199730-17-1Relevant academic research and scientific papers
Chlorocatechelins A and B from streptomyces sp.: New siderophores containing chlorinated catecholate groups and an acylguanidine structure
Kishimoto, Shinji,Nishimura, Shinichi,Hattori, Akira,Tsujimoto, Masafumi,Hatano, Masaki,Igarashi, Masayuki,Kakeya, Hideaki
, p. 6108 - 6111 (2014)
Two novel siderophores, chlorocatechelins A and B, were isolated from a culture broth of Streptomyces sp. Their structures were determined by spectroscopic analysis and degradation study. They contain chloro-substituted catecholate that has not been reported in natural products, whereas this group was conjugated to guanidine to form acylguanidine in chlorocatechelin A. This acylguanidine decomposed in weakly acidic solutions to furnish a less potent siderophore chlorocatechelin B. Chemical and biological insights into acylguanidine are also discussed.
Argicyclamides A-C Unveil Enzymatic Basis for Guanidine Bis-prenylation
Balloo, Nandani,Fujita, Kei,Matsuda, Kenichi,Okino, Tatsufumi,Phan, Chin-Soon,Wakimoto, Toshiyuki
supporting information, p. 10083 - 10087 (2021/07/26)
Guanidine prenylation is an outstanding modification in alkaloid and peptide biosynthesis, but its enzymatic basis has remained elusive. We report the isolation of argicyclamides, a new class of cyanobactins with unique mono- and bis-prenylations on guanidine moieties, from Microcystis aeruginosa NIES-88. The genetic basis of argicyclamide biosynthesis was established by the heterologous expression and in vitro characterization of biosynthetic enzymes including AgcF, a new guanidine prenyltransferase. This study provides important insight into the biosynthesis of prenylated guanidines and offers a new toolkit for peptide modification.
New cytotoxic callipeltins from the Solomon Island marine sponge Asteropus sp.
Stierhof, Marc,Hansen, Kine ?stnes,Sharma, Mukesh,Feussner, Klaus,Subko, Karolina,Díaz-Rullo, Fernando Fernández,Isaksson, Johan,Pérez-Victoria, Ignacio,Clarke, David,Hansen, Espen,Jaspars, Marcel,Tabudravu, Jioji N.
, p. 6929 - 6934 (2016/10/14)
Four new callipeltin A derivatives (N–Q) have been isolated from the Solomon Island marine sponge Asteropus sp. Their structures were established by spectroscopic techniques followed by acid hydrolysis and derivatisation of the free amino acids, and subsequent LCMS analysis of the derivatives. The compounds were evaluated for their activity against cancer cell lines A2058 (melanoma), HT-29 (colorectal adenocarcinoma) and MCF-7 (breast adenocarcinoma) and non-malignant MRC-5 fibroblast cells. While the acyclic callipeltins P and Q were inactive the cyclic callipeltins N and O showed significant cytotoxicity against all exposed cell lines with IC50values as low as 0.16?μM confirming the role of cyclic configuration in biological activity.
Application of 3D NMR for Structure Determination of Peptide Natural Products
Zhang, Fan,Adnani, Navid,Vazquez-Rivera, Emmanuel,Braun, Doug R.,Tonelli, Marco,Andes, David R.,Bugni, Tim S.
, p. 8713 - 8719 (2015/09/15)
Despite the advances in NMR, structure determination is often slow and constitutes a bottleneck in natural products discovery. Removal of this bottleneck would greatly improve the throughput for antibiotic discovery as well as other therapeutic areas. Overall, faster structure methods for structure determination will serve the natural products community in a broad manner. This report describes the first application of 3D NMR for elucidation of two microbially produced peptide natural products with novel structures. The methods are cost-effective and greatly improve the confidence in a proposed structure.
Stictamides A-C, MMP12 inhibitors containing 4-amino-3-hydroxy-5- phenylpentanoic acid subunits
Liang, Zhibin,Sorribas, Analia,Sulzmaier, Florian J.,Jimenez, Jorge I.,Wang, Xin,Sauvage, Thomas,Yoshida, Wesley Y.,Wang, Guangyi,Ramos, Joe W.,Williams, Philip G.
experimental part, p. 3635 - 3643 (2011/06/24)
An extensive study of the secondary metabolites produced by a new Sticta sp. of lichen has led to the isolation of three new compounds containing the 4-amino-3-hydroxy-5-phenylpentanoic acid residue (Ahppa). The structures of stictamides A-C (1-3) were as
