Triterpenes from the Twigs of Mesua kunstleri
Abstract
The methanol extract from the twigs of Mesua kunstleri was dissolved with chloroform. The chloroform soluble portion was purified by chromatographic methods to yield eight known triterpenes: lupeol (1), betulin (2), lup-20(29)-en-3β,16β,28-triol (3), lupenone (4), lup-20(29)-en-3β,16β-diol (5), betulinaldehyde (6), betulinic acid (7) and 2a,3β-dihydroxylup-20(29)-en-28-oic acid (8). All structures were determined by 1D (1H and 13C) and 2D (HMQC and HMBC) NMR spectroscopic data. For known compounds were compared with those reported in literatures. Eight compounds (1-8) were isolated for the first time from the twigs of M. kunstleri.Keywords : Mesua kunstleri, Guttiferae, triterpenesReferences
Chan, G., Awang, K., Hadi, H. A. and Ng S. W. (2008). 6-[(E)-3,7-Dimethylocta-2,6-dienyl]-5,7-dihydroxy-8-(2-methylbutanoyl)-4-phenyl-2H-chromen-2-one from Mesua kunstleri King (Kosterm). Acta Crystallographica Section E, 64 (7), o1332.
Chan, G., Kamarudin, M. N. A., Hua, W. D. Z., Ismail, N. H., Abdul, L. F., Hasan, A., Awang, K. and Abdul, K. H. (2012). Mitigation of H2O2-induced mitochondrial-mediated apoptosis in NG108-15 cells by novel mesuagenin C from Mesua kunstleri (King) Kosterm. Evidence-Based Complementary and Alternative Medicin. 2012, 1-19.
De Barnardi, M., Vidari, G., Vita-Finzi, P., Mellerio, G., Gabetta, B. and Scilingo, A. (1987). New coumarins from Mesua ferrrea L. Pharmaceutisch Weekblad, Scientific Education, 9 (4), 231.
Gritsanapan, W. (1996). Plants, Medicinal Herbs versatile. Department of Pharmacognosy, Mahidol University, Bangkok, 25. (in Thai)
Gritsanapan, W., Sommanabandhu, A. and Suriyapananont, S. (1998). Gardening Herbs. Bangkok. Medical Media Printing House, 1. (in Thai)
Gunasekera, S. P. and Sultanbawwa, M. U. S. (1977). Chemical investigation of ceylonese plants. Part 20. Extractives of Mesua myrtifolia. Isolation and structure of a new triterpene hydroxyl-acid, myrtifolic acid. Journal of the Chemical Society, Perkin Transactions I, 6.
Kumar, N. S., Muthukuda, P. M. and Wazeer, M. I. M. (1985). A lupenediol from Euonymus revolutus. Phytochemistry, 24 (6), 1337-1340.
Ministry of Public Health, Office of the Basic Health Commission, (1998). Herb Garden in Primary Health Care. War Veteran's Welfare Publishing House, 28. (in Thai)
Monaco, P. and Previtera, L. (1984). Isoprenoids from the leaves of Quercus suber. Journal of Natural Products, 47 (4), 673-676.
Pongpangan, S. and Poobrasert, S. (1991). Edible and poisonous plants in Thai forests. O. S. Printing House, Bangkok, 9. (in Thai)
Razden, T. K., Harkar, S., Qadri, B., Qurishi, M. A., and Khuroo, M. A. (1988). Lupane derivatives from Skimmia laureola. Phytochemistry, 27 (6), 1890-1892.
Reynolds, W. F., Mclean, S., Popawski, J., Enriquez, R. G., Escobar, L. I. and Leon, I. (1986). Total assignment of 13C and 1H spectra of three isomeric triterpenol derivatives by 2D NMR: an investigation of the potential utility of 1H chemical shifts in structural investigations of complex natural products. Tetrahedron, 42 (13), 3419-3428.
Rittiwigrom, T. (2002). Xanthones from the stem bark of Garcinia nigrolineata. Master of Science Thesis in Organic Chemistry, Prince of Songkla University.
Singh, R., Gray, A. I. and Waterman, P. G. (1993). Mesuabixanthone-A and mesuabixanthone-B: novel bis-xanthones from the stembark of Mesua ferea (Guttiferae). Natural Products Letters, 3 (1), 53-58.
Sholichin, M., Yamasaki, K., Kasai, R. and Tanaka, O. (1980) 13C Nuclear magnetic resonance of lupane-type triterpenes, lupeol, betulin and betulinic acid. Chemical and Pharmaceutical Bulletin, 28, 1006-1008.
Tinto, W. F., Blair, L. C., Alli, A., Reynolds, W. F. and Mclean, S. (1992). Lupane triterpenoids of Salacia cordata. Journal of Natural Products, 55 (3), 395-398.
