Antiproliferative Constituents of the Roots of Conyza canadensis

Boglárka Csupor-Löffler; Zsuzsanna Hajdú; István Zupkó; Judit Molnár; Peter Forgo; Andrea Vasas; Zoltán Kele; Judit Hohmann

doi:10.1055/s-0030-1270714

Planta Medica, Inhaltsverzeichnis

Planta Med 2011; 77(11): 1183-1188
DOI: 10.1055/s-0030-1270714

Lectures GA Conference

Original Papers
© Georg Thieme Verlag KG Stuttgart · New York

Antiproliferative Constituents of the Roots of Conyza canadensis

Boglárka Csupor-Löffler¹ , Zsuzsanna Hajdú¹ , István Zupkó² , Judit Molnár² , Peter Forgo¹ , Andrea Vasas¹ , Zoltán Kele³ , Judit Hohmann¹

¹Department of Pharmacognosy, University of Szeged, Szeged, Hungary
²Department of Pharmacodynamics and Biopharmacy, University of Szeged, Szeged, Hungary
³Department of Medical Chemistry, University of Szeged, Szeged, Hungary

Abstract

Bioassay-guided fractionation of the n-hexane and CHCl₃ phases of the methanol extract of the roots of Conyza canadensis (L.) Cronquist led to the isolation of two new dihydropyranones named conyzapyranone A (1) and B (2), and the known 4Z,8Z-matricaria-γ-lactone (3), 4E,8Z-matricaria-γ-lactone (4), 9,12,13-trihydroxy-10(E)-octadecenoic acid (5), epifriedelanol (6), friedeline (7), taraxerol (8), simiarenol (9), spinasterol (10), stigmasterol, β-sitosterol, and apigenin. The structures were determined by means of ESIMS and 1D and 2D NMR spectroscopy, including ¹H-¹H COSY, NOESY, HSQC, and HMBC experiments. The isolated compounds were evaluated for their antiproliferative activities and were demonstrated to exert considerable cell growth-inhibitory activity against human cervix adenocarcinoma (HeLa), skin carcinoma (A431), and breast adenocarcinoma (MCF-7) cells. Some of the active components, including 2, 4, and 10, proved to be substantially more potent against these cell lines than against noncancerous human foetal fibroblasts (MRC-5) and can therefore be considered selective antiproliferative natural products.

Key words

Conyza canadensis - Asteraceae - conyzapyranone A - B - antiproliferative activity - 2D NMR

Volltext

Referenzen

References

1 Grünwald J. Canadian fleabane. PDR for herbal medicines. Oxford; Wiley 2000: 144-145
2 Li T S C. Chinese and related North American herbs – phytopharmacology and therapeutic values. Boca Raton, London, New York, Washington; CRC Press 2002: 179-180
3 Duke J A, Bogenschutz-Godwin M J, Ottesen A R. Canada fleabane. Duke's handbook of medicinal plants of Latin America. Boca Raton, London, New York; CRC Press 2009: 225-227
4 Bohlmann F, Jakupovic J. 8-Oxo-α-Selinen und neue Scopoletin-Derivate aus Conyza-Arten. Phytochemistry. 1979; 18 1367-1370
5 Xie W D, Gao X, Jia Z J. A new acetylene and a new triterpenoid from Conyza canadensis. Arch Pharm Res. 2007; 30 547-551
6 Lenfeld J, Motl O, Trka A. Anti-inflammatory activity of extracts from Conyza canadensis. Pharmazie. 1986; 41 268-269
7 Czeczot H, Tudek B, Kusztelak J, Szymczyk T, Dobrowolska B, Glinkowska G, Malinowski J, Strzelecka H. Isolation and studies of the mutagenic activity in the Ames test of flavonoids naturally occurring in medical herbs. Mutat Res. 1990; 240 209-216
8 Mukhtar N, Iqbal K, Anis I, Malik A. Sphingolipids from Conyza canadensis. Phytochemistry. 2002; 61 1005-1008
9 Mukhtar N, Iqbal K, Malik A. Novel sphingolipids from Conyza canadensis. Chem Pharm Bull. 2002; 50 1558-1560
10 Ding X, Su Y, Guo H, Yang F, Mao H, Gao X, Zhu Z, Tu G. Phenylpropanoid esters from horseweed (Conyza canadensis) and their inhibitory effects on catecholamine secretion. J Nat Prod. 2010; 73 270-274
11 Hrutfiord B F, Hatheway W H, Smith D B. Essential oil of Conyza canadensis. Phytochemistry. 1988; 27 1858-1860
12 Réthy B, Csupor-Löffler B, Zupkó I, Hajdú Z, Máthé I, Hohmann J, Rédei T, Falkay G. Antiproliferative activity of Hungarian Asteraceae species against human cancer cell lines. Part I. Phytother Res. 2007; 21 1200-1208
13 Mossmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods. 1983; 65 55-63
14 Lam J. Polyacetylenes of Solidago virgaurea: their seasonal variation and NMR long-range spin coupling constants. Phytochemistry. 1971; 10 647-653
15 Oueslati M H, Jannet H B, Mighri Z, Chriaa J, Abreu P M. Phytochemical constituents from Salsola tetrandra. J Nat Prod. 2006; 69 1366-1369
16 Kundu J K, Rouf A S S, Nazmul Hossain M, Hasan C M, Rashid M A. Antitumor activity of epifriedelanol from Vitis trifolia. Fitoterapia. 2000; 71 577-579
17 Mahato S B, Kundu A P. ¹³C NMR spectra of pentacyclic triterpenoids – a compilation and some salient features. Phytochemistry. 1994; 37 1517-1575
18 Jutiviboonsuk A, Zhang H J, Kondratyuk T P, Herunsalee A, Chaukul W, Pezzuto J M, Fong H H S, Bunyapraphatsara N. Isolation and characterization of cancer chemopreventive compounds from Barringtonia maunwongythiae. Pharm Biol. 2007; 45 185-194
19 Yoo N H, Jang D S, Kim J S. Phytochemical constituents of the roots of Erigeron annuus. J Korean Soc Appl Biol Chem. 2008; 51 305-308
20 Kojima H, Sato N, Hatano A, Ogura H. Sterol glycosides from Prunella vulgaris. Phytochemistry. 1990; 29 2351-2355
21 Zheng G Q. Cytotoxic terpenoids and flavonoids from Artemisia annua. Planta Med. 1994; 60 54-57
22 Li X, Pan J, Gao K. γ-Pyranone derivatives and other constituents from Erigeron annuus. Pharmazie. 2006; 61 474-477
23 Christensen L P, Lam J. Acetylenes and related compounds in Asteraceae. Phytochemistry. 1991; 30 2453-2476

Prof. Judit Hohmann

Department of Pharmacognosy
University of Szeged

Eotvos u.6.

6720 Szeged

Hungary

Telefon: +36 62 54 64 53

Fax: +36 62 54 57 04

eMail: hohmann@pharm.u-szeged.hu