Home>>Herboxidiene
Herboxidiene Catalog No.GC40103

Size Price Stock Qty
500μg
$258.00
In stock
1mg
$413.00
In stock

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Sample solution is provided at 25 µL, 10mM.

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Chemical Properties

Cas No. 142861-00-5 SDF Download SDF
Synonyms N/A
Chemical 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
Canonical 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
Formula C25H42O6 M.Wt 438.6
Solubility Soluble in ethanol or methanol or DMSO or dichloromethane Storage Store at -20°C
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
Shipping Condition Evaluation sample solution : ship with blue ice
All other available size: ship with RT , or blue ice upon request

Background

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] It also exhibits herbicidal activity against wild buckwheat, morning glory, maize, hemp sesbania, and rapeseed when applied at 0.069 kg/hectare.[1]

Reference:
[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).