생약학회지 (Korean Journal of Pharmacognosy)

  • 제42권2호
  • /
  • Pages.117-126
  • /
  • 2011
  • /
  • 0253-3073(pISSN)
  • /
  • 2288-9299(eISSN)
한국생약학회 (The Korean Society of Pharmacognosy)
권호 표지

숙지황(熟地黃)의 성분연구

Phytochemical Studies on Rehmanniae Radix Preparata

  • 이주영 (서울대학교 약학대학 천연물과학연구소) ;
  • 이은주 (서울대학교 약학대학 천연물과학연구소) ;
  • 김주선 (서울대학교 약학대학 천연물과학연구소) ;
  • 이제현 (동국대학교 한의과대학) ;
  • 강삼식 (서울대학교 약학대학 천연물과학연구소)
  • 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)
  • 투고 : 2011.04.14
  • 심사 : 2011.06.16
  • 발행 : 2011.06.30
PDF 다운로드
⟨ 이전 논문 다음 논문 ⟩

초록

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.

키워드

참고문헌

  1. 한국약학대학협의회 약전분과회 (1998) 대한약전, 7개정, 문성사, 서울.
  2. 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
  3. 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. https://doi.org/10.1055/s-2006-962064
  4. 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
  5. 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.
  6. 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
  7. 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.
  8. 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. https://doi.org/10.1016/0308-8146(88)90071-4
  9. 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. https://doi.org/10.1016/0009-8981(73)90315-X
  10. 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. https://doi.org/10.1021/np000401s
  11. Martin, D. and Lichtenthaler, F. W. (2006) Versatile building blocks from disaccharides: glycosylated 5-hydroxymethylfurfurals. Tetrahedron: Asymmetry 17: 756-762. https://doi.org/10.1016/j.tetasy.2005.12.010
  12. 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.
  13. 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
  14. 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. https://doi.org/10.1007/s11418-007-0206-z
  15. 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. https://doi.org/10.1016/j.fct.2010.05.076
  16. 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. https://doi.org/10.1016/j.fct.2009.01.022
  17. 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. https://doi.org/10.1016/j.foodchem.2008.11.097
  18. Brieskorn, C. H. and Wunderer, H. (1967) Pomol- und Pomonsäure. Chem. Ber. 100: 1252-1265. https://doi.org/10.1002/cber.19671000426
  19. Brieskorn, C. H. and Suss, H. P. (1974) Die Triterpenoide der Birnen- und Apfelschale. Arch. Pharm. 307: 949-960. https://doi.org/10.1002/ardp.19743071211
  20. Cheng, D.-L. and Cao, X.-P. (1992) Pomolic acid derivatives from the root of Sanguisorba officinalis. Phytochemistry 31: 1317-1320. https://doi.org/10.1016/0031-9422(92)80499-5
  21. 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. https://doi.org/10.1248/bpb.28.1103
  22. 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
  23. Calis, I., Saracoglu, I., Basaran, A. A. and Sticher, O. (1992) Two phenethyl alcohol glycosides from Scutellaria orientalis subsp. pinnatifida. Phytochemistry 32: 1621-1623.
  24. Kanchannapoon, T., Kasai, R., Chumsri, P., Hiraga, Y. and Yamasaki, K. (2001) Megastigmane and iridoid glucosides from Clerodendrum inerme. Phytochemistry 58: 333-336. https://doi.org/10.1016/S0031-9422(01)00208-4
  25. 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. https://doi.org/10.1016/0031-9422(90)85306-Z
  26. 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.
  27. Oshio, H., Naruse, Y. and Inouye, H. (1981) Quantitative analysis of iridoid glycosides of Rehmanniae Radix. Shoyakugaku Zasshi 35: 291-294.
  28. 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.
  29. 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. https://doi.org/10.1248/cpb.59.546