Cladobotric acids: Metabolites from cultures of Cladobotryum sp., semi-synthetic analogues and antibacterial activity

Trong Tuan Dao; Kathrine Williams; Kate M J de Mattos-Shipley; Zhongshu Song; Yuiko Takebayashi; Thomas J Simpson; James Spencer; Andrew M. Bailey; Chris L Willis

doi:10.1021/acs.jnatprod.1c01063

Cladobotric acids: Metabolites from cultures of Cladobotryum sp., semi-synthetic analogues and antibacterial activity

Trong Tuan Dao, Kathrine Williams, Kate M J de Mattos-Shipley, Zhongshu Song, Yuiko Takebayashi, Thomas J Simpson, James Spencer, Andrew M. Bailey, Chris L Willis

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Abstract

Three new polyketide-derived natural products, cladobotric acids G–I (1–3), and six known metabolites (4, 5, 8–11) were isolated from fermentation of the fungus Cladobotryum sp. grown on rice. Their structures were elucidated by extensive spectroscopic methods. Two metabolites, cladobotric acid A (4) and pyrenulic acid A (10), were converted to a series of new products (12–20) by semisynthesis. The antibacterial activities of all these compounds were investigated against the Gram-positive pathogen Staphylococcus aureus including methicillin-susceptible (MSSA), methicillin-resistant and vancomycin-intermediate (MRSA/VISA), and heterogeneous vancomycin-intermediate (hVISA) strains. Results of these antibacterial assays revealed structural features of the unsaturated decalins important for biological activity.

Original language	English
Pages (from-to)	572-580
Number of pages	9
Journal	Journal of Natural Products
Volume	85
Issue number	3
DOIs	https://doi.org/10.1021/acs.jnatprod.1c01063
Publication status	Published - 16 Feb 2022

Bibliographical note

Funding Information:
We are very grateful to MRC (MR/N029909/1) for financial support (for K.W., K.M.J.M.S., Z.S., and T.T.D.) as well as to BBSRC and EPSRC for funding instrumentation via the Bristol Centre for Synthetic Biology (BB/L01386X/1). We would also like to thank Dr. Katja M. Fisch for obtaining the strain Cladobotryum sp. CANU E1042.

Publisher Copyright:
© 2022 American Chemical Society and American Society of Pharmacognosy.

Research Groups and Themes

Bristol BioDesign Institute

Keywords

synthetic biology

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title = "Cladobotric acids: Metabolites from cultures of Cladobotryum sp., semi-synthetic analogues and antibacterial activity",

abstract = "Three new polyketide-derived natural products, cladobotric acids G–I (1–3), and six known metabolites (4, 5, 8–11) were isolated from fermentation of the fungus Cladobotryum sp. grown on rice. Their structures were elucidated by extensive spectroscopic methods. Two metabolites, cladobotric acid A (4) and pyrenulic acid A (10), were converted to a series of new products (12–20) by semisynthesis. The antibacterial activities of all these compounds were investigated against the Gram-positive pathogen Staphylococcus aureus including methicillin-susceptible (MSSA), methicillin-resistant and vancomycin-intermediate (MRSA/VISA), and heterogeneous vancomycin-intermediate (hVISA) strains. Results of these antibacterial assays revealed structural features of the unsaturated decalins important for biological activity.",

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author = "Dao, {Trong Tuan} and Kathrine Williams and {de Mattos-Shipley}, {Kate M J} and Zhongshu Song and Yuiko Takebayashi and Simpson, {Thomas J} and James Spencer and Bailey, {Andrew M.} and Willis, {Chris L}",

note = "Funding Information: We are very grateful to MRC (MR/N029909/1) for financial support (for K.W., K.M.J.M.S., Z.S., and T.T.D.) as well as to BBSRC and EPSRC for funding instrumentation via the Bristol Centre for Synthetic Biology (BB/L01386X/1). We would also like to thank Dr. Katja M. Fisch for obtaining the strain Cladobotryum sp. CANU E1042. Publisher Copyright: {\textcopyright} 2022 American Chemical Society and American Society of Pharmacognosy.",

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AU - Dao, Trong Tuan

AU - Williams, Kathrine

AU - de Mattos-Shipley, Kate M J

AU - Song, Zhongshu

AU - Takebayashi, Yuiko

AU - Simpson, Thomas J

AU - Spencer, James

AU - Bailey, Andrew M.

AU - Willis, Chris L

N1 - Funding Information: We are very grateful to MRC (MR/N029909/1) for financial support (for K.W., K.M.J.M.S., Z.S., and T.T.D.) as well as to BBSRC and EPSRC for funding instrumentation via the Bristol Centre for Synthetic Biology (BB/L01386X/1). We would also like to thank Dr. Katja M. Fisch for obtaining the strain Cladobotryum sp. CANU E1042. Publisher Copyright: © 2022 American Chemical Society and American Society of Pharmacognosy.

PY - 2022/2/16

Y1 - 2022/2/16

N2 - Three new polyketide-derived natural products, cladobotric acids G–I (1–3), and six known metabolites (4, 5, 8–11) were isolated from fermentation of the fungus Cladobotryum sp. grown on rice. Their structures were elucidated by extensive spectroscopic methods. Two metabolites, cladobotric acid A (4) and pyrenulic acid A (10), were converted to a series of new products (12–20) by semisynthesis. The antibacterial activities of all these compounds were investigated against the Gram-positive pathogen Staphylococcus aureus including methicillin-susceptible (MSSA), methicillin-resistant and vancomycin-intermediate (MRSA/VISA), and heterogeneous vancomycin-intermediate (hVISA) strains. Results of these antibacterial assays revealed structural features of the unsaturated decalins important for biological activity.

AB - Three new polyketide-derived natural products, cladobotric acids G–I (1–3), and six known metabolites (4, 5, 8–11) were isolated from fermentation of the fungus Cladobotryum sp. grown on rice. Their structures were elucidated by extensive spectroscopic methods. Two metabolites, cladobotric acid A (4) and pyrenulic acid A (10), were converted to a series of new products (12–20) by semisynthesis. The antibacterial activities of all these compounds were investigated against the Gram-positive pathogen Staphylococcus aureus including methicillin-susceptible (MSSA), methicillin-resistant and vancomycin-intermediate (MRSA/VISA), and heterogeneous vancomycin-intermediate (hVISA) strains. Results of these antibacterial assays revealed structural features of the unsaturated decalins important for biological activity.

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JO - Journal of Natural Products

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ER -

Cladobotric acids: Metabolites from cultures of Cladobotryum sp., semi-synthetic analogues and antibacterial activity

Abstract

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