Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Antimicrobial ambiguine isonitriles from the cyanobacterium Fischerella ambigua.

Literature DB >> 19371071

Antimicrobial ambiguine isonitriles from the cyanobacterium Fischerella ambigua.

Shunyan Mo¹, Aleksej Krunic, George Chlipala, Jimmy Orjala.

Abstract

Five new antibacterial ambiguine K-O isonitriles (1-5) and eight previously described indole alkaloids were isolated from the cultured cyanobacterium Fischerella ambigua (UTEX 1903) by bioassay-guided fractionation. The planar structures of the new compounds were determined by spectroscopic analysis including MS and 1D and 2D NMR. X-ray crystallography was used to determine the absolute stereoconfiguration of ambiguine K isonitrile. The isolates were evaluated for their antibacterial activities against a set of bacterial targets, including Mycobacterium tuberculosis and Bacillus anthracis. Ambiguine K and M isonitriles showed the most potent activity against M. tuberculosis, with MIC values of 6.6 and 7.5 microM, respectively. Ambiguine A isonitrile showed the most potent activity against B. anthracis, with a MIC of 1.0 microM.

Entities: CellLine Chemical Disease Mutation Species

Mesh：

Substances：

Year: 2009 PMID： 19371071 PMCID： PMC2765494 DOI： 10.1021/np800751j

Source DB: PubMed Journal: J Nat Prod ISSN： 0163-3864 Impact factor: 4.050

23 in total

1. Biochemical and pharmacological investigations of selected cyanobacteria.

Authors: S Mundt; S Kreitlow; A Nowotny; U Effmert
Journal: Int J Hyg Environ Health Date: 2001-05 Impact factor: 5.840

Review 2. Bioactive compounds from cyanobacteria and microalgae: an overview.

Authors: Sawraj Singh; Bhushan N Kate; U C Banerjee
Journal: Crit Rev Biotechnol Date: 2005 Jul-Sep Impact factor: 8.429

3. Natural products from cyanobacteria: Exploiting a new source for drug discovery.

Authors: Heike Sielaff; Guntram Christiansen; Torsten Schwecke
Journal: IDrugs Date: 2006-02

4. Brunsvicamides A-C: sponge-related cyanobacterial peptides with Mycobacterium tuberculosis protein tyrosine phosphatase inhibitory activity.

Authors: Daniela Müller; Anja Krick; Stefan Kehraus; Christian Mehner; Mark Hart; Frithjof C Küpper; Krishna Saxena; Heino Prinz; Harald Schwalbe; Petra Janning; Herbert Waldmann; Gabriele M König
Journal: J Med Chem Date: 2006-08-10 Impact factor: 7.446

5. Antimycobacterial cycloartanes from Borrichia frutescens.

Authors: C L Cantrell; T Lu; F R Fronczek; N H Fischer; L B Adams; S G Franzblau
Journal: J Nat Prod Date: 1996-12 Impact factor: 4.050

6. Total synthesis of (+/-)-welwitindolinone a isonitrile.

Authors: Sarah E Reisman; Joseph M Ready; Atsushi Hasuoka; Catherine J Smith; John L Wood
Journal: J Am Chem Soc Date: 2006-02-08 Impact factor: 15.419

7. Enantioselective total syntheses of welwitindolinone A and fischerindoles I and G.

Authors: Phil S Baran; Jeremy M Richter
Journal: J Am Chem Soc Date: 2005-11-09 Impact factor: 15.419

8. Direct coupling of indoles with carbonyl compounds: short, enantioselective, gram-scale synthetic entry into the hapalindole and fischerindole alkaloid families.

Authors: Phil S Baran; Jeremy M Richter
Journal: J Am Chem Soc Date: 2004-06-23 Impact factor: 15.419

9. Selection of Bacillus anthracis isolates resistant to antibiotics.

Authors: A Athamna; M Athamna; N Abu-Rashed; B Medlej; D J Bast; E Rubinstein
Journal: J Antimicrob Chemother Date: 2004-06-17 Impact factor: 5.790

10. Microscale LC-MS-NMR platform applied to the identification of active cyanobacterial metabolites.

Authors: Yiqing Lin; Susan Schiavo; Jimmy Orjala; Paul Vouros; Roger Kautz
Journal: Anal Chem Date: 2008-10-04 Impact factor: 6.986

38 in total

1. Synthetic Studies on the Ambiguine Family of Alkaloids: Construction of the ABCD Ring System.

Authors: Ryan J Rafferty; Robert M Williams
Journal: Tetrahedron Lett Date: 2011-04-27 Impact factor: 2.415

2. Ambiguine I Isonitrile from Fischerella ambigua Induces Caspase-Independent Cell Death in MCF-7 Hormone Dependent Breast Cancer Cells.

Authors: Ulyana Muñoz Acuña; Jiachen Zi; Jimmy Orjala; Esperanza J Carcache de Blanco
Journal: Int J Cancer Res (Tortola) Date: 2015-03

3. Pathway from N-Alkylglycine to Alkylisonitrile Catalyzed by Iron(II) and 2-Oxoglutarate-Dependent Oxygenases.

Authors: Tzu-Yu Chen; Jinfeng Chen; Yijie Tang; Jiahai Zhou; Yisong Guo; Wei-Chen Chang
Journal: Angew Chem Int Ed Engl Date: 2020-03-10 Impact factor: 15.336

4. Hapalindole H Induces Apoptosis as an Inhibitor of NF-ĸB and Affects the Intrinsic Mitochondrial Pathway in PC-3 Androgen-insensitive Prostate Cancer Cells.

Authors: Ulyana Muñoz Acuña; Shunyan Mo; Jiachen Zi; Jimmy Orjala; Esperanza J Carcache DE Blanco
Journal: Anticancer Res Date: 2018-06 Impact factor: 2.480