A mycotoxin
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(+)-Rugulosin

Item No. 23558

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(5aS,6R,13aS,14R,17S,18R,19R,20S)-1,7,9,15,17,20-hexahydroxy-3,11-dimethyl-5H,6H-6,13a,5a,14-[1,2,3,4]butanetetraylcycloocta[1,2-b:5,6-b']dinaphthalene-5,8,13,16(14H)-tetrone
CAS Number
23537-16-8
Synonyms
  • NSC 160880
  • NSC 249990
  • Rugulosin A
Molecular Formula
C30H22O10
Formula Weight
542.5
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: SolubleEthanol: SolubleMethanol: Soluble
SMILES
CC1=CC(O)=C(C(C2=C(O)[C@]3([H])[C@]4(C(C5=CC(C)=CC(O)=C5C6=O)=O)C6=C(O)[C@@]([H])([C@](O)([H])[C@]4([H])[C@@]7([H])[C@]3([H])O)[C@]27C8=O)=O)C8=C1
InChi Code
InChI=1S/C30H22O10/c1-7-3-9-13(11(31)5-7)21(33)17-25(37)20-23(35)15-16-24(36)19(29(15,17)27(9)39)26(38)18-22(34)14-10(28(40)30(16,18)20)4-8(2)6-12(14)32/h3-6,15-16,19-20,23-24,31-32,35-38H,1-2H3/t15-,16-,19+,20+,23-,24-,29+,30+/m0/s1
InChi Key
OYNIPTDPTUSUAY-PUTAFCBNSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    (+)-Rugulosin is a pigment and mycotoxin produced by certain fungi.1 It inhibits HIV-1 integrase activity with IC50 values of 19 and 25 µM in coupled and strand transfer assays, respectively.2 It also inhibits ribonuclease H in rat liver by 83% at a concentration of 157 µM and ribonucleases H1, H2, and H3 in T. pyriformis by 100, 99, and 100%, respectively, at a concentration of 313 µM.3 (+)-Rugulosin leads to hepatic injury and liver cell hyperplasia in mice when administered in the diet.1 It is cytotoxic to insect cells but not mammalian C6/36, L929, and HepG2 cells (ID50s = 1.2, >200, 23.7, and >200 µg/ml, respectively).4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Uneo, Y., Sato, N., Ito, T., et al. Chronic toxicity and hepatocarcinogenicity of (+) rugulosin, an anthraquinoid mycotoxin from penicillium species: Preliminary surveys in mice. J. Toxicol. Sci. 5(4), 295-302 (1980).

    2. Singh, S.B., Jayasuriya, H., Dewey, R., et al. Isolation, structure, and HIV-1-integrase inhibitory activity of structurally diverse fungal metabolites. J. Ind. Microbiol. Biotechnol. 30(12), 721-731 (2003).

    3. Tashiro, F., Hiral, K., and Ueno, Y. Inhibitory effects of carcinogenic mycotoxins on deoxyribonucleic acid-dependent ribonucleic acid polymerase and ribonuclease H. Appl. Environ. Microbiol. 38(2), 191-196 (1979).

    4. Watts, P., Kittakoop, P., Veeranondha, S., et al. Cytotoxicity against insect cells of entomopathogenic fungi of the genera Hypocrella (anamorph Aschersonia): Possible agents for biological control. Mycol. Res. 107(Pt 5), 581-586 (2003).