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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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Abstract

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.

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References

  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 39:1171–1176

    CAS  Google Scholar 

  2. Jiangsu Xinyiyuan (1979) Great dictionary of chinese medicine, vol 2. Kexue Jishu Chubanshe, Shanghai, p 2626

  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 94

  4. Morota T, Sasaki H, Sugama K, Nishimura H, Chin M, Mitsuhashi H (1990) Chemical and biological studies on Rehmanniae radix. Part 6. Two nonglycosidic iridoids from Rehmannia glutinosa. Phytochemistry 29:523–526

    Article  CAS  Google Scholar 

  5. Oshio H, Inouye H (1981) Iridoid glycosides of Rehmannia glutinosa. Phytochemistry 21:133–138

    Article  Google Scholar 

  6. Morota T, Sasaki H, Nishimura H, Sugama K, Chin M, Mitsuhashi H (1989) Chemical and biological studies on Rehmanniae radix. Part 4. Two iridoid glycosides from Rehmannia glutinosa. Phytochemistry 28:2149–2153

    Article  CAS  Google Scholar 

  7. Nishimura H, Sasaki H, Morota T, Chin M, Mitsuhashi H (1989) Chemical and biological studies on Rehmanniae radix. Part 3. Six iridoid glycosides from Rehmannia glutinosa. Phytochemistry 28:2705–2709

    Article  CAS  Google 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 34:2294–2297

    CAS  Google Scholar 

  9. Sasaki H, Morota T, Nishimura H, Ogino T, Katsuhara T, Sugama K, Chin M, Matsuhashi H (1991) Chemical and biological studies on Rehmanniae radix. Part 8. Norcarotenoids of Rehmannia glutinosa var. hueichingensis. Phytochemistry 30:1997–2001

    Article  CAS  Google Scholar 

  10. Sasaki H, Morota T, Nishimura H, Morota T, Katsuhara T, Chin M, Matsuhashi H (1991) Chemical and biological studies on Rehmanniae radix. Part 9. Norcarotenoid glycosides of Rehmannia glutinosa var. purpurea. Phytochemistry 30:1639–1664

    Article  CAS  Google 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 2659–2660

  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 967–974

  13. Martin D, Lichtenthaler FW (2006) Versatile building blocks from disaccharides: glycosylated 5-hydroxymethylfurfurals. Tetrahedron Asymmetry 17:756–762

    Article  CAS  Google Scholar 

  14. Matsuda E, Yoshizawa Y, Yokosawa Y, Watanabe N, Kawaii S, Murofushi N (2006) Effects of Eucommia ulmoides Oliver leaf extract on 3T3-L1 differentiation into adipocytes. J Natl Med 60:126–129

    Article  CAS  Google 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 23:230–231

    CAS  Google Scholar 

  16. Abdulmalik O, Safo MK, Chen Q, Yang J, Brugnara C, Ohene-Frempong K, Abraham D, Asakura T (2005) 5-Hydroxymethyl-2-furfural modifies intracellular sickle haemoglobin and inhibits sickling of red blood cells. Br J Hematology 128:552–561

    Article  CAS  Google Scholar 

  17. Safo M, Danso-Danquah R, Joshi G, Abraham D (2006) U.S. Patent No. 7119208B2

  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 23:291–293

    CAS  Google Scholar 

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Acknowledgments

This investigation was supported by the Hong-Yen and Lin-Run Charitable Foundation awarded to K.H. Lee.

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Authors and Affiliations

  1. Natural Products Research Laboratories, School of Pharmacy, University of North Carolina, Chapel Hill, NC, 27599, USA

    An-Shen Lin, Keduo Qian, Yoshihide Usami, Li Lin, Hideji Itokawa, Susan L. Morris-Natschke & Kuo-Hsiung Lee

  2. Sun Ten Laboratories, Inc., 9250 Jeronimo Road, Irvine, CA, 92618, USA

    Charleson Hsu

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  1. An-Shen Lin
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  2. Keduo Qian
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  3. Yoshihide Usami
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  4. Li Lin
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  5. Hideji Itokawa
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  6. Charleson Hsu
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  7. Susan L. Morris-Natschke
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  8. Kuo-Hsiung Lee
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Correspondence to Kuo-Hsiung Lee.

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Lin, AS., Qian, K., Usami, Y. et al. 5-Hydroxymethyl-2-furfural, a clinical trials agent for sickle cell anemia, and its mono/di-glucosides from classically processed steamed Rehmanniae Radix. J Nat Med 62, 164–167 (2008). https://doi.org/10.1007/s11418-007-0206-z

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  • DOI: https://doi.org/10.1007/s11418-007-0206-z

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