationPlace | WASHINGTON |
| PublicationPlace_xml | – name: WASHINGTON – name: Northbrook, IL – name: United States |
| PublicationTitle | Journal of natural products (Washington, D.C.) |
| PublicationTitleAbbrev | J NAT PROD |
| PublicationTitleAlternate | J. Nat. Prod |
| PublicationYear | 2011 |
| Publisher | American Chemical Society and American Society of Pharmacognosy Amer Chemical Soc American Society of Pharmacognosy |
| Publisher_xml | – name: American Chemical Society and American Society of Pharmacognosy – name: Amer Chemical Soc – name: American Society of Pharmacognosy |
| References | Winssinger N. (ref3/cit3) 2007 Dong J. (ref8/cit8) 2007; 33 Thiyagarajan V. (ref14/cit14) 2003; 143 Shier W. T. (ref6/cit6) 2001; 39 Fromtling R. A. (ref15/cit15) 1993; 37 Nair M. S. R. (ref2/cit2) 1981; 37 Isaka M. (ref7/cit7) 2009; 65 Nair M. S. R. (ref1/cit1) 1980; 21 Wang S. (ref17/cit17) 2006; 69 Tatsuta K. (ref11/cit11) 2001 Wickramaratne D. B. (ref12/cit12) 1988; 29 Ellestad G. A. (ref10/cit10) 1978; 43 Xu L. X. (ref5/cit5) 2010; 73 Arango V. (ref13/cit13) 2010; 73 Isaka M. (ref4/cit4) 2002; 67 Sugawara F. (ref9/cit9) 1992; 31 Grever M. R. (ref16/cit16) 1992; 19 Shier, WT (WOS:000169518600022) 2001; 39 Wang, S (WOS:000242298300019) 2006; 69 WICKRAMARATNE, DBM (WOS:A1988R317900037) 1988; 29 Thiyagarajan, V (WOS:000185672200014) 2003; 143 Tatsuta, K (WOS:000167144100040) 2001 NAIR, MSR (WOS:A1980JU32700003) 1980; 21 Dong, JY (WOS:000246478200018) 2007; 33 NAIR, MSR (WOS:A1981LZ29600004) 1981; 37 Arango, V (WOS:000278080900044) 2010; 73 FROMTLING, RA (WOS:A1993KF24700007) 1993; 37 Isaka, M (WOS:000174399200020) 2002; 67 SUGAWARA, F (WOS:A1992HZ54800025) 1992; 31 Isaka, M (WOS:000266296100018) 2009; 65 Winssinger, N (WOS:000243380800001) 2007 ELLESTAD, GA (WOS:A1978FC53300007) 1978; 43 GREVER, MR (WOS:A1992KC78500003) 1992; 19 Xu, LX (WOS:000278080900017) 2010; 73 J Nat Prod. 2013 Feb 22;76(2):302 |
| References_xml | – volume: 19 start-page: 622 year: 1992 ident: ref16/cit16 publication-title: Semin. Oncol. – volume: 31 start-page: 1987 year: 1992 ident: ref9/cit9 publication-title: Phytochemistry doi: 10.1016/0031-9422(92)80346-G – volume: 143 start-page: 543 year: 2003 ident: ref14/cit14 publication-title: Mar. Biol. (Berlin) doi: 10.1007/s00227-003-1077-9 – volume: 73 start-page: 885 year: 2010 ident: ref5/cit5 publication-title: J. Nat. Prod. doi: 10.1021/np900853n – volume: 69 start-page: 1622 year: 2006 ident: ref17/cit17 publication-title: J. Nat. Prod. doi: 10.1021/np060248n – volume: 39 start-page: 1435 year: 2001 ident: ref6/cit6 publication-title: Toxicon doi: 10.1016/S0041-0101(00)00259-2 – volume: 65 start-page: 4396 year: 2009 ident: ref7/cit7 publication-title: Tetrahedron doi: 10.1016/j.tet.2009.03.050 – volume: 29 start-page: 6153 year: 1988 ident: ref12/cit12 publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(00)82292-3 – volume: 33 start-page: 1115 year: 2007 ident: ref8/cit8 publication-title: J. Chem. Ecol. doi: 10.1007/s10886-007-9256-7 – volume: 67 start-page: 1561 year: 2002 ident: ref4/cit4 publication-title: J. Org. Chem. doi: 10.1021/jo010930g – start-page: 172 year: 2001 ident: ref11/cit11 publication-title: Chem. Lett. doi: 10.1246/cl.2001.172 – start-page: 22 year: 2007 ident: ref3/cit3 publication-title: Chem. Commun. doi: 10.1039/B610344H – volume: 37 start-page: 39 year: 1993 ident: ref15/cit15 publication-title: Antimicrob. Agents Chemother. doi: 10.1128/AAC.37.1.39 – volume: 37 start-page: 2445 year: 1981 ident: ref2/cit2 publication-title: Tetrahedron doi: 10.1016/S0040-4020(01)88900-6 – volume: 21 start-page: 2011 year: 1980 ident: ref1/cit1 publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(00)71472-9 – volume: 43 start-page: 2339 year: 1978 ident: ref10/cit10 publication-title: J. Org. Chem. doi: 10.1021/jo00406a007 – volume: 73 start-page: 1012 year: 2010 ident: ref13/cit13 publication-title: J. Nat. Prod. doi: 10.1021/np100146y – volume: 143 start-page: 543 year: 2003 ident: WOS:000185672200014 article-title: Energy content at metamorphosis and growth rate of the early juvenile barnacle Balanus amphitrite publication-title: MARINE BIOLOGY doi: 10.1007/s00227-003-1077-9 – volume: 67 start-page: 1561 year: 2002 ident: WOS:000174399200020 article-title: Aigialomycins A-E, new resorcylic macrolides from the marine mangrove fungus Aigialus parvus publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo010930g – volume: 37 start-page: 2445 year: 1981 ident: WOS:A1981LZ29600004 article-title: METABOLITES OF PYRENOMYCETES .14. STRUCTURE AND PARTIAL STEREOCHEMISTRY OF THE ANTIBIOTIC MACROLIDES HYPOTHEMYCIN AND DIHYDROHYPOTHEMYCIN publication-title: TETRAHEDRON – volume: 31 start-page: 1987 year: 1992 ident: WOS:A1992HZ54800025 article-title: ZEARALENONE DERIVATIVES PRODUCED BY THE FUNGUS DRECHSLERA-PORTULACAE publication-title: PHYTOCHEMISTRY – volume: 73 start-page: 885 year: 2010 ident: WOS:000278080900017 article-title: β-Resorcylic Acid Lactones from a Paecilomyces Fungus publication-title: JOURNAL OF NATURAL PRODUCTS doi: 10.1021/np900853n – volume: 29 start-page: 6153 year: 1988 ident: WOS:A1988R317900037 article-title: ACID REARRANGEMENTS OF THE MURRANGATINS publication-title: TETRAHEDRON LETTERS – volume: 33 start-page: 1115 year: 2007 ident: WOS:000246478200018 article-title: Nematicidal resorcylides from the aquatic fungus Caryospora callicarpa YMF1.01026 publication-title: JOURNAL OF CHEMICAL ECOLOGY doi: 10.1007/s10886-007-9256-7 – volume: 43 start-page: 2339 year: 1978 ident: WOS:A1978FC53300007 article-title: NEW ZEARALENONE RELATED MACROLIDES AND ISOCOUMARINS FROM AN UNIDENTIFIED FUNGUS publication-title: JOURNAL OF ORGANIC CHEMISTRY – volume: 65 start-page: 4396 year: 2009 ident: WOS:000266296100018 article-title: Aigialomycins and related polyketide metabolites from the mangrove fungus Aigialus parvus BCC 5311 publication-title: TETRAHEDRON doi: 10.1016/j.tet.2009.03.050 – start-page: 172 year: 2001 ident: WOS:000167144100040 article-title: The first total synthesis of a macrocyclic anti-protozoan, LL-Z1640-2 publication-title: CHEMISTRY LETTERS – start-page: 22 year: 2007 ident: WOS:000243380800001 article-title: Chemistry and biology of resorcylic acid lactones publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/b610344h – volume: 37 start-page: 39 year: 1993 ident: WOS:A1993KF24700007 article-title: MULTICENTER EVALUATION OF A BROTH MACRODILUTION ANTIFUNGAL SUSCEPTIBILITY TEST FOR YEASTS publication-title: ANTIMICROBIAL AGENTS AND CHEMOTHERAPY – volume: 39 start-page: 1435 year: 2001 ident: WOS:000169518600022 article-title: Structure-activity relationships for human estrogenic