New tryptamine derivatives isolated from wax of green coffee beans

Abstract

the presence of 2,4-disubstituted-1,3-dioxolanes since they are specific for this type of compound.These substituted 1,3-dioxolanes do not appear in all mixtures containing aldehydes and propylene glycol, although it has been noted that the frequency of their appearance in flavors has been increasing. The reason may be due to the increasing use of organic acids as flavorants. However, with the growing availability of mass spectroscopic instrumentation in commercial laboratories the above procedure will provide a rapid means for detection so that corrective action can be taken.

Tryptamine Derived Amides and Acetogenins from the Seeds of Rollinia mucosa

“…Its UV spectrum showed absorptions typical of indole derivatives. 23,24 The NMR spectra (Table 1) clearly indicated that compound 6 was an amide of tryptamine and lignoceric acid. A prominent peak at m/z 143 (base peak) in the FABMS and EIMS further confirmed the tryptamine moiety.…”

“…N -Lignoceroyltryptamine ( 6 ) was obtained as a white solid that exhibited a [M + H] peak in the HRFABMS at m / z 511.4628, appropriate for a molecular formula of C 34 H 58 N 2 O. Its UV spectrum showed absorptions typical of indole derivatives. , The NMR spectra (Table ) clearly indicated that compound 6 was an amide of tryptamine and lignoceric acid. A prominent peak at m / z 143 (base peak) in the FABMS and EIMS further confirmed the tryptamine moiety.…”

Quantitation of βN-Alkanoyl-5-hydroxytryptamides in Coffee by Means of LC-MS/MS-SIDA and Assessment of Their Gastric Acid Secretion Potential Using the HGT-1 Cell Assay

“…Addition of petroleum ether (20 mL) led to the precipitation of the target compounds which were isolated by centrifugation and recrystallized from methanol, yielding the β N-d 2 -alkanoyl-5-hydroxytryptamides in a purity of more than 99% (LC-MS, 1 m/z (%) 160.1 (100), 177 (12). 1 H NMR (400 MHz, d 6 -DMSO): δ/ppm 0.84 (t, 3H, J = 7.1 Hz, H-C(28)), 1.15-1.30 (m, 12 Â 2H, 2 Â 1H, H-C (14)(15)(16)(17)(18)(20)(21)(22)(23)(24)(25)(26)(27), H-C (19,20)), 1.47 (m, 2H, H-C(13)), 2.03 (t, 2H, J = 7.4 Hz, H-C(12)), 2.69 (t, 2H, J = 7.4 Hz, H-C(8)), 3.25 (q, 2H, J = 6.6 Hz, H-C(9)), 6.56 (dd, 1H, J = 8.56 Hz, J = 2.02 Hz, H-C(6)), 6.80 (d, 1H, J = 2.02 Hz, H-C(4)), 6.99 (d, 1H, J = 1.77 Hz, H-C(2)), 7.10 (d, 1H, J = 8.6 Hz, H-C(7)), 7.82 (t, 1H, J = 5.56 Hz, H-N(10)), 8.54 (s, 1H, HO-C(5)), 10.44 (d, 1H, J = 1.77 Hz, H-N(1)). 13 C NMR (100 MHz, d 6 -DMSO): δ/ppm 14.08 (CH 3 , C(28)), 25.35 (CH 2 , C(8,13)), 22.17-34.47 (CDH, CH 2 , C(14-27)), 35.53 (CH 2 , C(12)), 39.75 (CH 2 , C(9)), 102.66 (CH, C(4)), 111.80 (CH, C(6,7)), 112.66 (C, C(3)), 123.39 (CH, C(2)), 128.06 (C, C(3 0 )), 131.07 (C, C(7 0 )), 150.84 (C-OH, C(5)), 172.32 (CdO, C(11)).…”

Effect of Dewaxed Coffee on Gastroesophageal Symptoms in Patients with GERD: A Randomized Pilot Study

“…Interestingly, a recent ongoing prospective US cohort study demonstrated a minimal change in upper gastrointestinal symptoms upon stratification by caffeine status among caffeinated beverages (coffee, soda, and tea) and a major association between decaffeinated tea and GERD symptoms [48]. In line with these findings, an older experimental study demonstrated a worsening of upper gastrointestinal symptoms after caffeinated coffee consumption, but not after caffeinated tap water consumption, suggesting a feasible involvement of other unknown components of coffee in inducing GERD symptoms [49].…”