Calothrixins A and B, novel pentacyclic metabolites from Calothrix cyanobacteria with potent activity against malaria parasites and human cancer cells

Rickards, Rodney W.; Rothschild, Jennifer M.; Willis, Anthony C.; Chazal, Nola M. de; Kirk, Julie; Kirk, Kiaran; Saliba, Kevin J.; Smith, Geoffrey D.

doi:10.1016/s0040-4020(99)00833-9

Cited by 237 publications

(159 citation statements)

References 16 publications

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“…In the context of a screening program against Plasmodium, twon ew indoloquinonones, calothrixin Aa nd B, were isolated from Calothrix in 1999. [35] These compounds contain an indolo[3,2-j]phenanthridine skeleton, which is unprecedented in other natural products, and theydisplay antiplasmodial and cytotoxic behavior.…”

Section: Active Inhibition Of Biofoulingmentioning

confidence: 99%

Cyanobacterial Natural Products for the Inhibition of Biofilm Formation and Biofouling

Gademann¹

2007

Chimia

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Biofouling is defined by the non-specific attachment of biological material (proteins, carbohydrates, prokaryotic cells and higher organisms) to surfaces upon their exposuret oa ny biological fluid. Biofouling is a serious problem in many areas ranging from marine technology,nuclear power plants, dentistry,food processing to biomedical implants. This process can be addressed either actively by chemical compounds inhibiting growth, settlement or biofilm formation, or passively by generating repellent or resistant surfaces. This highlight article gives an overview over different secondary metabolites from cyanobacteria useful in this context. Acandidate for active antifouling is nostocarboline, acarboline alkaloid from Nostoc.Ithas distinct and powerful activities against both prokaryotic and eukaryotic photosynthetic organisms. This compound is acandidate for the replacement of toxic tributyltin (TBT) antifouling coatings. Another passive strategy is presented utilizing the strong binding of anachelin to metal oxide surfaces. This anchor binds polyethyleneglycol (PEG) efficiently to surfaces and renders TiO 2 protein resistant. This anchor displays superior properties when compared to dopamine or DOPA, ak ey constituent in mussel adhesive proteins (MAP). Implications for biomaterials design arediscussed.

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Section: Active Inhibition Of Biofoulingmentioning

confidence: 99%

Cyanobacterial Natural Products for the Inhibition of Biofilm Formation and Biofouling

Gademann¹

2007

Chimia

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“…The known alkaloid 12-epi-hapalindole E isonitrile and the novel calothrixin A were isolated from cyanobacterial Fischerella [4] and Calothrix species [5], respectively, following a screening program [6]. The hapalindole is bioactive against a range of cell types ; calothrixin A is active at nanomolar concentrations against human cancer cells and the malaria parasite Plasmodium falciparum in culture [5].…”

Section: Introductionmentioning

confidence: 99%

Inhibition of bacterial RNA polymerase by the cyanobacterial metabolites 12-epi-hapalindole E isonitrile and calothrixin A

Doan

2001

FEMS Microbiology Letters

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The alkaloid 12-epi-hapalindole E isonitrile, from a cyanobacterial Fischerella species, and the indolophenanthridine calothrixin A, from Calothrix, inhibited Escherichia coli RNA polymerase competitively with respect to ATP, and non-competitively with respect to UTP. The inhibition was dependent on the order of addition of the inhibitors. The K I values, with ATP as the variable substrate, were 1.3 þ 0.2 mM and 0.23 þ 0.11 mM, respectively. Based on comparisons with the sensitivity of whole cells to these inhibitors, it is concluded that other targets in addition to RNA polymerase may also be implicated in their action. ß

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“…(22). [149] These compounds contain an indolo [3,2-j] Cyanobacteria populate many different habitats. In particular, they evolved either to cope with little sunlight (i.e.…”

Section: In the Context Of A Screening Program Of Cyanobacterial Metamentioning

confidence: 99%

Secondary Metabolites from Cyanobacteria: Complex Structures and Powerful Bioactivities

Gademann¹,

Portmann

2008

COC

235

168

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This review presents natural products from cyanobacteria. Several classes of secondary metabolites are highlighted. Toxic metabolites from these prokaryotic photosynthetic organisms include compounds such as microcystin, anatoxin and saxitoxin, which display hepatotoxicity and neurotoxicity. Their potential as drugs in cancer therapy is discussed based on the cryptophycin class of potent cytotoxic agents. The next part of this review highlights iron chelators from cyanobacteria, including schizokinen, synechobactin and anachelin. The biogenesis of anachelin is investigated as its mechanism of iron acquisition. Several indole alkaloids are then reviewed, from simple carbolines such as bauerines and nostocarboline to complex polycyclic structures such as hapalindole, welwitindolinone and ambiguine. The latter compounds present fascinating structure combined with powerful bioactivities and interesting biogenetic pathways. In the last part, protease inhibitors from cyanobacteria are discussed (cyanopeptolins, micropeptin and oscillapeptin) and their structure/activity relationships and selectivity for trypsin / chymotrypsin are presented. All these examples highlight the large structural variety of cyanobacterial metabolites combined with powerful biological activities. Cyanobacteria can thus be considered a prime source both for novel bioactive compounds and for leads for drugs.

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Calothrixins A and B, novel pentacyclic metabolites from Calothrix cyanobacteria with potent activity against malaria parasites and human cancer cells

Cited by 237 publications

References 16 publications

Cyanobacterial Natural Products for the Inhibition of Biofilm Formation and Biofouling

Cyanobacterial Natural Products for the Inhibition of Biofilm Formation and Biofouling

Inhibition of bacterial RNA polymerase by the cyanobacterial metabolites 12-epi-hapalindole E isonitrile and calothrixin A

Secondary Metabolites from Cyanobacteria: Complex Structures and Powerful Bioactivities

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