Structure of thermozymocidin

Aragozzini, Fabrizio; Manachini, P. L.; Craveri, R.; Rindone, B.; Scolastico, Carlo

doi:10.1007/bf01924918

Cited by 13 publications

(4 citation statements)

References 4 publications

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“…4: compound 36 in Fig. 4, which has been named ISP-1 (from Isaria sinclairii ) (76, 84, 86), myriocin (isolated from Myrioccocum albomyces ) (87), and thermozycidin (from Mycelia sterilia ) (88); sulfamisterin from Pycnidiella species ( 37 in Fig. 4) (89), a sulfated, 18 carbon myriocin-like analog (minus the 4-hydroxyl group); sphingofungins produced by Aspergillus and Paecilomyces (76, 86, 90–92) and other compounds with similar structural features (Table 1), the mycestericins (from Mycelia sterilia ) (85), malonofungin (from Phaeramularia fusimaculans ) (93), and fumifungin from Aspergillus fumigatus (94).…”

Section: Sphingoid Bases and Sphingoid Base-like Compounds That Disrumentioning

confidence: 99%

Thematic Review Series: Sphingolipids. Biodiversity of sphingoid bases (“sphingosines”) and related amino alcohols

Pruett

Bushnev

Hagedorn

et al. 2008

Journal of Lipid Research

415

341

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“Sphingosin” was first described by J. L. W. Thudichum in 1884 and structurally characterized as 2S,3R,4E-2-aminooctadec-4-ene-1,3-diol in 1947 by Herb Carter, who also proposed the designation of “lipides derived from sphingosine as sphingolipides.” This category of amino alcohols is now known to encompass hundreds of compounds that are referred to as sphingoid bases and sphingoid base-like compounds, which vary in chain length, number, position, and stereochemistry of double bonds, hydroxyl groups, and other functionalities. Some have especially intriguing features, such as the tail-to-tail combination of two sphingoid bases in the α,ω-sphingoids produced by sponges. Most of these compounds participate in cell structure and regulation, and some (such as the fumonisins) disrupt normal sphingolipid metabolism and cause plant and animal disease. Many of the naturally occurring and synthetic sphingoid bases are cytotoxic for cancer cells and pathogenic microorganisms or have other potentially useful bioactivities; hence, they offer promise as pharmaceutical leads. This thematic review gives an overview of the biodiversity of the backbones of sphingolipids and the broader field of naturally occurring and synthetic sphingoid base-like compounds.

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Section: Sphingoid Bases and Sphingoid Base-like Compounds That Disrumentioning

confidence: 99%

Thematic Review Series: Sphingolipids. Biodiversity of sphingoid bases (“sphingosines”) and related amino alcohols

Pruett

Bushnev

Hagedorn

et al. 2008

Journal of Lipid Research

415

341

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“…Structurally, Myriocin features a carbonyl-modified polymethylene hydrophobic tail and a complex, multifunctional head group that carries two hydroxyl groups and the amino acid substructure of serine (Aragozzini et al, 1972). This complex of conflicting chemical properties (a zwitterionic, tri-hydroxylated hydrophilic "head" and a hydrophobic "tail") imparts to the molecule a limited solubility in water and in common organic solvents, a factor that complicates chemical manipulations and administration of the drug (Caretti et al, 2014, Gasco & Gasco, 2007.…”

Section: Introductionmentioning

confidence: 99%

Determination of the serine palmitoyl transferase inhibitor myriocin by electrospray and Q‐trap mass spectrometry

Campisi

Signorelli

Rizzo

et al. 2017

Biomedical Chromatography

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“…20 The structure of thermozymocidin was reported separately in 1972 as 10. 21 Thermozymocidin 10 was also separately isolated from the thermophilic fungus Myriococcum albomyces and renamed myriocin. Synthetic studies confirmed the stereochemistry of the three stereogenic centres.…”

Section: Secondary Metabolitesmentioning

confidence: 99%