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Rugulosin (+ form) (CAS 23537-16-8)

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Alternate Names:
Radicalisin
Application:
Rugulosin (+ form) is an intense yellow pigment produced by Penicillium and Aspergillus
CAS Number:
23537-16-8
Purity:
>98%
Molecular Weight:
542.5
Molecular Formula:
C30H22O10
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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Rugulosin, particularly its (+) form, has garnered significant interest in scientific research due to its diverse biological activities and potential applications in chemical biology and drug discovery. This compound, isolated from various fungi species, exhibits potent inhibitory effects on the enzyme squalene epoxidase (SE), a key enzyme in the biosynthesis of ergosterol, an essential component of fungal cell membranes. Rugulosin′s mechanism of action involves the specific binding to the active site of squalene epoxidase, thereby inhibiting its enzymatic activity and disrupting ergosterol synthesis. Research has explored the structural features of rugulosin and its binding interactions with squalene epoxidase, providing insights into its mechanism of action and potential for structure-based drug design. Additionally, rugulosin has shown promising antifungal activity against a wide range of fungal pathogens, including both yeast and filamentous fungi, suggesting its potential as a lead compound for the development of novel antifungal agents. Furthermore, studies have investigated the potential of rugulosin derivatives and analogs as scaffolds for the development of new antifungal drugs with improved potency and pharmacological properties. Overall, rugulosin represents a valuable tool in chemical biology research, offering insights into fungal membrane biology and serving as a potential starting point for the development of new antifungal therapies.


Rugulosin (+ form) (CAS 23537-16-8) References

  1. Cytotoxicity against insect cells of entomopathogenic fungi of the genera Hypocrella (anamorph Aschersonia): possible agents for biological control.  |  Watts, P., et al. 2003. Mycol Res. 107: 581-6. PMID: 12884955
  2. Studies in the biochemistry of micro-organisms. 95. Rugulosin, a crystalline colouring matter of Penicillium rugulosum Thom.  |  BREEN, J., et al. 1955. Biochem J. 60: 618-26. PMID: 13249956
  3. Metabolic products of fungi. IV. Isolation of the coloring matters of Endothia spp. and the respective identities of endothianin and redicalisin with skyrin and rugulosin.  |  SHIBATA, S., et al. 1955. Pharm Bull. 3: 274-7. PMID: 13289272
  4. The respective identities of endothianin and radicalisin with skyrin and rugulosin; and the structure of skyrin.  |  SHIBATA, S., et al. 1955. Pharm Bull. 3: 160-1. PMID: 14394822
  5. Measurement of a rugulosin-producing endophyte in white spruce seedlings.  |  Sumarah, MW., et al. 2005. Mycologia. 97: 770-6. PMID: 16457346
  6. Total syntheses of 2,2'-epi-cytoskyrin A, rugulosin, and the alleged structure of rugulin.  |  Nicolaou, KC., et al. 2007. J Am Chem Soc. 129: 4001-13. PMID: 17355133
  7. Effect of a rugulosin-producing endophyte in Picea glauca on Choristoneura fumiferana.  |  Miller, JD., et al. 2008. J Chem Ecol. 34: 362-8. PMID: 18266038
  8. Spread and persistence of a rugulosin-producing endophyte in Picea glauca seedlings.  |  Sumarah, MW., et al. 2008. Mycol Res. 112: 731-6. PMID: 18487038
  9. Full Genome of Phialocephala scopiformis DAOMC 229536, a Fungal Endophyte of Spruce Producing the Potent Anti-Insectan Compound Rugulosin.  |  Walker, AK., et al. 2016. Genome Announc. 4: PMID: 26950333
  10. Production of respiratory-deficient mutants of Saccharomyces cerevisiae by (-) luteoskyrin and (+) rugulosin.  |  Ueno, Y. and Nakajima, M. 1974. Chem Pharm Bull (Tokyo). 22: 2258-62. PMID: 4619580
  11. Inhibition of phage growth by an antibiotic rugulosin isolated from Myrothecium verucaria. I. Properties of the anti-phage effect.  |  Nakamura, S., et al. 1971. Jpn J Microbiol. 15: 113-20. PMID: 4930806
  12. Specific and non-specific interactions of two carcinogenic mycotoxins, luteoskyrin and rugulosin with nucleic acids.  |  Bouhet, JC. and Pham van Chuong, P. 1977. Ann Nutr Aliment. 31: 811-30. PMID: 566070
  13. Isolation and characterization of luteoskyrin and rugulosin, two hepatotoxic anthraquinonoids from Penicillium islandicum Sopp. and Penicillium rugulosum Thom.  |  Bouhet, JC., et al. 1976. J Agric Food Chem. 24: 964-72. PMID: 987085

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

Rugulosin (+ form), 1 mg

sc-202327
1 mg
$287.00