Korean Journal of Pharmacognosy (생약학회지)

The Korean Society of Pharmacognosy (한국생약학회)
권호 표지

Phytochemical Studies on Rehmanniae Radix

지황 (地黃)의 성분연구

  • 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)
  • 이소영 (서울대학교 약학대학 천연물과학연구소) ;
  • 연민혜 (서울대학교 약학대학 천연물과학연구소) ;
  • 김주선 (서울대학교 약학대학 천연물과학연구소) ;
  • 이제현 (동국대학교 한의과대학) ;
  • 강삼식 (서울대학교 약학대학 천연물과학연구소)
  • Received : 2011.04.14
  • Accepted : 2011.06.16
  • Published : 2011.06.30
Download PDF
⟨ Previous Next ⟩

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

References

  1. 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.
  2. Zhang, R.-X., Li, M.-X. and Jia, Z.-P. (2008) Rehmannia glutinosa: Review of botany, chemistry and pharmacology. J. Ethnopharmacol. 117: 199-214. https://doi.org/10.1016/j.jep.2008.02.018
  3. Tang, W. and Eisenbrand, G. (1992) Chinese Drugs of Plant Origin, 849-854, Springer-Verlag, Berlin.
  4. 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.
  5. 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. https://doi.org/10.1248/cpb.39.1171
  6. 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. https://doi.org/10.1248/cpb.34.1399
  7. 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. https://doi.org/10.1248/cpb.43.1096
  8. 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. https://doi.org/10.1248/cpb.34.1403
  9. 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. https://doi.org/10.1248/cpb.44.41
  10. 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. https://doi.org/10.1248/cpb.34.2294
  11. 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. https://doi.org/10.1080/14786410410001704787
  12. Oshima, Y., Tanaka, K. and Hikino, H. (1993) Sesquiterpenoid from Rehmannia glutinosa roots. Phytochemistry 33: 233-234. https://doi.org/10.1016/0031-9422(93)85431-P
  13. Oh, H. C. (2005) Remophilanetriol: A new eremophilane from the roots of Rehmannia glutinosa. Bull. Korean Chem. Soc. 26: 1303-1305. https://doi.org/10.5012/bkcs.2005.26.8.1303
  14. 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.
  15. Oshio, H. and Inouye, H. (1981) Iridoid glycosides of Rehmannia glutinosa. Phytochemistry 21: 133-138.
  16. 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. https://doi.org/10.1016/0031-9422(90)85110-2
  17. Morota, T., Sasaki, H., Nishimura, H., Sugama, K., Chin, M. and Mitsuhashi, H. (1989) Two iridoid glycosides from Rehmannia glutinosa. Phytochemistry 28: 2149-2153. https://doi.org/10.1016/S0031-9422(00)97934-2
  18. Nishimura, H., Sasaki, H., Morota, T., Chin, M. and Mitsuhashi, H. (1989) Six iridoid glycosides from Rehmannia glutinosa. Phytochemistry 28: 2705-2709. https://doi.org/10.1016/S0031-9422(00)98072-5
  19. Sasaki, H., Nishimura, H., Chin, M. and Mitsuhashi, H. (1989) Hydroxycinnamic acid esters of phenethyl alcohol glycosides from Rehmannia glutinosa. Phytochemistry 28: 875-879. https://doi.org/10.1016/0031-9422(89)80134-7
  20. Nishimura, H., Sasaki, H., Morota, T., Chin, M. and Mitsuhashi, H. (1990) Six glycosides from Rehmannia glutinosa var. purpurea. Phytochemistry 29: 3303-3306. https://doi.org/10.1016/0031-9422(90)80204-T
  21. 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.
  22. 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. https://doi.org/10.1016/0031-9422(91)84224-G
  23. 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. https://doi.org/10.1016/0031-9422(91)85055-5
  24. 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. https://doi.org/10.1248/cpb.19.1455
  25. 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. https://doi.org/10.1248/cpb.19.2411
  26. Shoyama, Y., Matsumoto, M. and Nishioka, I. (1986) Four caffeoyl glycosides from callus tissue of Rehmannia glutinosa. Phytochemistry 25: 1633-1636. https://doi.org/10.1016/S0031-9422(00)81224-8
  27. Shoyama, Y., Matsumoto, M. and Nishioka, I. (1987) Phenolic glycosides from diseased roots of Rehmannia glutinosa var. purpurea. Phytochemistry 26: 983-986. https://doi.org/10.1016/S0031-9422(00)82331-6
  28. 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. https://doi.org/10.1016/S0031-9422(00)97978-0
  29. Anh, N. T. H., Sung, T. V., Franke, K. and Wessjohann, L. A. (2003) Phytochemical studies of Rehmannia glutinosa rhizomes. Pharmazie 58: 593-595.
  30. 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. https://doi.org/10.1016/j.jep.2008.12.015
  31. 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. https://doi.org/10.1016/j.jep.2010.11.050
  32. 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.
  33. 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. https://doi.org/10.1007/s12263-007-0065-y
  34. 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. https://doi.org/10.1142/S0192415X08006491
  35. 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.
  36. 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.
  37. 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.
  38. 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. https://doi.org/10.1016/j.lfs.2004.07.032
  39. 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. https://doi.org/10.5483/BMBRep.2004.37.5.618
  40. 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. https://doi.org/10.1016/S0009-8981(03)00238-9
  41. 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. https://doi.org/10.1248/cpb.59.742
  42. 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.
  43. Inoue, K., Inouye, H. and Chen, C.-C. (1981) A naphthoquinone and a lignan from the wood of Kigelia pinnata. Phytochemistry 20: 2271-2276. https://doi.org/10.1016/0031-9422(81)80128-8
  44. 강삼식, 이승호, 최재수, 김진웅, 이동웅, 이강노, 서은경, 배기환, 손건호 (2008) 한약재성분 분광분석 자료집, 158- 163, 도서출판 우림, 서울.
  45. 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. https://doi.org/10.1080/14786410802391120
  46. 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.
  47. 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. https://doi.org/10.1016/j.bse.2005.07.004
  48. Kanchanapoom, T., Kasai, R. and Yamasaki, K. (2002) Phenolic glycosides from Markhamia stipulata. Phytochemistry 59: 557-563. https://doi.org/10.1016/S0031-9422(01)00466-6
  49. 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.
  50. 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. https://doi.org/10.1016/S0031-9422(00)97989-5
  51. 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.
  52. 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.
  53. 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. https://doi.org/10.1080/713604303
  54. 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.