Characterization of New Ent-kaurane Diterpenoids of Yunnan Arabica Coffee Beans

Abstract

Five new ent-kaurane diterpenoids, named mascaroside III–V (1–3), and 20-nor-cofaryloside I–II (4–5), together with seven known diterpenoids, were isolated from methanol extracts of the green coffee beans of Yunnan Arabica Coffee. Their chemical structures were elucidated by extensive spectroscopic analyses. Meanwhile, cytotoxicity assay against HL-60, A-549, SMMC-7721, MCF-7 and SW480 cell lines showed that they have not evident inhibition of cytotoxicity.Graphical AbstractElectronic supplementary materialThe online version of this article (doi:10.1007/s13659-016-0099-1) contains supplementary material, which is available to authorized users.

Metabolomics fingerprint of coffee species determined by untargeted-profiling study using LC-HRMS

“…The other feature, m/z 299.1997, has been identified as a possible derivative of a ent-kaurane diterpenoid derivative like a methyl-atractylgenin or the aglycone of 20-nor-cofaryloside I which has been described before in coffee but in others organs (Chu et al, 2016;Kučera, Papoušek, Kurka, Barták, & Bednář, 2016). It is interesting to highlight that after a search of the 299.1997 m/z in the sample data, several peaks were observed and always in parallel to other m/z values that included one or two H 2 O (317.2093, 335.2209, respectively) and one or two hexoses (497.2742 and 659.3270, respectively).…”

“…Finally, the last class of key metabolites, which caught our attention, concerned ent-kaurane diterpenoids that were described as key metabolites to discriminate the species (see section 3.3 above). Coffee beans are known for containing nearly 90 diterpenoids (Chu et al, 2016). An which exhibit various biological activities (Chu et al, 2016;Lang et al, 2013).…”

“…Coffee beans are known for containing nearly 90 diterpenoids (Chu et al, 2016). An which exhibit various biological activities (Chu et al, 2016;Lang et al, 2013). Several of these compounds are known to have therapeutic or toxic effects.…”

“…Nevertheless, these compounds have to be monitored either in leaves and in (roasted-) beans of coffee before further large human consumption as already mentioned (Chu et al, 2016;Lang et al, 2013).…”

Synthesis and Cytotoxicity Evaluation of Tropinone Derivatives

“…Thus we designed and synthesized a series of tropinone derivatives, and their preliminary biological evaluation was performed for their inhibitory activities in five human cancer cell lines (HL-60, A-549, SMMC-7721, MCF-7 and SW480) using MTS [3-(4, 5-dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfopheny)-2H-tetrazolium] method. The pattern of apoptosis in vitro against cancer depended upon cell line and dose of the compound [26, 27] and the dose was established according to the related literatures [28–30]. …”