activity in zearalenone mycotoxins publication-title: TOXICON – volume: 19 start-page: 622 year: 1992 ident: WOS:A1992KC78500003 article-title: THE NATIONAL-CANCER-INSTITUTE - CANCER DRUG DISCOVERY AND DEVELOPMENT PROGRAM publication-title: SEMINARS IN ONCOLOGY – volume: 73 start-page: 1012 year: 2010 ident: WOS:000278080900044 article-title: Coumarins from Galipea panamensis and Their Activity against Leishmania panamensis publication-title: JOURNAL OF NATURAL PRODUCTS doi: 10.1021/np100146y – volume: 21 start-page: 2011 year: 1980 ident: WOS:A1980JU32700003 article-title: METABOLITES OF PYRENOMYCETES .13. STRUCTURE OF (+) HYPOTHEMYCIN, AN ANTIBIOTIC MACROLIDE FROM HYPOMYCES-TRICHOTHECOIDES publication-title: TETRAHEDRON LETTERS – volume: 69 start-page: 1622 year: 2006 ident: WOS:000242298300019 article-title: Chaetopyranin, a benzaldehyde derivative, and other related metabolites from Chaetomium globosum, an endophytic fungus derived from the marine red alga Polysiphonia urceolata publication-title: JOURNAL OF NATURAL PRODUCTS doi: 10.1021/np060248n – reference: - J Nat Prod. 2013 Feb 22;76(2):302 |
| SSID | ssj0003095 |
| Score | 2.4102347 |
| Snippet | Three new 14-membered resorcylic acid lactones, two with a rare natural acetonide group and one with a 5-chloro-substituted lactone, named cochliomycins A−C... Three new 14 membered resorcylic acid lactones, two with a rare natural acetonide group and one with a 5-chloro-substituted lactone, named cochliomycins A-C... Three new 14-membered resorcylic acid lactones, two with a rare natural acetonide group and one with a 5-chloro-substituted lactone, named cochliomycins A-C... Three new 14-membered resorcylic acid lactones, two with a rare natural acetonide group and one with a 3-chloro-substituted lactone, named cochliomycins A-C... |
| Source | Web of Science |
| SourceID | proquest pubmed pascalfrancis webofscience crossref acs |
| SourceType | Aggregation Database Index Database Enrichment Source Publisher |
| StartPage | 629 |
| SubjectTerms | Animals Anthozoa - chemistry Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - isolation & purification Anti-Bacterial Agents - pharmacology Antineoplastic Agents - chemistry Antineoplastic Agents - isolation & purification Antineoplastic Agents - pharmacology Ascomycota - chemistry Bacillus subtilis - drug effects Biofouling - prevention & control Biological and medical sciences Chemistry, Medicinal Drug Screening Assays, Antitumor Escherichia coli - drug effects General pharmacology Hep G2 Cells Humans Hydroxybenzoates Lactones - chemistry Lactones - isolation & purification Lactones - pharmacology Larva - drug effects Life Sciences & Biomedicine Medical sciences Microbial Sensitivity Tests Micrococcus - drug effects Molecular Structure Pharmacognosy. Homeopathy. Health food Pharmacology & Pharmacy Pharmacology. Drug treatments Plant Sciences Science & Technology Staphylococcus aureus - drug effects Thoracica - chemistry |
| Title | Potent Antifouling Resorcylic Acid Lactones from the Gorgonian-Derived Fungus Cochliobolus lunatus |
| URI | http://dx.doi.org/10.1021/np100641b http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000289742300013 https://www.ncbi.nlm.nih.gov/pubmed/21348465 https://www.proquest.com/docview/863431422 https://www.proquest.com/docview/896853916 |
