Isothiocyanates: Translating the Power of Plants to People

Abstract

Isothiocyanates from cruciferous vegetables have been studied extensively in cells and in animals for their disease preventive and therapeutic effects. However, translating their utility to human populations has been both limited and challenging. Herein, clinical trials employing two isothiocyanates, sulforaphane (SFN; 1-isothiocyanato-4-(methylsulfinyl) butane) and phenethyl isothiocyanate (PEITC; 2-isothiocyanatoethylbenzene) that are isolated principally from broccoli and watercress, respectively, are summarized and discussed. Both of these compounds have been used in small human clinical trials, either within food matrices or as single agents, against a variety of diseases ranging from cancer to autism. Results suggest an opportunity to incorporate them, or more likely preparations derived from their source plants, into larger human disease mitigation efforts. The context for the applications of these compounds and plants in evidence-based food and nutritional policy is also evaluated.

Nitro-fatty acids: New drug candidates for chronic inflammatory and fibrotic diseases

“…Whereas bardoxolone-me was chemically engineered to strongly increase its electrophilicity, plant-derived sulforaphane is a less reactive electrophile obtained from broccoli sprouts upon enzymatic hydrolysis of glucoraphanin by the enzyme myrosinase (57). Large clinical trials have shown that sulforaphane is a promising therapy for preventing liver carcinogenesis induced by aflatoxin in endemic areas of the province of Qidong in China (58).…”

The Glucosinolates: A Sulphur Glucoside Family of Mustard Anti-Tumour and Antimicrobial Phytochemicals of Potential Therapeutic Application

“…Plants produce a myriad of phytochemicals and many of these have valuable nutritive, medicinal and health promoting properties [1][2][3] (Tables 1-3). Anecdotal evidence often points to these beneficial properties however in this report we will concentrate on two members of the glucosinolates (Figure 1), Glucoraphanin and Sinigrin, with a very extensive scientific and nutritional literature illustrating their potential therapeutic applications [3][4][5][6][7][8][9][10][11][12] (Table 2).…”

Evaluation of 2‐Thiothiazolidine‐4‐Carboxylic Acid, a Common Metabolite of Isothiocyanates, as a Potential Biomarker of Cruciferous Vegetable Intake

“…It is recognized that plants have a well‐evolved stress response mechanism that allows for them to protect themselves against environmental threats . In fact, the glucosinolate–isothiocyanate axis may exist precisely for this purpose in the cruciferous plant—to generate a tightly controlled antipathogenic response, given the potent antibacterial and antifungal properties of isothiocyanates . However, upon formation of these bioactive isothiocyanates, they have to be effectively neutralized and eliminated from plant cells, a process that may include the formation of the inactive metabolite TTCA.…”

“…[33,34] In fact, the glucosinolateisothiocyanate axis may exist precisely for this purpose in the cruciferous plant [35] -to generate a tightly controlled antipathogenic response, given the potent antibacterial and antifungal properties of isothiocyanates. [36] However, upon formation of these bioactive isothiocyanates, they have to be effectively neutralized and eliminated from plant cells, a process that may include the formation of the inactive metabolite TTCA. Nevertheless, the exact mechanism by which this isothiocyanate cycling or removal occurs in plants is not well understood.…”