Isolation, structure elucidation, and biological screening of bioactive natural products from selected traditional vegetables in China

• Applicant: Professor Dr. Peter Winterhalter
• Subject Area: Plant Cultivation, Plant Nutrition, Agricultural Technology
• Term: from 2003 to 2011
• Project identifier: Deutsche Forschungsgemeinschaft (DFG) - Project number 5410659

• Final Report Year: 2007

Final Report Abstract

The principal focus of the project was the isolation and structural characterization of bioactive natural products recoverable from five selected traditional vegetables of China. In this process, fractionation and isolation of plant compounds with High-Speed Countercurrent Chromatography (HSCCC) was of principal interest. Structure elucidation was performed by means of nuclear magnetic resonance spectroscopy (1D-/2D-NMR) and mass-spectrometiy experiments (EI-MS, HREI-MS and ESI-MS-MS) and resulted in the isolation of 31 substances from five different plant species. Partly, the isolated components were new for the investigated vegetable plants and one natural product was a novel structure. Preparatively recovered components are summarized below. Bioassay-guided fractionation and isolation and also evaluation of purified substances was performed by using the TEAC-assay (antioxidant activity) and the 'brine-shrimp'-assay (cytotoxic activity). Compounds recovered from Chinese Eggplant (Solanum melongena): Chlorogenic acid (5-caffeoyl quinic acid) (E1), neo-Chlorogenic acid (3-caffeoyl quinic acid) (E2), krypto-Chlorogenic acid (4-caffeoyl quinic acid (E3), N1,N10-di-dihydro-caffeoyl-spermidine (E5), Delphinidin-3-(p-coumaroylrutinoside)-5-glucoside (nasunin) (E4). Compounds from Black Rice (Oryza sativa): Cyanidin-3-O-ß-D-glucoside (B1), Peonidin-3-O-ß-C-glucoside (B2), Protocatechuic acid (B3). Compounds from Perilla frutescens: 7-O-Diglucuronyl-apigenin (P1), 7-O-Diglucuronyl-luteolin (P2), 7-O-Diglucuronyl-scutellarein (P3), Malonylshisonin (P4), Shisonin (P5), Syrinic acid ß-D-glucopyranosyl ester (P6), Peonidin-3-O-ß-D-glucoside (P7). Isolated compounds from leaves and stems of Amaranthus tricolor (Chinese spinach): Trianthenol (A5), Amaranthenol (A6), 132-Hydroxy-(132-S)-phaeophytin-a (A1), Chlorophyll b methoxylactone (A2), Chlorophyll a (A3), Chlorophyll b (A4), (5a)-Stigmasta-7,22-dien-3ß-ol (A7), 3/3- Hydroxy-5or,6or-epoxy-7-megastigmen-9-one (A8), Adenosin (A9), Quercetin 3-O-rutinoside (A10), p-Caffeoyl-isocitric acid (A11), L-Phenylafanine A12), all-trans-Lutein (A13), ß-Carotene (A14), Dotriacontan-1-ol (A15), Octacosanol (A16), Amaranthine/ Isoamaranthine (A17). Isolated compounds from violet stemmed Taro (Xanthosoma violaceum): (-)-Epicatechin (X1), Procyanidin A1 (X2)

Publications

• Sino German Symposium, Bioactive compounds and mycotoxins in vegetables as affected by environment and nutrient status, Hangzhou, China, 03th - 06th Dezember 2003. Isolation, structure elucidation, and biological screening of bioactive natural products from selected traditional vegetables in China'
  G. Jerz, Q. Du, P. Winterhalter
  
• Isolation of two Anthocyanin-sambubiosides from Bilberry (Vaccinium myrtillus) by High-speed Countercurrent Chromatography. J. Chromatogr. A 1045 (2004) 59-63
  Q. Du, G. Jerz, P. Winterhalter
  
• Preparation of Ursane Triterpenoids from Centella asiatica Using High-speed Countercurrent Chromatography with Step-Gradient Elution. Journal of Liquid Chromatography & Related Technologies, (2004)2201-2215
  Q. Du, G. Jerz, P. Chen, P. Winterhalter
  
