Coffee cafestol

The synthesis of cafestol, an antiinflammatory agent which occurs in coffee beans along with related diterpenoids such as actractyloside and kahweol, was accomplished by the same strategic approach which was applied to its companion atractyligenin. 

Kahweol, a "coffee" diterpenoid, was synthesized from the co-occurring natural product cafestol. 

Several diterpenes, free, as their esters or as their glycosides, have been recognized in green coffee beans. Cafestol (a furokaurane) and kahweol (a furokaurene) are the predominant diterpenes. They have been recog-... 

Cafestol from robusta coffee as well as kahweol from arabica coffee were both recognized as capable of elevating serum cholesterol levels.124... 

Large amounts of diterpene mono- and di-alcohols have been found in both Arabic and Robusta coffees, including cafestol, kahweol, and 16-O-methylcafestol.126 The characteristic differences can be used to quantify the Robusta content of commercial blends with Arabica.127... 

Lam, L. K. T., Sparnins, V. L., Wattenberg, L. W., Isolation and identification of kahweol palmitate and cafestol palmitate as active constituents of green coffee beans that enhance glutathione-S transferase activity in the mouse, Cancer Res., 42, 1193, 1982. (CA96 198149d)... 

To identify further which substance, cafestol or kahweol, or both, was inducing changes in serum cholesterol, the investigators attempted, but failed due to technical limitations, to separate the two chemical compounds. Alternatively, they compared coffee oil from Arabica vs. Robusta coffee beans. Arabica beans contain both cafestol and kahweol, while Robusta beans contain cafestol, but almost no kahweol. The investigators found that Arabica and Robusta oils both increased serum cholesterol and triglyceride levels comparably. They thus concluded that cafestol is, and kahweol might be, a serum cholesterol raising factor. 

Finally, a recently published crossover study of coffee oil lipid extracts by Urgert et al.27 compared the effects of 60 mg/day of cafestol with a mixture of 60 mg/day of cafestol plus 50 mg/day of kahweol. These doses were comparable to consuming 10 to 20 cups of boiled Turkish or French-press coffee. In 10 healthy men, 18 days of cafestol alone resulted in significant increases in total cholesterol (0.79 mmol/L [31 mg/dL]), LDL-C (0.57 mmol/L [22 mg/dL]), and TG (0.65 mmol/L [58 mg/dL]), relative to baseline. Compared to cafestol alone, the cafestol/kahweol mixture resulted in additional increases in total cholesterol (0.23 mmol/L [9 mg/dL), LDL-C (0.23 mmol/L [9 mg/dL]), and TG (0.09 mmol/L [8... 

In summary, these investigations suggest that the diterpenoid alcohol content of coffee, primarily cafestol and kahweol, is the cholesterol raising fraction. It can be present in either oil droplets or floating fines found predominantly in boiled coffee. Studies have shown that the use of a filter in coffee preparation can trap most of the diterpenoid material and the fines, thereby producing coffee without these cholesterol raising factors. 

Arabica beans coffee oil 3 weeks/ Rx Ages 20-26 Robusta differences 72 mg / d cafestol... 

Urgert, R., Essed, N., van der Weg, G., Kosmeijer-Schuil, T. G., Katan, M. B., Separate effects of the coffee diterpenes cafestol and kahweol on serum lipids and liver aminotransferases, Am J Clin Nutr, 65, 519, 1997... 

Lipoprotein modification. Decoction of the seed, administered orally to 22 adults at a dose of five to six strong cups for 1 day, was active. Consumption of cafestol and kahweol resulted in decreased lipoprotein A levels. Filtering coffee removed the diterpenes " . Decoction of the dried stem bark, administered orally to 150 healthy adults of both sexes who consumed five or more cups of boiled coffee and 159 filter coffee consumers at a dose of 1.2 L/day, was active on human serum. Median level of serum lipoprotein was higher in the boiled coffee drinkers ". ... 

Urinary diterpenes excretion. Absorption and excretion of the cholesterol-raising coffee diterpenes cafestol and kahweol were observed in nine healthy patients with ileostomies. Ileostomy effluent was collected for 14 hours, and urine was collected for 24 hours. Approximately 70% of the ingested cafestol and kahweol was absorbed. Only small part of the diterpene was excreted as a conjugate of glucuronic acid or sulphate in urine, mean excretion was 1.2% of the ingested amount for cafesterol and 0.4% for kahweol . 

De Roos, B., S. Meyboom, T. G. Kosmeijer-Schiul, and M. B. Katan. Absorption and urinary excretion of CA072 the coffee diterpenes cafestol and kahweol in healthy ileostomy volunteers. J Intern Med 1998 244(6) ... 

If the ketone is symmetrical, as here, or can form an enolate on one side only, or if we are dealing with an ester, enolate formation and hence alkylation is unambiguous. In Corey s synthesis of cafestol,13 an anti-inflammatory agent from coffee beans, he first alkylated ketone 44 on the only possible side and converted the product 45 into the new alkylating agent 46. 

Di79 Cafestol Green coffee beans Skin-6, CYP, GSH, GST [102-105]... 

The chemistry of atractyloside has been reviewed. A further relative (87) of cafestol has been isolated from green coffee beans. Sideritis (Labiatae) species have continued to attract attention as a source of diterpenoids. The comparative phytochemistry of Canary Island species has been reviewed. A number of 15-hydroxykaurenes (88)—(90) have been isolated from S. crispata, S. ilicifolia, and S. tragoriganum together with the atisine (91) and beyerene (92) derivatives, ent-18-Acetoxy-3/8,7a,15/S-trihydroxykaur-16-ene has also been obtained from S. scardica. 

Other compounds, the diterpenes cafestol and kahweol (see Section 2.1.3), have been shown to increase cholesterol levels, this effect being drastically reduced by drinking filtered coffee. Anyway, they have also been recognized as chemoprotective agents. 

The extraction of lipids from the roasted coffee into the brew has received special attention because of the tendency of cafestol, and possibly also kahweol, to increase the (total and low-density lipoprotein) cholesterol level (the intake of 16-O-methylcafestol is too low to be taken into account). This effect of the coffee beverage, already suspected in 1963 (reference quoted in Katan and Urgert, 1995), was later confirmed (for example Thelle, 1992, and earlier work many publications appeared on the subject) and the brewing method was especially examined. The conclusion was that there is no problem when the brew is... 

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