Coffee diterpene

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... 

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) ... 

One of the most significant differences between Arabica and Robusta coffees is in the caffeine content. Robusta coffees contain almost twice the caffeine found in Arabica coffees. There are some other differences recognized thus far Robustas contain almost no sucrose and only very small amounts of the kaurane and furokaurane-type diterpenes they contain higher proportions of phenols, complex carbohydrates (both soluble and hydrolyzable), volatile fatty acids on roasting, and sulfur compounds, all in comparison with Arabicas. References to these distinctions can be found in Chapter 6 of this book. 

Methods for the decaffeination of green coffee beans, mainly with solvents after a steaming, have already been described. Even with the selective adsorption techniques to remove only caffeine, it is unlikely that the full character of the starting beans can be realized in a final decaffeinated beverage the result is that Robusta coffees are generally used to prepare decaffeinated coffee. The cost is kept down and the treatment, anyway, reduces any harsh or bitter flavor that the Robusta coffee may have had. The resulting beverage will be relatively caffeine-free, but Robusta coffee will contribute more soluble carbohydrates, phenols, and volatile fatty acids, and much less of the diterpenes found in Arabica coffees. 

Several alicyclic compounds identifiable in roasted coffee are terpenes and these contribute presumably to the coffee oil. The kaurane and furokaurane type diterpenes are discussed in Section VIII.D. 

Coffee bean lipids include triglycerides, sterols, tocopherols, and diterpenes, all of which are mainly found in the coffee oils. The Np-alkanoyl-5-hydroxytryptamides are concentrated in the outer coating of coffee bean wax. 

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-... 

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... 

Wurziger, J., Diterpenes in coffee oils for the evaluation of raw coffee according to type and processing, Fette Seiffen Anstrichm., 79, 334, 1977. (CA88 103392a)... 

Ludwig, H., Obermann, H., Spiteller, G., Diterpenes recently found in coffee, Colloq. Int. Chlm. Cafe, 7, 205, 1975. 

Arabica/Robusta beans used in different countries ranges from 1.5 1 in Italy, 4 1 to 3 1 in the U.S., and 20 1 in Sweden and Norway.2 As described in Chapter 6, coffee contains a number of physiologically active components, including caffeine, diterpene alcohols, sterols, hydrocarbons, squalene, and others. 

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 ". ... 

Pettitt Jr, B. C. Identification of the diterpene esters in arabica and cane-phora coffees. J Agr Food Chem 1987 35(4) 549-551. 

Speer, K. 16-O-methylcafestrol, anew diterpene in coffee. Food Chem Con-sum Proc Eur Conf Food Chem 5th 1989 1989(1) 302-306. 

Diterpenes in coffee leaves. Colloq Sci CA092 Int Cafe 1997 17(15) 1-154. 

Maier, H. G. and H. Wewetzer. Determination of diterpene glycosides in coffee. Z Lebensm-Unters Forsch... 

A. C. Beynen, and M. B. Catan. CA156 Diterpenes from coffee beans decrease serum levels of lipoprotein (A) in CA157 humans results from four randomized controlled trials. Eur J Clin Nutr 1997 ... 

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. 

Gross G., Jaccaud E. and Huggett A.C. (1997) Analysis of the content of the diterpenes cafestol and Kahweol in coffee brews. Food Chem. Toxic. 35, 547-54. 

Speer K. (1989) 16-O-Methylcafestol—ein neues Diterpen im Kaffee. Z. Lebensm. Unters. Forsch. 189, 326-30. Speer K. (1995) Fatty acid esters of 16-O-methylcafestol. 16th Int. Colloq. Chem. Coffee (Kyoto, 9 14.4.1995) (ASIC, 1995), 224-31. 

Speer K., Tewis R. and Montag A. (1991) 16-O-Methylcafestol—a new diterpene in coffee. Free and bound 16-O-methylcafestol. Z. Lebensm. Unters. Forsch. 192 (5), 451 —4. 

Speer K., Hruschka A., Kurzrock T. and Kolling-Speer I. (2000a) Diterpenes in coffee. Am. Chem. Soc. Symp. Ser. 754, 241-51. 

The potential anti-inflammatory properties of southern African soft coral metabolites were further exemplified by the isolation of five diterpene esters valdivones A (101), B (102), their corresponding methoxy ketals (103, 104) and dihydrovaldivone A (105) from Alcyonium valdivae (Family Alcyoniidae) collected off Coffee Bay on the warm temperate east coast of southern Africa (Figure 1) [94]. The structures of these compounds were determined from analysis of their 2D-NMR data with coupling constant analysis and nOe data providing the relative stereochemistry of 101 and 102. Valdivones A and B showed fairly strong inhibition of chemically-induced inflammation in the mouse ear assay (93% and 72% inhibition at 50 pg/ear respectively) but did not significantly inhibit bee venom phospholipase A2 (ca. 43% at 16 pgmL1) [94]. 

Two diterpenes, cafestol and kahweol, were isolated fi om brewed coffees and separated on a C g column (A = 230 nm and 290 nm) using a 20-min 30/70 - 5/95 water/methanol gradient [362]. Peak shapes were excellent and baseline resolution was obtained. Detection limits of 50pg/L were reported and standards of 40-300 pg/g were easily detected. 

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