Subscribe to RSS
DOI: 10.1055/s-0030-1250020
© Georg Thieme Verlag KG Stuttgart · New York
Cloning and Characterization of a cDNA Coding a Hydroxycinnamoyl-CoA Quinate Hydroxycinnamoyl Transferase Involved in Chlorogenic Acid Biosynthesis in Lonicera japonica
Publication History
received January 20, 2010
revised May 3, 2010
accepted May 6, 2010
Publication Date:
10 June 2010 (online)
![](https://www.thieme-connect.de/media/plantamedica/201016/lookinside/thumbnails/10.1055-s-0030-1250020-1.jpg)
Abstract
The flower buds of Lonicera japonica are widely used in Chinese medicine for their anti-inflammatory properties. The reason why L. japonica has potent and significant effects is that it contains various active components, especially chlorogenic acid (CGA). In the present study, we isolated a hydroxycinnamoyl-CoA quinate hydroxycinnamoyl transferase (HQT) gene encoding a protein of 439 amino acids from L. japonica. The RT‐PCR results showed that tissue distribution of HQT was in accordance with the pattern of CGA content. The corresponding cDNAs were expressed in Escherichia coli as fusion proteins. Recombinant HQT exhibited catalysis activity in esterification of quinic acid with caffeoyl-CoA to generate CGA. Purified proteins demonstrated similar kinetic properties as HQT isolated from other species. This work is of significance for further studies concerned with strengthening the efficacy of L. japonica by means of improved CGA content and exploring the biosynthesis of CGA in vitro.
Key words
Lonicera japonica - Caprifoliaceae - chlorogenic acid - hydroxycinnamoyl‐CoA quinate hydroxycinnamoyl transferase - thermal asymmetric interlaced PCR - tissue distribution - enzyme assay
References
- 1 State Pharmacopoeia Committee .Pharmacopoeia of China, Part 1. Beijing; Chemical Industry Press 2005: 152-153
- 2 Larson B M H, Catling P M, Waldron G E. The biology of Canadian weeds. 135. Lonicera japonica Thunb. Can J Plant Sci. 2007; 87 423-438
- 3 Teng H L. Synthetically study on medicinal materials of Lonicera japonica. J Chin Med Mat. 2007; 30 744-748
- 4 Zhang S P, Xin L, Wang L P. Progress about the chemical constitution and quality control of Lonicera japonica. Chin J Info TCM. 2007; 14 84-86
- 5 Zang L Y, Cosma G, Gardner H, Castranova V, Vallyathan V. Effect of chlorogenic acid on hydroxyl radical. Mol Cell Biochem. 2003; 247 205-210
- 6 Tamura H, Akioka T, Ueno K, Chujyo T, Okazaki K, King P J, Robinson W E. Anti-human immunodeficiency virus activity of 3,4,5-tricaffeoylquinic acid in cultured cells of lettuce leaves. Mol Nutr Food Res. 2006; 50 396-400
- 7 Chiang L C, Chiang W, Chang M Y, Ng L T, Lin C C. Antiviral activity of Plantago major extracts and related compounds in vitro. Antiviral Res. 2002; 55 53-62
- 8 Olthof M R, Hollman P C, Katan M B. Chlorogenic acid and caffeic acid are absorbed in humans. J Nutr. 2001; 131 66-71
- 9 Laranjinha J A, Almeida L M, Madeira V M. Reactivity of dietary phenolic acids with peroxyl radicals: antioxidant activity upon low density lipoprotein peroxidation. Biochem Pharmacol. 1994; 48 487-494
- 10 Niggeweg R, Michael A J, Martin C. Engineering plants with increased levels of the antioxidant chlorogenic acid. Nat Biotechnol. 2004; 22 746-754
