Search Log for Part II: ScienceDirect: Terms: Hits: ----------------------------------------------------------------------------------------- “Chlorogenic Acid isolation” 21 Articles "Chlorogenic acid” 228 articles “Chlorogenic acid” 84 articles “Luteolin” 144 articles “Luteolin” Search within Results:“Isolation” Search within Results: “Purification” 111 articles “Chlorogenic Acid” Search within results: “Lonicera japonica” Search within Resutls: “synthesis” 1 article “Chlorogenic Acid” Search within results: “Synthesis” 191 articles ----------------------------------------------------------------------------------------- Pub Med: Terms: Hits: ----------------------------------------------------------------------------------------- “Chlorogenic acid isolation” 135 “Chlorogenic Acid Synthesis” 228 ----------------------------------------------------------------------------------------- Plant Science: Terms: Hits: ----------------------------------------------------------------------------------------- Advanced Search “Chlorogenic acid” and “isolation” 14 journals ----------------------------------------------------------------------------------------- Science Direct: “Chlorogenic Acid isolation” Hits: 21 Articles Second Article Listed – had both key words “Chlorogenic Acid” and “Isolation” pH-gradient Counter-Current Chromatography Isolation of Natural Antioxidant Chlorogenic Acid from Lonicera japonica Thumb. using an Upright Coil Plant Centrifuge with Three Multi-layer Coils Connected in Series Tingting Wang, Xinhang Jiang, Lu Yang, and Shihua Wu. Zhejiang University, Research Center of Siyuan Natural Pharmacy and Biotoxicology, College of Life Sciences, Ziginggang Campus, Hangzhou 310058, China. Received September 2, 2007; revised November 29, 2007; accepted November 30, 2007. Available online December 8, 2007. Date Visited March 17, 2008. http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6TG8-4R9GGTX-D&_user=650615&_coverDate=02%2F08%2F2008&_alid=707542633&_rdoc=2&_fmt=full&_orig=search&_cdi=5248&_sort=d&_docanchor=&view=c&_ct=21&_acct=C000035118&_version=1&_urlVersion=0&_userid=650615&md5=b197f3ec7960df3032a3a1901a01f416 Abstract: A new pH-gradient counter-current chromatography method for the isolation of chlorogenic acid from flowers and buds of Lonicera japonica Thumb. has been successfully established using a novel upright coil planet centrifuge with three multi-layer coils connected in series with 600 mL capacity. The crude extracts were first prepared by direct extraction with hot water and following concentration to remove the solution. Then the two-phase solvent system composed of ethyl acetate–n-butanol–water (2:1:3, v/v) was applied to the separation. Its neutral upper phase was used as stationary phase, whereas both its neutral lower phase and base lower phase with 10 mM NH3 were employed as mobile phase with gradient elution in the head to tail mode. As a result, 330 mg quantity of crude extract was purified in one-step separation for 180 min, yielding 20.5 mg chlorogenic acid with over 98% purity. Structure of the compound is further identified by electrospray ionization tandem mass spectrometry (ESI-MS/MS) and nuclear magnetic resonance (NMR). -Contains information on isolating Chlorogenic acid. ----------------------------------------------------------------------------------------- Science Direct: “Chlorogenic acid” search within results “characterization” Hits: 228 articles Sort By Relevance First article listed, it has the key words “Characterization” and “Chlorogenic Acid,” along with “Purification.” Purification and characterization of a chlorogenic acid hydrolase from Aspergillus niger catalysing the hydrolysis of chlorogenic acid. Michčle Asther, Maria Isabel Estrada Alvarado, Mireille Haon, David Navarro, Marcel Asther, Laurence Lesage-Meessen and Eric Record. UMR 1163 INRA/Université de Provence de Biotechnologie des Champignons Filamenteux, IFR 86-IBAIM, Universités de Provence et de la Méditerranée, ESIL, 163 avenue de Luminy, Case Postale 925, 13288 Marseille Cedex 09, France. Received January 5, 2004; revised July 28 2004; accepted July 30, 2004; Available online September 16, 2004. Visited March 17, 2008. Abstract: Among 15 Aspergillus strains, Aspergillus niger BRFM 131 was selected for its high chlorogenic acid hydrolase activity. The enzyme was purified and characterized with respect to its physico-chemical and kinetic properties. Four chromatographic steps were necessary to purify the protein to homogeneity with a recovery of 2%. Km of the chlorogenic acid hydrolase was estimated to be 10 µM against chlorogenic