Browse > Article

Phytochemical Studies on Rehmanniae Radix Preparata  

Lee, Joo-Young (Natural Products Research Institute and College of Pharmacy, Seoul National University)
Lee, Eun-Ju (Natural Products Research Institute and College of Pharmacy, Seoul National University)
Kim, Ju-Sun (Natural Products Research Institute and College of Pharmacy, Seoul National University)
Lee, Je-Hyun (Department of Korean Medicine, Dongguk University)
Kang, Sam-Sik (Natural Products Research Institute and College of Pharmacy, Seoul National University)
Publication Information
Korean Journal of Pharmacognosy / v.42, no.2, 2011 , pp. 117-126 More about this Journal
Abstract
Twenty-two compounds were isolated from the 70% ethanolic extract of Rehmanniae Radix Preparata (Scrophulariaceae) and their structures were identified as three triterpenoids [oleanolic acid (1), pomonic acid (2) and ursolic acid (5)], an iridoid, catalpol (13), four furan derivatives [5-hydroxymethyl-2-furaldehyde acetate (3), 5-hydroxymethyl-2-furfural (6), 5-hydroxymethyl-2-furancarboxylic acid (7), and 5-(${\alpha}$-D-galactopyranosyloxymethyl)-2-furancarboxaldehyde (15)], three phenethyl alcohol glycosides [darendoside B (14), phenethyl alcohol 2-O-${\beta}$-D-xylopyranosyl(1${\rightarrow}$6)-${\beta}$-D-glucopyranoside (17), and salidroside (19)], four sugar derivatives [L-arabinose (11), raffinose (20), stachyose (21), and mannitol (22)], and seven others [2,5-dihydroxyacetophenone (4), succinic acid (8), daucosterol (9), ${\beta}$-sitosterol (10), adenosine (16), uridine (18) jio-cerebroside (12)]. The chemical structures of these compounds were identified on the basis of spectroscopic methods and comparison with literature values. This is the first report of the triterpenoids oleanolic acid (1), pomonic acid (2), and ursolic acid (5) from the genus Rehmannia, as well as the first report of compounds 5-hydroxymethyl-2-furaldehyde acetate (3), 2,5-dihydroxyacetophenone (4), daucosterol (9), darendoside B (14), 5-(${\alpha}$-D-galactopyranosyloxymethyl)-2-furancarboxaldehyde (15), adenosine (16), phenethyl alcohol 2-O-${\beta}$-D-xylopyranosyl(1${\rightarrow}$6)-${\beta}$-D-glucopyranoside (17), and salidroside (19) from the Rehmanniae Radix Preparata.
Keywords
Rehmanniae Radix Preparata; Scrophulariaceae; Isolation and identification;
Citations & Related Records
Times Cited By KSCI : 1  (Citation Analysis)
Times Cited By SCOPUS : 2
연도 인용수 순위
1 Kubo, M., Asano, T., Matsuda, H., Yutani, S. and Honda, S. (1996) Studies on Rehmanniae Radix. III. The relation between changes of constituents and improvable effects on hemorheology with the processing of roots of Rehmannia glutinosa. Yakugaku Zasshi 116: 158-168.
2 Oshio, H., Naruse, Y. and Inouye, H. (1981) Quantitative analysis of iridoid glycosides of Rehmanniae Radix. Shoyakugaku Zasshi 35: 291-294.
3 Seto, T., Yasuda, I., Hamano, T., Takano, I., Takahashi, N., Watanabe, Y. and Akiyama, K. (1991) Processing influence on the constituents of crude drugs (I). Analysis on the phenethyl alcohol glycosides in various processed roots of Rehmannia glutinosa. Ann. Rep. Tokyo Metr. Res. Lab. P. H. 42: 21-26.
4 Chang, W.-T., Choi, Y. H., Van der Heijden, R., Lee, M.-S., Lin, M.-K., Kong, H.-W., Kim, H. K., Verpoorte, R., Hankemeier, T., Van der Greef, J. and Wang, M. (2011) Traditional processing strongly effects metabolite composition by hydrolysis in Rehmannia glutinosa roots. Chem. Pharm. Bull. 59: 546-552.   DOI   ScienceOn
5 Cheng, D.-L. and Cao, X.-P. (1992) Pomolic acid derivatives from the root of Sanguisorba officinalis. Phytochemistry 31: 1317-1320.   DOI   ScienceOn
6 Lee, S.-H., Shim, S. H., Kim, J. S., Shin, K. H. and Kang, S. S. (2005) Aldose reductase inhibitors from the fruiting bodies of Ganoderma applanatum. Biol. Pharm. Bull. 28: 1103- 1105.   DOI   ScienceOn
7 Nishimura, H., Sasaki, H., Morota, T., Chin, M. and Mitsuhashi, H. (1990) Six glycosides from Rehmannia glutinosa var. purpurea. Phytochemistry 29: 3303-3306.   DOI   ScienceOn
8 Calis, I., Saracoglu, I., Basaran, A. A. and Sticher, O. (1992) Two phenethyl alcohol glycosides from Scutellaria orientalis subsp. pinnatifida. Phytochemistry 32: 1621-1623.
