Distribution of (-)-Yatein in Cupressaceae Family Analysed by High Performance liquid Chromatography

  • Published : 2004.01.01

Abstract

The method for the chiral analysis of (-)-yatein was developed and the distribution of this component in the plants of three genera like Juniperus, Thuja and Chamaecyparis belonging to Cupressaceae family was examined. The chiral analysis of (-)-yatein from the plants was carried out by high performance liquid chromatography on (R,R)-Whelk-O1 column using 81 v/v% methanol as mobile phase. The yatein content in the leaves of Juniperus was the highest in compare with that of the other two genera, providing the possibility of the chemical discrimination of the plants in Juniperus from the other plants in the Cupressaceae family. In general, the yatein content in the leaves was much higher than that in the twigs. This method could be applied for the quality control of (-)-yatein in the plants belonging to Cupressaceae family.

Keywords

References

  1. Ali, A. M., Mackeen, M. M., Intan-Safinar, I., Hamid, M., Lajis., N. H., and Sharkoshi, S. H. E., Antitumour-promoting and antitumour activities of the crude extract from the leaves of Juniperus chinensis. J. Ethnopharmacol., 53, 165-169 (1996) https://doi.org/10.1016/0378-8741(96)01434-1
  2. Burits, M., Asres, K., and Bucar, F., The antioxidant activity of the essential oils of Artemisia afra, Artemisia abyssinica and Juniperus procera. Phytother. Res., 15, 103-108 (2001) https://doi.org/10.1002/ptr.691
  3. Cairnes, D. A., Ekundayo, O., and Kingston, D. G., Plant anticancer agents. X. Lignans from Juniperus phoenicea. J. Nat. Prod., 43, 495-497 (1980) https://doi.org/10.1021/np50010a010
  4. Cairnes, D. A., Kingston, D. G. I., and Rao, M. M., High performance liquid chromatography of podophyllotoxines and related lignans. J. Nat. Prod., 44, 34-37 (1981) https://doi.org/10.1021/np50013a006
  5. Chang, L. C., Song, L. L., Park, E. J., Lee, L. L., Farnsworth, N. R., Pezzuto, J. M., and Kinghorn, A. D., Bioactive constituents of Thuja occidentalis. J. Nat. Prod., 63, 1235-1238 (2000) https://doi.org/10.1021/np0001575
  6. Digrak, M., IIcim, A., and Hakki, A. M., Antimicrobial activities of several parts of Pinus brutia, Juniperus oxycedrus, Abies cilicia, Cedrus libani and Pinus nigra. Phytother. Res., 13, 584-587 (1999) https://doi.org/10.1002/(SICI)1099-1573(199911)13:7<584::AID-PTR508>3.0.CO;2-S
  7. Gerhauser, C., Leonhardt, K., Tan, G. T., Pezzuto, J. M., and Wagner, H., What is the active antiviral principle of Thuja occidentalis L. Pharm. Pharmacol. Lett., 2,127-130 (1992)
  8. Honda, T., Kimura, N., Sato, S., Kato, D., and Tominaga, H., Chiral synthesis of lignan lactones, (-)-hinokinin, (-)-deoxypodorhizone, (-)-isohibalactone and (-)-savinin by means of enantioselective deprotonation strategy. J. Chem. Soc. Perkin Trans., 1, 1043-1046 (1994)
  9. Kawai, S., Sugishita, K., and Ohashi, H., Identification of Thuja occidentalis Iignans and its biosynthetic relationship. Phytachem., 51, 243-247 (1999) https://doi.org/10.1016/S0031-9422(99)00004-7
  10. Kim, Y, You, Y. J., Nam, N. H., and Ahn, B. Z., 2,3-Dibenzylbutyrolactones and 1,2,3,4-tetrahydro-2-naphthoic acid gamma-Iactones: structure and activity relationship in cytotoxic activity. Arch. Pharm. Res., 25, 240-249 (2002) https://doi.org/10.1007/BF02976621
  11. Koulman, A., Bos, R., Medarde, M., Pras, N., and Quax, W. J., A fast and simple GC-MS method for lignan profiling in Anthriscus sylvestris and biosynthetically related plant species. Planta Med., 67, 858-862 (2001) https://doi.org/10.1055/s-2001-18849
  12. Lee, C. K. and Cheng, Y S., Diterpenoids from the leaves of Juniperus chinensis var. kaizuka. J. Nat. Prod., 64, 511-514 (2001) https://doi.org/10.1021/np0004505
  13. Lee, T. B., Illustrated flora of Korea, Hyangmoonsa, Korea, pp. 65-68, (1989)
  14. Lim, H. M., Kim, Y., Kim, Y. H., Ahn, B. Z., and Kang, J. S., Stereoselective determination of (-)-yatein in the plant of the Cupressaceae family by capillary electrophoresis. J. Sep. Sci., 25, 1070-1072 (2002) https://doi.org/10.1002/1615-9314(20021101)25:15/17<1070::AID-JSSC1070>3.0.CO;2-H
  15. McDoniel, P. B. and Cole. J. R., Antitumor activity of Bursera schlechtendalii (Burseraceae): Isolation and structure determination of two new Iignans. J. Pharm. Sci., 61, 1992-1994 (1972) https://doi.org/10.1002/jps.2600611224
  16. Medarde, M., Clairac, R. P., Lopez, J. L., Gravalos, D. G., and San Feliciano, A., Synthesis, antitumoral and antiviral evaluation of halo- and demethyl-yatein derivatives. Arch. Pharm., 328, 640-644 (1995) https://doi.org/10.1002/ardp.19953280903
  17. Miyata, M., Itoh, K., and Tachibana, S., Extractives of Juniperus chinensis L. 1: Isolation of podophyllotoxin and yatein from the leaves of J. chinensis. J. Wood Sci., 44, 397-400 (1998) https://doi.org/10.1007/BF01130454
  18. Moreno, L., Bello, R., Beltran, B., Calatayud, S., Primo-Yufera, E., and Esplugues, J., Pharmacological screening of different Juniperus oxycedrus L. extracts. Pharmacol. Toxicol., 82, 108-112 (1998) https://doi.org/10.1111/j.1600-0773.1998.tb01407.x
  19. Neidigh, K. A., Kingston, D., Lewis, G. I., and Norman, G., Synthesis of stereospecifically deuterated matairesinol, podorhizol, epipodorhizol, and yatein. J. Nat. Prod., 57, 791-800 (1994) https://doi.org/10.1021/np50108a016
  20. Perry, L. M., Medicinal Plants of East and Southeast Asia. The MIT Press, Cambridge, pp. 311-312, (1980)
  21. San Feliciano, A., Gordaliza, M., Miguel del Corral, J. M., Castro, M. A., Garcia-Gravalos, M. D., and Ruiz-Lazaro, P., Antineoplastic and antiviral activities of some cyclolignans. Planta Med., 59, 246-249 (1993) https://doi.org/10.1055/s-2006-959660
  22. Teng, C. M., Lin, C. H., Kuo, Y. H., Lin, Y. L., and Huang, T. F., Antiplatelet and vasorelaxing actions of the acetoxy derivative of cedranediol isolated from Juniperus squamata. Planta Med., 60, 209-213 (1994) https://doi.org/10.1055/s-2006-959460
  23. Topcu, G., Erenler, R., Cakmak, O., Johansson, C. B., Celik, C., Chai, H. B., and Pezzuto, J. M., Diterpenes from the berries of Juniperus excelsa. Phytochem., 50, 1195-1199 (1999) https://doi.org/10.1016/S0031-9422(98)00675-X