| Veraguamides A-G, cyclic hexadepsipeptides from a dolastatin 16-producing cyanobacterium Symploca cf. hydnoides from Guam. | |
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MedLine Citation:
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PMID: 21446699 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Cytotoxicity-directed purification of a Symploca cf. hydnoides sample from Cetti Bay, Guam, afforded seven new cyclic depsipeptides, veraguamides A-G (1-7), together with the known compound dolastatin 16. The planar structures of 1-7 were elucidated using NMR and MS experiments, while enantioselective HPLC and Mosher's analysis of acid and base hydrolysates, respectively, were utilized to assign the absolute configurations of the stereocenters. Veraguamides A-G (1-7) are characterized by the presence of an invariant proline residue, multiple N-methylated amino acids, an α-hydroxy acid, and a C8-polyketide-derived β-hydroxy acid moiety with a characteristic terminus as either an alkynyl bromide, alkyne, or vinyl group. These compounds and a semisynthetic analogue (8) showed moderate to weak cytotoxic activity against HT29 colorectal adenocarcinoma and HeLa cervical carcinoma cell lines. Preliminary structure-activity relationship analysis identified several sensitive positions in the veraguamide scaffold that affect the cytotoxic activity of this compound class. Dolastatin 16 showed only weak cytotoxic activity on both cell lines tested. The complete stereostructure of dolastatin 16 was proposed for the first time through degradation followed by a combination of advanced Marfey's analysis and modified Mosher's analysis using phenylglycine methyl ester as a chiral anisotropic reagent. |
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Authors:
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Lilibeth A Salvador; Jason S Biggs; Valerie J Paul; Hendrik Luesch |
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Publication Detail:
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Type: Journal Article; Research Support, N.I.H., Extramural Date: 2011-03-29 |
Journal Detail:
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Title: Journal of natural products Volume: 74 ISSN: 1520-6025 ISO Abbreviation: J. Nat. Prod. Publication Date: 2011 May |
Date Detail:
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Created Date: 2011-05-27 Completed Date: 2011-08-17 Revised Date: 2013-05-24 |
Medline Journal Info:
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Nlm Unique ID: 7906882 Medline TA: J Nat Prod Country: United States |
Other Details:
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Languages: eng Pagination: 917-27 Citation Subset: IM |
Affiliation:
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Department of Medicinal Chemistry, University of Florida, 1600 SW Archer Road, Gainesville, Florida 32610, United States. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Antineoplastic Agents
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chemistry,
isolation & purification*,
pharmacology Cyanobacteria / chemistry* Depsipeptides / chemistry, isolation & purification*, pharmacology Drug Screening Assays, Antitumor Female Guam HT29 Cells HeLa Cells Humans Molecular Structure Nuclear Magnetic Resonance, Biomolecular Structure-Activity Relationship |
| Grant Support | |
ID/Acronym/Agency:
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P41 GM086210-01S1/GM/NIGMS NIH HHS; P41 GM086210-02/GM/NIGMS NIH HHS; P41 GM086210-03/GM/NIGMS NIH HHS; P41GM086210/GM/NIGMS NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/Antineoplastic Agents; 0/Depsipeptides; 0/dolastatin 16; 0/veraguamide A |
| Comments/Corrections | |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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