New Cytotoxic Benzopyrans from the Leaves of Mallotus apelta

  • Kiem Phan Van (Institute of Natural Products Chemistry, Vietnamese Academy of Science and Technology) ;
  • Dang Nguyen Hai (Institute of Natural Products Chemistry, Vietnamese Academy of Science and Technology) ;
  • Bao Ha Viet (Institute of Natural Products Chemistry, Vietnamese Academy of Science and Technology) ;
  • Huong Hoang Thanh (Institute of Natural Products Chemistry, Vietnamese Academy of Science and Technology) ;
  • Minh Chau Van (Institute of Natural Products Chemistry, Vietnamese Academy of Science and Technology) ;
  • Huong Le Mai (Institute of Natural Products Chemistry, Vietnamese Academy of Science and Technology) ;
  • Lee Jung Joon (Korea Research Institute of Bioscience and Biotechnology) ;
  • Kim Young Ho (College of Pharmacy, Chungnam National University)
  • Published : 2005.10.01

Abstract

Two new benzopyrans 6-[1'-oxo-3'(R)-hydroxy-butyl]-5,7 -dimethoxy-2,2-dimethyl-2H-1-ben-zopyran (1) and 6-[1'-oxo-3'(R)-methoxy-butyl]-5,7 -dimethoxy-2,2-dimethyl-2H-1-benzopyran (2) were isolated from the leaves of Mallotus apelta Muell.-Arg., (Euphorbiaceae). Their chemical structures were elucidated by spectroscopic analyses, especially by 1D-, 2D-NMR and MS spectra. Compound 1 was found to have strong cytotoxic effect against two human cancer cell lines as human hepatocellular carcinoma (Hep-2, $IC_{50}\;:\;0.49\;{\mu}g/mL$) and rhabdosarcoma (RD, $IC_{50}\;:\;0.54\;{\mu}g/mL$), while compound 2 showed moderate activity against Hep-2 cell line ($IC_{50}\;:\;4.22\;{\mu}g/mL$) by in vitro assay.

Keywords

References

  1. An, T. Y., Hu, L. H., Cheng, X. F., and Chen, Z. L., Benzopyran derivatives from Maflotus apelta. Phytochemistry, 57, 273-278 (2001) https://doi.org/10.1016/S0031-9422(00)00512-4
  2. An, T. Y., Hu, L. H., Cheng, X. F., and Chen, Z. L., Two new benzopyran derivatives from Maflotus apelta. Nat. Prod. Res., 17, 325-328 (2003) https://doi.org/10.1080/1057563031000072569
  3. Cheng, X. F., Meng, Z. M., and Chen, Z. L., A pyridine-type alkaloid from Mallotus apelta. Phytochemistry, 49, 2193-2194 (1998) https://doi.org/10.1016/S0031-9422(98)00395-1
  4. Cheng, X. F., Chen, Z. L., and Meng, Z. M., Two new diterpenoids from Mallotus apelta. J. Asian Nat. Prod. Res., 1, 163-168 (1999a) https://doi.org/10.1080/10286029908039860
  5. Cheng, X. F. and Chen, Z. L., Three new diterpenoids from Mallotus apelta. J. Asian Nat. Prod. Res., 1, 319-325 (1999b) https://doi.org/10.1080/10286029908039881
  6. Cheng, X. F. and Chen, Z. L., Coumarinofignoids of Maflotus apelta.Fitoterapia, 71, 341-342 (2000) https://doi.org/10.1016/S0367-326X(99)00160-4
  7. Chi, V. V. (ed.), 'Vietnamese Medical Plant Dictionary'. Ha Noi Medicine Pub., 1997
  8. Hori, K., Satake, T., Saiki, Y., and Murakami, K., Chemical and chemotaxonomical studies of Filices. LXXIX. An acylphloro-glucinol glycoside from Diplezium nipponicum TAGAWA. Yakugaku Zasshi, 110, 315-320 (1990)
  9. Kamperdick, C., Van, N. H., Sung, T. V., and Adam, G., Benzopyrans from Melicope ptelefolia leaves. Phytochemistry, 45, 1049-1056 (1997) https://doi.org/10.1016/S0031-9422(97)00059-9
  10. Kiem, P. V., Minh, C. V., Huong, H. T., Nam, N. H., Lee, J. J., and Kim, Y. H., Pentacyclic triterpenoids from Mallotus apelta. Arch. Pharm. Res., 27, 1109-1113 (2004) https://doi.org/10.1007/BF02975113
  11. Lee, H. J., Park, S. Y., Kim, J. S., Song, H. M., Suh, M. E., and Lee, C. O., Synthesis and cytotoxicity evaluation of pyridin 2,3-f indole-2,4,9-trione and benz f indole-2,4,9-trione derivaties. Bioorg. Med. Chem., 11, 4791-4796 (2003) https://doi.org/10.1016/j.bmc.2003.08.005
  12. Likhitwitayawuid K., Angerhofer C. K., Cordell G. A., and Pezzuto J. M., Cytotoxic and antimalarial bisbenzylisoquinoline alkaloids from Stephania erecta. J. Nat. Prod., 56, 30-38 (1993) https://doi.org/10.1021/np50091a005
  13. Loi, D. T. (ed.), 'Glossary of Vietnamese Medicinal Plants'. Hanoi S&T Pub., 2001
  14. Ono, K., Nakane, H., Meng, Z. M., Ose, Y., Sakai, Y., and Mizuno, M., Differential inhibitory effects of various herb extracts on the activities of reverse transcriptase and various deoxyribonucleic acid (DNA) polymerases. Chem. Pharm. Bull., 37, 1810-1812 (1989) https://doi.org/10.1248/cpb.37.1810
  15. Shan, X. Q. and Feng, L. B., Chemical constituents of the roots of Mallotus apelta (Lour.) Muell-Arg.Acta Botanica Sinica, 27, 192-195 (1985)
  16. Zhao, J., Wang, X., and Zhang, X., The study on the antioxidant effect of root of Mallotus apelta in the rat model of liver fibrosis. Zhong Yao Cai, 25, 185-187 (2002)