Antimicrobial activity of alkaloids from amphibian venoms and effects on the ultrastructure of yeast cells

Preusser, H.-J.; Habermehl, Gerhard; Sablofski, M.; Schmall-Haury, D.

doi:10.1016/0041-0101(75)90135-x

Cited by 58 publications

(30 citation statements)

References 11 publications

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“…Lipids with antibiotic activity, present on the skin of many species of animals, are represented principally by sphingolipids (5), fatty acids (4,5), and both fatty acid esters (31) and 0-alkyl ethers (32,33) of polyhydric alcohols. Alkaloids form a third chemical class and have been isolated from amphibian skin secretions (6)(7)(8). They include metabolites of histidine and tryptophan, such as spinaceamine and bufotenine, and more complex molecules such as samandarine (7).…”

Section: Discussionmentioning

confidence: 99%

“…Alkaloids form a third chemical class and have been isolated from amphibian skin secretions (6)(7)(8). They include metabolites of histidine and tryptophan, such as spinaceamine and bufotenine, and more complex molecules such as samandarine (7).…”

Section: Discussionmentioning

confidence: 99%

“…Over the past several years, an increasing number of low molecular weight antibiotic substances, believed to play a role in defense against environmental microbes, have been isolated from diverse species of animals. These molecules include peptides (1)(2)(3), lipids (4,5), and alkaloids (6)(7)(8).…”

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confidence: 99%

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Squalamine: an aminosterol antibiotic from the shark.

Moore

Wehrli

Röder

et al. 1993

Proc. Natl. Acad. Sci. U.S.A.

386

250

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In recent years, a variety of low molecular weight antibiotics have been isolated from diverse animal species. These agents, which include peptides, lipids, and alkaloids, exhibit antibiotic activity against environmental microbes and are thought to play a role in innate immunity. We report here the discovery of a broad-spectrum steroidal antibiotic isolated from tissues of the dogfish shark Squalus acanthias. This water-soluble antibiotic, which we have named squalamine, exhibits potent bactericidal activity against both Gram-negative and Gram-positive bacteria. In addition, squalamine is fungicidal and induces osmotic lysis of protozoa. The chemical structure of the antibiotic 313-N-1-{N-[3-(4-aminobutyl)]-1,3-diaminopropane}-7a,24'-dihydroxy-Sacholestane 24-sulfate has been determined by fast atom bombardment mass spectroscopy and NMR. Squalamine is a cationic steroid characterized by a condensation of an anionic bile salt intermediate with spermidine. The discovery of squalamine in the shark implicates a steroid as a potential host-defense agent in vertebrates and provides insights into the chemical design of a family of broad-spectrum antibiotics.Animals must defend themselves against environmental microbes if they are to survive. Multiple mechanisms of host defense against microbes have been described such as the array of humoral and cellular responses of the classical vertebrate immune system and less-specific physical and chemical barriers. Over the past several years, an increasing number of low molecular weight antibiotic substances, believed to play a role in defense against environmental microbes, have been isolated from diverse species of animals. These molecules include peptides (1-3), lipids (4, 5), and alkaloids (6-8).In the course of our studies exploring the diversity of antibiotics from animal sources, we have surveyed tissues from a number of animal species (9, 10). We focused our search for antibiotic substances on the gastrointestinal tract of various animals after the recent discovery of peptide antibiotics in the gut of frogs (11), pigs (12, 13), mice (14), and humans (34). In the course of our survey, we discovered that stomach extracts of the shark Squalus acanthias exhibited potent antimicrobial activity, prompting efforts to purify and identify the responsible molecule.In this report we describe the isolation, structural determination, and characterization of a water-soluble cationic steroid from the shark that exhibits potent antimicrobial activity against fungi, protozoa, and both Gram-negative and Gram-positive bacteria. This molecule is shown to be an unusual adduct of spermidine with an anionic bile salt intermediate that, to our knowledge, is without precedent in vertebrates. We have named the aminosterol "squalamine," derived from the genus Squalus and its chemical structure as an amine. MATERIALS AND METHODSPurification of Squlamine. Squalus acanthias sharks were captured off the New England coast. The shark stomach tissue (400 g) was frozen immediately after dissectio...

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

See 1 more Smart Citation

Squalamine: an aminosterol antibiotic from the shark.

Moore

Wehrli

Röder

et al. 1993

Proc. Natl. Acad. Sci. U.S.A.

386

250

View full text Add to dashboard Cite

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“…Although it has been reported that spinaceamine and 5-methylspinaceamine possess antimicrobial activity (Preusser et al, 1975), the bioactivity of 4-MSPA is not known. Hence, the biological significance of 4-MSPA in the human body is unknown at present and further investigations are required.…”

Section: Discussionmentioning

confidence: 99%

Identification of 4-methylspinaceamine - a Pictet – Spengler condensation reaction product of histamine with acetaldehyde - in human urine

Ohya

Niitsu

2005

Life Sciences

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“…Their secretions have a protective function against bacterial and fungal infection as well as predators (Preusser et al 1975). Main types of amphibian skin biologically active compounds are: biogenic amines, bufodienolides (bufogenines and bufotoxins=steroids), alkaloids, peptides and proteins (Daly et al 1987;Habermehl 1981).…”

Section: Innothink Center For Research In Biomedical Innovation and Tmentioning

confidence: 99%

An Overview of Brevinin Superfamily: Structure, Function and Clinical Perspectives

Savelyeva

Ghavami

Davoodpour

et al. 2014

Advances in Experimental Medicine and Biology

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SummaryAntimicrobial peptides are the backbone of first-line defense against various microorganisms in the animal kingdom. Thus, not surprisingly, they are gaining attention in the science and medical fields as a rich repository of new pro-drugs. Below, we focus our attention on the Brevinin family of anuran peptides. While most of them show strong antibacterial activities, some, e.g. Brevinin-2R, appear to be promising anticancer molecules, exhibiting better a therapeutic window than widely-use anticancer drugs like doxorubicin. We briefly introduce the field, followed by highlighting the promising therapeutic properties of Brevinins. Next, we provide information about the cloning and phylogenetic aspects of Brevinin genes. In the final paragraphs of this chapter, we discuss possible large-scale production methods of Brevinins, giving examples of some systems that are already in use. Towards the end, we discuss various means of modification of biologic properties of Brevinins, either by chemical modifications or by amino acid substitution and sequence rearrangements. In this context, also other unique properties of Brevinins are briefly mentioned. Finally, we discuss the future of the Brevinin field,particularly highlighting yet to be answered biologic questions, like for example presumed anti-viral and antitumor activities of Brevinin family members.2

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Antimicrobial activity of alkaloids from amphibian venoms and effects on the ultrastructure of yeast cells

Cited by 58 publications

References 11 publications

Squalamine: an aminosterol antibiotic from the shark.

Squalamine: an aminosterol antibiotic from the shark.

Identification of 4-methylspinaceamine - a Pictet – Spengler condensation reaction product of histamine with acetaldehyde - in human urine

An Overview of Brevinin Superfamily: Structure, Function and Clinical Perspectives

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