Cafestol, Kahweol and Their Acylated Derivatives: Antitumor Potential, Pharmacokinetics, and Chemopreventive Profile

Extraction of Diterpene-Phytochemicals in Raw and Roasted Coffee Beans and Beverage Preparations and Their Relationship

“…Figure 3 shows the structures of 12 of the 16 substances mentioned above that would be produced from C&K during roasting. Of all these, only three were isolated using the countercurrent chromatography technique followed by preparative HPLC and had their structures confirmed by 1 H and 13 C NMR-namely, the derivatives 16-O-methyl-cafestol, 15,16-dehydro-cafestol (#15) and 15,16-dehydro-kahweol (#12) [52].…”

“…Figure 3 shows the structures of 12 of the 16 substances mentioned above that would be produced from C&K during roasting. Of all these, only three were isolated using the countercurrent chromatography technique followed by preparative HPLC and had their structures confirmed by 1 H and 13 C NMR-namely, the derivatives 16-O-methyl-cafestol, 15,16-dehydro-cafestol (#15) and 15,16-dehydro-kahweol (#12) [52]. The justification for these proposals is due to the more intense ion m/z 267 in the first structure due to the sum of the losses of methyl groups linked to carbons 10 and 16 (Figure 4A), while the second structure has only one methyl loss from carbon 10 (Figure 4B).…”

“…Two other degradation products of cafestol (#1 and #2) were also observed in the elution region of fatty acids and methyl esters, with ions characteristic of the furan group (m/z 133, 147 and 161) and apparent molecular ions of m/z 282 (Figure 4A,B). These are anhydrous derivatives of cafestol, likely resulting from an intramolecular and an intermolecular elimination, that is, the loss of water and a hydroxyl with a rearrangement for the presence of only one unsaturation, with a probable location between carbons 15-16 (or [13][14][15][16] for the first detected molecule and 16-17 for the second.…”

“…A broad bioactive profile of these diterpenes is characterized by antioxidant, antiinflammatory, anti-adipogenic, anti-diabetic and anti-carcinogenic activity [10][11][12][13], which leads coffee oil to be seen differently in terms of its potential, already demonstrated in studies of photoprotective effect, healing, moisturizing and hypoglycemic properties [14][15][16][17]. The esterified form of C&K diterpenes is the most abundant in coffee beans (99.6%), and it is an analytical challenge due to the structural similarity of the 26 C&K esters.…”

On the Cholesterol Raising Effect of Coffee Diterpenes Cafestol and 16-O-Methylcafestol: Interaction with Farnesoid X Receptor

“…These are mainly present in coffee as esters of palmitic acid or other fatty acids at the C17 position, while the free form is only in 0.4% w / w of the coffee lipid fraction [ 12 ]. They possess both positive and negative effects on human health, and considering the high consumption of the coffee brew, it is important to understand the impact on the human health of coffee diterpenes [ 13 ]. Anti-carcinogenic, anti-angiogenic, anti-inflammatory, anti-diabetic, and anti-oxidative stress effects were observed in subjects drinking a moderate amount of coffee or a brew with a moderate diterpene content.…”