5-Hydroxymethyl-2-furfural, a clinical trials agent for sickle cell anemia, and its mono/di-glucosides from classically processed steamed Rehmanniae Radix
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Rehmanniae Radix (Di Huang) is one of the most important traditional Chinese medicines (TCM), and is used for multiple therapeutic purposes. In our investigation of the chemical constituents of Rehmanniae Radix, steamed roots were prepared by the classical processing method. Reversed-phase HPLC of the 50% MeOH extract of steamed Rehmanniae Radix yielded three 5-hydroxymethylfurfural derivatives. The new furfural disaccharide 5-(α-d-glucopyranosyl-(1→6)-α-d-glucopyranosyloxymethyl)-2-furancarboxaldehyde (1) was isolated and characterized, together with its known aglycone 5-hydroxymethyl-2-furfural (3), which is currently in sickle cell anemia Phase I clinical trials, and its corresponding monosaccharide 5-(α-d-glucopyranosyloxymethyl)-2-furancarboxaldehyde (2), which was isolated as a natural product for the first time. The presence of these three compounds, particularly 3, which were not found in the unprocessed extract of Rehmanniae Radix, could substantiate the traditional medicinal use of steamed Rehmanniae Radix.
KeywordsRehmanniae Radix Traditional Chinese medicine (TCM) 5-Hydroxymethylfurfural (5-HMF) Reversed-phase HPLC
This investigation was supported by the Hong-Yen and Lin-Run Charitable Foundation awarded to K.H. Lee.
- 1.Kitagawa I, Fukuda Y, Taniyama T, Yoshikawa M (1991) Chemical studies on crude drug processing. VII. On the constituents of Rehmanniae radix. (1): absolute stereostructures of rehmaglutins A, B, and D isolated from Chinese Rehmanniae radix, the dried root of Rehmannia glutinosa Libosch. Chem Pharm Bull 39:1171–1176Google Scholar
- 2.Jiangsu Xinyiyuan (1979) Great dictionary of chinese medicine, vol 2. Kexue Jishu Chubanshe, Shanghai, p 2626Google Scholar
- 3.Pharmacopoeia Commission of the People’s Republic of China (2000) The pharmacopoeia of the people’s Republic of China, vol 1. Chemical Industry Publishing House, Beijing, p 94Google Scholar
- 8.Yoshikawa M, Fukuda Y, Taniyama T, Cha BC, Kitagawa I (1986) Absolute configurations of rehmaionosides A, B, and C and rehmapicroside three new ionone glucosides and a new monoterpene glucoside from Rehmanniae radix. Chem Pharm Bull 34:2294–2297Google Scholar
- 11.Papadogianakis G, Matt L, Sheldon RA (1994) Catalytic conversions in water: a novel carbonylation reaction catalyzed by palladium trisulfonated triphenylphosphine complexes. J Chem Soc Chem Commun 2659–2660Google Scholar
- 12.Lichtenthaler FW, Martin D, Weber T, Schiweck H (1993) 5-(α-d-Glucosyloxymethyl)furfural: preparation from isomaltulose and exploration of its ensuing chemistry. Liebigs Ann Chem 967–974Google Scholar
- 15.Xia Y, Li Z, Zhu D, Yan Y (1998) Research on chemical dynamic changes and drug efficacy of Shengmaisan (complex prescription). Chin J Chin Mater Med 23:230–231Google Scholar
- 17.Safo M, Danso-Danquah R, Joshi G, Abraham D (2006) U.S. Patent No. 7119208B2Google Scholar
- 18.Xechem, Inc. http://www.xechem.com/100406.html
- 19.Zhu D, Li Z, Yan Y (1998) Research on chemical dynamic changes and drug efficacy of Shengmaisan (complex prescription) (II). Chin J Chin Mater Med 23:291–293Google Scholar