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Phytochemical Studies on Rehmanniae Radix  

Lee, So-Young (Natural Products Research Institute and College of Pharmacy, Seoul National University)
Yean, Min-Hye (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. 127-137 More about this Journal
Abstract
Twenty-four compounds were isolated from the 70% ethanolic extract of Rehmanniae Radix (Scrophulariaceae) cultivated in Ubo-myeon, Gunwi-gun, Gyeongbuk province, Korea and their structures were identified as four iridoids [6-O-(4''-O-${\alpha}$-L-rhamnopyranosyl) vanilloyl ajugol (17), ajugol (18), aucubin (19), and catalpol (20)], three phenethyl alcohol glycosides [decaffeoyl acteoside (15), isoacteoside (16), and acteoside (21)], five sugar derivatives [ethyl ${\beta}$-D-fructofuranoside (7), eleutheroside C (14), mannitol (22), raffinose (23), and stachyose (24)], two terpenoids [remophilanetriol (4) and glutinolic acid (11)], a lignan, paulownin (2), and eight others [${\beta}$-sitosterol (1), daucosterol (6), monopalmitin (3), pinellic acid (9), uracil (5), adenosine (12), jio-cerebroside (10), aeginetic acid 5-O-${\beta}$-D-quinovoside (8), aeginetoyl ajugol 5''-O-${\beta}$-D-quinovoside (13)]. The chemical structures of these compounds were identified on the basis of spectroscopic methods and comparison with literature values. Among these compounds, paulownin (2), monopalmitin (3), uracil (5), daucosterol (6), ethyl ${\beta}$-D-fructo-furanoside (7), and eleutheroside C (14) were isolated from this plant for the first time.
Keywords
Rehmannia glutinosa Liboschitz ex Steudel; Scrophulariaceae; Isolation and identification;
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1 Jung, H. S., Lee, E. J., Lee, J.-H., Kim, J. S. and Kang, S. S. (2008) Phytochemical Studies on Astragalus Root (3) - Triterpenoids and Sterols. Kor. J. Pharmacogn. 39: 186-193.
2 Agostini, A., Guiso, M., Marini-Bettolo, R. and Martinazzo, G. (1982) 5-Deoxylamioside, a new iridoid glucoside from Lamium amplexicaule L. and reassignment of OH-6 configuration of ajugol. Gazz. Chim. Ital. 112: 9-12.
3 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
4 Bladt, S., Wagner, H. and Woo, W. S. (1990) Taiga-Wurzel. DC- und HPLC-Analyse von Eleutherococcus- bzw. Acanthopanax- Extrakten und diese enthaltenden Phytoprparaten. Dtsch. Apoth. Ztg. 130: 1499-1508.
5 Lee, E. J., Lee, J. Y., Kim, J. S. and Kang, S. S. (2010) Phytochemical studies on Lonicerae Flos (1) - Isolation of iridoid glycosides and other constituents. Nat. Prod. Sci. 16: 32-38.
6 Silvestre, A. J. D., Evtugun, D. V., Mendes Sousa, A. and Silva, A. M. S. (2005) Lignans from a hybrid Paulownia wood. Biochem. System. Ecol. 33: 1298-1302.   DOI   ScienceOn
7 Kanchanapoom, T., Kasai, R. and Yamasaki, K. (2002) Phenolic glycosides from Markhamia stipulata. Phytochemistry 59: 557-563.   DOI   ScienceOn
8 Choi, D. G., Yoo, N. H., Yu, C. Y., de los Reyes, B. and Yun, S. J. (2004) The activities of antioxidant enzymes in response to oxidative stresses and hormones in paraquit-tolerant Rehmannia glutinosa plants. J. Biochem. Mol. Biol. 37: 618-624.   DOI
9 Kim, J. S., Yean, M. H., Seo, H. K., Lee, J.-H. and Kang, S. S. (2009) Phytochemical studies on Lonicera Caulis (2) - Aliphatic and Phenolic compounds. Kor. J. Pharmacogn. 40: 326-333.
10 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
11 Oh, K.-O., Kim, S.-W., Kim, J.-Y., Ko, S.-Y., Kim, H.-M., Baek, J.-H., Ryoo, H.-M. and Kim, J.-K. (2003) Effect of Rehmannia glutinosa Libosch extracts on bone metabolism. Clin. Chim. Acta 334: 185-195.   DOI
12 Lee, S. Y., Kim, J. S., Choi, R. J., Kim, Y. S., Lee, J.-H. and Kang, S. S. (2011) A new polyoxygenated triterpene and two new aeginetic acid quinovosides from the roots of Rehmannia glutinosa. Chem. Pharm. Bull. 59: 742-746.   DOI   ScienceOn
13 Zhang, Z., Wang, D., Zhao, Y., Gao, H., Hu, Y.-H. and Hu, J.- F., (2009) Fructose-derived carbohydrates from Alisma orientalis. Nat. Prod. Res. 23: 1013-1020.   DOI   ScienceOn
14 Park, Y. M., Jang, S. K., Kim, Y. S. and Kim, B.-K. (1991) The constituents of Paulownia tomentosa stem. Yakhak Hoeji 35: 301-307.