| Volume | 74 |
| WOS | 000289742300013 |
| WOSCitedRecordID | wos000289742300013 |
| hasFullText | 1 |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjZ3bb9MwFIePxhBiEuJSNgiXyoJp4mEZ9SVO_FhllAkhVIlN2ltk5wIVVVotCVL56zmuk3QTZfCSl55Wjn3s89XH_h2Aw3yUZjST1G5U4cNo7qtQhX5oBZ8iw6wCjD1t8UWeXYhPl8HlDrz9Swaf0fflktq4Sc0duMskTl7LP_HXfrnlI-XOKUru80iKTj7o-ldt6EmrG6HnwVJX2AuFK1-xjS-3hqJ12Jk8gtPu8o47bfLjpKnNSfrrTy3H297oMTxssZOMnZ88gZ28HMA9V4hyNYD7cVf3bQBHU6dmvTom55vLWdUxOSLTjc716imY6QKBuyZje97IFlYvvxGbDbhKV_NZSsbpLCOfbTkfXE2JvcZCEDbJR2wjriO69E_R-X_mGZngetNUJF6k3-ezhcG5UJF5YxVHq324mHw4j8_8tmSDr4VgtR_R3BRKUzPiJhRZlo1YISKmuVZGh4EJ8rCQSpkg4tLYrCvPEDmiFEdPZqEc8QPYLbFZz4Hg_55CiFAWLDQiyFWEbIYsFWkEkEAY6sEQxzRpp1yVrLPpjCZ973rwrhvuJG0Fz23djfk20ze96dKpfGwzGt7wmd4SIQghTWGLSOdECY6ZzbzoMl80VRJJjqAmGLvFREkkJ4R1D545_9v8PuUCMTHw4PC6Q_afu3SxTbmvid4D-j9mcdslVvugfvGvznwJe243XfgseAW79VWTv0Ycq81wPR1_A4vGKwI |
| linkProvider | American Chemical Society |
| linkToHtml | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV3rb9MwELdgCG0S4lFe4VEsNE18WEb8iBN_rAKlQJkq0Un7Ftl5sIoqreYEqfz1nOO03VAF-5IvuUSX853vF5_9O4QOiyDLSS6IXaiCi1bMl5GM_MgSPsWaWgYYu9viVIzO-Jfz8LyjybFnYUAJA28ybRF_yy5A3ldLYtMn0bfRHQAh1HrzIPm-mXVZIN12RcF8Fgu-ZhG6-qjNQJm5loHuLZUBY5Sui8UumLkzI7XZZ_jAtTFq9W43nfw8aWp9kv3-i9LxZh_2EN3vQCgeOK95hG4VVQ_ddW0pVz20n6y7wPXQ0cRxW6-O8XR7VMsc4yM82bJerx4jPVkA_K7xwO4-sm3Wqx_Y1gYus9V8luFBNsvx2Db3gbkV20MtGKAn_gR6wqyiKv8DhMKvIsdDmH0ag5NFdjGfLTREhsHzxvKPmifobPhxmoz8roGDrzintR-TQpdSER0wHfE8zwNa8pgqpqRWUajDIiqFlDqMmdC2BstyACBxBoMo8kgE7Cnaq0Ct5wjDX1DJeSRKGmkeFjIGpAbIKlYAR0KuiYf6YNy0C0CTtrV1StKNdT30bj3qadbRn9suHPNdom83okvH-bFLqH_NdTaSAIkAsknQCK99KYUxs3UYVRWLxqSxYADbOKX_EJECcBRAdw89c264fT9hHEBj6KHDq365ue-Kx7YA3-J7D5GbiCWdSSwTQv3if8Z8g_ZH02_jdPz59OtLdODW2blPw1dor75sitcA1GrdbyP0D4MxM2M |
| linkToPdf | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV1Lb5tAEB61qfqQqj7cF324qyqKcggJyy4LHC1SN22j1FITKTfEstBYtbAVoJL76zsDGCeV1ebChQENszM7Hzu73wBsZ05quFGcFqrwohNhh37o2z4RPgXaJQYY2m1xoo7O5Jdz77z7UaSzMKhEiW8qmyI-RfXC5B3DAD8oFpxSKNe34Q6V68ijR9H3fuYVTthuWVTCFoGSKyahq49SFkrLa1no4SIp0SB528liE9TcmJWaDDR-DN963ZuNJz_360rvp7__onW8-cc9gUcdGGWj1nuewq2sGMDdtj3lcgD3o1U3uAHsTFqO6-UeO10f2Sr32A6brNmvl89AT-YIwys2ol1I1G69-MGoRnCZLmfTlI3SqWHH1OQH51hGh1sYQlD2CXXF2SUp7EMMiV-ZYWOcheqSRfP0Yjada4yQks1q4iEtn8PZ-ONpdGR3jRzsREq3sgOe6TxMuHaE9qUxxnFzGbiJSEKd-J72Mj9XYai9QChNtVhhEIgEKQ6kMr5yxAvYKlCtV8DwbyiX0le562vpZWGAiA0RVpAgLPGk5hYM0cBxF4hl3NTYXR731rVgdzXycdrRoFM3jtkm0Q-96KLl_tgkNLzmPr0kQiOEbiFqxFb-FOOYUT0mKbJ5XcaBEgjfpOv-QyRUiKcQwlvwsnXF9fu5kAgePQu2r_pmf78tIlMhvsH5FvCbiEWdSYgRoXr9P2O-h3uTw3F8_Pnk6xt40C63S9v13sJWdVln7xCvVXrYBOkfdow15g |
| openUrl | ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Potent+antifouling+resorcylic+acid+lactones+from+the+gorgonian-derived+fungus+Cochliobolus+lunatus&rft.jtitle=Journal+of+natural+products+%28Washington%2C+D.C.%29&rft.au=Shao%2C+Chang-Lun&rft.au=Wu%2C+Hui-Xian&rft.au=Wang%2C+Chang-Yun&rft.au=Liu%2C+Qing-Ai&rft.date=2011-04-25&rft.eissn=1520-6025&rft.volume=74&rft.issue=4&rft.spage=629&rft_id=info:doi/10.1021%2Fnp100641b&rft_id=info%3Apmid%2F21348465&rft.externalDocID=21348465 |
| thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0163-3864&client=summon |
| thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0163-3864&client=summon |
| thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0163-3864&client=summon |