5 541 Coffea arabica L. C. canephora 3 Robusta C. liberica GC /MS 57 C. dewevrei % GC /MS

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1 ~550 Plant Science Journal DOI /PSJ * Q A Review of Research on the Chemical Constituents and Bioactivities of Coffee QIU Ming-Hua 1 2* ZHANG Zhi-Run 1 2 LI Zhong-Rong 1 2 ZHOU Lin 2 CHU Rui 1 2 LIU Jie-Qing 2 WANG Wei-Hua Coffee Engineering Research Centre of China Mangshi Dehong Prefecture Yunnan China 2. State Key Laboratory of Phytochemistry and Plant Resources in West China Kunming Institute of Botany CAS Kunming China Abstract Coffee has been used as a functional drink for hundreds of years and is considered as the first beverage. Due to its various chemical constituents and biological activities coffee has attracted increasing scientific attention. In this paper we review the latest research progress on the chemical structures of coffee and their bioactivities as well as the technological methods used in the coffee research of chemical constituents. Key words Coffee Constituents Caffeine Trigonelline Chlorogenic acid Bioactivities Coffea spp ~20 1 Rubiaceae Coffeoideae Coffea SB2007 FY400 KSCX2- YW-G-038 P2008ZZ mhchiu@mail. kib. ac. cn * Author for correspondence

2 5 541 Coffea arabica L. C. canephora 3 Robusta C. liberica GC /MS 57 C. dewevrei % GC /MS C-1 C-3 C-7 C-8 trigonelline 1 nicotinic acid 2 SPME GC / MS caffeine theobromine theophylline theacrine liberine O tri methyluric acid methyllibe- tine O tetramethyluric acid 1 GC-MS a b Fig. 1 GC-MS total ion current spectra of coffee chemical composition a Coffee sample from Wanning County b Coffee sample from Chengmai County

3 Fig. 2 2 Main metabolic pathway of caffeine β- β sitosterol stigmasterol scopeletin campesterol cholesterol - ρ-hydroxybenzoic acid 5- Δ5-avenasterol 7- vanillic acid - ρ-coumaric acid ferulicacid chlorogenic acid caffeic acid ursolic acid acid oleic acid linoleic acid acid palmitic acid stearic 3-O 4-O- 5-O- caffeoylquinic acid 3 4-O-3 5-O- 4 5-O- Arabica dicaffeoy1quinic acid 3-O % ~ 14. 0% Robusta 3-O-feruloyl-4-O-caffeoylquinic acid 3-O- -4-O- 3-O-caffeoyl-4-Oferuloylquinic acid C % ~10. 9% 6 Arabica Ro Δ7-avenasterol 7- - Δ7-stigmasterol myristic arachidic acid Derbesy 5 3-O-feruloylquinic acid 3-O- -4-O- 7. 6% ~ 9. 5% C % ~34% C % ~ 46. 5% C % ~ 17. 2% busta Robusta GC /MS

4 Arabica Robusta 3. 1 caffeine Robusta ~ 40% > ~ 30% > ~20% 3 Kahweol Shu ~ 5 mascaroside Ⅰ 3 1 mascaroside Ⅱ 3 2 aglycone E 3 3 cofaryloside Ⅰ 3 4 villanovane Moy 8 Ⅰ OH brain derived neurotrophic factor BDNF 4! A!! caspase Chu 9 3 AD Fig. 3 3 New diterpenoids from the roasted beans of Yunnan Arabica coffee

5 HFD HFDC + CDC + CD HFD High fat diet HFDC High fat diet plus caffeine CDC Control diet plus caffeine CD Control diet. 8 4 A p-akt 473 Akt B Glu T4 Glu T4 Fig. 4 A Mean density ratio of hippocampal p-akt Ser473 to total Akt ratios were normalized to beta-actin. B. Mean density ratio of plasma membrane Glu T4 to total Glu T4. C and D Representative blots for Akt and Glu T4 respectively 5 9 CC Caff A! Fig. 5 Crude caffeine and caffeine protection against neuronal death induced by A! trigonelline Yoshinari 10 trigonelline TRG TRG 9 6 Allred 11 Trig MCF-7 7 Shimoyama 14 CGA 3. 3 chlorogenic acid Nishi 12 2 ~3 4 Xu DNA

6 5 545 Fig TRG Model illustrating the effect of feeding TRG on antioxidant enzymes and glutathione 7 Trig 11 MCF-7 Fig. 7 Trigonelline increasing cellular proliferation of MCF-7 cells 13 8 Fig. 8 Reducing power of different chlorogenic acid isomers HPLC Gordillo-Delgado 16 - high performance liquid chromatography HPLC FTIR-photoacoustic spectrometry PAS HPLC 4 Caturra Castilla Tipica

