Natural Product Sciences

The Korean Society of Pharmacognosy (한국생약학회)
권호 표지

Neuroprotective Lignans from Biota orientalis leaves

  • Yoon, Jeong-Seon (College of Pharmacy and Research Institute of Pharmaceutical Science, Seoul National University) ;
  • Koo, Kyung-Ah (Biohealth Product Research Center (BPRC), Inje University) ;
  • Ma, Choong-Je (School of Bioscience and Biotechnology, Kangwon National University) ;
  • Sung, Sang-Hyun (College of Pharmacy and Research Institute of Pharmaceutical Science, Seoul National University) ;
  • Kim, Young-Choong (College of Pharmacy and Research Institute of Pharmaceutical Science, Seoul National University)
  • Published : 2008.09.30
Download PDF
⟨ Previous Next ⟩

Abstract

We previously reported that 90% MeOH fraction of Biota orientalis leaves (L.) ENDL. had significant neuroprotective activity against glutamate-induced neurotoxicity in primary cultures of rat cortical cells. In the present study, (-)-savinin (1), (-)-hinokinin (2), dehydroheliobuphthalmin (3) were isolated by bioactivity-guided fractionation from the 90% MeOH fraction. All three lignans had significant neuroprotective activities against glutamate-induced neurotoxicity at the concentrations ranging from 0.1 to 10.0 ${\mu}M$.