15 Inoue, K., Inouye, H. and Chen, C.-C. (1981) A naphthoquinone and a lignan from the wood of Kigelia pinnata. Phytochemistry 20: 2271-2276.   DOI   ScienceOn
16 강삼식, 이승호, 최재수, 김진웅, 이동웅, 이강노, 서은경, 배기환, 손건호 (2008) 한약재성분 분광분석 자료집, 158- 163, 도서출판 우림, 서울.
17 Hung, T. M., Manh, H. D., Minh, P. T. H.,, Youn, U. J., Na, M.-K., Oh, W. K., Min, B. S. and Bae, K.-H. (2007) $\alpha$-Amylase and protein tyrosine phophatase 1B inhibitory of some Vietnamese medicinal plants used to treat diabetes. Nat. Prod. Sci. 13: 311-316.
18 Park, U., Shin, Y.-C. and Ko, S.-G. (2006) Rehmannia Radix (RR) extracts inhibit IGF-II induced VEGF and HIF-$1{\alpha}$ expressions in HaCaT keratinocyte cells. Kor. J. Oriental Prev. Med. Soc. 10: 51-62.
19 Chae, H. J., Kim, H.-R., Kim, D.-S., Woo, E.-R., Cho, Y.-G. and Chae, S.-W. (2005) Saeng-Ji-Hwang has a protective effect on adriamycin- induced cytotoxicity in cardiac muscle cells. Life Sci. 76: 2027-2042.   DOI   ScienceOn
20 Kim, S.-B. and Kim, K.-J. (2006) The effects of Rehmannia glutinosa on the protein expression related to the angiogenesis, cell survival and inflammation. J. Kor. Oriental Med. Ophthal. Orolaryngol. Dermatol. 19: 22-33.
21 Matsumoto, M., Shoyama, Y., Nishioka, I. and Irino, N. (1989) Constituents of regenerated shoot and cultured root tissue of Rehmannia glutinosa. Phytochemistry 28: 2331- 2332.   DOI   ScienceOn
22 Anh, N. T. H., Sung, T. V., Franke, K. and Wessjohann, L. A. (2003) Phytochemical studies of Rehmannia glutinosa rhizomes. Pharmazie 58: 593-595.
23 Lee, B.-C., Choi, J.-B., Cho, H.-J. and Kim, Y.-S. (2009) Rehmannia glutinosa ameliorates the progressive renal failure induced by 5/6 nephrectomy. J. Ethnopharmacol. 122: 131- 135.   DOI   ScienceOn
24 Shin, S. W., Park, C. I., Yang, C. H. and Park, J. W. (2008) Protective effect of Rehmannia glutinosa on the UV-induced apoptosis in U937 cells. Am. J. Chin. Med. 36: 1159-1170.   DOI   ScienceOn
25 Sung, Y.-Y., Yoon, T. S., Jang, J. Y., Park, S.-J. and Kim, H. K. (2011) Topical application of Rehmannia glutinosa extract inhibits mite allergen-induced atopic dermatitis in NC/Nga mice. J. Ethnopharmacol. 134: 37-44.   DOI   ScienceOn
26 Woo, K. S., Hwang, I. G., Song, D. S., Lee, Y. R., Lee, J. S. and Jeong, H. S. (2008) Changes in antioxidant activity of Rehmannia Radix Libosch with heat treatment. Food Sci. Biotechnol. 17: 1387-1390.
27 Park, S. M., Hong, S. M., Sung, S. R., Lee, J. E. and Kwon, D. Y. (2008) Extracts of Rehmanniae radix, Ginseng radix and Scutellariae radix improve glucose-stimulated insulin secretion and $\beta$-cell proliferation through IRS2 induction. Genes. Nutr. 2: 347-351.   DOI   ScienceOn
28 Sasaki, H., Nishimura, H., Chin, M. and Mitsuhashi, H. (1989) Hydroxycinnamic acid esters of phenethyl alcohol glycosides from Rehmannia glutinosa. Phytochemistry 28: 875-879.   DOI   ScienceOn
29 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
30 Kitagawa, I., Hori, K., Kawanishi, T., Kobayashi, M. and Kawanishi, F. (1998) On the constituents of the root of Fukuchiyama- jio, the hybrid of Rehmannia glutinosa var. purpurea and R. glutinosa forma hueichingensis. Yakugaku Zasshi 118: 464-475.
