Isothiocyanates

Watercress (Nasturtium officinale), a cruciferous vegetable, is rich in isothiocyanate compounds. These compounds exhibit anticancer properties and can induce Phase II detoxifying enzyme activity. The primary bioactive component of watercress is phenethyl isothiocyanate (PEITC), followed by 7-Methylsulfinylheptyl Isothiocyanate (MSH) and 8-Methylsulfinyloctyl Isothiocyanate (MSO).

Figure 1. Chemical Structure of Phenethyl Isothiocyanate

Major Bioactivities:

1. Anticancer and Chemopreventive Effects

PEITC exhibits chemopreventive and chemotherapeutic activities in multiple models.

In prostate cancer cells, PEITC induces apoptosis by inhibiting oxidative phosphorylation, depleting ATP, and generating ROS.

In prostate cancer xenograft animal models, PEITC suppresses PECAM-1 and various integrin family proteins in tumors, inhibiting angiogenesis and tumor growth.

2. Induction of Phase II Detoxifying Enzymes

PEITC induces quinone reductase activity and regulates ROS levels.

MSH and MSO also induce quinone reductase and may be more potent in activating Phase II enzyme activity.

3. Inhibition of Tumor Invasion and Matrix-Degrading Enzymes

Isothiocyanates such as (R)-sulforaphane, PHITC, and R-(-)-Iberin inhibit TPA-induced MMP-9 activity and breast cancer cell invasion.

4. Epigenetic Regulation

PEITC and sulforaphane can directly act on histones and chromatin remodeling proteins, potentially inhibiting histone deacetylase activity and DNA methylation.

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References

1. Xiao D, Powolny AA, Moura MB, et al. J Biol Chem. 2010 Aug 20;285(34):26558-69.

2. Hudson TS, Perkins SN, Hursting SD, et al. Int J Oncol. 2012 Apr;40(4):1113-21.

3. Gerhauser C. Curr Opin Clin Nutr Metab Care. 2013 Jul;16(4):405-10.

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