Herbal Medicines and Infectious Diseases: Characterization by LC-SPE-NMR of Some Medicinal Plant Extracts Used against Malaria

Abstract

The extracts of two medicinal plants used in traditional medicine against malaria were characterized by means of an LC-SPE-NMR and LC-MS platform. The structure of a series of major constituents from Bafodeya benna, as well as minor constituents from Ormocarpum kirkii, was determined. Bafodeya benna was found to contain (2R,3R)-taxifolin-3-O-α-L-rhamnoside or astilbin, and its isomers neoastilbin, neoisoastilbin, and isoastilbin, as well as quercetin-3-O-α-L-rhamnoside. From Ormocarpum kirkii, a series of known flavonoids and biflavonoids was obtained, as well as three new compounds, i.e., 7,7′′-di-O-β-D-glucosyl-(−)-chamaejasmin, 7-O-β-D-glucosyl-(I-3,II-3)-biliquiritigenin, and isovitexin-(I-3,II-3)-naringenin. The isolated constituents may explain, at least in part, the traditional use against malaria. LC-SPE-NMR, in combination with LC-MS, is a powerful tool for the fast characterization of plant extracts, in order to define priorities at an early stage of a fractionation procedure. In addition, herbal medicinal products can completely be characterized, both with regard to their major as well as their minor constituents.

Key words

LC-SPE-NMR - malaria - Bafodeya benna - Chrysobalanaceae - Ormocarpum kirkii - Papilionaceae

