Archives of Pharmacal Research

, Volume 34, Issue 4, pp 527–531 | Cite as

C-7 oxygenated coumarins from the fruits of Micromelum minutum

  • Ratsami Lekphrom
  • Somdej Kanokmedhakul
  • Veerapol Kukongviriyapan
  • Kwanjai Kanokmedhakul
Research Articles Drug Design and Discovery

Abstract

A new 7-oxygenated coumarin, 7-demethylmurralonginol isovalerate (1), and a new natural product, murralonginol (2), together with seven known 7-oxygenated coumarins, murralonginol isovalerate (3), murralongin (4), micromelin (5), scopoletin (6), microminutin (7), murrangatin (8), and minumicrolin (9), were isolated from the fruits of Micromelum minutum. The structures of these compounds were established on the basis of their 1D and 2D NMR spectroscopic data. Among these isolates, compounds 2 and 49 exhibited cytotoxicity against cholangiocarcinoma cell line, KKU-100.

Key words

Micromelum minutum Rutaceae Coumarin Cytotoxicity Cholangiocarcinoma 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Asmah Susidarti, R., Rahmani, M., Ismail, H. B. M., Sukari, M. A., Yun Hin, T.-Y., Ee Cheng Lian, G., Ali, A. M., Kulip, J., and Waterman, P. G., A new coumarin and triterpenes from Malaysian Micromelum minutum. Nat. Prod. Res., 20, 145–151 (2006).PubMedCrossRefGoogle Scholar
  2. Cassady, J. M., Ojima, N., Chang, C., and McLaughlin, J. L., An investigation of the antitumor activity of Micromelum integerrimum (Rutaceae). J. Nat. Prod., 42, 274–278 (1979).PubMedCrossRefGoogle Scholar
  3. Collins, L. and Franzblau, S. G., Microplate alamar blue assay versus BACTEC 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium. Antimicrob. Agents Chemother., 4, 1004–1009 (1997).Google Scholar
  4. Das, S., Baruah, R. H., Sharma, R. P., Barua, J. N., Kulanthaivel, P., and Herz, W., 7-Methoxycoumarins from Micromelum minutum. Phytochemistry, 23, 2317–2321 (1984).CrossRefGoogle Scholar
  5. Imai, F., Kinoshita, T., Itai, A., and Sankawa, U., Acidcatalyzed rearrangement of an epoxy coumarin phebalosin the revised structure of murrlongin. Chem. Pharm. Bull., 34, 3978–3981 (1986).Google Scholar
  6. Ito, C., Furukawa, H., Ishii, H., Ishikawa, T., and Haginiwa, J., The chemical composition of Murraya paniculata. The structure of five new coumarins and one new alkaloid and the stereochemistry of murrangatin and related coumarins. J. Chem. Soc. Perkin Trans. 1, 2047–2055 (1990).CrossRefGoogle Scholar
  7. Kamperdick, C., Phuong, N. M., Sung, V. T., Schmidt, J., and Adam, G., Coumarins and dihydrocinnamic acid derivatives from Micromelum falcatum. Phytochemistry, 52, 1671–1676 (1999).CrossRefGoogle Scholar
  8. Lamberton, J. A., Price, J. R., and Redcliffe, A. H., Micromelin, a new coumarin from Micromelum minutum. Aust. J. Chem., 20, 973–979 (1967).CrossRefGoogle Scholar
  9. Lee, K. H. and Soine, T. O., Coumarins. X. Spectral studies on some linear furanocoumarins. J. Pharm. Sci., 58, 681–683 (1969).PubMedCrossRefGoogle Scholar
  10. Pongboonrod, S., Maitet Muang Thai. Kasembunakij Press, Bangkok, pp. 624, (1958).Google Scholar
  11. Rahmani, M., Susidarti, R. A., Ismail, H. B. M., Sukari, M. A., Yun Hin, T.-Y., Ee Cheng Lian, G., Ali, A. M., Kulip, J., and Waterman, P. G., Coumarins from Malaysian Micromelum minutum. Phytochemistry, 64, 873–877 (2003).PubMedCrossRefGoogle Scholar
  12. Skehan, P., Storeng, R., Scudiero, D., Monks, A., McMahon, J., Vistica, D., Warren, J. T., Bokesch, H., Kenney, S., and Boyd, M. R., New colorimetric cytotoxicity assay for anticancer-drug screening. J. Natl. Cancer Inst., 82, 1107–1112 (1990).PubMedCrossRefGoogle Scholar
  13. Smitinand, T., Thai Plant Names. Revised Edition, Prachachon Co. Limited, Bangkok, pp. 357, (2001).Google Scholar
  14. Tantishaiyakul, V., Pummangura, S., Chaichantipyuth, C., Ma, W. W., and McLaughlin, J. L., Phebalosin from the bark of Micromelum minutum. J. Nat. Prod., 49, 180–181 (1986).PubMedCrossRefGoogle Scholar
  15. Tantivatana, P., Ruangrungsi, N., Vaisiriroj, V., Lankin, D. C., Bhacca, N. S., Borris, R. P., Cordell, G. A., and Johnson, L. F., Microminutin, a novel cytotoxic coumarin from Micromelum minutum (Rutaceae). J. Org. Chem., 48, 268–270 (1983).CrossRefGoogle Scholar

Copyright information

© The Pharmaceutical Society of Korea and Springer Netherlands 2011

Authors and Affiliations

  • Ratsami Lekphrom
    • 1
  • Somdej Kanokmedhakul
    • 1
  • Veerapol Kukongviriyapan
    • 2
  • Kwanjai Kanokmedhakul
    • 1
  1. 1.Natural Products Research Unit, Department of Chemistry, and Center for Innovation in Chemistry, Faculty of ScienceKhon Kaen UniversityKhon KaenThailand
  2. 2.Department of Pharmacology, Faculty of MedicineKhon Kaen UniversityKhon KaenThailand

Personalised recommendations