199729-86-7Relevant academic research and scientific papers
Microseiramide from the freshwater cyanobacterium Microseira sp. UIC 10445
Luo, Shangwen,Krunic, Aleksej,Chlipala, George E.,Orjala, Jimmy
, p. 47 - 52 (2015/06/08)
Abstract Microseiramide (1), a cyclic heptapeptide, was isolated from a sample of the freshwater cyanobacterium Microseira sp. UIC 10445 collected in a shallow lake in Northern Indiana. Taxonomic identification of UIC 10445 was performed by a combination of morphological and phylogenetic characterization. Phylogenetic analysis revealed that UIC 10445 was a member of the recently described genus Microseira, which is phylogenetically distinct from the morphologically similar genera, Moorea and Lyngbya. The planar structure of microseiramide (1) was determined by extensive 1D and 2D NMR experiments as well as HRESIMS analysis. The absolute configurations of amino acid residues were determined using acid hydrolysis followed by the advanced Marfey's analysis. Microseiramide (1) is the first cyclic peptide reported from a Microseira sp., and the structure of microseiramide (1) is distinct from the previously known metabolites from cyanobacteria of the genera Moorea and Lyngbya.
Structures and solution conformational dynamics of stylissamides G and H from the Bahamian Sponge Stylissa caribica
Wang, Xiao,Morinaka, Brandon I.,Molinski, Tadeusz F.
supporting information, p. 625 - 630 (2014/04/17)
Two new peptides, stylissamides G and H, were isolated from extracts of a sample of Stylissa caribica collected in deep waters of the Caribbean Sea. A single sample of S. caribica among a collection of 10 samples that were examined by LC-MS appeared to be a different chemotype from the others in that it lacked the familiar pyrrole-2-aminoimidazole alkaloids, stevensine and oroidin, and contained peptides of the stylissamide class. The structures of the title compounds were solved by integrated analysis of the MS and NMR spectra and chemical degradation. The solution conformation of stylissamide G was briefly examined by electronic circular dichroism and temperature-dependent 1H NMR chemical shifts of amide NH signals, which supported a conformationally rigid macrocycle.
Astins K-P, six new chlorinated cyclopentapeptides from Aster tataricus
Xu, Hui-Min,Zeng, Guang-Zhi,Zhou, Wen-Bing,He, Wen-Jun,Tan, Ning-Hua
supporting information, p. 7964 - 7969 (2013/08/23)
During further investigation on the methanol extract of roots and rhizomes of Aster tataricus, six new chlorinated cyclopentapeptides, designated as astins K-P (9-14), together with eight known derivatives, astins A-H (1-8), were isolated. Structures of the new cyclopeptides were established using extensive spectroscopic methods, and the absolute configurations were determined by the advanced Marfey's method. Astin P (14) represents a unique cyclopentapeptide linking as cyclo-(l-Pro (Cl2)1-l-allo-Thr 2-l-Ser3-l-β-Phe4-l-Ava5). Astin B (2) showed cytotoxicity against BGC-823 cell with IC50 value of 19.2 μg/ml. Astin C (3) exhibited cytotoxicity on HCT-116 and BGC-823 cells with IC50 values of 13.4 and 3.3 μg/ml, respectively.
Tataricins A and B, two novel cyclotetrapeptides from Aster tataricus, and their absolute configuration assignment
Xu, Hui-Min,Yi, Hua,Zhou, Wen-Bing,He, Wen-Jun,Zeng, Gang-Zhi,Xu, Wen-Yan,Tan, Ning-Hua
supporting information, p. 1380 - 1383 (2013/04/23)
Two novel cyclotetrapeptides, tataricins A and B, with a unique cyclopeptide backbone and aδ 2,4Pro side chain, were isolated from the traditional Chinese medicine Aster tataricus. Their structures and absolute configurations were determined using a combination of spectroscopic data, the advanced Marfey's method, and a total synthesis. Copyright
Biosynthetic origin of the 3-amino-2,5,7,8-tetrahydroxy-10-methylundecanoic acid moiety and absolute configuration of pahayokolides A and B
Liu, Li,Bearden, Daniel W.,Rein, Kathleen S.
experimental part, p. 1535 - 1538 (2011/08/22)
Pahayokolides A (1) and B (2) are cyclic undecapeptides that were isolated from the cyanobacterium Lyngbya sp. They contain the unusual α-hydroxy-β-amino acid 3-amino-2,5,7,8-tetrahydroxy-10- methylundecanoic acid (Athmu). The absolute configurations of the amino acids of the pahayokolides, except for the four oxygen-bearing stereocenters of Athmu, have been determined by Marphy's method. Incorporation of labeled leucine and acetate precursors into the pahayokolides has established that Athmu is derived from a leucine or α-keto isocaproic acid starter unit, which is further extended with three acetate units.
