Planta Med 2013; 79(05): 361-364
DOI: 10.1055/s-0032-1328286
Natural Product Chemistry
Letters
Georg Thieme Verlag KG Stuttgart · New York

Phenolic Constituents from the Twigs of Euonymus alatus and Their Cytotoxic and Anti-inflammatory Activity

Ki Hyun Kim
1   Natural Products Laboratory, School of Pharmacy, Sungkyunkwan University, Suwon, Korea
,
Sang Keun Ha
2   Korea Food Research Institute, Sungnam, Korea
,
Sang Un Choi
3   Korea Research Institute of Chemical Technology, Daejeon, Korea
,
Sun Yeou Kim
4   College of Pharmacy, Gachon University, Incheon, Korea
,
Kang Ro Lee
1   Natural Products Laboratory, School of Pharmacy, Sungkyunkwan University, Suwon, Korea
› Author Affiliations
Further Information

Publication History

received 14 November 2012
revised 24 January 2013

accepted 30 January 2013

Publication Date:
06 March 2013 (online)

Abstract

A bioassay-guided fractionation and chemical investigation of the MeOH extract of the twigs of Euonymus alatus resulted in the isolation and identification of five new phenolic compounds, named alatusols A−E (15), together with six known compounds (611). The structures of these new compounds were elucidated through spectral analysis, including extensive 2D-NMR data, and their absolute configurations were determined by the modified Mosherʼs method. Compounds 13 and 79 showed consistent cytotoxicity against A549, SK-OV-3, SK-MEL-2, and HCT-15 cell lines with IC50 values of 15.20–29.81 µM. In addition, compounds 5 and 7 inhibited nitric oxide production in lipopolysaccharide-activated BV-2 cells with IC50 values of 22.77 and 32.52 µM, respectively.

Supporting Information

 
  • References

  • 1 Pack JH, Sung SH. Medicinal plants. Seoul: Shinil Books Co.; 2007: 446-447
  • 2 Jeong EJ, Yang H, Kim SH, Kang SY, Sung SH, Kim YC. Inhibitory constituents of Euonymus alatus leaves and twigs on nitric oxide production in BV2 microglia cells. Food Chem Toxicol 2011; 49: 1394-1398
  • 3 Lee TK, Kim DI, Han JY, Kim CH. Inhibitory effects of Scutellaria barbata D. Don. and Euonymus alatus Sieb. on aromatase activity of human leiomyomal cells. Immunopharmacol Immunotoxicol 2004; 26: 315-328
  • 4 Parka WH, Kim SH, Kim CH. A new matrix metalloproteinase-9 inhibitor 3, 4-dihydroxycinnamic acid (caffeic acid) from methanol extract of Euonymus alatus: isolation and structure determination. Toxicology 2005; 207: 383-390
  • 5 Chung TW, Moon SK, Chang YC, Ko JH, Lee YC, Cho G, Kim SH, Kim JG, Kim CH. Novel and therapeutic effect of caffeic acid and caffeic acid phenyl ester on hepatocarcinoma cells: complete regression of hepatoma growth and metastasis by dual mechanism. FASEB J 2004; 18: 1670-1681
  • 6 Ishikawa T, Fujimatu E, Kitajima J. Water-soluble constituents of anise: new glucosides of anethole glycol and its related compounds. Chem Pharm Bull 2002; 50: 1460-1466
  • 7 Kim KH, Choi SU, Kim YC, Lee KR. Tirucallane triterpenoids from Cornus walteri . J Nat Prod 2011; 74: 54-59
  • 8 Yang XW, Zhao PJ, Ma YL, Xiao HT, Zuo YQ, He HP, Li L, Hao XJ. Mixed lignan-neolignans from Tarenna attenuate . J Nat Prod 2007; 70: 521-525
  • 9 Otsuka H, Takeuchi M, Inoshiri S, Sato T, Yamasaki K. Phenolic compounds from Coix lachryma-jobi var. ma-yuen . Phytochemistry 1989; 28: 883-886
  • 10 Huang Z, Zhang W, Lin S, Liu C, Huang D, Song T, Lu L, Pei Y. Chemical constituents from roots of Incarvillea mairei . Zhongguo Zhongyao Zazhi 2009; 34: 1672-1675
  • 11 Sadhu SK, Khatun A, Ohtsuki T, Ishibashi M. Constituents from Hoya parasitica and their cell growth inhibitory activity. Planta Med 2008; 74: 760-763
  • 12 Lin RC, Skaltsounis AL, Seguin E, Tillequin F, Koch M. Phenolic constituents of Selaginella doederleinii . Planta Med 1994; 60: 168-170
  • 13 Kisiel W, Zielinska K. Sesquiterpenoids and phenolics from Lactuca perennis . Fitoterapia 2000; 71: 86-87
  • 14 Barakat HH, Nawwar AM, Buddrus J, Linscheid M. Niloticol, a phenolic glyceride and two phenolic aldehydes from the roots of Tamarix nilotica . Phytochemistry 1987; 26: 1837-1838
  • 15 Chen CY, Chang FR, Teng CM, Wu YC. Cheritamine, a new N-fatty acyl tryptamine and other constituents from the stems of Annona cherimola . J Chin Chem Soc 1999; 46: 77-86
  • 16 Skehan P, Storeng R, Scudiero D, Monks A, Mcmahon J, Vistica D, Warren JT, Bokesch H, Kenney S, Boyd MR. New colorimetric cytotoxicity assay for anticancer-drug screening. J Natl Cancer Inst 1990; 82: 1107-1112