- 11 Comino C, Hehn A, Moglia A, Menin B, Bourgaud F, Lanteri S, Portis E. The isolation and mapping of a novel hydroxycinnamoyltransferase in the globe artichoke chlorogenic acid pathway. BMC Plant Biol. 2009; 9 30
- 12 Ulbrich B, Zenk M H. Partial purification and properties of hydroxycinnamoyl-CoA: quinate hydroxycinnamoyl transferase from higher plants. Phytochemistry. 1979; 18 929-933
- 13 Lofty S, Fleuriet A, Macheix J J. Partial purification and characterization of hydroxycinnamoyl CoA: transferases from apple and date fruits. Biochemistry. 1992; 13 767-772
- 14 Liu Y G, Chen Y. High-efficiency thermal asymmetric interlaced PCR for amplification of unknown flanking sequences. Biotechniques. 2007; 43 649-656
- 15 Comino C, Lanteri S, Portis E, Acquadro A, Romani A, Hehn A, Larbat R, Bourgaud F. Isolation and functional characterization of a cDNA coding a hydroxycinnamoyltransferase involved in phenylpropanoid biosynthesis in Cynara cardunculus L. BMC Plant Biol. 2007; 7 14
- 16 Beuerle T, Pichersky E. Enzymatic synthesis and purification of aromatic coenzyme A esters. Anal Biochem. 2002; 302 305-312
- 17 Lepelley M, Cheminade G, Tremillon N, Simkin A, Caillet V, McCarthy J. Chlorogenic acid synthesis in coffee: an analysis of CGA content and real-time RT-PCR expression of HCT, HQT, C3H1, and CCoAOMT1 genes during grain development in C. canephora. Plant Sci. 2007; 172 978-996
- 18 Brown N F, Anderson R C, Caplan S L, Foster D W, McGarry J D. Catalytically important domains of rat carnitine palmitoyltransferase II as determined by site-directed mutagenesis and chemical modification. Evidence for a critical histidine residue. J Biol Chem. 1994; 269 19157-19162
- 19 St-Pierre B, Laflamme P, Alarco A M, Luca V D. The terminal O-acetyltransferase involved in vindoline biosynthesis defines a new class of proteins responsible for coenzyme A-dependent acyl transfer. Plant J. 1998; 14 703-713
- 20 Liu Y G, Whittier R F. Thermal asymmetric interlaced PCR: automatable amplification and sequencing of insert end fragments from P1 and YAC clones for chromosome walking. Genomics. 1995; 25 674-681
- 21 Zhao Y, Blumer S E, Sundin G W. Identification of Erwinia amylovora genes induced during infection of immature pear tissue. J Bacteriol. 2005; 187 8088-8103
- 22 Sessions A, Burke E, Presting G, Aux G, McElver J, Patton D, Dietrich B, Ho P, Bacwaden J, Ko C, Clarke J D, Cotton D, Bullis D, Snell J, Miguel T, Hutchison D, Kimmerly B, Mitzel T, Katagiri F, Glazebrook J, Law M, Goff S A. A high-throughput Arabidopsis reverse genetics system. Plant Cell. 2002; 14 2985-2994
- 23 Chen Z Y. Analysis of the chlorogenic acid content in flower buds, stems and leaves of Lonicera japonica. Chin Clin New Med. 2006; 6 354-355
- 24 Jiang B, Wang F Y, Zeng Y E, Zhan L L, Lai X P, Zhang J. The study on impact factors of the stability of chlorogenic acid in extract from Artemisia scoparia medicinal materials. Chin Tradit Pat Med. 2007; 29 359-362
- 25 Liu H J, Qiu A Y. Study on technique of extraction and purification chlorogenic acid in Eucommia ulmoides leaves. J Chin Med Mat. 2004; 12 942-946
Prof. Dr. Genben Bai
Department of Biopharmaceutics
School of Chinese Medicine
Beijing University of Chinese Medicine
No. 6 South Wangjing Zhonghuan Road
Beijing 100102
China
Phone: +86 10 84 73 86 11
Fax: +86 10 84 73 86 11
Email: pxxjuve@yahoo.cn
Weidong Li
Email: liweidong2005@126.com