Cytotoxic Phenolic Constituents of Acer tegmentosum Maxim

  • Park, Ki-Myun (Natural Products Laboratory, College of Pharmacy, Sungkyunkwan University) ;
  • Yang, Min-Cheol (Natural Products Laboratory, College of Pharmacy, Sungkyunkwan University) ;
  • Lee, Kyu-Ha (Natural Products Laboratory, College of Pharmacy, Sungkyunkwan University) ;
  • Kim, Kyung-Ran (Natural Products Laboratory, College of Pharmacy, Sungkyunkwan University) ;
  • Choi, Sang-Un (Korea Research Institute of Chemical Technology) ;
  • Lee, Kang-Ro (Natural Products Laboratory, College of Pharmacy, Sungkyunkwan University)
  • Published : 2006.12.31


The chromatographic separation of the MeOH extract from the twigs of Acer tegmentosum led to the isolation of ten phenolic compounds. The structures of these compounds were determined using spectroscopic methods as 3,7,3',4'-tetramethyl-quercetin (1), 5,3'-dihydroxy-3,7,4'-trimethoxy flavone (2), 2,6-dimethoxy-p-hydroquinone (3), (-)-catechin (4), morin-3-O-${\alpha}$-L-lyxoside (5), p-hydroxy phenylethyl-O-${\beta}$-D-glucopyranoside (6), 3,5-dimethoxy-4-hydroxy phenyl-1-O-${\beta}$-D-glucoside (7), fraxin (8), 3,5-dimethoxy-benzyl alcohol 4-O-${\beta}$-D-glucopyranoside (9) and 4-(2,3-dihydroxy propyl)-2,6-dimethoxy phenyl ${\beta}$-D-glucopyranoside (10). The compounds were examined for their cytotoxic activity against five cancer cell lines. Compound 3 exhibited good cytotoxic activity against five human cancer cell lines with $ED_{50}$ values ranging from $1.32\;to\;3.85\;{\mu}M$.


  1. Ahn, D. K., Illustrated Book of Korean Medicinal Herbs. Kyo- Hak publishing, Seoul, p 523 (1998)
  2. Adolf, H., Peter, P., and Eric, E. Conn., Dhurrin, (-)-catechin, flavonol glycosides and flavones from Chamaebatia foliolosa. Phytochemistry, 26, 1546-1547 (1987)
  3. Bilia, A. R., Morelli, I., Hamburger M., and Hostettmann, K., Flavanes and a-type proanthocyanidins from Prunus prostrata., Phytochemistry, 43, 887-892 (1996)
  4. Emi, O., Tetsuya, H., Takamitsu, M., Haruhiro, F., Masami, I., and Mikio, Y., Analgesic Components of Saposhnikovia Root (Saposhnikovia divaricata)., Chem. Pharm. Bull., 49, 154- 160 (2001)
  5. Hatano, T., Hattori, S., Ikeda, Y., Shingu, T., and Okuda, Y., Tannins of Aceraceous plants. Part II. Gallotannins having a 1,5-anhydro-D-glucitol core and some ellagitannins from Acer species., Chem. Pharm. Bull., 38, 1902-1905 (1990)
  6. Hefeng, P. and Lennart, N. L., Phenolics from inner bark of Pinus sylvestris., Phytochemistry, 42, 1185-1189 (1996)
  7. Hideaki, O., Mami, T., Shogo, I., Tomohiro, S., and Kazuo, Y., Phenolic compounds from Coix lachryma-jobi var. ma-yuen., Phytochemistry, 28, 883-886 (1989)
  8. Hidetoshi, A. and Gen, I. D., Isolation of antimicrobial compounds from Guava (Pisdium guajava L.) and their structural elucidation. Biosci. Biotechnol. Biochem., 66, 1727-1730 (2002)
  9. Hideyuki, M., Hiroyuki, M., Chikako, A., Midori, A., Teruhiko, Y., and Junya, M., Isolation of ${\alpha}$-glucosidase inhibitors from hyssop (Hyssopus officinalis). Phytochemistry, 65, 91-97 (2004)
  10. Jorn, L., Alfred, B., Thomas, D., Turgen, S., Vidtor, W., Dierk, S., Dieter, S., and Sabine, R., Accumulation of tyrosol glucoside in transgenic potato plants expressing a parsley tyrosine decarboxylase. Hiroko Oguchi, Ionone and lignan glycosides from Epimedium diphyllum. Phytochemistry, 60, 683-689 (2002)
  11. Junichi, K., Toru, I., Yasuko, T., Masateru, O., Yasuyuki, I., and Toshihiro, N., Water soluble constituents of Fennel. V Glycosides of Aromatic compounds. Chem. Pharm. Bull., 46, 1587-1590 (1998)
  12. Kangi, I., Gen, I. N., and Itsuo, N., Flavan-3-ol and procyanidin glycosides from Quercus miygii., Phytochemistry, 26, 1167- 1170 (1987)
  13. Kanji, I., Hiroshi, S., Motoyoshi, S., and Koichiro, S., Phenyl glucosides from hairy root culture of Swertia jponica. Phytochemistry, 29, 3823-3825 (1990)
  14. Kubo, M., Inoue, T., and Nagai, M., Studies on the constituents of aceraceae plants. III. Structure of acerogenin B from Acer nikoense Maxim. Chem. Pharm. Bull., 28, 1300-1303 (1980)
  15. Kubo, M., Nagai, M., and Inoue, T., Studies on the constituents of ceraceae plants. Carbon-13 nuclear magnetic resonance spectra of acerogenin A, rhododendrol, and related compounds, and structure of aceroside from Acer nikoense. Chem. Pharm. Bull., 31, 1917-1922 (1983)
  16. Masataka, S. and Masao, K., Studies on the constituents of Osmantus species. X. Structures of phenolic glucosides form the leaves of Osmanthus asiaticus Nakai. Chem. Pharm. Bull., 40, 325-326 (1992)
  17. Renmin, L., Qinghua, S., Ailing, S., and Jichun, C., Isolation and purification of coumarin compounds from Cortex fraxinus by high-speed counter-current chromatography. J. Chromatogr. A., 1072, 195-199 (2005)
  18. Stephen, J. P., Louise, N. J., and David, C. P., High-resolution $^1H$- and $^{13}C$-NMR. Spectra of D-glucopyranose, 2-acetamido- 2-deoxy-D-glucopyranose, and related compounds in aqueous media. Carbohydrate Research, 59, 19-34 (1977)
  19. Ying, W., Matthias, H., Joseph, G., and Kurt, H., Antimicrobial flavonoids from Psiadia trinervia and their methylated and acetylated derivatives. Phytochemistry, 28, 2323-2327 (1989)