9 Kanchannapoon, T., Kasai, R., Chumsri, P., Hiraga, Y. and Yamasaki, K. (2001) Megastigmane and iridoid glucosides from Clerodendrum inerme. Phytochemistry 58: 333-336.   DOI   ScienceOn
10 Otsuka, H., Takeda, Y. and Yamasaki, K. (1990) Xyloglucosides of benzyl and phenethyl alcohols and Z-hex-3-en-1- ol from leaves of Alangium platanifolium var. trilobum. Phytochemistry 29: 3681-3683.   DOI   ScienceOn
11 Gaspar, E. M. S. M. and Lucena, A. F. F. (2009) Improved HPLC methodology for food control - furfurals and patulin as markers of quality. Food Chemistry 114: 1576-1582.   DOI   ScienceOn
12 Lin, A.-S., Qian, K., Usami, Y., Lin, L., Itokawa, H., Hsu, C., Morris-Natschke, S. L. and Lee, K.-H. (2008) 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.   DOI   ScienceOn
13 Khalil, M. I., Sulaiman, S. A. and Gan, S. H. (2010) High 5- hydroxymethylfurfural concentrations are found in Malaysian honey samples stored for more than one year. Food Chem. Toxicol. 48: 2388-2392.   DOI   ScienceOn
14 Durling, L. J. K., Busk, L. and Hellman, B. E. (2009) Evaluation of the DNA damaging effect of the heat-induced food toxicant 5-hydroxymethylfurfural (HMF) in various cell lines with different activities of sulfotransferases. Food Chem. Toxicol. 47: 880-884.   DOI   ScienceOn
15 Brieskorn, C. H. and Wunderer, H. (1967) Pomol- und Pomonsäure. Chem. Ber. 100: 1252-1265.   DOI
16 Brieskorn, C. H. and Suss, H. P. (1974) Die Triterpenoide der Birnen- und Apfelschale. Arch. Pharm. 307: 949-960.   DOI   ScienceOn
17 Jadulco, R., Proksch, P., Wray, V., Sudarsono, Berg, A. and Grfe, U. (2001) New macrolides and furan carboxylic acid derivative from the sponge-derived fungus Cladosporium herbarum. J. Nat. Prod. 64: 527-530.   DOI   ScienceOn
18 Khan, K. M., Perveen, S., Ayattollahi, S. A. M., Saba, N., Rashid, A., Firdous, S., Haider, S. M., Ullah, Z., Rahat, S. and Khan, Z. (2002) Isolation and structure elucidation of three glycosides and a long chain alcohol from Polianthes tuberosa Linn. Nat. Prod. Lett. 16: 283-290.   DOI   ScienceOn
19 Martin, D. and Lichtenthaler, F. W. (2006) Versatile building blocks from disaccharides: glycosylated 5-hydroxymethylfurfurals. Tetrahedron: Asymmetry 17: 756-762.   DOI   ScienceOn
20 Aplin, R. T., Durham, L. J., Kanazawa, Y. and Safe, S. (1967) 2-O-$\alpha$-D-galactopyranosylglycerol from Laurencia pinnatifida. J. Chem. Soc. (C) 1346-1347.
21 Zhang, R.-X., Li, M.-X. and Jia, Z.-P. (2008) Rehmannia glutinosa: Review of botany, chemistry and pharmacology. J. Ethnopharmacol. 117: 199-214.   DOI   ScienceOn
22 Lee, S. Y., Yean, M. H., Kim, J. S., Lee, J.-H. and Kang, S. S. (2011) Phytochemical Studies on Rehmanniae Radix. Kor. J. Pharmacogn. 42: 127-137.
23 Morota, T., Nishimura, H., Sasaki, H., Chin, M., Sugama, K., Katsuhara, T. and Mitsuhashi, H. (1989) Five cyclopentanoid monoterpenes from Rehmannia glutinosa. Phytochemistry 28: 2385-2391.   DOI   ScienceOn
24 Urashima, T., Suyama, K. and Adachi, S. (1988) The condensation of 5-(hydroxymethyl)-2-furfuraldehyde with some aldoses on heating. Food Chemistry 29: 7-17.   DOI   ScienceOn
25 Jellum, E., Borrensen, H. C. and Eldjarn, L. (1973) The presence of furan derivatives in patients receiving fructose-containing solutions intravenously. Clin. Chim. Acta 47: 191- 201.   DOI   ScienceOn
26 한국약학대학협의회 약전분과회 (1998) 대한약전, 7개정, 문성사, 서울.
27 Sasaki, H., Nishimura, H., Morota, T., Chin, M., Mitsuhashi, H., Komatsu, Y., Maruyama, H., Tu, G.-R., He, W. and Xiong, Y.-L. (1989) Immunosuppressive principles of Rehmannia glutinosa var. hueichingensis. Planta Medica 55: 458-462.   DOI
28 Kitagawa, I., Fukuda, Y., Taniyama, T. and Yoshikawa, M. (1995) Chemical studies on crude drug processing. X. On the constituents of Rehmanniae Radix (4): Comparison of the constituents of various Rehmanniae Radixes originating in China, Korea, and Japan. Yakugaku Zasshi 115: 992-1003.
29 Sasaki, H., Morota, T., Nishimura, H., Ogino, T., Katsuhara, T., Sugama, K., Chin, M. and Mitsuhashi, H. (1991) Norcarotenoids of Rehmannia glutinosa var. hueichingensis. Phytochemistry 30: 1997-2001.   DOI   ScienceOn