Taxonomy Driven Discovery of Polyketides from Aspergillus californicus

Yaojie Guo; Ling Ding; Simone Ghidinelli; Charlotte Held Gotfredsen; Mercedes de la Cruz; Thomas A. Mackenzie; Maria C. Ramos; Pilar Sánchez; Francisca Vicente; Olga Genilloud; Sonia Coriani; René W. Larsen; Jens C. Frisvad; Thomas O. Larsen

doi:10.1021/acs.jnatprod.0c00866

Taxonomy Driven Discovery of Polyketides from Aspergillus californicus

Yaojie Guo, Ling Ding, Simone Ghidinelli, Charlotte Held Gotfredsen, Mercedes de la Cruz, Thomas A. Mackenzie, Maria C. Ramos, Pilar Sánchez, Francisca Vicente, Olga Genilloud, Sonia Coriani, René W. Larsen, Jens C. Frisvad, Thomas O. Larsen^*

^*Corresponding author for this work

Research output: Contribution to journal › Journal article › Research › peer-review

Abstract

Five new polyketides were isolated from the rare filamentous fungus Aspergillus californicus IBT 16748 including calidiol A (1); three phthalide derivatives califuranones A₁, A₂, and B (2-4); and a pair of enantiomers (-)-calitetralintriol A (-5) and (+)-calitetralintriol A (+5) together with four known metabolites (6-9). The structures of the new products were established by extensive spectroscopic analyses including HRMS and 1D and 2D NMR. The absolute configurations of two diastereomers 2 and 3 and the enantiomers (-5) and (+5) were assigned by comparing their experimental and calculated ECD data, whereas the absolute configuration of 4 was proposed by analogy. Compound 1 showed moderate activity against methicillin-resistant Staphylococcus aureus.

Original language	English
Journal	Journal of Natural Products
Volume	84
Issue number	4
Pages (from-to)	979-985
Number of pages	7
ISSN	0163-3864
DOIs	https://doi.org/10.1021/acs.jnatprod.0c00866
Publication status	Published - 2021

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Guo, Y., Ding, L., Ghidinelli, S., Gotfredsen, C. H., de la Cruz, M., Mackenzie, T. A., Ramos, M. C., Sánchez, P., Vicente, F., Genilloud, O., Coriani, S., Larsen, R. W., Frisvad, J. C., & Larsen, T. O. (2021). Taxonomy Driven Discovery of Polyketides from Aspergillus californicus. Journal of Natural Products, 84(4), 979-985. https://doi.org/10.1021/acs.jnatprod.0c00866

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title = "Taxonomy Driven Discovery of Polyketides from Aspergillus californicus",

abstract = "Five new polyketides were isolated from the rare filamentous fungus Aspergillus californicus IBT 16748 including calidiol A (1); three phthalide derivatives califuranones A1, A2, and B (2-4); and a pair of enantiomers (-)-calitetralintriol A (-5) and (+)-calitetralintriol A (+5) together with four known metabolites (6-9). The structures of the new products were established by extensive spectroscopic analyses including HRMS and 1D and 2D NMR. The absolute configurations of two diastereomers 2 and 3 and the enantiomers (-5) and (+5) were assigned by comparing their experimental and calculated ECD data, whereas the absolute configuration of 4 was proposed by analogy. Compound 1 showed moderate activity against methicillin-resistant Staphylococcus aureus.",

author = "Yaojie Guo and Ling Ding and Simone Ghidinelli and Gotfredsen, {Charlotte Held} and {de la Cruz}, Mercedes and Mackenzie, {Thomas A.} and Ramos, {Maria C.} and Pilar S{\'a}nchez and Francisca Vicente and Olga Genilloud and Sonia Coriani and Larsen, {Ren{\'e} W.} and Frisvad, {Jens C.} and Larsen, {Thomas O.}",

year = "2021",

doi = "10.1021/acs.jnatprod.0c00866",

language = "English",

volume = "84",

pages = "979--985",

journal = "Journal of Natural Products",

issn = "0163-3864",

publisher = "American Chemical Society",

number = "4",

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TY - JOUR

T1 - Taxonomy Driven Discovery of Polyketides from Aspergillus californicus

AU - Guo, Yaojie

AU - Ding, Ling

AU - Ghidinelli, Simone

AU - Gotfredsen, Charlotte Held

AU - de la Cruz, Mercedes

AU - Mackenzie, Thomas A.

AU - Ramos, Maria C.

AU - Sánchez, Pilar

AU - Vicente, Francisca

AU - Genilloud, Olga

AU - Coriani, Sonia

AU - Larsen, René W.

AU - Frisvad, Jens C.

AU - Larsen, Thomas O.

PY - 2021

Y1 - 2021

N2 - Five new polyketides were isolated from the rare filamentous fungus Aspergillus californicus IBT 16748 including calidiol A (1); three phthalide derivatives califuranones A1, A2, and B (2-4); and a pair of enantiomers (-)-calitetralintriol A (-5) and (+)-calitetralintriol A (+5) together with four known metabolites (6-9). The structures of the new products were established by extensive spectroscopic analyses including HRMS and 1D and 2D NMR. The absolute configurations of two diastereomers 2 and 3 and the enantiomers (-5) and (+5) were assigned by comparing their experimental and calculated ECD data, whereas the absolute configuration of 4 was proposed by analogy. Compound 1 showed moderate activity against methicillin-resistant Staphylococcus aureus.

AB - Five new polyketides were isolated from the rare filamentous fungus Aspergillus californicus IBT 16748 including calidiol A (1); three phthalide derivatives califuranones A1, A2, and B (2-4); and a pair of enantiomers (-)-calitetralintriol A (-5) and (+)-calitetralintriol A (+5) together with four known metabolites (6-9). The structures of the new products were established by extensive spectroscopic analyses including HRMS and 1D and 2D NMR. The absolute configurations of two diastereomers 2 and 3 and the enantiomers (-5) and (+5) were assigned by comparing their experimental and calculated ECD data, whereas the absolute configuration of 4 was proposed by analogy. Compound 1 showed moderate activity against methicillin-resistant Staphylococcus aureus.

U2 - 10.1021/acs.jnatprod.0c00866

DO - 10.1021/acs.jnatprod.0c00866

M3 - Journal article

C2 - 33656895

SN - 0163-3864

VL - 84

SP - 979

EP - 985

JO - Journal of Natural Products

JF - Journal of Natural Products

IS - 4

ER -

Taxonomy Driven Discovery of Polyketides from Aspergillus californicus

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