Date published: 2025-10-15

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Skyrin (CAS 602-06-2)

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Alternate Names:
Skirin
Application:
Skyrin is a non-peptidic anthraquinone, mycotoxin
CAS Number:
602-06-2
Purity:
≥97%
Molecular Weight:
538.46
Molecular Formula:
C30H18O10
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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Skyrin is a non-peptidic anthraquinone, mycotoxin with in vitro cytotoxic activity. It suppresses the growth of HeLa, Vero, K562, Raji, Wish and Calu-1 cell lines. Skyrin treatment induces DNA fragmentation and other morphological changes leading to apoptosis in Human HL-60 promyelotic leukemia cells. Skyrin was found to serve as an anti-diabetic agent by selectively binding to the glucagon receptor acting as its antagonist. Regular binding of glucagon to its receptor on hepathocyte plasma membrane activates adenylate cyclase indirectly. As a result, the cAMP produced activates protein kinase A with a consequent increase in both glycogen breakdown and gluconeogenesis leading to glucose output. Skyrin was shown to block this signal transduction sequence, such that the interaction of glucagons with its receptor does not result in an increase in cAMP production. Skyrin was also found to efficiently scavenge free radical species as •OH, •R and of singlet oxygen (1O2). Based on Skyrin selective toxicity towards insect cell line Sf9, it may be useful as an agent for pest control.


Skyrin (CAS 602-06-2) References

  1. Effects of skyrin, a receptor-selective glucagon antagonist, in rat and human hepatocytes.  |  Parker, JC., et al. 2000. Diabetes. 49: 2079-86. PMID: 11118010
  2. Studies in the biochemistry of micro-organisms. 91. The colouring matters of Penicillium islandicum Sopp. 3. Skyrin and flavoskyrin.  |  HOWARD, BH. and RAISTRICK, H. 1954. Biochem J. 56: 56-65. PMID: 13126093
  3. Metabolic products of fungi. V. The structure of skyrin.  |  SHIBATA, S., et al. 1955. Pharm Bull. 3: 278-83. PMID: 13289273
  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. Synthesis and Evaluation of 131I-Skyrin as a Necrosis Avid Agent for Potential Targeted Radionuclide Therapy of Solid Tumors.  |  Wang, C., et al. 2016. Mol Pharm. 13: 180-189. PMID: 26647005
  6. Secondary Metabolites from Endophytic Fungus Penicillium pinophilum Induce ROS-Mediated Apoptosis through Mitochondrial Pathway in Pancreatic Cancer Cells.  |  Koul, M., et al. 2016. Planta Med. 82: 344-55. PMID: 26848704
  7. Linking secondary metabolites to biosynthesis genes in the fungal endophyte Cyanodermella asteris: The anti-cancer bisanthraquinone skyrin.  |  Jahn, L., et al. 2017. J Biotechnol. 257: 233-239. PMID: 28647529
  8. Phenotyping the genus Hypericum by secondary metabolite profiling: emodin vs. skyrin, two possible key intermediates in hypericin biosynthesis.  |  Kimáková, K., et al. 2018. Anal Bioanal Chem. 410: 7689-7699. PMID: 30291388
  9. MALDI-HRMS Imaging Maps the Localization of Skyrin, the Precursor of Hypericin, and Pathway Intermediates in Leaves of Hypericum Species.  |  Revuru, B., et al. 2020. Molecules. 25: PMID: 32878122
  10. Death Receptor 5 (TNFRSF10B) Is Upregulated and TRAIL Resistance Is Reversed in Hypoxia and Normoxia in Colorectal Cancer Cell Lines after Treatment with Skyrin, the Active Metabolite of Hypericum spp.  |  Babinčák, M., et al. 2021. Cancers (Basel). 13: PMID: 33916015
  11. Intertwined Biosynthesis of Skyrin and Rugulosin A Underlies the Formation of Cage-Structured Bisanthraquinones.  |  Han, YB., et al. 2021. J Am Chem Soc. 143: 14218-14226. PMID: 34432466
  12. Comparison of Cytotoxic, Genotoxic, and DNA-Protective Effects of Skyrin on Cancerous vs. Non-Cancerous Human Cells.  |  Zajičková, T., et al. 2022. Int J Mol Sci. 23: PMID: 35628149
  13. A comparative study on cytotoxicities and biochemical properties of anthraquinone mycotoxins emodin and skyrin from Penicillium islandicum Sopp.  |  Kawai, K., et al. 1984. Toxicol Lett. 20: 155-60. PMID: 6320499

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

Skyrin, 1 mg

sc-364139
1 mg
$209.00