acid as substrate. Under native conditions, the protein presented a molecular mass of 170 kDa, and SDS-PAGE analysis suggested the presence of two identical 80 kDa subunits. Isoelectric point was 6.0; pH optimum for activity was determined to be 6.0 and temperature optima to be 55 °C. The N-terminal sequence did not present any homology with other cinnamoyl ester hydrolases previously described suggesting the purification of a new protein. The chlorogenic acid hydrolase was used successfully for the production of caffeic acid, which possesses strong antioxidant properties, from natural substrates specially rich in chlorogenic acid like apple marc and coffee pulp. -Talks about purifying Chlorogenic acid. ----------------------------------------------------------------------------------------- Science Direct: “Chlorogenic acid” search within results “laboratory synthesis” Hits: 84 articles –Sort by Relevance It was the second article listed and it has the key words in the title “Synthesis” and “Chlorogenic acid” Synthesis of Chlorogenic Acid Derivatives with Promicing Antifungal Activity. Chao-Mai Ma, Maureen Kully, Jehangir K. Khan, Masao Hattori, and Mohsen Daneshtalab. School of Pharmacy, Memorial University of Newfoundland, St. John’s, NL, Canada A1C 3V6. NAEJA Pharmaceutical Co. Ltd, 4290-91 A Street, Edmonton, AB, Canada T6E 5V2. Institute of Natural Medicine, University of Toyama, Sugitani 2630, Toyama 930-0194, Japan. Received 22 May 2007; revised 11 July 2007; accepted 13 July 2007. Available online 22 August 2007. Visited March 17, 2008. http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6TF8-4PGGP0Y-F&_user=650615&_coverDate=11%2F01%2F2007&_alid=708934459&_rdoc=2&_fmt=full&_orig=search&_cdi=5220&_sort=r&_docanchor=&view=c&_ct=84&_acct=C000035118&_version=1&_urlVersion=0&_userid=650615&md5=965c1e8d99bca7e8f714df06f7759997 Abstract: Derivatives of chlorogenic acid or its analogues were synthesized by coupling protected chlorogenic acid or its analogues with p-octyloxyaniline and selected amino acids. Most of the compounds exhibited significant potency against Cryptococcus neoformans and Candida species with low toxicity to brine shrimps. The 4,5-dihydroxyl groups in the quinic acid moiety were necessary for the activity and introduction of a free amino group increased the inhibitory activity against Aspergillus fumigatus. Graphic Abstract: The synthesis of the chlorogenic acid derivatives with in vitro antifungal activity is reported. Keywords: Chlorogenic acid; p-Octyloxyaniline; Candida albicans; Cryptococcus neoformans; Aspergillus fumigates; H2N-aa-4-(octyloxy) aniline; Brine shrimp lethality assay; Echinocadin B; 1,3-ß-Glucan; H NMR; ESI-MS; FAB-MS. ----------------------------------------------------------------------------------------- Plant Science: CSA ILLUMINA: Advanced Search: “Chlorogenic acid” and “isolation” Hits: 14 journals – Sort by Relevance Rank -It was the first article listed and it contained the keywords “Chlorogenic Acid” and “Isolation.” A Phenolic Compound, 5-caffeoylquinic acid (Chlorogenic acid), is a New Type and Strong Matrix Metalloproteinase-9 Inhibitor: Isolation and Identification from Methanol Extract of Euonymus alatus. Jin, UH; Lee, JY; Kang, SK; Kim, JK; Park, WH; Kin, JG; Moon, SK; Kim, CH. Department of Biochemistry and Molecular Biology, Dongguk University College of Oriental Medicine, National Research Laboratory for Glycobiology, Kyungju, Kyungbuk 780-714, South Korea. Visited March 17, 2008. http://www-ca5.csa.com/ids70/view_record.php?id=4&recnum=0&log=from_res&SID=363bc6f251c8bff5baa5524d5d4086c8&mark_id=search%3A4%3A26%2C0%2C10. Abstract: A phenolic compound responsible for anti-MMP-9, which is known to be involved in tumor cell invasion and metastasis, has been isolated from methanol extracts prepared from stem barks of Euonymus alatus by assay-guided fractionation. The compound has been identified as 5-caffeoylquinic acid (chlorogenic acid; CHA) by NMR and FAB-MS. CHA showed a strong inhibitory effect of matrix metalloproteinase (MMP)-9 activity in a concentration-dependent manner on zymography. The purified CHA inhibited MMP-9 activity with the IC 50 of 30-50 nM. Furthermore, the cytotoxic survival curve showed that CHA does not have cytotoxic effects on cellular proliferation, when Hep3B cells were treated with various concentrations of CHA and cell viability was measured using the XTT assay. The present data suggest a clue for possible mechanisms of cancer chemoprevention by CHA and other naturally occurring phenolic compounds. The results also imply that useful cancer chemopreventive