7 Fig EtOH /HCl CGA Effects of CGA on gastric ulcer area in Et /HCl-treated mice Fig A B HPLC HPLC chromatogram of roasted coffee A and roasted coffee residue B FT-MIR-PAS FT-MIR- kahweol σ 12 PAS ν max 600 ~ ~ ~3900 cm -1 kahweol σ ka FTIR-PAS 2D-NMR Keidel Wei

8 A Caturra FTIR-PAS B Tipica FTIR-PAS Fig. 11 A FTIR-PAS spectra of organic solid lines and conventional dotted lines Caturra coffee B FTIR-PAS spectra of organic solid lines and conventional dotted lines Tipica coffee Fig kahweol σ ka Spectral kahweol index σ ka determined from Raman spectra of various coffee samples 18 D 2 O 1 h NMR 2D-NMR 90% 1 H 13 C 13 NMR 24 3 NMR NMR NMR

9 Fig. 13 A "c B "c53-87 C "c C NMR Expansion of the 13 C NMR spectrum of roasted coffee bean extract

10 5 549 A. 1 5-CQA 2 4-CQA 3 3-CQA B. 1 Quinic acid 2 γ-quinide 3 syllo-quinic acid C. Sucrose D. 1 L-glutamic acid 2 L-alanine 3 L-asparagine 4 GABA E. 1 Trigonelline 2 N-methylpyridinium 3 Nicotinic acid F. 1 Citric acid 2 Malic acid 3 Lactic acid 4 Acetic acid 5 Formic acid G. 1 β D-mannopyranose 2 α larabinofuranose 3 α L-arabinofuranose 4 β D-galactopyranose 5 β D-galactopyranose H. 1 myo-inositol 2 Choline 3 2-furylmethanol 4 γ-butyrolactone 5 5-hydroxymethylfurfural. The integral value of the signal of caffeine was set to a constant of 100. Fig A ~ H Evolution of coffee components A- H during the roasting process

11 Allred KF Yackley KM Vanamala J Allred CD. Trigonelline is a novel phytoestrogen in coffee beans J. J Nutr Nishi Ahad A Kumar P. Hypolipidemic effect of chlorogenic acid in a hypercholesterolemic rat 1. model J. Int J Pharm Bio Sci J Xu JG Hu QP Liu Y. Antioxidant and DNA-pro-. tective activities of chlorogenic acid isomers J. J J Agric Food Chem Oliveira e Silva AM de Melo IL Mancini-Filho J J Farsky SH. Antiulcerogenic activity of chlorogenic acid in different models of gastric ulcer J. Nau- 4 nyn-schmiedeberg's Arch Pharmacol J Derbesy M Venot C dos Santos AC. Green coffees of Angola chemical study J. Quality Plant Material and Vegetables DM Mejía-Morales C García-Salcedo AJ. Discrimination of organic coffee via Fourier. 3 J. transform Shu Y Liu JQ Peng XR Wan LS Zhou L Zhang T Qiu MH. Characterization of diterpenoid glucosides in roasted pure coffee beans J. J Agric Food Chem Moy GA McNay EC. Caffeine prevents weight gain and cognitive impairment caused by a highfat diet while elevating hippocampal BDNF J. Physiol Behavior Chu YF Chang WH Black RM Liu JR Sompol P Chen YM Wei HL Zhao QY Cheng IH. Crude caffeine reduces memory impairment and amyloid! 1-42 levels in an Alzheimer's mouse model J. Food Chem Yoshinari O Takenake A Igarashi K. Trigonelline ameliorates oxidative stress in type 2 diabetic Goto-Kakizaki rats J. J Med Food Shimoyama AT Santin JR Machado ID de 15 Olthof MR van Dijk AE Deacon CF Heine RJ van Dam RM. Acute effects of decaffeinated coffee and the major coffee components chlorogenic acid and trigonelline on incretin hormones J. NutrMetab Lond Gordillo-Delgado F Marín E Cortés-Hernández infrared - photoacoustic spectroscopy J. J Sci Food Agric Keidel A von Stetten D Rodrigues C Máguas C Hildebrandt P. Discrimination of green Arabica and Robusta coffee beans by Raman spectroscopy J. J Agric Food Chem Wei FF Furihata K Hu FY Miyakawa T Tanokura M. Two-dimensional 1 H- 13 C nuclear magnetic resonance NMR -based comprehensive analysis of roasted coffee bean extract J. J Agric Food Chem Wei FF Furihata K Koda M Hu FY Miyakawa T Tanokura M. Roasting process of coffee beans as studied by nuclear magnetic resonance time course of changes in composition J. J Agric Food Chem

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中国农学通报 2013,29(04):39-43 Chinese Agricultural Science Bulletin 中药荆芥最新研究进展 1,2 1,2 赵立子, 魏建和 ( 1 北京协和医学院药用植物研究所, 北京 100193; 2 中草药物质基础与资源利用教育部重点实验室, 北京