References

• 1 World Malaria Report 2008. Geneva; World Health Organization 2008: viii-x http://whqlibdoc.who.int/publications/2008/9789241563697_eng.pdf
• 2 World Health Organization Fact Sheet No. 134: Traditional Medicine. Geneva; World Health Organization 2008
• 3 Vlietinck A, Pieters L, Apers S. Legal requirements for the quality of herbal substances and herbal preparations for the manufacturing of herbal medicinal products in the European Union.  Planta Med. 2009;  75 683-688
• 4 Pieters L, Vlietinck A. Bioguided isolation of pharmacologically active plant components, still a valuable strategy for the finding of new lead compounds?.  J Ethnopharmacol. 2005;  100 57-60
• 5 Wolfender J L, Ndjoko K, Hostettmann K. Liquid chromatography with ultraviolet absorbance – mass spectrometric detection and with nuclear magnetic resonance spectroscopy: a powerful combination for the on-line structural investigation of plant metabolites.  J Chromatogr A. 2003;  1000 437-455
• 6 Verpoorte R, Choi Y H, Kim H K. NMR-based metabolomics at work in phytochemistry.  Phytochem Rev. 2007;  6 3-14
• 7 Jaroszewski J. Hyphenated NMR methods in natural products research, part 2: HPLC-SPE-NMR and other trends in NMR hyphenation.  Planta Med. 2005;  71 795-802
• 8 Magassouba F B, Diallo A, Kouyaté M, Mara F, Mara O, Bangoura O, Camara A, Traoré S, Diallo A K, Zaoro M, Lamah K, Diallo S, Camara G, Traoré S, Kéita A, Camara M K, Barry R, Kéita S, Oularé K, Barry M S, Donzo M, Camara K, Toté K, Berghe D V, Totté J, Pieters L, Vlietinck A J, Baldé A M. Ethnobotanical survey and antibacterial activity of some plants used in Guinean traditional medicine.  J Ethnopharmacol. 2010;  128 705-708
• 9 Maregesi S M, Ngassapa O D, Pieters L, Vlietinck A J. Ethnopharmacological survey of the Bunda district, Tanzania: plants used to treat infectious diseases.  J Ethnopharmacol. 2007;  113 457-470
• 10 Maregesi S, Van Miert S, Pannecouque C, Feiz Haddad M H, Hermans N, Wright C W, Vlietinck A J, Apers S, Pieters L. Screening of Tanzanian medicinal plants against Plasmodium falciparum and human immunodeficiency virus.  Planta Med. 2010;  76 195-201
• 11 Dhooghe L, Maregesi S, Mincheva I, Ferreira D, Marais J, Lemiere F, Matheeusen A, Cos P, Maes L, Vlietinck A, Apers S, Pieters L. Antiplasmodial activity of (I-3,II-3)-biflavonoids from Ormocarpum kirkii.  Phytochemistry. 2010;  71 785-791
• 12 Kuspradini H, Mitsunaga T, Ohashi H. Antimicrobial activity against Streptococcus sobrinus and glucosyltransferase inhibitory activity of taxifolin and some flavanonol rhamnosides from kempas (Koompassia malaccensis) extracts.  J Wood Sci. 2009;  55 308-313
• 13 Chosson E, Chaboud A, Chulia A J, Raynaud J. Dihydroflavonol glycosides from Rhododendron ferrugineum.  Phytochemistry. 1998;  49 1431-1433
• 14 Zhou X, Xu Q, Li J X, Chen T. Structural revision of two flavanonol glycosides from Smilax glabra.  Planta Med. 2009;  75 654-655
• 15 Cintra P, Malaspina O, Petacci F, Fernandes J B, Bueno O C, Vieira P C, Da Silva M F D. Toxicity of Dimorphandra mollis to workers of Apis mellifera.  J Braz Chem Soc. 2002;  13 115-118
• 16 Du Q Z, Li L, Jerz G. Purification of astilbin and isoastilbin in the extract of Smilax glabra rhizome by high-speed counter-current chromatography.  J Chromatogr A. 2005;  1077 98-101
• 17 Arot L O M, Williams L A D. A flavonol glycoside from Embelia schimperi leaves.  Phytochemistry. 1997;  44 1397-1398
• 18 Chen L, Yin Y, Yi H W, Xu Q, Chen T. Simultaneous quantification of five major bioactive flavonoids in Rhizoma Smilacis Glabrae by high-performance liquid chromatography.  J Pharm Biomed Anal. 2007;  43 1715-1720
• 19 Kasai R, Hirono S, Chou W H, Tanaka O, Chen F H. Sweet dihydroflavonol rhamnoside from leaves of Engelhardtia chrysolepis, a Chinese folk medicine, Hung-qi.  Chem Pharm Bull. 1988;  36 4167-4170
• 20 Kraft C, Jenett-Siems K, Siems K, Solis P N, Gupta M P, Bienzle U, Eich E. Andinermals A–C, antiplasmodial constituents from Andira inermis.  Phytochemistry. 2001;  58 769-774
• 21 Gupta A M, Saxena S, Saxena M. Integrated ligand and structure based studies of flavonoids as fatty acid biosynthesis inhibitors of Plasmodium falciparum.  Bioorg Med Chem Lett. 2010;  20 4779-4781
• 22 Tsanuo M K, Hassanali A, Hooper A M, Khan Z, Kaberia F, Pickett J A, Wadhams L J. Isoflavanones from the allelopathic aqueous root exudate of Desmodium uncinatum.  Phytochemistry. 2003;  64 265-273
• 23 Kinoshita T, Tamura Y, Mizutani K. The isolation and structure elucidation of minor isoflavonoids from licorice of Glycyrrhiza glabra origin.  Chem Pharm Bull. 2005;  53 847-849
• 24 Nunome S, Ishiyama A, Kobayashi M, Otoguro K, Kiyohara H, Yamada H, Omura S. In vitro antimalarial activity of biflavonoids from Wikstroemia indica.  Planta Med. 2004;  70 76-78
• 25 Yang G H, Liao Z X, Xu Z Y, Zhang H P, Chen D F. Antimitotic and antifungal C-3/C-3′′-biflavanones from Stellera chamaejasme.  Chem Pharm Bull. 2005;  53 776-779
• 26 Shoeb M, MacManus S M, Jaspars M, Trevidu J, Nahar L, Kong-Thoo-Lin P, Sarker S D. Montamine, a unique dimeric indole alkaloid, from the seeds of Centaurea montana (Asteraceae), and its in vitro cytotoxic activity against the CaCo2 colon cancer cells.  Tetrahedron. 2006;  62 11172-11177
• 27 Liu L, Liu Q, Wu M, Zhang H. Study on powder characteristics and in vitro dissolution rate of Exocarpium Citri Grandis in different diameters.  Guangdong Yaoxueyuan Xuebao. 2010;  26 20-22