Putaminoxins D and E from phoma putaminum

Evidente, Antonio; Capasso, Renato; Andolfi, Anna; Vurro, Maurizio; Zonno, Maria Chiara

doi:10.1016/s0031-9422(97)00879-0

Cited by 28 publications

(57 citation statements)

References 4 publications

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“…The latter observation can be connected with a change of propyl group at C-9 in stagonolide to a methyl group in stagonolide C. These results confirm that modifications at the C(2)À ÀC(4) moiety of the nonenolide ring induces a decrease or total loss of phytotoxicity. Furthermore, stagonolides C-F differ from the phytotoxic herbarumins I-III 168 or putaminoxins, nonenolides produced by Phoma putaminum, 169,171,172 pathogenic for the pasture weed Erigeron annus, in having a methyl group at C-9 instead of an n-propyl group, which appears to be an important structural feature for the latter two groups of phytotoxins. The functionality and conformation of the nonenolide ring are important for the activity of putaminoxins as well as closely related pinolidoxins, which are phytotoxic nonenolides isolated from cultures of Ascochyta pinodes Jones, a fungal pathogen for pea (Pisum sativum L.).…”

Section: Nonenolides Produced By Stagonospora Cirsiimentioning

confidence: 99%

Relationships between the stereochemistry and biological activity of fungal phytotoxins

2011

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Toxins produced by phytopathogenic fungi assume great importance because of their involvement in several plant diseases. Although such pathogens are known to have seriously damaged crops, forest, and environmental resources, they represent a very important tool to develop new environmentally friendly herbicides and fungicides. This review deals with the relationships between the biological activity of some phytotoxins produced by pathogenic fungi for major forest plants and for damaging weeds and their stereochemistry. In particular, the methods used to determine their relative and/or absolute configuration will be illustrated. These include the application of Mosher's and Murata's methods, X-ray diffractometric analysis, circular dichroism, and the use of computational methods to determine the theoretical optical rotatory power as well as the CD spectrum. The importance of determining the absolute configuration to achieve the total synthesis of some phytotoxins, interesting for their potential practical application, is also discussed.

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Section: Nonenolides Produced By Stagonospora Cirsiimentioning

confidence: 99%

Relationships between the stereochemistry and biological activity of fungal phytotoxins

2011

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“…Putaminoxin (35), putaminoxins B, D, E (36)(37)(38) Phoma putaminum Fungal pathogen [15][16][17] Colletofragarones A1, A2 (50,51) Colletotrichum fragariae Fungus [18] Mueggelone (gloeolactone) (39) Aphanizomenon flos-aquae (Gloeotrichia sp.) Cyanobacterium [8,9] Aspinolides A-C (1-3) Aspergillus chraceus (DSM-7428) Fungus [19] Sporostatin (M5032) (53) Sporormiella sp.…”

Section: Simple Nonanolides With Methyl and Oxygen Substituentsmentioning

confidence: 99%

“…; Penicillium canescens Fungus [12][13][14] Unnamed nonanolides 10-12 Cordyceps militaris (BCC 2816) Entomopathogenic fungus [29] Dictyosphaeric acids A, B (59, 60) Penicillium sp. (F01V25) Fungus [30] 8-O-Acetylmultiplolide A (13) 8-O-Acetyl-5,6-dihydro-5,6-epoxy-multiplolide A (14) 5,6-Dihydro-5,6-epoxymultiplolide A (15) 3,4-Deoxy-3,4-didehydromultiplolide A (16) Phomopsis sp. (NXZ-05) Endophytic fungus [31] Stagonolides A-I (44, 45, 17-23) Stagonospora cirsii Fungal pathogen [32][33][34] Curvulides A, B1, B2 (24)(25)(26) Unnamed nonanolide 27…”

Section: Simple Nonanolides With Methyl and Oxygen Substituentsmentioning

confidence: 99%

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Nonanolides of Natural Origin: Structure, Synthesis, and Biological Activity

Sun¹,

Lu²,

Ree³

et al. 2012

curr med chem

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Naturally occurring nonanolides (synonym decanolides) are a large family of secondary metabolites with an interesting 10- membered macrolide subunit. Metabolites of the nonanolide family have been found to have various biological activities, including cytotoxic, phytotoxic, antimalarial, antifungal, antibacterial, and antimicrofilament activities. An early review of the chemistry and bioactivity of nonanolides was presented in 1996, covering the literature published between 1975 and 1995. During the past decades, the broad spectrum of bioactivity and the intriguing structure of the medium-sized ring in nonanolide analogues have continuously drawn the attention of biologists and natural product and synthetic chemists, resulting in a great number of publications. This review summarizes in whole the recent progress in the field of the nonanolides of natural origin, aiming to give the readers a brief view of the compounds, concerning their natural occurrence, structural elucidation, biological activities, total synthesis, and structure-activity relationships. The article covers the literature published in the period from the beginning of 1996 to July 2011.

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“…It produced necrotic lesions in leaves of the globe artichoke, Cynara cardunculus at a concentration of 8 mg per droplet. 135,136 Shake-flask cultures of Paecilomyces varietii produce a phytotoxin 59 which is highly active against broadleaf weeds. It is named hydroxycornestin, a new member of the nonadride class.…”

Section: Phytotoxinsmentioning

confidence: 99%

Recent advances in chemical ecology

Harborne¹

1999

Nat. Prod. Rep.

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Putaminoxins D and E from phoma putaminum

Cited by 28 publications

References 4 publications

Relationships between the stereochemistry and biological activity of fungal phytotoxins

Relationships between the stereochemistry and biological activity of fungal phytotoxins

Nonanolides of Natural Origin: Structure, Synthesis, and Biological Activity

Recent advances in chemical ecology

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