Bartanol and bartallol, novel macrodiolides from Cytospora sp. ATCC 20502

Hanson, Karen L.; O'Neill, John A.; Simpson, Thomas J.; Willis, Christine L.

doi:10.1039/p19940002493

Cited by 10 publications

(4 citation statements)

References 10 publications

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“…7a ). Similar rearrangements have been suggested in the cases of aspyrone 23 42 and bartanol 24 43 (Fig. 7b ), and are also involved in ring-contracting mechanisms in the case of xenovulene A 44 , 45 .…”

Section: Discussionsupporting

confidence: 78%

Strobilurin biosynthesis in Basidiomycete fungi

et al. 2018

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Strobilurins from fungi are the inspiration for the creation of the β-methoxyacrylate class of agricultural fungicides. However, molecular details of the biosynthesis of strobilurins have remained cryptic. Here we report the sequence of genomes of two fungi that produce strobilurins and show that each contains a biosynthetic gene cluster, which encodes a highly reducing polyketide synthase with very unusual C-terminal hydrolase and methyltransferase domains. Expression of stpks1 in Aspergillus oryzae leads to the production of prestrobilurin A when the fermentation is supplemented with a benzoyl coenzyme A (CoA) analogue. This enables the discovery of a previously unobserved route to benzoyl CoA. Reconstruction of the gene cluster in A. oryzae leads to the formation of prestrobilurin A, and addition of the gene str9 encoding an FAD-dependent oxygenase leads to the key oxidative rearrangement responsible for the creation of the β-methoxyacrylate toxophore. Finally, two methyltransferases are required to complete the synthesis.

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Section: Discussionsupporting

confidence: 78%

Strobilurin biosynthesis in Basidiomycete fungi

et al. 2018

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“…including colletodiol 1,' colletoketol (or grahamimycin A) 2, configuration of the natural product but also provides valuable graham&ycin A, 3, grahamimycin B 4' colletallol 5 and colletol 6. 3 The structures of these metabolites have been elucidated by a combination of spectroscopic method^,^ X-ray crystallography and total synthesk6 Biosynthetic studies have established that colletodiol 1 is polyketide derived and is formed via c 6 -and C,-hydroxy acids of tri-and tetra-ketide origins respectively.' In the course of studies on the later stages of colletodiol biosynthesis in Cytospora,8 extracts of the culture filtrate were examined for the presence of minor metabolites which might provide further information on the biosynthetic pathway.…”

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confidence: 99%

Enantioselective synthesis of the 13-membered macrodiolide bartanol

O'Neill¹,

Lindell²,

Simpson³

et al. 1996

J. Chem. Soc., Perkin Trans. 1

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The enantioselective synthesis of the unusual 13-membered ring macrodiolide bartanol7 from poly [(R)hydroxybutyrate] is described confirming the 6R,llR,13R configuration of the natural product. The use of a novel ylide 29 with a MEM-ester protecting group is developed to enable a mild, one-pot cleavage of both the acid and alcohol protecting groups in 30 prior to macrocyclisation to the bartanol framework. The outcome of a Wittig chain extension reaction on a mixture of lactols 19 and 22 using this ylide was found to be dependent on the solvent.

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“…Several related polyketide macrodiolides were isolated from diverse microorganisms, including 2, colletoketol (grahamimysins A), colletoll, and colletallol from Colletotrichum capsici [6]; grahamimysins A 1 and B from Cytospora sp. [7][8][9]; 9,10-dihydrocolletodiol from Varicosporina ramulosa [10]; clonostachydiol from Clonostachys cylindrospora [11]; Gliocladium sp. [12] and Xylaria sp.…”

Section: Introductionmentioning

confidence: 99%

Halosmysin A, a Novel 14-Membered Macrodiolide Isolated from the Marine-Algae-Derived Fungus Halosphaeriaceae sp.

et al. 2020

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Halosmysin A, a new 14-membered macrodiolide with an unprecedented skeleton, was isolated from the fungus Halosphaeriaceae sp. OUPS-135D-4, which, in turn, was obtained from the marine algae Sargassum thunbergii. The chemical structure of the macrodiolide was elucidated using 1D and 2D NMR, as well as high resolution fast atom bombardment mass (HRFABMS) spectral analysis. The absolute stereochemistry was determined via chemical derivatization and comparison with a known compound, (6R,11R,12R,14R)-colletodiol. Additionally, halosmysin A was shown to be very potent against murine P388 leukemia, human HL-60 leukemia, and murine L1210 leukemia cell lines, with IC50 values ranging from 2.2 ± 3.1 to 11.7 ± 2.8 μM.

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Bartanol and bartallol, novel macrodiolides from Cytospora sp. ATCC 20502

Cited by 10 publications

References 10 publications

Strobilurin biosynthesis in Basidiomycete fungi

Strobilurin biosynthesis in Basidiomycete fungi

Enantioselective synthesis of the 13-membered macrodiolide bartanol

Halosmysin A, a Novel 14-Membered Macrodiolide Isolated from the Marine-Algae-Derived Fungus Halosphaeriaceae sp.

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