Minor Pyranonaphthoquinones from the Apothecia of the Lichen Ophioparma ventosa

  • J Nat Prod. 2016 Apr 22;79(4):1005-11. doi: 10.1021/acs.jnatprod.5b01073.
Pierre Le Pogam  1 ,  Anne-Cécile Le Lamer  1  2 ,  Bandi Siva  3 ,  Béatrice Legouin  1 ,  Arnaud Bondon  4 ,  Jérôme Graton  5 ,  Denis Jacquemin  5  6 ,  Isabelle Rouaud  1 ,  Solenn Ferron  1 ,  Walter Obermayer  7 ,  K Suresh Babu  3 ,  Joël Boustie  1
Affiliations
  • 1. UMR CNRS 6226 ISCR PNSCM, Université de Rennes 1 , 2 Avenue du Professeur Léon Bernard, 35043 Rennes, France.
  • 2. Université Paul Sabatier Toulouse 3 , 118 Route de Narbonne, 31062 Toulouse, France.
  • 3. Division of Natural Products Chemistry CSIR, Indian Institute of Chemical Technology , Uppal Road, Hyderabad 500607, India.
  • 4. UMR CNRS 6226 ISCR ICMV, Université de Rennes 1 , Plate-forme PRISM, CS 34317, 35043 Rennes, France.
  • 5. UMR CNRS 6230, Chimie et Interdisciplinarité: Synthèse, Analyse et Modélisation (CEISAM), Université de Nantes , 2 Rue de la Houssinière, BP 92208, 44322 CEDEX 3 Nantes , France.
  • 6. Institut Universitaire de France , 1 Rue Descartes, 75231 CEDEX 05 Paris, France.
  • 7. Institut für Pflanzenwissenschaften, Karl-Franzens-Universität , Holteigasse 6, A-8010 Graz, Austria.
PMID: 26934105 DOI: 10.1021/acs.jnatprod.5b01073
Abstract

Four new quinonoid naphthopyranones, ophioparmin (1), 4-methoxyhaemoventosins (2a and 2b), and 4-hydroxyhaemoventosin (3), together with anhydrofusarubin lactone (4) and haemoventosin (5) were isolated from the fruiting bodies of Ophioparma ventosa, a crustose Lichen. Their structures were determined by spectroscopic analyses, and the absolute configurations of 1 and 2 were elucidated through experimental and calculated electronic circular dichroism analyses. Compounds 1, 2, and 5 exhibited moderate to strong antioxidant activities. The main pigment haemoventosin exhibited significant cytotoxicity toward a panel of nine cell lines.