Health benefits associated with Mediterranean diets are due to the significantly large intake of functional plant foods and beverages, i.e., fruits, vegetables, cereals, legumes, nuts, wine, beer, and olive oil, containing a great array of bioactive phytochemicals or nutraceutical compounds. Therefore, the low risk of chronic diseases, such as coronary hearth disease and certain cancers, observed in some population groups, results from a diversified eating style, either in term of foods and food components. The paradigm of the relationship between the chemical diversity of a particular food and the array of its biological activities may be symbolized by grape. Despite the extensive knowledge about phenylpropanoids, principally polyphenols (stilbenes and anthocyanins) and condensed tannins (proanthocyanidins), in grape and wine, little it is known about the other compounds, such as tetrahydro-beta-carbolines. Recently, it has been attached importance to the dietary indoleamines, melatonin, and serotonin, in different plant foods, including grape, thus further supporting the hypothesis that health benefits, associated with Mediterranean dietary style, are due to plant food chemical diversity.