Verticilide, a new ryanodine-binding inhibitor, produced by Verticillium sp. FKI-1033

Shiomi, Kazuro; Matsui, Ryosuke; Kakei, Atsuo; Yamaguchi, Yuichi; Masuma, Rokuro; Hatano, Hiroko; Arai, Noriko; Isozaki, Miki; Tanaka, Haruo; Kobayashi, Susumu; Turberg, Andreas; Ōmura, Satoshi

doi:10.1038/ja.2009.126

Cited by 44 publications

(43 citation statements)

References 18 publications

(16 reference statements)

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“…The IR absorption at 1650-1754 cm À1 suggested the presence of carbonyl groups in their structures. These data were similar to those of verticilide A1, 20,21 indicating that they were also likely to be cyclodepsipeptides.…”

Section: Isolationsupporting

confidence: 74%

“…20,21 Verticilides A2, A3 and B1 did not, however, inhibit this binding event at concentrations up to 100 mM. Verticilide B1 had the broad antimicrobial activity; active against Bacillus subtilis, …”

Section: Inhibition Of Cholesteryl Ester (Ce) Synthesis In Acat1-and mentioning

confidence: 99%

“…From the taxonomic study, strain FKI-2679 appeared very similar to strain FKI-1033, which was previously reported as a producer of the insecticidal verticilide A1. 20,21 Though they may be classified to the same species, strain FKI-2679 was isolated from a soil sample collected from Okinawa, Japan, whereas strain FKI-1033 was isolated from a sample collected from Kagoshima, Japan. 20,21 Furthermore, their secondary metabolites and productivity were different.…”

Section: Taxonomy Of Strain Fki-2679mentioning

confidence: 99%

“…14 During our screening programme, 18,19 four structurally related compounds were isolated from the culture broth of a fungal strain FKI-2679 as inhibitors of both ACAT isozymes in cell-based assays. One was identified as verticilide (verticilide A1 in this study), which had previously been reported to have insecticidal activity, 20,21 but the others were new compounds, named verticilides A2, A3 and B1 ( Figure 1). They are members of the cyclodepsipeptide family such as beauveriolides, [22][23][24] beauvericin, 25 enniatins 26 and bassianolide.…”

Section: Introductionmentioning

confidence: 99%

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New verticilides, inhibitors of acyl-CoA:cholesterol acyltransferase, produced by Verticillium sp. FKI-2679

et al. 2012

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Verticillium sp. FKI-2679, a soil isolate, was found to produce inhibitors of acyl-CoA:cholesterol acyltransferase (ACAT) in a cell-based assay using ACAT1-and ACAT2-expressing CHO cells. Three new compounds, verticilides A2, A3 and B1, were isolated along with a known compound, verticilide A1, from the fermentation broth of the fungus by solvent extraction, ODS column chromatography, silica gel column chromatography and preparative HPLC. Structure elucidation showed that these compounds were new cyclic depsipeptide. Verticilides A1, A2, A3 and B1 showed a degree of selectivity towards ACAT2, with IC 50 s 8.5-11-fold more potent than observed against ACAT1.

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Section: Isolationsupporting

confidence: 74%

Section: Inhibition Of Cholesteryl Ester (Ce) Synthesis In Acat1-and mentioning

confidence: 99%

Section: Taxonomy Of Strain Fki-2679mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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New verticilides, inhibitors of acyl-CoA:cholesterol acyltransferase, produced by Verticillium sp. FKI-2679

et al. 2012

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“…2) is a 24-membered cyclodepsipeptide isolated by Omura and coworkers in 2006 (24,25). Its ability to selectively inhibit insect RyR led to a 14-step synthesis (24) from the (R)-oxazolidone chiral auxiliary and N-Me-N-Boc alanine.…”

Section: Resultsmentioning

confidence: 99%

Rapid synthesis of cyclic oligomeric depsipeptides with positional, stereochemical, and macrocycle size distribution control

Batiste

Johnston

2016

Proc. Natl. Acad. Sci. U.S.A.

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Macrocyclic small molecules are attractive tools in the development of sensors, new materials, and therapeutics. Within early-stage drug discovery, they are increasingly sought for their potential to interact with broad surfaces of peptidic receptors rather than within their narrow folds and pockets. Cyclization of linear small molecule precursors is a straightforward strategy to constrain conformationally mobile motifs, but forging a macrocycle bond typically becomes more difficult at larger ring sizes. We report the development of a general approach to discrete collections of oligomeric macrocyclic depsipeptides using an oligomerization/macrocyclization process governed by a series of Mitsunobu reactions of hydroxy acid monomers. Ring sizes of 18, 24, 30, and 36 are formed in a single reaction from a didepsipeptide, whereas sizes of 24, 36, and 60 result from a tetradepsipeptide. The ring-size selectivity inherent to the approach can be modulated by salt additives that enhance the formation of specific ring sizes. Use of chemical synthesis to prepare the monomers suggests broad access to functionally and stereochemically diverse collections of natural product-like oligodepsipeptide macrocycles. Two cyclodepsipeptide natural products were prepared along with numerous unnatural oligomeric congeners to provide rapid access to discrete collections of complex macrocyclic small molecules from medium (18) to large (60) ring sizes.Mitsunobu | total synthesis | collective | macrocycle | oligomerization I nterest in the preparation and use of small molecules exhibiting macrocyclic rings is growing at a tremendous pace, driving the development of new approaches, new chemical reactions, and the underlying chemistry and tools (catalysts) to support them. Historically, studies of macrocyclization reactions have been guided by natural products bearing unusually large carbocycles or mediumand large-ring lactones, amides, and ethers. Fragmentation reactions of polycyclic molecules have long played a role in access to medium-sized macrocycles, whereas macrocyclizations to lactones and amides are often accomplished from linear precursors at high dilution. Insofar as these efforts were typically driven by the goal to prepare a specific macrocycle, often in the form relevant to a natural product synthesis or an engineered constraint to a peptide, absent from the field is an approach that provides rapid access to collections (1) of natural product-like macrocycles, particularly from stereochemically complex, functionally rich, linear precursors (2-6).Pioneers in this area have recorded some success (Fig. 1). Esterification reactions of activated hydroxy acids have led predominantly to diolides, (7-10) and in a single case, oligolides (11). Amidation reactions of activated polypeptides were central to the preparations of macrocyclic peptides by Rothe and Kreiss (12,13) and Wipf and coworkers (14, 15), but they were low yielding and size nonselective. Burke and coworkers (16,17) have shown that the efficiency of an 18-membered oligol...

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Mechanism‐Based Screening Strategies for Anthelmintic Discovery

Geary

2012

Parasitic Helminths

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Verticilide, a new ryanodine-binding inhibitor, produced by Verticillium sp. FKI-1033

Cited by 44 publications

References 18 publications

New verticilides, inhibitors of acyl-CoA:cholesterol acyltransferase, produced by Verticillium sp. FKI-2679

New verticilides, inhibitors of acyl-CoA:cholesterol acyltransferase, produced by Verticillium sp. FKI-2679

Rapid synthesis of cyclic oligomeric depsipeptides with positional, stereochemical, and macrocycle size distribution control

Mechanism‐Based Screening Strategies for Anthelmintic Discovery

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