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. 2010 Apr;71(5-6):635-40.
doi: 10.1016/j.phytochem.2010.01.012. Epub 2010 Feb 25.

Bioactivity-guided isolation of cytotoxic sesquiterpenes of Rolandra fruticosa

Li Pan  1 , Daniel D Lantvit, Soedarsono Riswan, Leonardus B S Kardono, Hee-Byung Chai, Esperanza J Carcache de Blanco, Norman R Farnsworth, Djaja Doel Soejarto, Steven M Swanson, A Douglas Kinghorn
Affiliations

Bioactivity-guided isolation of cytotoxic sesquiterpenes of Rolandra fruticosa

Li Pan et al. Phytochemistry. 2010 Apr.

Abstract

Cytotoxicity-guided fractionation of a methanol extract of the leaves and twigs of Rolandra fruticosa using the HT-29 human colon cancer cell line led to the isolation of seven sesquiterpene lactones, including the hitherto unknown isorolandrolide, 13-methoxyisorolandrolide (1), and bourbonenolide, 2alpha,13-diacetoxy-4alpha-hydroxy-8alpha-isobutyroyloxybourbonen-12,6alpha-olide (2), as well as five known compounds, 13-acetoxyrolandrolide (3), 8-desacyl-13-acetoxyrolandrolide-8-O-tiglate (4), 2-epi-glaucolide E (5), 2alpha,13-diacetoxy-4alpha-hydroxy-8alpha-methacryloyloxybourbonen-12,6alpha-olide (6), and 2alpha,13-diacetoxy-4alpha-hydroxy-8alpha-tigloyloxybourbonen-12,6alpha-olide (7). The structures of the two sesquiterpenes were elucidated on the basis of spectroscopic methods. All isolates were evaluated for their cytotoxicity using the HT-29 cell line, and only 13-acetoxyrolandrolide (3) was found to possess a potent inhibitory effect against this cell line. Compounds 3, 5 and 6 were also tested in a NF-kappaB (p65) inhibition assay, and 3 was assessed in an in vivo hollow fiber assay.

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Key NOESY correlations of 1 and 2
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