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 Hapalindole-related alkaloids from the cultured cyanobacterium Fischerella ambigua.

Literature DB >> 20965528

Hapalindole-related alkaloids from the cultured cyanobacterium Fischerella ambigua.

Shunyan Mo¹, Aleksej Krunic, Bernard D Santarsiero, Scott G Franzblau, Jimmy Orjala.

Abstract

Four hapalindole-related alkaloids, namely fischambiguines A and B, ambiguine P, ambiguine Q nitrile as well as ambiguine G nitrile were identified from the cultured cyanobacterium Fischerella ambigua (UTEX 1903). The structures were determined by spectroscopic analysis including MS, 1D and 2D NMR and X-ray crystallography. The alkaloids possessed fused pentacyclic and hexacyclic carbon skeletons. Fischambiguine B displayed a strong inhibitory activity against Mycobacterium tuberculosis with an MIC value of 2 μM, with no detectable cytotoxicity in a Vero cell line.

Entities: CellLine Chemical Disease Mutation Species

Mesh：

Substances：

Year: 2010 PMID： 20965528 PMCID： PMC2981615 DOI： 10.1016/j.phytochem.2010.09.004

Source DB: PubMed Journal: Phytochemistry ISSN： 0031-9422 Impact factor: 4.072

22 in total

Review 1. Microalgal metabolites.

Authors: Yuzuru Shimizu
Journal: Curr Opin Microbiol Date: 2003-06 Impact factor: 7.934

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

Review 4. Panning for chemical gold: marine bacteria as a source of new therapeutics.

Authors: Philip G Williams
Journal: Trends Biotechnol Date: 2008-11-18 Impact factor: 19.536

5. In vitro and in vivo activities of macrolide derivatives against Mycobacterium tuberculosis.

Authors: Kanakeshwari Falzari; Zhaohai Zhu; Dahua Pan; Huiwen Liu; Poonpilas Hongmanee; Scott G Franzblau
Journal: Antimicrob Agents Chemother Date: 2005-04 Impact factor: 5.191

6. 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

7. 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

8. 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

9. 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

10. 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

18 in total

1. Nitrile-Containing Fischerindoles from the Cultured Cyanobacterium Fischerella sp.

Authors: Hyunjung Kim; Aleksej Krunic; Daniel Lantvit; Qi Shen; David J Kroll; Steven M Swanson; Jimmy Orjala
Journal: Tetrahedron Date: 2012-04-15 Impact factor: 2.457

2. Hapalindole/Ambiguine Biogenesis Is Mediated by a Cope Rearrangement, C-C Bond-Forming Cascade.

Authors: Shasha Li; Andrew N Lowell; Fengan Yu; Avi Raveh; Sean A Newmister; Nathan Bair; Jeffrey M Schaub; Robert M Williams; David H Sherman
Journal: J Am Chem Soc Date: 2015-12-02 Impact factor: 15.419

3. Structural basis of the Cope rearrangement and cyclization in hapalindole biogenesis.

Authors: Sean A Newmister; Shasha Li; Marc Garcia-Borràs; Jacob N Sanders; Song Yang; Andrew N Lowell; Fengan Yu; Janet L Smith; Robert M Williams; K N Houk; David H Sherman
Journal: Nat Chem Biol Date: 2018-03-12 Impact factor: 15.040

4. Scalable Total Syntheses of (-)-Hapalindole U and (+)-Ambiguine H.

Authors: Thomas J Maimone; Yoshihiro Ishihara; Phil S Baran
Journal: Tetrahedron Date: 2015-05-02 Impact factor: 2.457

5. Total Synthesis of Pentacyclic (-)-Ambiguine P Using Sequential Indole Functionalizations.

Authors: Rebecca E Johnson; Hwisoo Ree; Marco Hartmann; Laura Lang; Shota Sawano; Richmond Sarpong
Journal: J Am Chem Soc Date: 2019-02-04 Impact factor: 15.419

6. FORMAL SYNTHESIS OF HAPALINDOLE O AND SYNTHETIC EFFORTS TOWARDS HAPALINDOLE K AND AMBIGUINE A.

Authors: Ryan J Rafferty; Robert M Williams
Journal: Heterocycles Date: 2012-05-01 Impact factor: 0.831

7. Application of high-field NMR spectroscopy for characterization and quantitation of submilligram quantities of isolated natural products.

Authors: Aleksej Krunić; Jimmy Orjala
Journal: Magn Reson Chem Date: 2015-08-20 Impact factor: 2.447

8. Indole alkaloids from two cultured cyanobacteria, Westiellopsis sp. and Fischerella muscicola.

Authors: Hyunjung Kim; Daniel Lantvit; Chang Hwa Hwang; David J Kroll; Steven M Swanson; Scott G Franzblau; Jimmy Orjala
Journal: Bioorg Med Chem Date: 2012-07-05 Impact factor: 3.641

Review 9. An invocation for computational evaluation of isomerization transforms: cationic skeletal reorganizations as a case study.

Authors: Alexander W Schuppe; Yannan Liu; Timothy R Newhouse
Journal: Nat Prod Rep Date: 2020-09-15 Impact factor: 13.423

10. Indole-fused spirochromenes as potential anti-tubercular agents: design, synthesis and in vitro evaluation.

Authors: Ashok Dogamanti; Pamula Chiranjeevi; Vikas Kumar Aamate; Siva Krishna Vagolu; Dharmarajan Sriram; Sridhar Balasubramanian; Madderla Sarasija
Journal: Mol Divers Date: 2020-05-30 Impact factor: 2.943