31 Sasaki, H., Nishimura, H., Morota, T., Katsuhara, T., Chin, M. and Mitsuhashi, H. (1991) Norcarotenoid glycosides of Rehmannia glutinosa var. purpurea. Phytochemistry 30: 1639- 1644.   DOI   ScienceOn
32 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
33 Tomoda, M., Kato, S. and Onuma, M. (1971) Water-soluble constituents of Rehmanniae Radix. I. Carbohydrates and acids of Rehmannia glutinosa f. hueichingensis. Chem. Pharm. Bull., 19: 1455-1460.   DOI
34 Tomoda, M., Tanaka, M. and Kondo, N. (1971) Water-soluble constituents of Rehmanniae Radix. II. Carbohydrates and acids of Rehmannia glutinosa var. purpurea. Chem. Pharm. Bull. 19: 2411-2413.   DOI
35 Shoyama, Y., Matsumoto, M. and Nishioka, I. (1986) Four caffeoyl glycosides from callus tissue of Rehmannia glutinosa. Phytochemistry 25: 1633-1636.   DOI   ScienceOn
36 Shoyama, Y., Matsumoto, M. and Nishioka, I. (1987) Phenolic glycosides from diseased roots of Rehmannia glutinosa var. purpurea. Phytochemistry 26: 983-986.   DOI   ScienceOn
37 Oshima, Y., Tanaka, K. and Hikino, H. (1993) Sesquiterpenoid from Rehmannia glutinosa roots. Phytochemistry 33: 233-234.   DOI   ScienceOn
38 Oshio, H. and Inouye, H. (1981) Iridoid glycosides of Rehmannia glutinosa. Phytochemistry 21: 133-138.
39 Oh, H. C. (2005) Remophilanetriol: A new eremophilane from the roots of Rehmannia glutinosa. Bull. Korean Chem. Soc. 26: 1303-1305.   DOI
40 Kitagawa, I., Nishimura, T., Furubayashi, A. and Yosioka, I. (1971) On the constituents of Rehmannia glutinosa Libosch. forma hueichingensis Hsiao. Yakugaku Zasshi 91: 593-596.
41 Morota, T., Sasaki, H., Sugama, K., Nishimura, H., Chin, M. and Mitsuhashi, H. (1990) Two non-glycosidic iridoids from Rehmannia glutinosa. Phytochemistry 29: 523-526.   DOI   ScienceOn
42 Morota, T., Sasaki, H., Nishimura, H., Sugama, K., Chin, M. and Mitsuhashi, H. (1989) Two iridoid glycosides from Rehmannia glutinosa. Phytochemistry 28: 2149-2153.   DOI   ScienceOn
43 Nishimura, H., Sasaki, H., Morota, T., Chin, M. and Mitsuhashi, H. (1989) Six iridoid glycosides from Rehmannia glutinosa. Phytochemistry 28: 2705-2709.   DOI   ScienceOn
44 Kitagawa, I., Fukuda, Y., Taniyama, T. and Yoshikawa, M., (1986) Absolute stereostructures of rehmaglutins A, B, and D. Three new iridoids isolated from Chinese Rehmanniae Radix. Chem. Pharm. Bull. 34: 1399-1402.   DOI
45 Yoshikawa, M., Fukuda, Y., Taniyama, T., Cha, B. C. and Kitagawa, I. (1986) Absolute stereostructures of rehmaionosides A, B, and C and rehmapicroside. Three new ionone glucosides and a monoterpene glucoside from Rehmanniae Radix. Chem. Pharm. Bull. 34: 2294-2297.   DOI
46 Kitagawa, I., Fukuda, Y., Taniyama, T. and Yoshikawa, M. (1995) Chemical studies on crude drug processing. VIII. On the constituents of Rehmanniae Radix (2): Absolute stereo structures of rehmaglutin C and glutinoside isolated from Chinese Rehmanniae Radix, the dried root of Rehmannia glutinosa Libosch. Chem. Pharm. Bull. 43: 1096-1100.   DOI   ScienceOn
47 Kitagawa, I., Fukuda, Y., Taniyama, T. and Yoshikawa, M. (1986) Absolute stereostructures of rehmaglutin C and glutinoside. A new iridoid lactone and a new chlorinated iridoid glucoside from Chinese Rehmanniae Radix. Chem. Pharm. Bull. 34: 1403-1406.   DOI
48 Yoshikawa M., Fukuda Y., Taniyama T. and Kitagawa I. (1996) Chemical studies on crude drug processing. IX. On the constituents of Rehmanniae Radix (3): Absolute stereostructures of rehmaionosides A, B, and C, and rehmapicroside, biologically active ionone glucosides and a monoterpene glucoside isolated from Chinese Rehmanniae Radix. Chem. Pharm. Bull., 44: 41-47.   DOI
49 Li, Y.-S., Chen, Z.-J. and Zhu, D.-Y. (2005) A novel bis-furan derivative, two new natural furan derivatives from Rehmannia glutinosa and their bioactivity. Nat. Prod. Res. 19: 165- 170.   DOI   ScienceOn
50 Takagi, K., Kimura, M., Harada, M. and Otsuka, Y. (1982) Pharmacology of Medicinal Herbs in East Asia (和漢藥物學), 74-75, Nanzando Company Limited (南山堂), Tokyo.
51 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
52 Tang, W. and Eisenbrand, G. (1992) Chinese Drugs of Plant Origin, 849-854, Springer-Verlag, Berlin.
53 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.
54 Kitagawa, I., Fukuda, Y., Taniyama, T. and 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.   DOI