Generic placeholder image

The Natural Products Journal

Author(s): GuiLin Hu, DeFu Hong, XiaoYuan Wang, YanBing Wang, Lin Zhou, ZhongRong Li and MingHua Qiu*

DOI: 10.2174/2210315511666210604164549

DownloadDownload PDF Flyer Cite As
Pyrrolomorpholine Spiroketal Alkaloids Present in Roasted Beans of Yunnan Arabica Coffee

Article ID: e040621193895 Pages: 4

  • * (Excluding Mailing and Handling)

Abstract

Background: Coffee is one of the most commonly consumed drinks around the world. During the coffee roasting process, sugars and amines undergo a violent Maillard reaction, resulting in a large number of volatile and non-volatile components. These ingredients have a huge impact on the formation of coffee flavor. In addition, many Maillard products in coffee have also been proven to exert antioxidative, anti-inflammatory effects, etc.

Objective: The objective of this research is to discover non-volatile Maillard reaction products in roasted coffee beans.

Methods: A pair of enantiomers pyrrolomorpholine spiroketal alkaloids 1a and 1b were isolated from roasted beans of Yunnan coffea Arabica. Their planar structures were elucidated by extensive spectroscopic analysis, HRESIMS spectra and X-Ray diffraction.

Results: Two pyrrolomorpholine spiroketal alkaloids were isolated from roasted Arabica coffee beans. And their formation pathway via Maillard reaction was deduced.

Conclusion: Their influence on the formation of coffee bitterness and biological functions is worthy of being further studied.

Keywords: Coffee, coffea arabica, roasted beans, pyrrolomorpholine spiroketal, alkaloid, maillard reaction.

Graphical Abstract

[1]
Moreira, A.S.P.; Nunes, F.M.; Domingues, M.R.; Coimbra, M.A. Coffee melanoidins: structures, mechanisms of formation and potential health impacts. Food Funct., 2012, 3(9), 903-915.
[http://dx.doi.org/10.1039/c2fo30048f] [PMID: 22584883]
[2]
Reineccius, G.A. The Maillard reaction and coffee flavor. 16th International Scientific Colloquium on Coffee, 1995, Vols I & Ii, pp. 249-257.
[3]
Ho, C.T.; Hwang, H.I.; Yu, T.H.; Zhang, J. An overview of the maillard reactions related to aroma generation in coffee. 15th International Scientific Colloquium on Coffee, 1993, Vols 1 and 2, pp. 519-527.
[4]
Liu, Y.Z.; Kitts, D.D. Confirmation that the Maillard reaction is the principle contributor to the antioxidant capacity of coffee brews. Food Res. Int., 2011, 44, 2418-2424.
[http://dx.doi.org/10.1016/j.foodres.2010.12.037]
[5]
Sauer, T.; Raithel, M.; Kressel, J.; Münch, G.; Pischetsrieder, M. Activation of the transcription factor Nrf2 in macrophages, Caco-2 cells and intact human gut tissue by Maillard reaction products and coffee. Amino Acids, 2013, 44(6), 1427-1439.
[http://dx.doi.org/10.1007/s00726-012-1222-1] [PMID: 22274738]
[6]
Fukushima, Y.; Kasuga, M.; Nakao, K.; Shimomura, I.; Matsuzawa, Y. Effects of coffee on inflammatory cytokine gene expression in mice fed high-fat diets. J. Agric. Food Chem., 2009, 57(23), 11100-11105.
[http://dx.doi.org/10.1021/jf901278u] [PMID: 19899759]
[7]
Hu, G.L.; Wang, X.; Zhang, L.; Qiu, M.H. The sources and mechanisms of bioactive ingredients in coffee. Food Funct., 2019, 10(6), 3113-3126.
[http://dx.doi.org/10.1039/C9FO00288J] [PMID: 31166336]
[8]
Tong, X.G.; Zhou, L.L.; Wang, Y.H.; Xia, C.; Wang, Y.; Liang, M.; Hou, F.F.; Cheng, Y.X. Acortatarins A and B, two novel antioxidative spiroalkaloids with a naturally unusual morpholine motif from Acorus tatarinowii. Org. Lett., 2010, 12(8), 1844-1847.
[http://dx.doi.org/10.1021/ol100451p] [PMID: 20329735]
[9]
Wood, J.M.; Furkert, D.P.; Brimble, M.A. 2-Formylpyrrole natural products: origin, structural diversity, bioactivity and synthesis. Nat. Prod. Rep., 2019, 36(2), 289-306.
[http://dx.doi.org/10.1039/C8NP00051D] [PMID: 30039828]
[10]
Jiang, D.; Peterson, D.G. Identification of bitter compounds in whole wheat bread. Food Chem., 2013, 141(2), 1345-1353.
[http://dx.doi.org/10.1016/j.foodchem.2013.03.021] [PMID: 23790923]
[11]
Wakamatsu, J.; Stark, T.D.; Hofmann, T. Taste-Active Maillard Reaction Products in Roasted Garlic (Allium sativum). J. Agric. Food Chem., 2016, 64(29), 5845-5854.
[http://dx.doi.org/10.1021/acs.jafc.6b02396] [PMID: 27381763]
[12]
Sudhakar, G.; Kadam, V.D.; Bayya, S.; Pranitha, G.; Jagadeesh, B. Total synthesis and stereochemical revision of acortatarins A and B. Org. Lett., 2011, 13(20), 5452-5455.
[http://dx.doi.org/10.1021/ol202121k] [PMID: 21955040]
[13]
Verano, A.L.; Tan, D.S. Family-level stereoselective synthesis and biological evaluation of pyrrolomorpholine spiroketal natural product antioxidants. Chem. Sci. (Camb.), 2017, 8(5), 3687-3693.
[http://dx.doi.org/10.1039/C6SC05505B] [PMID: 28845229]