agents can be further identified by combinations of in vitro (as a first screen) and in vivo studies. (copyright) 2005 Elsevier Inc. All rights reserved. ----------------------------------------------------------------------------------------- PubMed: “Chlorogenic acid isolation” Hits: 135 The second article listed – it had the keywords “Chlorogenic acid” in the title. The first article listed did not. Gene Overexpression and Biochemical Characterization of the Biotechnologically Relevant Chlorogenic Acid Hydrolase from Aspergillus niger. Isabelle Benoit, Michele Asther, Yves Bourne, David Navarro, Stephane Canaan, Laurence Lesage-Meessen, Marga Herweijer, Pedro M. Coutinho, Marcel Asther, and Eric Record. UMR-1163, INRA de Biotechnologie des Champignons Filamenteux, IFR86-BAIM, Universites de Provence et de la Mediterranee, ESIL, 163 avenue de Luminy, CP 965, 13288 Marseille Cedex 09, France, UMR 6098, Architecture et Fonction des Macromolecules Biologiques, CNRS/Universites de Provence et de la Mediterranee, 163 avenue de Luminy, CP 932, 13288 Marseille Cedex 09, France, UPR 9025, CNRS Laboratoire d'Enzymologie Interfaciale et de la Physiologie de la Lipolyse, 31 chemin Joseph Aiguier, 13402 Marseille Cedex 20, France, DSM Food Specialties, P.O. Box 1, 2600 MA Delft, The Netherlands. Received February 16, 2007; Accepted June 30, 2007. Visited March 17, 2008. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2042068. Abstract: The full-length gene that encodes the chlorogenic acid hydrolase from Aspergillus niger CIRM BRFM 131 was cloned by PCR based on the genome of the strain A. niger CBS 513.88. The complete gene consists of 1,715 bp and codes for a deduced protein of 512 amino acids with a molecular mass of 55,264 Da and an acidic pI of 4.6. The gene was successfully cloned and overexpressed in A. niger to yield 1.25 g liter-1, i.e., 330-fold higher than the production of wild-type strain A. niger CIRM BRFM131. The histidine-tagged recombinant ChlE protein was purified to homogeneity via a single chromatography step, and its main biochemical properties were characterized. The molecular size of the protein checked by mass spectroscopy was 74,553 Da, suggesting the presence of glycosylation. ChlE is assembled in a tetrameric form with several acidic isoforms with pIs of around 4.55 and 5.2. Other characteristics, such as optimal pH and temperature, were found to be similar to those determined for the previously characterized chlorogenic acid hydrolase of A. niger CIRM BRFM 131. However, there was a significant temperature stability difference in favor of the recombinant protein. ChlE exhibits a catalytic efficiency of 12.5 × 106 M-1 s-1 toward chlorogenic acid (CGA), and its ability to release caffeic acid from CGA present in agricultural by-products such as apple marc and coffee pulp was clearly demonstrated, confirming the high potential of this enzyme. ----------------------------------------------------------------------------------------- PubMed: “Chlorogenic Acid Synthesis” Hits: 228 It was the first article listed and the title contained the keyword “Chlorogenic acid.” Effect of chlorogenic acid on antioxidant activity of Flos Lonicerae extracts. Lan Wu Department of Horticulture, Beijing Vocational College of Agriculture, Beijing 102442, China. Received December 6, 2006; Accepted June 22, 2007. Visited March 17, 2008. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1963434. Abstract: Flos Lonicerae is a medically useful traditional Chinese medicine herb. However, little is known about the antioxidant properties of Flos Lonicerae extracts. Here the antioxidant capacity of water, methanolic and ethanolic extracts prepared from Flos Lonicerae to scavenge 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical and reduce Fe3+ to Fe2+ is examined. Chlorogenic acid, a major component of Flos Lonicerae, is identified and further purified from 70% ethanolic extract with high performance liquid chromatography (HPLC) and its antioxidant capacity is characterized. The total phenolic compounds and chlorogenic acid contents in Flos Lonicerae are determined. The present results demonstrate that the Flos Lonicerae extracts exhibit antioxidant activity and chlorogenic acid is a major contributor to this activity. ----------------------------------------------------------------------------------------- Science Direct: “Luteolin” Search within Results: “synthesis” Hits: 144 articles –Sort by Relevance Fifth article listed – it contained the key words in the title “Synthesis” and “Luteolin.” Synthesis and Biological Evaluation of Novel Luteolin Derivatives as Antibacterial Agents. Peng-Cheng Lv, Huan-Qiu Li, Jia-Yu Xue, Lei Shi, and Hai-Liang Zhu. Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing 210093, People's Republic of China. Received 21 July 2007; revised 13 December 2007; accepted 10 January 2008. Available online 25 January 2008. Visited March 17, 2008. http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6VKY-4RNR6TV-F&_user=650615&_coverDate=01%2F25%2F2008&_alid=708937312&_rdoc=5&_fmt=full&_orig=search&_cdi=6135&_sort=r&_docanchor=&view=c&_ct=144&_acct=C000035118&_version=1&_urlVersion=0&_userid=650615&md5=9c97deacea48c608a41739e65111d673 Abstract: A series of luteolin derivatives 2–20 were prepared, 3–20 of which were first reported. The chemical structures of these compounds were confirmed by means of 1H NMR, ESI-MS and elemental analyses. The compounds were assayed for antibacterial (Bacillus subtilis, Staphylococcus aureus, Pseudomonas fluorescens and Escherichia coli) activities by MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl trtrazolium bromide) method. Among the compounds tested, most of them displayed significant activity against the tested strains, and 2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-5-hydroxy-7-(2-(3-morpholinopropylamino)ethoxy)-4H-chromen-4-one (17) showed the most favorable antibacterial activity in vitro with MICs of 1.562, 3.125, 3.125, and 6.25 µg/mL against B. subtilis, S. aureus, P. fluorescens and E. coli, respectively. Structure–activity relationships (SAR) were also discussed based on the obtained experimental data. Graphical Abstract: A series of luteolin derivatives containing a 2-carbon spacer at C-7 position and potential pharmacophore 1,4-benzodioxin were prepared and evaluated for antibacterial activity against four bacteria. ----------------------------------------------------------------------------------------- ScienceDirect: “Luteolin” Search within Results:“Isolation” Search within Results: “Purification” Hits:111 articles –Sort by Date It was the first article listed. Determination of polyphenolic compounds in commercial herbal drugs and spices from Lamiaceae: thyme, wild thyme and sweet marjoram by chromatographic techniques. Izabela Fecka and Sebastian Turek. Department of Pharmacognosy, Wroclaw Medical University. Received 26 April 2007; revised 3 October 2007; accepted 6 November 2007. Available online 23 November 2007. Visited March 17, 2008. http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6T6R-4R6B2T9-1&_user=650615&_coverDate=06%2F01%2F2008&_alid=708939441&_rdoc=1&_fmt=full&_orig=search&_cdi=5037&_sort=d&_docanchor=&view=c&_ct=111&_acct=C000035118&_version=1&_urlVersion=0&_userid=650615&md5=e7c9ee032eba3e09932e7bb48805a3b8. Abstract: HPLC and HPTLC methods were used for a qualitative and quantitative determination of luteolin -7-O-B-glucuronide, lithospermic acid, rosmarinic acid and mthyl rosmarinate, together with other known compounds, in commercial herbal drugs and spices from lamiaceous species: Thymi herba, Serpylli herba and Majoranae herba. The contents of analyzed compounds in the studied hydrophilic extracts, prepared form herbal sources, were established using a C18 column with acetonitrile–water–formic acid as a mobile phase. The HPLC method was validated for linearity, precision and accuracy. Luteolin-7-O-ß-glucuronide and lithospermic acid were identified as new wild thyme constituents, luteolin-7-O-B-glucuronide and methyl rosmarinate as new compounds in sweet marjoram. Methyl rosmarinate was isolated for the first time from thyme. The investigated herbal drugs and spices provide polyphenols in high amounts, even up to 84.3 mg per 1 g of a dried herb. ----------------------------------------------------------------------------------------- ScienceDirect: “Chlorogenic Acid” Search within results: “Lonicera japonica” Search within Resutls: “synthesis” Hits: 1 Scavenging and antioxidant properties of compound derived from chlorogenic acid in South-China honeysuckle. Zhinan Xiang and Zhengxiang Ning. College of Light Industry and Food Science, South China University of Technology, Guangzhou 510640, China. Received 16 April 2007; revised 8 August 2007; accepted 22 August 2007. Available online 1 September 2007. Visited March 17, 2008. http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6WMV-4PJM9VV-2&_user=650615&_coverDate=09%2F01%2F2007&_alid=708942127&_rdoc=1&_fmt=full&_orig=search&_cdi=6944&_sort=d&_st=13&_docanchor=&_ct=1&_acct=C000035118&_version=1&_urlVersion=0&_userid=650615&md5=b4fad273f993cdf2c40a5efa85acf936. Abstract: Chlorogenic acid (CGA) is a natural antioxidant, and