5-Hydroxymethyl-2-furfural, a clinical trials agent for sickle cell anemia, and its mono/di-glucosides from classically processed steamed Rehmanniae Radix

• Published in: Journal of natural medicines Vol. 62; no. 2; pp. 164 - 167
• Main Authors: Lin, An-Shen, Qian, Keduo, Usami, Yoshihide, Lin, Li, Itokawa, Hideji, Hsu, Charleson, Morris-Natschke, Susan L., Lee, Kuo-Hsiung
• Format: Journal Article
• Language: English
• Published: Japan Springer Japan 01.04.2008
• Subjects: Anemia, Sickle Cell - drug therapy; Biomedical and Life Sciences; Biomedicine; Chromatography, High Pressure Liquid; Complementary & Alternative Medicine; Disaccharides - analysis; Drugs, Chinese Herbal - chemistry; Furaldehyde - analogs & derivatives; Furaldehyde - analysis; Furaldehyde - therapeutic use; Furans - analysis; Glucosides - analysis; Hot Temperature; Humans; Medicinal Chemistry; Original Paper; Pharmacology/Toxicology; Pharmacy; Plant Roots - chemistry; Plant Sciences; Rehmannia - chemistry; Reversed-phase HPLC; 5-Hydroxymethylfurfural (5-HMF); Rehmanniae Radix; Traditional Chinese medicine (TCM)
• ISSN: 1340-3443; 1861-0293; 1861-0293
• DOI: 10.1007/s11418-007-0206-z

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.