Acremines A–F, novel secondary metabolites produced by a strain of an endophytic Acremonium, isolated from sporangiophores of Plasmopara viticola in grapevine leaves

Assante, Gemma; Dallavalle, Sabrina; Malpezzi, Luciana; Nasini, Gianluca; Burruano, Santa; Torta, Livio

doi:10.1016/j.tet.2005.05.094

Cited by 32 publications

(48 citation statements)

References 13 publications

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“…Further studies are needed to identify and characterize the secondary metabolites active in the antagonism produced by the strains of A. persicinum and A. sclerotigenum tested in this study. In this respect, only from A. persicinum strain A20, formerly named A. byssoides A20, twelve novel secondary metabolites (acremines A-N), involved in the inhibition of P. viticola sporangia germination, have been identified and characterized (Assante et al 2005;Arnone et al 2008Arnone et al , 2009. Moreover, in vivo tests are required to confirm the suitability of these organisms or their metabolites in the biocontrol of P. viticola in field.…”

Section: Discussionmentioning

confidence: 99%

“…& Curtis) Berl. & De Toni (Falk et al 1996;Kortekamp 1997;Bakshi et al 2001;Assante et al 2005;Musetti et al 2006;Burruano et al 2008). In this regard, Acremonium sp.…”

Section: Introductionmentioning

confidence: 99%

“…In this regard, Acremonium sp. strain A20, isolated from a leaf of asymptomatic grapevine cultivar Inzolia and identified wrongly as Acremonium byssoides W. Gams & G. Lim, has been reported as hyperparasite of P. viticola gamic and agamic structures (Burruano et al 2008) and producer of secondary metabolites, named acremines (A-N), that inhibit sporangia germination (Assante et al 2005;Arnone et al 2008Arnone et al , 2009.…”

Section: Introductionmentioning

confidence: 99%

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Identification of Acremonium isolates from grapevines and evaluation of their antagonism towards Plasmopara viticola

et al. 2015

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Some endophytic fungal genera in Vitis vinifera, including Acremonium, have been reported as antagonists of Plasmopara viticola. Endophytic Acremonium isolates from an asymptomatic grapevine cultivar Inzolia from Italy were identified by morphological features and multigene phylogenies of ITS, 18S and 28S genes, and their intra-specific genomic diversity was analyzed by RAPD analysis. Culture filtrates (CFs) obtained from Acremonium isolates were tested in vitro for their inhibitory activity against the P. viticola sporangia germination. Among 94 isolates, 68 belonged to the Acremonium persicinum and 26 to the Acremonium sclerotigenum. RAPD analysis grouped the A. persicinum isolates into 15 clusters and defined 31 different strains. The A. sclerotigenum isolates, instead, were clustered into 22 groups and represented 25 strains. All A. persicinum CFs inhibited sporangia germination of P. viticola, while not all those of A. sclerotigenum had inhibitory effect. A different degree of inhibition was observed between strains of the same species, while some strains of different species showed identical inhibitory effect. No correlation was found between RAPD groups and inhibitory activity in both Acremonium species.

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Section: Discussionmentioning

confidence: 99%

“…& Curtis) Berl. & De Toni (Falk et al 1996;Kortekamp 1997;Bakshi et al 2001;Assante et al 2005;Musetti et al 2006;Burruano et al 2008). In this regard, Acremonium sp.…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Identification of Acremonium isolates from grapevines and evaluation of their antagonism towards Plasmopara viticola

et al. 2015

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“…Fungi from the genus Acremonium have been reported from both terrestrial [1][2][3] and marine sources [4][5][6] and produce unique and biologically active secondary metabolites, the most well known being the antibiotic cephalosporin C. 7 Antioxidant hydroquinone derivatives 8 and a chlorinated polyketide 6 have been reported from an algal-derived Acremonium sp., while isolates derived from marine sponges have yielded alkaloids, 4,9 peptides, 10,11 or oxygenated metabolites. 12 In 2005, Nasini et al reported a series of 12 meroterpenoids, including acremines A (1), F (2), and N (3), from an endophytic strain of Acremonium byssoides isolated from sporangiospores of Plasmopara viticola in grapevine leaves.…”

mentioning

confidence: 99%

“…12 In 2005, Nasini et al reported a series of 12 meroterpenoids, including acremines A (1), F (2), and N (3), from an endophytic strain of Acremonium byssoides isolated from sporangiospores of Plasmopara viticola in grapevine leaves. 1,13,14 Malik et al described the isolation of a "norterpenoid" from the plant Periploca aphylla, 15 however the structure of this compound was later revised to that of acremine A (1) based on a synthetic study. 16 Acremine A has also been isolated from the fungus Myceliopthora lutea by Smetanina et al along with isoacremine D and two spiroacremines.…”

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confidence: 99%

Secondary Metabolites of the Sponge-Derived Fungus Acremonium persicinum

et al. 2013

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This study reports the isolation and characterization of six new acremine metabolites, 5-chloroacremine A (4), 5-chloroacremine H (5), and acremines O (6), P (7), Q (8), and R (9), together with the known acremines A (1), F (2), and N (3) from the fungus Acremonium persicinum cultured from the marine sponge Anomoianthella rubra. The relative configuration of acremine F (2) was determined by analyses of proton coupling constant values and NOESY data, and the absolute configuration confirmed as (1S, 4S, 6R) by X-ray crystallographic analysis of the borate ester derivative 15. Acremines O, P, and R were each shown to be of 8R configuration by 1H NMR analyses of MPA esters. The relative configurations suggested for acremines P and Q were each deduced by molecular modeling together with NOESY and coupling constant data. The 3 J H–C values in acremine P were measured using the pulse sequence EXSIDE, and the observed 3 J H8–C4 of 5.4 Hz and small 3 J H–C values (<1.5 Hz) from H-8 to C-10 and C-11 were fully consistent with stereoisomer 7a. For acremine Q, NOESY data combined with molecular modeling established the preferred diastereomer 8a.

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Secondary Mould Metabolites. Part 64. Acremines A—F, Novel Secondary Metabolites Produced by a Strain of an Endophytic Acremonium, Isolated from Sporangiophores of Plasmopara viticola in Grapevine Leaves.

et al. 2005

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Acremines A–F, novel secondary metabolites produced by a strain of an endophytic Acremonium, isolated from sporangiophores of Plasmopara viticola in grapevine leaves

Cited by 32 publications

References 13 publications

Identification of Acremonium isolates from grapevines and evaluation of their antagonism towards Plasmopara viticola

Identification of Acremonium isolates from grapevines and evaluation of their antagonism towards Plasmopara viticola

Secondary Metabolites of the Sponge-Derived Fungus Acremonium persicinum

Secondary Mould Metabolites. Part 64. Acremines A—F, Novel Secondary Metabolites Produced by a Strain of an Endophytic Acremonium, Isolated from Sporangiophores of Plasmopara viticola in Grapevine Leaves.

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