4.7 Article

First Enantiospecific Syntheses of Marine Merosesquiterpenes Neopetrosiquinones A and B: Evaluation of Biological Activity

Journal

JOURNAL OF NATURAL PRODUCTS
Volume 78, Issue 5, Pages 1026-1036

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/np500975b

Keywords

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Funding

  1. Spanish Ministry of Science and Innovation [CTQ 2009-09932]
  2. Regional Government of Andalucia [P11-CTS-7651]
  3. Spanish Agency of International Cooperation and Development (AECID)
  4. FPU predoctoral fellowship (Ministry of Education, Culture and Sport)

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The first enantiospecific syntheses of neopetrosiquinones A (6) and)3 (7), two merosesquiterpenes isolated from the deep-water sponge Neopetrosia cf proxima, from the labdane diterpene trans-communic acid (10) have been achieved. A key step of the synthetic sequence is the simultaneous aromatization of the C ring and the benzylic oxidation on C-7 of an advanced intermediate, mediated by the oxygen-DDQ system. The in vitro antiproliferative activities of neopetrosiquinone B (7) and of the synthetic intermediates 8 and 9 against human breast (MCF-7), lung (A-549), and colon (T-84) tumor cell lines have been assayed. The most potent was compound 9 (IC50 = 4.1 mu M), which was twice as active as natural compound 7 (IC50 = 8.3 mu M) against A-549 cells. In addition, the treatment with these compounds resulted in an induction of apoptosis. These findings indicate that the terpene benzoquinones reported here might be potentially useful as anticancer agents.

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