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Planta Med 2004; 70(3): 244-249
DOI: 10.1055/s-2004-815542
Original Paper
Natural Product Chemistry
© Georg Thieme Verlag Stuttgart · New York

Euphopubescenol and Euphopubescene, Two New Jatrophane Polyesters, and Lathyrane-type Diterpenes from Euphorbia pubescens

Cláudia Valente1 , Madalena Pedro2 , José R. Ascenso3 , Pedro M. Abreu4 , Maria São José Nascimento2 , Maria-José U. Ferreira1
  • 1Centro de Estudos de Ciências Farmacêuticas (CECF), Faculdade de Farmácia da Universidade de Lisboa, Lisboa, Portugal
  • 2CEQOFFUP, Centro de Estudos de Química Orgânica, Fitoquímica e Farmacologia da Universidade do Porto, Faculdade de Farmácia, Porto, Portugal
  • 3Centro de Química Estrutural, Instituto Superior Técnico, Lisboa, Portugal
  • 4CQFB/REQUIMTE, Faculdade de Ciências e Tecnologia da Universidade Nova de Lisboa, Caparica, Portugal
This work was supported by FCT (grants: SFRH/BM/161/2000 SFRH/BD/1456/2000; I&D Nº226/94), POCTI (QCA III) and FEDER
Further Information

Publication History

Received: August 5, 2003

Accepted: November 22, 2003

Publication Date:
23 March 2004 (online)

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Abstract

The structures of euphopubescenol and euphopubescene, two new macrocyclic jatrophane diterpene polyesters, isolated from the whole dried plant of Euphorbia pubescens, were established as 5α,8α,15β-triacetoxy-3α-benzoyloxy-4α-hydroxy-9,14-dioxo-13βH-jatropha-6(17),11E-diene (1) and 3β,7β,8β,9α,14α,15β-hexaacetoxy-2βH-jatropha-5E,11E-diene (2) by 1D- and 2D-NMR (COSY, HMQC, HMBC and NOESY), IR, EI-MS and EI-FTICR-MS. Two known lathyrane derivatives, jolkinol A (3) and jolkinol A (4), whose 13C-NMR spectra were assigned, were also isolated. Compounds 1 - 3 have been evaluated for their ability to inhibit the in vitro growth of three human tumour cell lines representing different tumour types, MCF-7 (breast adenocarcinoma), NCI-H460 (non-small cell lung cancer) and SF-268 (CNS cancer). They inhibited both MCF-7 and NCI-H460 cell lines, with GI50 values ranging between 40.9 μM and 95.3 μM, but were found to be ineffective as growth inhibitors of the SF-268 cell line.

Key words

Euphorbia pubescens - Euphorbiaceae - jatrophane diterpenes - antitumour activity

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Prof. Maria José Umbelino Ferreira

Centro de Estudos de Ciências Farmacêuticas

Faculdade de Farmácia da Universidade de Lisboa

Av. das Forças Armadas

1600-083 Lisboa

Portugal

Fax: +351-21-7946470

Email: mjuferreira@ff.ul.pt