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Cytotoxic Sesquiterpenoid from the Seeds of Amomum xanthioides  

Kim, Ki-Hyun (Natural Products Laboratory, School of Pharmacy, Sungkyunkwan University)
Choi, Jung-Wook (Natural Products Laboratory, School of Pharmacy, Sungkyunkwan University)
Choi, Sang-Un (Korea Research Institute of Chemical Technology)
Lee, Kang-Ro (Natural Products Laboratory, School of Pharmacy, Sungkyunkwan University)
Publication Information
Natural Product Sciences / v.17, no.1, 2011 , pp. 10-13 More about this Journal
Abstract
As parts of our continuing search for biologically active compounds from medicinal plants, we investigated the constituents of the seeds of Amomum xanthioides and isolated a sesquiterpenoid, a nerolidol derivative from its MeOH extract. The chemical structure was determined by spectroscopic methods, including 1D and 2D NMR to be ($2S^*$,$2,$5)-2-(5'-ethenyltetrahydro-5'-methylfuran-2'-yl)-6-methylhept-5en-2-ol (1). Compound 1 was isolated for the first time from nature source. Compound 1 exhibited a good cytotoxicity against SK-OV-3 and SK-MEL-2 cells ($IC_{50}$: 16.7 and $8.6\;{\mu}M$, respectively) using a SRB bioassay. In this study, we also determined the absolute configuration of 2 reported in previous paper.
Keywords
Amomum xanthioides; Zingiberaceae; Sesquiterpenoid; Cytotoxicity;
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Times Cited By KSCI : 2  (Citation Analysis)
Times Cited By SCOPUS : 1
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1 Zhang, S., Lan, Y., and Qin, X., Gas chromatography analysis of the volatile oil of the imported amomi semen (Amomum xanthioides Wall ex Bak.) and adulterants (Hong Ke Sha, Cao Dou Kou, Hong Dou Kou, and Zhu Mu Sha). Yaowu Fenxi Zazhi 9, 219-222 (1989).
2 Kaiser, R. and Lamparsky, D., Constituents of Osmanthus absolute. Part 6. The (7S,10S,5E)- and (7R,10S,5E)-2,6,10-trimethyl-7,10-epoxy-2,5,11-dodecatrienes. Helv. Chim. Acta 62, 1887-1892 (1979).   DOI
3 Kim, K.H., Choi, J.W., Choi, S.U., Seo, E.-K., and Lee, K. R., Amoxantin A: A new bisnorlabdane diterpenoid from Amomum xanthioides. Bull. Korean Chem. Soc. 31, 1035-1037 (2010a).   DOI
4 Kim, K.H., Choi, J.W., Choi, S.U., and Lee, K.R., Terpene glycosides and cytotoxic constituents from the seeds of Amomum xanthioides. Planta Med. 76, 461-464 (2010b).   DOI
5 Kitajima, J. and Ishikawa, T., Water soluble constituents of Amomum seed. Chem. Pharm. Bull. 51, 890-893 (2003).   DOI   ScienceOn
6 Morikawa, T., Matsuda, H., Sakamoto, Y., Ueda, K., and Yoshikawa, M., New farnesane-type sesquiterpenes, hedychiols A and B 8,9-diacetate, and inhibitors of degranulation in RBL-2H3 cells from the rhizome of Hedychium coronarium. Chem. Pharm. Bull. 50, 1045-1049 (2002).   DOI   ScienceOn
7 Park, B.H. and Park, J.W., The protective effect of Amomum xanthoides extract against alloxan-induced diabetes through the suppression of NFkappaB activation. Exp. Mol. Med. 33, 64-68 (2001).   DOI   ScienceOn
8 Skehan, P., Stroreng, 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 anticacer-drug screening. J. Natl. Cancer Inst. 82, 1107-1112 (1990).   DOI
9 Blanc, M.C., Bradesi, P., and Casanova, J., Enantiomeric differentiation of acyclic terpenes by $^{13}C$ NMR spectroscopy using a chiral lanthanide shift reagent. Magn. Res. Chem. 43, 176-179 (2005).   DOI   ScienceOn
10 Choi, J.W., Kim, K.H., Lee, I.K., Choi, S.U., and Lee, K. R., Phytochemical Constituents of Amomum xanthioides. Nat. Prod. Sci. 15, 44-49 (2009).
11 Holmes, D.S., Ashworth, D.M., and Robinson, J.A., The bioconversion of (3RS,E)- and (3RS,Z)-nerolidol into oxygenated products by Streptomyces cinnamonensis. Possible implications for the biosynthesis of the polyether antibiotic monensin A?. Helv. Chim. Acta 73, 260-271 (1990).   DOI