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Cytotoxic Activity of Parthenin, a Sesquiterpene Isolated from a Crinum ensifolium  

Khoi, Nguyen Minh (National Institute of Medicinal Materials)
Dat, Nguyen Tien (Institute of Marine Biochemistry, Vietnam Academy of Science and Technology)
Na, Min-Kyun (College of Pharmacy, Yeungnam University)
Thuong, Phuong Thien (National Institute of Medicinal Materials)
Min, Byung-Sun (College of Pharmacy, Catholic University of Daegu)
Bae, Ki-Hwan (College of Pharmacy, Chungnam National University)
Publication Information
Natural Product Sciences / v.17, no.2, 2011 , pp. 100-103 More about this Journal
Abstract
Phytochemical study on the ethanol extract of a Crinum species by bioassay-guided fractionation resulted in the isolation of an active principle, which was determined as parthenin (1) on the basis of physicochemical and spectroscopic analyses. This is the first report on the existence of a sesquiterpenoid from Crinum ensifolium. Compound 1 was found to show strong cytotoxic activity against some cancer cell lines and strongly inhibit NF-${\kappa}$B activity with the $IC_{50}$ value of 1.82 ${\mu}M$.
Keywords
Crinum ensifolium; Amaryllidaceae; parthenin; cytotoxic activity; NF-${\kappa}$B inhibition;
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1 Luqman, S. and Pezzuto, J.M., NFkappaB: a promising target for natural products in cancer chemoprevention. Phytother. Res. 24, 949-963 (2010).
2 Herz, W., Watanabe, H., Miyazaki, M., and Kishida, Y., The structure of parthenin and ambrosin. J. Am. Chem. Soc. 84, 2601-2610 (1962).   DOI
3 Hooper, M., Kirby, G.C., Kulkarni, M.M., Kulkarni, S.N., Nagasampagi, B.A., O'Neill, M.J., Phillipson, J.D., Rojatkar, S.R., and Warhurst, D.C., Antimalarial activity of parthenin and its derivatives. Eur. J. Med. Chem. 25, 717-723 (1990).   DOI   ScienceOn
4 Ghosal, S., Saini, K.S., and Razdan, S., Crinum alkaloids: their chemistry and biology. Phytochemistry 24, 2141-2156 (1985).   DOI   ScienceOn
5 Cui, L., Thuong, P.T., Lee, H.S., Njamen, D., Mbafor, J.T., Fomum, Z.T., Lee, J., Kim, Y.H., and Oh, W.K., Four new chalcones from Erythrina abyssinica. Planta Med. 74, 422-426 (2008).   DOI   ScienceOn
6 Hehner, S.P., Hofmann, T.G., Dröge, W., and Schmitz, M.L., The antiinflammatory sesquiterpene lactone parthenolide inhibits NFkappa B by targeting the I kappa B kinase complex. J. Immunol. 163, 5617-5623 (1999).
7 Do, H.B., Dang, Q.C., Bui, X.C., Nguyen, T.D., and Do, T.D., The medicinal plants and animals of Vietnam. Publishing House for Science and Technology, Hanoi, Vietnam. Vol 2, pp. 351-353, 1018- 1020 (2004).
8 Do, T.L., The Vietnamese medicinal plants and remedies. Medicinal Publishing House, Eleventh edition, pp. 509-512 (2003).
9 Fennell, C.W. and Staden, J., Crinum species in traditional and modern medicine. J. Ethnopharmacol. 78, 15-26 (2001).   DOI   ScienceOn
10 Fernandes, M.B., Scotti, M.T., Ferreira, M.J.P., and Emerenciano, V.P., Use of self-organizing maps and molecular descriptors to predict the cytotoxic activity of sesquiterpene lactones. Eur. J. Med. Chem. 43, 2197-2205 (2008).   DOI   ScienceOn
11 Mabberly, D.J., 1990. The plant book. Cambridge University Press.
12 Dat, N.T., Lee, J.H., Lee, K., Hong, Y.S., Kim, Y.H., and Lee, J.J., Phenolic constituents of Amorpha fruticosa that inhibit $NF-{\kappa}B$ activation and related gene expression. J. Nat. Prod. 71, 1696-1700 (2008).   DOI   ScienceOn
13 Biswanath, D., Reddy, V.S., Krishnaiah, M., Sharma, A.V.S., Kumar, K.R., Rao, J.V., and Sridhar, V., Acetylated pseudoguaianolides from Parthenium hysterophorus and their cytotoxic activity. Phytochemistry 68, 2029-2034 (2007).   DOI   ScienceOn
14 Chen, Y., Bean, M.F., Chambers, C., Francis, T., Huddleston, M.J., Offen, P., Westley, J.W., and Carté, B.K., Timmermann, B.N., Arrivacins, novel pseudoguaianolide esters with potent angiotensin II binding activity from Ambrosia psilostachya. Tetrahedron 47, 4869-4878 (1991).   DOI   ScienceOn
15 Ramesh, C., Ravindranath, N., Biswanath, D., Prabhakar, A., Bharatam, J., Ravikumar, K., Kashinatham, A., and McMorris, T.C., Pseudoguaianolides from the flowers of Parthenium hysterophorus. Phytochemistry 64, 841-844 (2003).   DOI   ScienceOn
16 Salam, A.N.A., Mahmoud, Z.F., Ziesche, J., and Jakupovic, J., Sesquiterpene lactones from Ambrosia maritima (Damssissa). Phytochemistry 23, 2851-2853 (1984).   DOI   ScienceOn
17 Sohma, I., Fujiwara, Y., Sugita, Y., Yoshioka, A., Shirakawa, M., Moon, J.H., Takiguchi, S., Miyata, H., Yamasaki, M., Mori, M., and Doki, Y., Parthenolide, an NF-{kappa}B inhibitor, suppresses tumor growth and enhances response to chemotherapy in gastric cancer. Cancer Genomics Proteomics 8, 39-47 (2011).
18 Sun, Q., Shen, Y.H., Tian, J.M., Tang, J., Su, J., Liu, R.H., Li, H.L., Xu, X.K., and Zhang, W.D., Chemical constituents of Crinum asiaticum L. var. sinicum Baker and their cytotoxic activities. Chem. Biodiver. 6, 1751-1757 (2009).   DOI   ScienceOn
19 Nguyen, T.N.T., Titorenkova, T.V., Bankova, V.S., Handjieva, N.V., and Popov, S.S., Crinum L. (Amaryllidaceae). Fitoterapia 73, 183-208 (2002).   DOI   ScienceOn
20 Picman, J. and Picman, A.K., Treatment of dermatitis from parthenin. Contact Dermatitis 13, 9-13 (1985).   DOI   ScienceOn
21 Mew, D., Balza, F., Towers, G.H., and Levy, J.G., Anti-tumour effects of the sesquiterpene lactone parthenin. Planta Med. 45, 23-27 (1982).   DOI
22 Morikawa, T., Abdel-Halim, O.B., Matsuda, H., Ando, S., Muraoka, O., and Yoshikawa, M., Pseudoguaiane-type sesquiterpenes and inhibitors on nitric oxide production from Dichrocephala integrifolia. Tetrahedron 62, 6435-6442 (2006).   DOI   ScienceOn
23 Nam, N.H., Kim, Y., You, Y.J., Hong, D.H., Kim, H.M., and Ahn, B.Z., New constituents from Crinum latifolium with inhibitory effects against tube-like formation of human umbilical venous endothelial cells. Nat. Prod. Res. 18, 485-491 (2004).   DOI   ScienceOn