Verotta, L. (2003). Are acylphloroglucinols lead structures for the treatment of degenerative diseases?. Phytochemistry Reviews, 1, 398-407.
Wenkert, E., Baddeley, G. V., Burfitt, I. R. and Moreno, L. N. (1978). Carbon-13 nuclear magnetic resonance spectroscopy of naturally-occurring substances. LVII Triterpenes related to lupane and hopane. Organic Magnetic Resonance, 11 (7), 337-343.
Wilkomirski, B. (1985). Pentacyclic triterpene triols from Calendula officinalis flowers. Phytochemistry, 24 (12), 3066-3067.
Chan, G., Kamarudin, M. N. A., Hua, W. D. Z., Ismail, N. H., Abdul, L. F., Hasan, A., Awang, K. and Abdul, K. H. (2012). Mitigation of H2O2-induced mitochondrial-mediated apoptosis in NG108-15 cells by novel mesuagenin C from Mesua kunstleri (King) Kosterm. Evidence-Based Complementary and Alternative Medicin. 2012, 1-19.
De Barnardi, M., Vidari, G., Vita-Finzi, P., Mellerio, G., Gabetta, B. and Scilingo, A. (1987). New coumarins from Mesua ferrrea L. Pharmaceutisch Weekblad, Scientific Education, 9 (4), 231.
Gritsanapan, W. (1996). Plants, Medicinal Herbs versatile. Department of Pharmacognosy, Mahidol University, Bangkok, 25. (in Thai)
Gritsanapan, W., Sommanabandhu, A. and Suriyapananont, S. (1998). Gardening Herbs. Bangkok. Medical Media Printing House, 1. (in Thai)
Gunasekera, S. P. and Sultanbawwa, M. U. S. (1977). Chemical investigation of ceylonese plants. Part 20. Extractives of Mesua myrtifolia. Isolation and structure of a new triterpene hydroxyl-acid, myrtifolic acid. Journal of the Chemical Society, Perkin Transactions I, 6.
Kumar, N. S., Muthukuda, P. M. and Wazeer, M. I. M. (1985). A lupenediol from Euonymus revolutus. Phytochemistry, 24 (6), 1337-1340.
Ministry of Public Health, Office of the Basic Health Commission, (1998). Herb Garden in Primary Health Care. War Veteran's Welfare Publishing House, 28. (in Thai)
Monaco, P. and Previtera, L. (1984). Isoprenoids from the leaves of Quercus suber. Journal of Natural Products, 47 (4), 673-676.
Pongpangan, S. and Poobrasert, S. (1991). Edible and poisonous plants in Thai forests. O. S. Printing House, Bangkok, 9. (in Thai)
Razden, T. K., Harkar, S., Qadri, B., Qurishi, M. A., and Khuroo, M. A. (1988). Lupane derivatives from Skimmia laureola. Phytochemistry, 27 (6), 1890-1892.
Reynolds, W. F., Mclean, S., Popawski, J., Enriquez, R. G., Escobar, L. I. and Leon, I. (1986). Total assignment of 13C and 1H spectra of three isomeric triterpenol derivatives by 2D NMR: an investigation of the potential utility of 1H chemical shifts in structural investigations of complex natural products. Tetrahedron, 42 (13), 3419-3428.
Rittiwigrom, T. (2002). Xanthones from the stem bark of Garcinia nigrolineata. Master of Science Thesis in Organic Chemistry, Prince of Songkla University.
Singh, R., Gray, A. I. and Waterman, P. G. (1993). Mesuabixanthone-A and mesuabixanthone-B: novel bis-xanthones from the stembark of Mesua ferea (Guttiferae). Natural Products Letters, 3 (1), 53-58.
Sholichin, M., Yamasaki, K., Kasai, R. and Tanaka, O. (1980) 13C Nuclear magnetic resonance of lupane-type triterpenes, lupeol, betulin and betulinic acid. Chemical and Pharmaceutical Bulletin, 28, 1006-1008.
Tinto, W. F., Blair, L. C., Alli, A., Reynolds, W. F. and Mclean, S. (1992). Lupane triterpenoids of Salacia cordata. Journal of Natural Products, 55 (3), 395-398.
Verotta, L. (2003). Are acylphloroglucinols lead structures for the treatment of degenerative diseases?. Phytochemistry Reviews, 1, 398-407.
Wenkert, E., Baddeley, G. V., Burfitt, I. R. and Moreno, L. N. (1978). Carbon-13 nuclear magnetic resonance spectroscopy of naturally-occurring substances. LVII Triterpenes related to lupane and hopane. Organic Magnetic Resonance, 11 (7), 337-343.
Wilkomirski, B. (1985). Pentacyclic triterpene triols from Calendula officinalis flowers. Phytochemistry, 24 (12), 3066-3067.
Downloads
Published
2018-02-15
Issue
Section
Research Article
