A polyketide with diverse biological activities
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Herboxidiene

Item No. 25136

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5,6-anhydro-6-C-[(2S,3E,5E)-6-[(2S,3S,6R)-6-(carboxymethyl)tetrahydro-3-methyl-2H-pyran-2-yl]-2-methyl-3,5-heptadien-1-yl]-1,4,7-trideoxy-4-methyl-3-O-methyl-L-glycero-L-gluco-heptitol
CAS Number
142861-00-5
Synonyms
  • GEX1A
  • Tan 1609
Molecular Formula
C25H42O6
Formula Weight
438.6
Purity
≥70%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Dichloromethane: solubleDMSO: solubleEthanol: solubleMethanol: solubleMethanol: Sparingly soluble: 1-10 mg/ml
SMILES
O=C(O)C[C@@H]1O[C@H](/C(C)=C/C=C/[C@@H](C)C[C@@]2(C)O[C@]2([H])[C@H](C)[C@@H](OC)[C@H](O)C)[C@@H](C)CC1
InChi Code
InChI=1S/C25H42O6/c1-15(14-25(6)24(31-25)18(4)23(29-7)19(5)26)9-8-10-16(2)22-17(3)11-12-20(30-22)13-21(27)28/h8-10,15,17-20,22-24,26H,11-14H2,1-7H3,(H,27,28)/b9-8+,16-10+/t15-,17+,18-,19-,20-,22-,23-,24-,25-/m1/s1
InChi Key
ISZXEMUWHQLLTC-LSIVYLFASA-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

    Herboxidiene is a polyketide originally isolated from S. chromofuscus that has diverse biological activities.1,2,3,4,5 It inhibits growth of HeLa S3, SK-MEL-2, PC3, A549, and EBC-1 cells with GI50 values ranging from 7.4 to 62 nM.3 Herboxidiene is cytostatic against human umbilical vein endothelial cells (HUVECs; (IC50 = 26 nM)) and inhibits VEGF-induced invasion and tube formation of serum-starved HUVECs in a concentration-dependent manner, indicating antiangiogenic activity.4 Herboxidiene (0.05 μM) inhibits HIF-1α mRNA splicing and reduces HIF-1α protein levels in HepG2 cells grown under hypoxic conditions. It also inhibits splicing of p27Kip mRNA in HeLa cells in a concentration-dependent manner via interaction with the SAP155 subunit of the SF3b complex.2 Herboxidiene (0.1 and 1 μM) increases LDL receptor promoter-driven transcription in a cell-based reporter assay.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Miller-Wideman, M., Makkar, N., tran, M.G.B., et al. Herboxidiene, a new herbicidal substance from Streptomyces chromofuscus A7847. Taxonomy, fermentation, isolation, physico-chemical and biological properties. J. Antibiot. (Tokyo) 45(6), 914-921 (1992).

    2. Hasegawa, M., Miura, T., Kuzuya, K., et al. Identification of SAP155 as the target of GEX1A (Herboxidiene), an antitumor natural product. ACS Chem Biol. 6(3), 229-233 (2011).

    3. Imaizumi, T., Nakagawa, H., Hori, R., et al. The synthesis and evaluation of the antiproliferative activity of deacidified GEX1A analogues. J Antibiot (Tokyo) 70(5), 675-679 (2017).

    4. Jung, H.J., Kim, Y., Shin, J.Y., et al. Antiangiogenic activity of herboxidiene via downregulation of vascular endothelial growth factor receptor-2 and hypoxia-inducible factor-1α. Arch. Pharm. Res. 38(9), 1728-1735 (2015).

    5. Koguchi, Y., Nishio, M., Kotera, J., et al. Trichostatin A and herboxidiene up-regulate the gene expression of low density lipoprotein receptor. J. Antibiot. (Tokyo). 50(11), 970-971 (1997).