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• Machado, F
• Yamamoto, R
• Zanoli, K
• Nocchi, S
• Novello, C
• Schuquel, I
• Sakuragui, C
• Luftmann, H
• Ueda-Nakamura, T
• Nakamura, C
• de Mello, J
• [+] on Google Scholar
• Machado, F
• Yamamoto, R
• Zanoli, K
• Nocchi, S
• Novello, C
• Schuquel, I
• Sakuragui, C
• Luftmann, H
• Ueda-Nakamura, T
• Nakamura, C
• de Mello, J
• [+] on PubMed
• Machado, F
• Yamamoto, R
• Zanoli, K
• Nocchi, S
• Novello, C
• Schuquel, I
• Sakuragui, C
• Luftmann, H
• Ueda-Nakamura, T
• Nakamura, C
• de Mello, J

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Molecules 2012, 17(2), 1852-1859; doi:10.3390/molecules17021852

Article

Evaluation of the Antiproliferative Activity of the Leaves from Arctium lappa by a Bioassay-Guided Fractionation

Fabio Bahls Machado ¹ , Rafael Eidi Yamamoto ² , Karine Zanoli ¹ , Samara Requena Nocchi ¹ , Cláudio Roberto Novello ³ , Ivânia Teresinha Albrecht Schuquel ⁴ , Cássia Mônica Sakuragui ⁵ , Heinrich Luftmann ⁶ , Tânia Ueda-Nakamura ¹ , Celso Vataru Nakamura ¹  and João Carlos Palazzo de Mello ^1,*

¹ Post-Graduate Program in Pharmaceutical Sciences, State University of Maringá, Av. Colombo, 5790, BR-87020-900, Maringá, PR, Brazil ² Department of Basic Sciences of Health, State University of Maringá, Av. Colombo, 5790, BR-87020-900, Maringá, PR, Brazil ³ Department of Pharmacy, State University of Maringá, Av. Colombo, 5790, BR-87020-900, Maringá, PR, Brazil ⁴ Department of Chemistry, State University of Maringá, Av. Colombo, 5790, BR-87020-900, Maringá, PR, Brazil ⁵ Federal University of Rio de Janeiro, Av. Pedro Calmon, 550, BR-21941-901, Rio de Janeiro, RJ, Brazil ⁶ Organic Chemistry Institute, University of Münster, Münster D-48149, Germany

* Author to whom correspondence should be addressed.

Received: 26 November 2011; in revised form: 17 January 2012 / Accepted: 1 February 2012 / Published: 14 February 2012

(This article belongs to the Section Natural Products)

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Abstract: Arctium lappa L. (Asteraceae) is used in folk medicine around the World, and shows several kinds of biological activity, particularly in vitro antitumor activity in different cell lines. This study evaluated the antiproliferative activity of the crude extract, semipurified fractions, and isolated compounds from the leaves of A. lappa, through bioassay-guided testing in Caco-2 cells. The crude extract was obtained with a 50% hydroethanolic extract and then partitioned with hexane, ethyl acetate, and n-butanol. The ethyl-acetate fraction (EAF) showed antiproliferative activity. This fraction was subjected to sequential column chromatography over silica gel to afford onopordopicrin (1), mixtures of 1 with dehydromelitensin-8-(4'-hydroxymethacrylate) (2), a mixture of 2 with dehydromelitensin (3), mixture of 1 with melitensin (4), dehydrovomifoliol (5), and loliolide (6). The compounds were identified by spectroscopic methods (NMR, MS) and comparison with literature data. This is the first description of compounds 2–5 from this species. The compounds tested in Caco-2 cells showed the following CC₅₀ (µg/mL) values: 1: 19.7 ± 3.4, 1 with 2: 24.6 ± 1.5, 2 with 3: 27 ± 11.7, 1 with 4: 42 ± 13.1, 6 30 ± 6.2; compound 5 showed no activity.

Keywords: Asteraceae; Arctium lappa; antiproliferative activity; sesquiterpene lactones

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