Sulforaphane

Sulforaphane is a naturally occurring compound found in cruciferous vegetables such as broccoli, cabbage, and arugula. It belongs to a class of plant-derived products containing an isothiocyanate functional group. Sulforaphane exhibits notable cancer chemopreventive effects and exerts its bioactivity through multiple mechanisms, including modulation of detoxifying enzyme activity, induction of apoptosis, inhibition of cell proliferation, and regulation of epigenetic markers.

Figure 1. Chemical Structure of Sulforaphane

Major Bioactivities:

1. Activation of Phase II Detoxifying Enzymes

Activates glutathione S-transferase, quinone reductase, and γ-glutamyl transpeptidase, enhancing their activity and expression.

In lymphoblasts and prostate cancer cells, induces apoptosis and inhibits cell growth.

2. Induction of Apoptosis in Various Cancer Cells

Colon cancer cells: Upregulates Bax expression, promotes cytochrome c release and PARP cleavage, leading to cell cycle arrest and apoptosis.

Melanoma cells: Activates caspases, Bax, and p53, downregulates Bcl-2, NF-κB, caspase-8, and Bid, inhibiting proliferation and promoting apoptosis.

3. Epigenetic Regulation

Inhibits histone deacetylase activity and promotes its degradation.

Increases the acetylation level of DNA repair enzymes and accelerates their degradation, thereby blocking DNA double-strand break repair and inducing cell cycle arrest, autophagy, and apoptosis.

4. Differences Between Synthetic and Natural Isomers

Synthetic R,S-sulforaphane: Effectively inhibits the occurrence and growth of breast tumors in animal models.

Natural R-sulforaphane: Optically active and exhibits pronounced biological activity.

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References

1. Misiewicz I, Skupińska K, Kowalska E, et al. Acta Biochim Pol. 2004;51(3):711-21.

2. Hamsa TP, Thejass P, Kuttan G. Drug Chem Toxicol. 2011 Jul;34(3):332-40.

3. Rajendran P, Kidane AI, Yu TW, et al. Epigenetics. 2013 Jun;8(6):612-23.

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