Herboxidiene

Names

[ Name ]:
Herboxidiene

[Synonym ]:
Herboxidiene
2H-Pyran-2-acetic acid,tetrahydro-6-(6-(3-(3-hydroxy-2-methoxy-1-methylbutyl)-2-methyloxiranyl)-1,5-dimethyl-1,3-hexadienyl)-5-methyl
2-((2R,5S,6S)-6-((S,2E,4E)-7-((2R,3R)-3-((2R,3R,4R)-4-hydroxy-3-methoxypentan-2-yl)-2-methyloxiran-2-yl)-6-methylhepta-2,4-dien-2-yl)-5-methyltetrahydro-2H-pyran-2-yl)acetic acid
herboxidiene 1

Biological Activity

[Description]:

Herboxidiene (GEX1A) is a potent phytotoxic polyketide from Streptomyces sp. A7847 with a diverse range of activities, including herbicidal, anti-cholesterol, anti-tumor effects. Herboxidiene inhibits the pre-mRNA splicing process by binding to spliceosome-associated protein (SAP) 155, a subunit of SF3b, in the splicesome[1][2].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Cell Cycle/DNA Damage >> DNA/RNA Synthesis

[In Vitro]

Herboxidiene (24 hours) induces both G1 and G2/M arrest in a human normal fibroblast cell line, WI-38, with an IC50 of 7.6 nM[3]. Herboxidiene exhibits cytotoxicity against A431, A549, and DLD-1 cells with IC50s of 3.7, 21, 51 nM, respectively[3].

[In Vivo]

Herboxidiene (GEX1A) (1 mg/kg; i.p.; once) shows significant antitumor activity[3]. Animal Model: BALB/c mice (bearing SVT2 murine fibrosarcoma)[3] Dosage: 1 mg/kg Administration: I.p.; once Result: Showed significant antitumor activity on day 4.

[References]

[1]. Pokhrel AR, et al. Herboxidiene biosynthesis, production, and structural modifications: prospect for hybrids with related polyketide. Appl Microbiol Biotechnol. 2015;99(20):8351‐8362.

[2]. Sakai Y, et al. GEX1 compounds, novel antitumor antibiotics related to herboxidiene, produced by Streptomyces sp. I. Taxonomy, production, isolation, physicochemical properties and biological activities. J Antibiot (Tokyo). 2002;55(10):855‐862.

[3]. Miller-Wideman M, et al. Herboxidiene, a new herbicidal substance from Streptomyces chromofuscus A7847. Taxonomy, fermentation, isolation, physico-chemical and biological properties. J Antibiot (Tokyo). 1992;45(6):914‐921.

Chemical & Physical Properties

[ Density]:
1.056g/cm3

[ Boiling Point ]:
567.9ºC at 760 mmHg

[ Molecular Formula ]:
C₂₅H₄₂O₆

[ Molecular Weight ]:
438.59700

[ Flash Point ]:
181.9ºC

[ Exact Mass ]:
438.29800

[ PSA ]:
88.52000

[ LogP ]:
4.36290

[ Vapour Pressure ]:
2.92E-15mmHg at 25°C

[ Index of Refraction ]:
1.497

Related Compounds

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