Keywords

References

  1. Aarts, M.M. and Tymianski, M., Novel treatment of excitotoxicity: targeted disruption of intracellular signaling from glutamate receptors. Biochem. Pharmacol. 66, 877-886 (2003) https://doi.org/10.1016/S0006-2952(03)00297-1
  2. Ban, H.S., Lee, S.H., Kim, Y.P., Yamaki, K., Shin, K.H., and Ohuchi, K., Inhibition of prostaglandin $E_2$ production by taiwanin C isolated from the root of Acanthopanax chiisanensis and the mechanism of action. Biochem. Pharmacol. 64, 1345-1354 (2002) https://doi.org/10.1016/S0006-2952(02)01348-5
  3. Bohlmann, F., Lonitz, T., and Knoll, K.H., Neue lignan-derivate aus der tribus heliantheae. Phytochemistry 17, 330-331 (1978) https://doi.org/10.1016/S0031-9422(00)94185-2
  4. Che, C.T., Ahmed, M.S., Kang, A.S., Waller, D.P., Bingel, A.S., Martin, A., Rajamahendran, P., Bunyapraphatara, N., Lankin, D.C., Cordell, G.A., Soejarto, D.D., Wijesekera, W., and Fong, H.H.S., Studies on Aristolochia III. Isolation and biological evaluation of constituents of Aristolochia indica roots for fertility-regulating activity. J. Nat. Prod. 47, 331-341 (1984) https://doi.org/10.1021/np50032a017
  5. Choi, D.W., Glutamate neurotoxicity and disease of the nervous system. Neuron 1, 623-634 (1988) https://doi.org/10.1016/0896-6273(88)90162-6
  6. Jakupovic, J., Huster, A., Bohlmann, F., King, R.M., and Robinson, H., New lignans and isobutylamides from Heliopsis buphthalmoides. Planta Med. 1, 18-20 (1986)
  7. Jang, Y.P., Kim, S.R., Choi, Y.H., Kim, J.W., Kim, S.G., Markelonis, G.J., Oh, T.H., and Kim, Y.C., Arctigenin protects cultured cortical neurons from glutamate-induced neurodegeneration by binding to kainate receptor. J. Neurosci. Res. 68, 233-240 (2002) https://doi.org/10.1002/jnr.10204
  8. Jang, Y.P., Kim, S.R., and Kim, Y.C., Neuroprotective dibenzylbutyrolactone lignans of Torreya nucifera. Planta Med. 67, 470-472 (2001) https://doi.org/10.1055/s-2001-15804
  9. Kato, M.J., Yoshida, M., and Gottlieb, O.R., Lignoids and arylalkanones from fruits of Virola elongata. Phytochemistry 29, 1799-1810 (1990) https://doi.org/10.1016/0031-9422(90)85020-G
  10. Kim, J.Y. and Yang, K.S., Antioxidative activities of triterpenoids and lignans from Acanthopanax divaricatus var. albeofructus. Yakhak Hoechi 48, 236-240 (2004)
  11. Kim, S.R. and Kim, Y.C., Neuroprotective phenylpropanoid esters of rhamnose isolated from roots of Scrophularia buergeriana. Phytochemistry 54, 503-509 (2000) https://doi.org/10.1016/S0031-9422(00)00110-2
  12. Kim, Y.C., Kim, S.R., Markelonis, G.J., and Oh, T.H., Ginsenosides $Rb_1$ and $Rg_3$ protect cultured rat cortical cells from glutamate-induced neurodegeneration. J. Neurosci. Res. 53, 426-432 (1998) https://doi.org/10.1002/(SICI)1097-4547(19980815)53:4<426::AID-JNR4>3.0.CO;2-8
  13. Koo, K.A., Sung, S.H., and Kim, Y.C., A new neuroprotective pinusolide derivative from the leaves of Biota orientalis. Chem. Pharm. Bull. 50, 834-836 (2002) https://doi.org/10.1248/cpb.50.834
  14. Lee, M.K., Yeo, H.S., Kim, J.W., Markelonis, G.J., Oh, T.H., and Kim, Y.C., Cynandione A from Cynanchum wilfordii protects cultured cortical neurons from toxicity induced by $H_2O_2$, L-glutamate, and kainite. J. Nurosci. Res. 59, 259-264 (2000) https://doi.org/10.1002/(SICI)1097-4547(20000115)59:2<259::AID-JNR12>3.0.CO;2-3
  15. Lee, S.H., Yoo, H.H., Piao, X.L., Kim, J.S., Kang, S.S., and Shin, K.H., Anti-estrogenic activity of lignans from Acanthopanax chiisanensis root. Arch. Pharm. Res. 28, 186-189 (2005a) https://doi.org/10.1007/BF02977713
  16. Lee, S.H., Ban, H.S., Kim, Y.P., Kim, B.K., Cho, S.H., Ohuchi, K., and Shin, K.H., Lignans from Acanthopanax chiisanensis having an inhibitory activity on prostaglandin $E_2$ prodution. Phytother. Res. 19, 103-106 (2005b) https://doi.org/10.1002/ptr.1220
  17. Lipton, S.A. and Rosenberg, P.A., Excitatory amino acids as a final common pathway for neurologic disorders. New Engl. J. Med. 330, 613-622 (1994) https://doi.org/10.1056/NEJM199403033300907
  18. Lopes, L.M.X., Yoshida, M., and Gottlieb, O.R., Dibenzylbutyrolactone lignans from Virola sebifera. Phytochemistry 22, 1516-1518 (1983) https://doi.org/10.1016/S0031-9422(00)84055-8
  19. Medola, J.F., Cintra, V.P, Pesqueira E Silva, E.P., de Andrade Royo, V., da Silva, R., Saraiva, J., Albuquerque, S., and Bastos, J.K., (−)-Hinokinin causes antigenotoxicity but genotoxicity in peripheral blood of Wistar rats. Food Chem. Toxicol. 45, 638-642 (2007) https://doi.org/10.1016/j.fct.2006.10.012
  20. Nissanka, A.P., Karunaratne, V., Bandara, B.M., Kumar, V., Nakanishi, T., Nishi, M., Inada, A., Tillekeratne, L.M., Wijesundara, D.S., and Gunatilaka, A.A., Antimicrobial alkaloids from zanthoxylum tetraspermum and caudatum. Phytochemistry 56, 857-861 (2001) https://doi.org/10.1016/S0031-9422(00)00402-7
  21. Ohmoto, T. and Yamaguchi, K., Constituents of Pollen. XV. Constituents of Biota orientalis (L.) ENDL. (1). Chem. Pharm. Bull. 36, 807-809 (1998)
  22. Pelter, A., Warren, R., Hameed, N., Khan, N.U., Ilyas, M., and Rahman, W., Biflavonyl pigments from Thuja orientalis (cupressaceae). Phytochemistry 9, 1897-1898 (1970) https://doi.org/10.1016/S0031-9422(00)85615-0
  23. Rehnberg, N. and Magnuson, G., Total synthesis of the lignans (−)- and (+)-burseran, (−)-cubebin, and (−)-hinokinin by diastereoselective conjugate addition of benzyl anions to 2-(R) and (s)-benzyloxy-2,5- dihydro-4-(3,4-methylenedioxybenzoyz-furan. Tetrahedron Lett. 29, 3599-3602 (1988) https://doi.org/10.1016/0040-4039(88)85304-8
  24. Sung, S.H., Koo, K.A., Lim, H.K., Lee, H.S., Cho, J.H., Kim, H.S., and Kim, Y.C., Diterpenes of Biota orientalis leaves. Kor. J. Pharmacogn. 29, 347-352 (1998)
  25. Yang, H.O., Suh, D.Y., and Han, B.H., Isolation and characterization of platelet-activating factor receptor binding antagonists from Biota orientalis. Planta Med. 61, 37-40 (1995) https://doi.org/10.1055/s-2006-957995
  26. Zhu, J.X., Wang, Y., Kong, L.D., Yang, C., and Zhang, X., Effects of Biota orientalis extract and its flavonoid constituents, quercetin and rutin on serum uric acid levels in oxonate-induced mice and xanthine dehydrogenase and xanthine oxidase activities in mouse liver. J. Ethnopharmacol. 93, 133-140 (2004) https://doi.org/10.1016/j.jep.2004.03.037