Synthesis of nor-anatoxin-<i>a</i> and anatoxin-<i>a</i>

Campbell, H. F.; Edwards, O. E.; Kolt, R. J.

doi:10.1139/v77-190

Cited by 76 publications

(19 citation statements)

References 11 publications

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“…Successful syntheses of analogues specific to neuronal subtypes could be of great value in the treatment of various neurological dysfunctions. The unique structure of anatoxin-a, and its powerful activity as a pharmacological tool, inspired a multitude of chemical synthetic pathways for anatoxin-a and its analogues [25]. The naturally occurring enantiomer, (+)-anatoxin-a, is much more potent than (-)-anatoxin-a [26].…”

Section: Anatoxinsmentioning

confidence: 99%

Alkaloids from Cyanobacteria with Diverse Powerful Bioactivities

Vasas¹,

Borbély²,

Nánási

2010

MRMC

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Alkaloid containing plants represent a heterogeneous group both taxonomically and chemically, a basic nitrogen being the unifying factor for the various classes. As most alkaloids are extremely toxic, organisms containing them do not feature strongly in medicine but they have always been important in the allopathic system. Typical alkaloids are derived from plant sources, they are basic, they contain one or more nitrogen, and they usually have marked physiological actions in humans or other mammalian species. This review will present various alkaloids generated by cyanobacteria, highlighting their complex structures, powerful bioactivities, and pharmacological properties. The main groups of cyanobacterial alkaloids include the neuromuscular transmission blocker anatoxins, the ion channel blocker saxitoxins, the degenerated amino acid β-methylamino-L-alanine, the protein synthesis inhibitor guanidine alkaloid cylindrospermopsins, and cyanobacterial indol alkaloids with antiviral, antifungal, and cytotoxic activity.

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Section: Anatoxinsmentioning

confidence: 99%

Alkaloids from Cyanobacteria with Diverse Powerful Bioactivities

Vasas¹,

Borbély²,

Nánási

2010

MRMC

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“…A synthesis of anatoxin-a from cocaine has now been achieved, colifirmillg both the structure and absolute stereochernistry (16). The activity of the toxin as a post-synaptic depolarizing ileurornuscular biocking agent has beell reported (17).…”

Section: Properties and Structurementioning

confidence: 99%

Anatoxin-a, a toxic alkaloid from Anabaena flos-aquae NRC-44h

Devlin¹,

Edwards²,

Gorham³

et al. 1977

Can. J. Chem.

376

151

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“…By spectra and crystallographic analysis (Huber, 1972;Devlin et al, 1977) and chemical synthesis (Campbell et al, 1977), anatoxin-a was confirmed to be an alkaloid of 2-acetyl-9-azabicyclo[4.2.1]non-2-ene and resembles acetylcholine in its structure. Further studies revealed that anatoxin-a acts as a potent postsynaptic depolarizing neuromuscular blocking agent by binding to the nicotinic acetylcholine receptors (Carmichael et al, 1975(Carmichael et al, , 1979Aronstam and Witkop, 1981).…”

Section: Introductionmentioning

confidence: 99%