nowadays its application has been distributed in medicine, food processing and cosmetic chemical industry. However, at a certain extent its application was restricted because of its only water solubility but no liposolubility. In this research, CGA is prepared from South-China honeysuckle and modified, undergoing efficient conjugation with lauroyl chloride in the presence of triethylamine (TEA) in non-water phase, to yield the adduct that has been identified as chlorogenic laurate (CGL) from its chromatographic behavior and spectral characteristics. The scavenging and antioxidant properties of CGL were evaluated using different antioxidant tests, including 2, 2'-diphenyl-1-picrylhydrazyl radical scavenging, hydroxyl radical scavenging, superoxide anion radical scavenging, reducing power, inhibition of peroxidation of linoleic acid and ferrous ions chelating activity. In the above six assays, CGL showed antioxidant potential to varying degrees in a concentration-dependent manner, and exhibited more antioxidant potency than CGA. Especially, the EC50 value of CGL in scavenging abilities on DPPH radicals was 70.5 µg/ml. The hydroxyl radicals scavenging compared with a-tocopherol was observed to high value in CGL. The antioxidant activity of CGL is not significantly different from BHT in a linoleic acid system. All the evaluations exhibited appreciable antioxidant potential for CGL. The data suggest that the modified CGA, CGL, may have a preventive effect against oxidation in liposoluble system, and would be a promising antioxidant. ----------------------------------------------------------------------------------------- CRC Handbook: Luteolin Hits: 1 CRC Handbook of Chemistry and Physics 88th Edition, 2007-2008. "Physical Constants of Organic Compounds.” Taylor and Francis Group: 2008. Page 3-322. Date Visited: March 17, 2008. http://www.hbcpnetbase.com/articles/03_01_88.pdf. ----------------------------------------------------------------------------------------- Chemfinder.com: “Chlorogenic Acid” Hits: 1 ChemFinder.com: Database and Internet Searching. “Chlorogenic Acid” Cambridge Software Corporation: 2004. http://chemfinder.cambridgesoft.com/result.asp ----------------------------------------------------------------------------------------- ScienceDirect: “Chlorogenic Acid” - Search within results: “Synthesis” Hits: 191 articles found. –Sort By Relevance -Second Article Listed had the key words “Purification,” “Separation,” and “Chlorogenic Acid.” Separation and Purification of Chlorogenic Acid by Molecularly Imprinting Polymer Monolithic Stationary Phase. Hui Li, Yingju Liu, Zhaohui Zhang, Haiping Liao, Lihua Nie, and Shouzhuo Yao. State Key Laboratory of Chemo/Bio Sensing & Chemometrics, Hunan University, Changsha 410082, China, College of Chemistry and Chemical Engineering, Jishou University, Hunan Jishou 416000, China, Received 26 March 2004; revised 4 August 2004; accepted 15 August 2005. Available online 31 August 2005. Date Visited March 18, 2008. http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6TG8-4H0S1H2-B&_user=650615&_coverDate=12%2F09%2F2005&_alid=708899127&_rdoc=2&_fmt=full&_orig=search&_cdi=5248&_sort=r&_docanchor=&view=c&_ct=191&_acct=C000035118&_version=1&_urlVersion=0&_userid=650615&md5=424eb9281232f3fd9c44f9f28fc64355. Abstract: Separation and purification of chlorogenic acid by removal of the impurities compounds co-existed in the product using molecular imprinting technique was firstly reported. In this work, an in situ synthesis method was utilized for the preparation of molecularly imprinted polymer monolithic stationary phase using the impurity molecule (caffeic acid) as template, the mixture of tetrahydrofuran and isooctane as solvent, and methacrylic acid and ethyl glycol dimethacrylate as functional monomer and cross-linker, respectively. The retention behavior of the monolithic polymer to chlorogenic acid molecule, the template and several main impurities compounds in the product was studied and the adsorption capacity of compounds on the stationary phase determined by frontal chromatographic technique. A relatively weak retention of the target product molecule (chlorogenic acid) on the polymer and a strong adsorption capability of the monolith to the template and several main impurities were observed. This might mainly result from the ‘shape’ difference of chlorogenic acid molecule with the impurities compounds molecules. This approach was shown to be successful for the separation and purification of chlorogenic acid from the extract of Eucommia ulmodies leaves. -Contains information on synthesizing Chlorogenic acid.