A fungal metabolite
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Stephacidin B

Item No. 31656

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(7cS,7dR,15aS,16aS,21aR,21bR,22R,22aR,27aS,28aS)-1,4,7c,11,15,15a,16,18,19,26,27,28,28a,29-tetradecahydro-1-hydroxy-4,4,11,11,15,15,29,29-octamethyl-17H,21H,21bH,25H-21a,16a-(Iminomethano)-22,27a-methano-23H-diindolizino[6,7-a:7′,6′-j]bispyrano[2′,3′:6,7]indolo[2,3-d:3′,2′-g]carbazole-21,23,30,32-tetrone, 14-oxide
CAS Number
360765-75-9
Synonyms
  • (–)-Stephacidin B
Molecular Formula
C52H54N6O8
Formula Weight
891.0
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: solubleMethanol: soluble
λmax
244 nm
SMILES
CC1(C(C2(C3=CC=C(O4)C(C=CC4(C)C)=C35)[C@@](C(C6=CC=C(O7)C(C=CC7(C)C)=C6N8O)=C8C9(C)C)([H])[C@]([C@@]9([H])C[C@@]%10%11C%12=O)(C(N%10CCC%11)=O)N%12[C@@]2([H])[C@]%13(NC%14=O)[C@@]1([H])CC%14%15N(CCC%15)C%13=O)=[N]5=O)C
InChi Code
InChI=1S/C52H54N6O8/c1-44(2)19-15-25-29(65-44)13-11-27-33-36-50-28-12-14-30-26(16-20-45(3,4)66-30)35(28)58(64)38(50)47(7,8)31-23-48-17-9-21-54(48)42(61)51(31,53-40(48)59)39(50)56-41(60)49-18-10-22-55(49)43(62)52(36,56)32(24-49)46(5,6)37(33)57(63)34(25)27/h11-16,19-20,31-32,36,39,63H,9-10,17-18,21-24H2,1-8H3,(H,53,59)/t31-,32-,36-,39+,48?,49-,50?,51+,52+/m0/s1
InChi Key
ZKJYVORSURCOMD-GSYUCZBGSA-N
Origin
Fungus/Aspergillus sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    2.5 mg

    $747

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    Product Description

    Stephacidin B is a fungal metabolite that has been found in A. ochraceus.1 Dimeric stephacidin B is rapidly converted to a monomer, avrainvillamide (Item No. 31655), in vitro.2 Stephacidin B is cytotoxic to a variety of cancer cells, including testosterone-independent PC3 and -sensitive LNCaP prostate cancer cells (IC50s = 0.37 and 0.06 µM, respectively) and estradiol-independent SK-BR-3 and -sensitive MCF-7 breast cancer cells (IC50s = 0.32 and 0.27 µM, respectively).1 It induces apoptosis in HepG2 and Huh7 hepatocellular carcinoma cells when used at a concentration of 4 µM.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Qian-Cutrone, J., Huang, S., Shu, Y.-Z., et al. Stephacidin A and B: Two structurally novel, selective inhibitors of the testosterone-dependent prostate LNCaP cells. J. Am. Chem. Soc. 124(49), 14556-14557 (2002).

    2. Wulff, J.E., Herzon, S.B., Siegrist, R., et al. Evidence for the rapid conversion of stephacidin B into the electrophilic monomer avrainvillamide in cell culture. J. Am. Chem. Soc. 129(16), 4898-4899 (2007).

    3. Hu, L., Zhang, T., Liu, D., et al. Notoamide-type alkaloid induced apoptosis and autophagy via a P38/JNK signaling pathway in hepatocellular carcinoma cells. RSC Adv. 9(34), 19855-19868 (2019).