A bacterial metabolite
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Neoaureothin

Item No. 28091

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-methoxy-3,5-dimethyl-6-[(2R,4Z)-tetrahydro-4-[(2E,4E,6E)-2,4,6-trimethyl-7-(4-nitrophenyl)-2,4,6-heptatrien-1-ylidene]-2-furanyl]-4H-pyran-4-one
CAS Number
59795-94-7
Synonyms
  • NSC 260179
  • Spectinabilin
Molecular Formula
C28H31NO6
Formula Weight
477.6
Purity
≥98%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMF: solubleDMSO: solubleEthanol: solubleMethanol: soluble
λmax
268, 368 nm
SMILES
CC(/C=C1CO[C@@H](C(OC(OC)=C2C)=C(C)C2=O)C\1)=C\C(C)=C\C(C)=C\C3=CC=C([N+]([O-])=O)C=C3
InChi Code
InChI=1S/C28H31NO6/c1-17(11-18(2)13-22-7-9-24(10-8-22)29(31)32)12-19(3)14-23-15-25(34-16-23)27-20(4)26(30)21(5)28(33-6)35-27/h7-14,25H,15-16H2,1-6H3/b17-11+,18-13+,19-12+,23-14-/t25-/m1/s1
InChi Key
IZICQJAGBLBAMJ-QDYRYYKCSA-N
Origin
Bacterium/Streptomyces sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

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    Product Description

    Neoaureothin is a bacterial metabolite that has been found in Streptomyces.1 It is an androgen receptor (AR) antagonist that inhibits binding of dihydrotestosterone (DHT) to ARs (IC50 = 13 μM) and inhibits DHT-induced expression of prostate-specific antigen in LNCaP cells (IC50 = 1.75 nM). Neoaureothin is cytotoxic to A549, HCT116, and HepG2 cells (IC50s = 34.3, 47, and 37.2 μg/ml, respectively).2 It also has nematocidal activity against the pine wood nematode B. xylophilus (LC50 = 0.84 μg/ml) and increases survival of P. densiflora trees inoculated with B. xylophilus.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kawamura, T., Fujimaki, T., Hamanaka, N., et al. Isolation and structure elucidation of a novel androgen antagonist, arabilin, produced by Streptomyces sp. MK756-CF1. J. Antibiot. (Tokyo) 63(10), 601-605 (2010).

    2. Liu, C.X., Liu, S.H., Zhao, J.W., et al. A new spectinabilin derivative with cytotoxic activity from ant-derived Streptomyces sp. 1H-GS5. J. Asian Nat. Prod. Res. 19(9), 924-929 (2017).

    3. Liu, M.J., Hwang, B.S., Jin, C.Z., et al. Screening, isolation and evaluation of a nematicidal compound from actinomycetes against the pine wood nematode, Bursaphelenchus xylophilus. Pest. Manag. Sci. 75(6), 1585-1593 (2019).