• Walberberg DFG-Workshop 16th, 17th July 2004, Verbundprojekte FlavoNet und LipidNet. Erschließung neuer Quellen für die Isolierung pharmakologisch aktiver Naturstoffe
  G. Jerz, P. Winterhalter
  
• Semi-industrial isolation of salicin and amygdalin from plant extracts using slow rotary counter-current chromatography. J. Chromatogr. A 1074 (2005) 43-46
  Q. Du, G. Jerz, Y. He, L. Li, Y. Xu, Q. Zhang, Q. Zheng, P. Winterhalter, Y. Ito
  
• Separation of anthocyanins and flavonoids from Perilla frutescens by high-speed countercurrent chromatography. Lebensmittelchemie 59, 1 (2005)21
  X.-D. Hu, G. Jerz, A. Körn, P. Winterhalter
  
• Technical Educational Institute (TEI), Crete, 25. May 2005. Preparative Isolation of Bioactive Natural Products from Medicinal Plants by 'High Speed Countercurrent Chromatography' (HSCCC)
  G. Jerz, Q. Du, M. del R. Ramos, O. Nehring, P. Winterhalter
  
• Antioxidant constituents in the fruits of Luffa cylindrica (L.) Roem. J. Agric. Food Chem., 54 (2006) 4186- 4190
  Q. Du, Y. Xu, L. Li, Y. Zhao, G. Jerz, P. Winterhalter
  
• Di-2-ethylhexyl phthalate in the fruits of Benincasa hispida. Food Addit Contam., 2 (6) (2006) 552-555
  Q. Du, L. Shen, L. Xiu, G. Jerz, P. Winterhalter
  
• Isolation and structure elucidation of nasunin and N1, N10-dihydrocaffeoylspermidine of Chinese eggplants. Lebensmittelchemie 60, 4 (2006) 91
  S. Stoll, G. Jerz, P. Winterhalter
  
• Isolation of 132-hydroxy-(132-S)- phaeophytin-a from leaves and stems of Amaranthus tricolor by high-speed countercurrent chromatography. (2006) Pigments in Food. A Challenge to Life Sciences. Abstract book p. 65-67 (Ed. R. Carle, A. Schieber, F. Stintzing), Shaker Verlag GmbH - Aachen, ISBN 3-8322-5479-X; Innovative Food Science & Emerging Technologies (2007)
  G. Jerz, T.N. Arrey, V. Wray, Q. Du, P. Winterhalter
  
• Isolierung und Strukturaufklärung von Anthocyanen aus chinesischem schwarzen Reis unter Anwendung der High-Speed Countercurrent Chromatography. Proceedings p. 275, 35. Deutscher Lebensmittelchemikertag, 18th - 20th September 2006, Dresden
  S. Stoll, G. Jerz, P. Winterhalter
  
• Lipophilic tetraterpenoids isolated from the leaves and stems of Amaranthus tricolor. Proceedings p. 143, 35. Deutscher Lebensmittelchemikertag, 18th -20th September 2006, Dresden
  G. Jerz, T.N. Arrey, V. Wray, Q. Du, P. Winterhalter
  
• Sino-German Workshop (Chinese biological active compounds), Graduiertenkolleg am Lehrstuhl für Lebensmitteltechnologie (Food Technology), Institut ür Humanernährung und Lebensmittelkunde Universität Kiel, 11th July 2006. Isolierung und Strukturaufklärung von Anthocyanen aus chinesischen Gemüse- und Getreidearten unter Anwendung der High-Speed Countercurrent Chromatography
  S. Stoll, G. Jerz, P. Winterhalter
  
• Sino-German Workshop (Chinese biological active compounds), Graduiertenkolleg am Lehrstuhl für Lebensmitteltechnologie (Food Technology), Institut ür Humanernährung und Lebensmittelkunde Universität Kiel, 11th July 2006. „Anwendung der High-Speed Countercurrent Chromatography (HSCCC) in der Naturstoffanalytik sowie Isolierung und Strukturaufklärung von Tetraterpenen und Chlorophyll- Abbauprodukten aus Amaranthus tricolor"
  G. Jerz, S. Stoll, T. N. Arrey, V. Wray, Q. Du, P. Winterhalter