Conformational Behavior and Absolute Stereostructure of Two Phytotoxic Nonenolides from the Fungus Phoma herbarum

Rivero-Cruz, J. Fausto; Garcı́a-Aguirre, Genoveva; Cerda-Garcı́a-Rojas, Carlos M.; Mata, Rachel

doi:10.1016/s0040-4020(00)00469-5

Cited by 104 publications

(153 citation statements)

References 19 publications

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“…13) isolated from the pathogenic fungus Phoma herbarum have been reported as phytotoxic, causing significant inhibition of radicle growth of plant seedlings [84]. It was shown that in these compounds, both the presence of the diol group and the propyl side chain are necessary to the phytotoxic activity.…”

Section: Studies In Natural Products Chemistrymentioning

confidence: 99%

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Diversity and Ecological Significance of Fungal Endophyte Natural Products

Prado¹,

Li²,

Nay³

2012

Studies in Natural Products Chemistry

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Section: Studies In Natural Products Chemistrymentioning

confidence: 99%

“…The rearranged polycyclic sequoiatones (e.g., 84,85) and sequoiamonascins (e.g., 86, 87) (Fig. 23) have been isolated through brine shrimp lethality-guided fractionation from Aspergillus parasiticus associated to the inner bark of Sequoia sempervirens, a coast redwood tree [128].…”

Section: Chapter 8 Diversity and Ecological Significance Of Endophytimentioning

confidence: 99%

Diversity and Ecological Significance of Fungal Endophyte Natural Products

Prado¹,

Li²,

Nay³

2012

Studies in Natural Products Chemistry

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“…Many polyhydroxylated 10-membered macrolides that contain a disubstituted trans CÀC bond have been isolated and identified since the 1980s, including decarestrictines, [1] herbarumins, [2] microcar-palide, [3] an unnamed nonenolide, [4] and achaetolide (1, Scheme 1). [5] Their interesting structures and, at least in some cases, their biological activities, have prompted a number of synthetic studies.…”

Section: Introductionmentioning

confidence: 99%

Unexpected Facile Formation of an Achaetolide Dimer

Zhang

2012

Asian J Org Chem

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Ring‐closing metathesis (RCM)‐based approaches to achaetolide usually lead to smooth ring closures. In contrast, lactonization gave none of the expected monolactone, but instead a diolide was obtained as the predominant product. This result not only illustrates that the current method is a facile “one‐pot” route to dilactones, but it also demonstrates an unnoticed advantage of RCM over lactonization for the formation of the given ring system.

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“…Our interest was reinforced by the resemblance of 1 to other nonenolides of fungal origin previously prepared in this laboratory (structures 2-4). [7,8] Pinolidoxin 2 [9] and the closely related herbarumins 3 and 4 [10] are promising phytotoxic agents interfering with the defense metabolism of higher plants; they consist of a similar (E)-configured nonenolide skeleton decorated with hydroxyl groups and a hydrophobic appendage. [11] Therefore, it seemed appropriate to investigate if 2-4 and selected derivatives thereof also exhibit any appreciable microfilament disrupting capacity and, if so, to compare their efficacy with that of microcarpalide (1) as the lead compound in this series.…”

Section: Introductionmentioning

confidence: 99%

Total Synthesis and Evaluation of the Actin‐Binding Properties of Microcarpalide and a Focused Library of Analogues

Fürstner

Nagano

Müller

et al. 2007

Chemistry A European J

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A comparative investigation shows that hydroxylated 10-membered lactones modeled around the fungal metabolites microcarpalide (1) and pinolidoxin (2) are endowed with selective actin-binding properties. Although less potent than the marine natural product latrunculin A, which represents the standard in the field, nonenolides of this type are significantly less toxic and accommodate substantial structural editing. Most notable is the fact that even an intramolecular transesterification with formation of a hydroxylated butanolide skeleton does not annihilate their microfilament disrupting capacity. This finding calls for a reinvestigation of the biological profile of other fungal metabolites that embody a similar motif. Microcarpalide (1) serving as the calibration point for this comparative study was prepared by total synthesis based on ring-closing metathesis (RCM) as the key step. The chosen route favorably compares to previous approaches to this target and provides further support for the notion that the (E,Z)-configuration of a medium-sized cycloalkene can be controlled by proper choice of the catalyst as previously outlined by our group. 9-epi-Microcarpalide 26 and furanone 27 as representative examples of the "natural productlike" compounds investigated herein have been characterized by crystal structure analysis.

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Conformational Behavior and Absolute Stereostructure of Two Phytotoxic Nonenolides from the Fungus Phoma herbarum

Cited by 104 publications

References 19 publications

Diversity and Ecological Significance of Fungal Endophyte Natural Products

Diversity and Ecological Significance of Fungal Endophyte Natural Products

Unexpected Facile Formation of an Achaetolide Dimer

Total Synthesis and Evaluation of the Actin‐Binding Properties of Microcarpalide and a Focused Library of Analogues

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