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SML0459

Sigma-Aldrich

Skyrin

≥98% (HPLC), from Penicillium islandicum

Synonym(s):

Endothianin, Rhodophyscin, Skirin

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About This Item

Empirical Formula (Hill Notation):
C30H18O10
CAS Number:
602-06-2
Molecular Weight:
538.46
UNSPSC Code:
51111800
NACRES:
NA.77

biological source

Penicillium islandicum

Quality Level

200

Assay

≥98% (HPLC)

storage condition

protect from light

solubility

DMSO: soluble
acetone: soluble
ethyl acetate: soluble

storage temp.

−20°C

InChI

1S/C30H18O10/c1-9-3-11-19(13(31)5-9)29(39)23-17(35)7-15(33)21(25(23)27(11)37)22-16(34)8-18(36)24-26(22)28(38)12-4-10(2)6-14(32)20(12)30(24)40/h3-8,31-36H,1-2H3

InChI key

MQSXZQXHIJMNAF-UHFFFAOYSA-N

Biochem/physiol Actions

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Jie Ma et al.
Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 37(16), 2408-2412 (2012-12-14)
To study the chemical constituents from Hypericum perforatum. Compouds were isolated by chromatographic techniques. Their structures were identified by spectral methods. The inhibitory activity of recombinant human PTP1B was evaluated. Nine compounds were elucidated as D-Mannitol (1), 1,2-benzenedicarboxylic acid bis(1-methylpropyl)
S Krivobok et al.
Mutation research, 279(1), 1-8 (1992-05-01)
Unsubstituted anthraquinone, 4 substituted anthraquinones (emodin, danthron, physcion, a new compound M-108-C) and 3 dimers (skyrin, rugulosin, rugulin) were tested using the Ames/Salmonella assay (strains TA98, TA100, TA1537 and TA102). Danthron and emodin were found to be mutagenic for TA1537
K Kawai et al.
Toxicology letters, 20(2), 155-160 (1984-02-01)
The anthraquinone mycotoxins emodin and skyrin were examined for the inhibitory effects on murine leukemia L1210 culture cells, oxidative phosphorylation of rat liver mitochondria, and Na+, K+-activated ATPase activity of rat brain microsomes to find the differences between their modes
K X Huang et al.
Current genetics, 28(6), 580-584 (1995-11-01)
Wild-type strains of Penicillium islandicum and Penicillium frequentans, which produce anthraquinone and related compounds, were transformed to benomyl and hygromycin B resistance. Plasmids pSV50 and pBT6, with benomyl-resistant beta-tublin genes, and plasmids pAN7-1 and pDH25, with a bacterial hygromycin phosphotransferase
Progress in the chemistry of organic natural products. The chemistry of mycotoxins.
S Bräse et al.
Progress in the chemistry of organic natural products, 97, v-xv (2013-06-21)
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