A fungal metabolite
Technical Support & Resources

Information provided in the product description is from published literature. Due to the nature of scientific experimentation, your results (e.g., selectivity and effective concentrations) or specific application for this product may differ. If you have questions about how this product fits your application, please contact our technical support staff.

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

(−)-Rugulosin

Item No. 25477

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
[5aR-(5aR*,6S*,13aR*,14S*,17R*,18S*,19S*,20R*)]-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
21884-45-7
Molecular Formula
C30H22O10
Formula Weight
542.5
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: solubleDMSO: 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+/m1/s1
InChi Key
OYNIPTDPTUSUAY-GBUXSVCISA-N
Origin
Fungus/Penicillium sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Recommended Products

Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    1 mg

    $248

    Add

    5 mg

    $799

    Add
    Cayman Chemical
    Visit Our Cancer Resource Center
    Find Tools & Resources to Study the Hallmarks of Cancer
    • Cancer cell signaling & regulation
    • Cancer metabolism
    • Tumor microenvironment
    EXPLORE NOW
    Product Description

    (–)-Rugulosin is a fungal metabolite that has been isolated from Penicillium species, including P. islandicum, which also produces the optical isomer and mycotoxin (+)-rugulosin (Item No. 23558).1 (–)-Rugulosin is 3-10-fold more cytotoxic to HeLa and L cells compared with (+)-rugulosin.2 It is protective against influenza in mice when administered via inhalation but not when administered intraperitoneally with 38.3 and 5% survival rates, respectively.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. 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).

    2. Umeda, M., Saito, M., and Shibata, S. Comparison of cytotoxic effects of various anthraquinonoids on cultured mammalian cells. Jpn. J. Exp. Med. 44(3), 249-255 (1974).

    3. Nakamura, S., Nii, F., Inoue, S., et al. Antiinfluenzal effect of rugulosin. Jpn. J. Microbiol. 18(1), 1-7 (1974).