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Diplopimarane, a 20-nor-ent-Pimarane produced by the oak pathogen Diplodia quercivora

Andolfi, Anna and Maddau, Lucia and Basso, Sara and Linaldeddu, Benedetto Teodoro and Cimmino, Alessio and Scanu, Bruno and Deidda, Antonio and Tuzi, Angela and Evidente, Antonio (2014) Diplopimarane, a 20-nor-ent-Pimarane produced by the oak pathogen Diplodia quercivora. Journal of Natural Products, Vol. 77 (11), p. 2352-2360. ISSN 0163-3864. eISSN 1520-6025. Article.

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DOI: 10.1021/np500258r

Abstract

In this study a new 20-nor-ent-pimarane, named diplopimarane, was isolated together with sphaeropsidins A (9) and C (10), and (+)-epiepoformin (11) from organic crude extracts of Diplodia quercivora, a recently described oak pathogen originally found on declining Quercus canariensis trees in Tunisia. Diplopimarane was characterized as (1S,2R)-2,8,8-trimethyl-2-vinyl-1,2,3,4,5,6,7,8-octahydrophenanthrene-1,9,10-triol by spectroscopic, X-ray, optical, and chemical methods. It exhibited a wide range of activities including remarkable phytotoxicity on nonhost plants such as tomato cuttings, moderate antifungal activity against important plant pathogens, and moderate zootoxicity against Artemia salina. Its derivatives (2–4 and 6) were also tested for their phytotoxic and zootoxic activities. All these derivatives proved to be active against A. salina at 200 μg/mL, while 2 and 6 were also active on tomato cuttings. The other secondary metabolites (9, 10, and 11) herein reported for D. quercivora exhibited phytotoxic, antifungal, and zootoxic activity. This is the first report on the secondary metabolites secreted in vitro by this oak pathogen that could be key components of its adaptative strategies.

Item Type:Article
ID Code:10714
Status:Published
Refereed:Yes
Uncontrolled Keywords:Oak Pathogen, Diplodia quercivora, 20-nor-ent-pimarane (diplopimarane)
Subjects:Area 07 - Scienze agrarie e veterinarie > AGR/12 Patologia vegetale
Divisions:001 Università di Sassari > 01-a Nuovi Dipartimenti dal 2012 > Agraria
Publisher:American Chemical Society
ISSN: 0163-3864
eISSN:1520-6025
Copyright Holders:© 2014 The American Chemical Society and American Society of Pharmacognosy
Deposited On:28 Jan 2015 15:33

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