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Mandelalides A-D, cytotoxic macrolides from a new Lissoclinum species of South African tunicate.

ABSTRACT: Mandelalides A-D are variously glycosylated, unusual polyketide macrolides isolated from a new species of Lissoclinum ascidian collected from South Africa, Algoa Bay near Port Elizabeth and the surrounding Nelson Mandela Metropole. Their planar structures were elucidated on submilligram samples by comprehensive analysis of 1D and 2D NMR data, supported by mass spectrometry. The assignment of relative configuration was accomplished by consideration of homonuclear and heteronuclear coupling constants in tandem with ROESY data. The absolute configuration was assigned for mandelalide A after chiral GC-MS analysis of the hydrolyzed monosaccharide (2-O-methyl-?-L-rhamnose) and consideration of ROESY correlations between the monosaccharide and aglycone in the intact natural product. The resultant absolute configuration of the mandelalide A macrolide was extrapolated to propose the absolute configurations of mandelalides B-D. Remarkably, mandelalide B contained the C-4' epimeric 2-O-methyl-6-dehydro-?-L-talose. Mandelalides A and B showed potent cytotoxicity to human NCI-H460 lung cancer cells (IC(50), 12 and 44 nM, respectively) and mouse Neuro-2A neuroblastoma cells (IC(50), 29 and 84 nM, respectively).

SUBMITTER: Sikorska J

PROVIDER: S-EPMC3549468 | biostudies-literature | 2012 Jul

REPOSITORIES: biostudies-literature

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Mandelalides A-D, cytotoxic macrolides from a new Lissoclinum species of South African tunicate.

Sikorska Justyna J Hau Andrew M AM Anklin Clemens C Parker-Nance Shirley S Davies-Coleman Michael T MT Ishmael Jane E JE McPhail Kerry L KL

The Journal of organic chemistry 20120703 14

Mandelalides A-D are variously glycosylated, unusual polyketide macrolides isolated from a new species of Lissoclinum ascidian collected from South Africa, Algoa Bay near Port Elizabeth and the surrounding Nelson Mandela Metropole. Their planar structures were elucidated on submilligram samples by comprehensive analysis of 1D and 2D NMR data, supported by mass spectrometry. The assignment of relative configuration was accomplished by consideration of homonuclear and heteronuclear coupling consta ...[more]

PMID: 22712890

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Project description:BackgroundThe previous species list of South African Mantodea, published in 1998, was largely compiled from the literature and did not incorporate data from the many insect museum collections available in the country. It is estimated that approximately 120 species of Mantodea occur in South Africa; however, since no historical museum records were previously incorporated, the current information is considered to be outdated and not a true reflection of the Mantodea fauna within this region. A checklist of species is an important benchmark for any insect group, especially in light of the worldwide declines of insect diversity reported over the last decade. Checklists that provide accurate information on insect diversity, especially for groups, such as the Mantodea which could be under threat and thus could provide important information that can be used in determining the threat status of species, as well as to aid in their conservation in general.New informationThis paper provides an updated checklist of the praying mantids (Insecta, Mantodea) species of South Africa. While 120 species were previously reported to occur in South Africa, this paper reports 157 species in 64 genera that represent eight different superfamilies, 14 families and 22 subfamilies. Additionally, five species are reported for the first time to occur in South Africa. This species list was generated from the approximately 4000 specimen records of which 3558 records reside within South Africa. The remaining 732 records represent 14 other African countries. Occurrence records from two citizen-science platforms (iNaturalist and Gbif.org), were also incorporated in this study, adding 1880 species records in South Africa. The low number of specimens in the national collections indicate that this group of insects is poorly collected and highlights the lack of knowledge about South Africa's mantid fauna, as well as a lack of taxonomic expertise as 1532 museum specimens remain unidentified to species level.

Dataset Information

Mandelalides A-D, cytotoxic macrolides from a new Lissoclinum species of South African tunicate.

Publications

Mandelalides A-D, cytotoxic macrolides from a new Lissoclinum species of South African tunicate.

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