Bioactive Ascochlorin Analogues from the Marine-Derived Fungus Stilbella fimetaria
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Bioactive Ascochlorin Analogues from the Marine-Derived Fungus Stilbella fimetaria. / Subko, Karolina; Kildgaard, Sara; Vicente, Francisca; Reyes, Fernando; Genilloud, Olga; Larsen, Thomas O.
In: Marine Drugs, Vol. 19, No. 2, 46, 2021.Research output: Contribution to journal › Journal article › Research › peer-review
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TY - JOUR
T1 - Bioactive Ascochlorin Analogues from the Marine-Derived Fungus Stilbella fimetaria
AU - Subko, Karolina
AU - Kildgaard, Sara
AU - Vicente, Francisca
AU - Reyes, Fernando
AU - Genilloud, Olga
AU - Larsen, Thomas O.
PY - 2021
Y1 - 2021
N2 - The marine-derived fungus Stilbella fimetaria is a chemically talented fungus producing several classes of bioactive metabolites, including meroterpenoids of the ascochlorin family. The targeted dereplication of fungal extracts by UHPLC-DAD-QTOF-MS revealed the presence of several new along with multiple known ascochlorin analogues (19-22). Their structures and relative configuration were characterized by 1D and 2D NMR. Further targeted dereplication based on a novel 1,4-benzoquinone sesquiterpene derivative, fimetarin A (22), resulted in the identification of three additional fimetarin analogues, fimetarins B-D (23-25), with their tentative structures proposed from detailed MS/HRMS analysis. In total, four new and eight known ascochlorin/fimetarin analogues were tested for their antimicrobial activity, identifying the analogues with a 5-chloroorcylaldehyde moiety to be more active than the benzoquinone analogue. Additionally, the presence of two conjugated double bonds at C-2'/C-3' and C-4'/C-5' were found to be essential for the observed antifungal activity, whereas the single, untailored bonds at C-4'/C-5' and C-8'/C-9' were suggested to be necessary for the observed antibacterial activity.
AB - The marine-derived fungus Stilbella fimetaria is a chemically talented fungus producing several classes of bioactive metabolites, including meroterpenoids of the ascochlorin family. The targeted dereplication of fungal extracts by UHPLC-DAD-QTOF-MS revealed the presence of several new along with multiple known ascochlorin analogues (19-22). Their structures and relative configuration were characterized by 1D and 2D NMR. Further targeted dereplication based on a novel 1,4-benzoquinone sesquiterpene derivative, fimetarin A (22), resulted in the identification of three additional fimetarin analogues, fimetarins B-D (23-25), with their tentative structures proposed from detailed MS/HRMS analysis. In total, four new and eight known ascochlorin/fimetarin analogues were tested for their antimicrobial activity, identifying the analogues with a 5-chloroorcylaldehyde moiety to be more active than the benzoquinone analogue. Additionally, the presence of two conjugated double bonds at C-2'/C-3' and C-4'/C-5' were found to be essential for the observed antifungal activity, whereas the single, untailored bonds at C-4'/C-5' and C-8'/C-9' were suggested to be necessary for the observed antibacterial activity.
KW - ascochlorin
KW - bioactivity
KW - dereplication
KW - meroterpenoids
KW - MS/HRMS
U2 - 10.3390/md19020046
DO - 10.3390/md19020046
M3 - Journal article
C2 - 33498522
AN - SCOPUS:85100511019
VL - 19
JO - Marine Drugs
JF - Marine Drugs
SN - 1660-3397
IS - 2
M1 - 46
ER -
ID: 258453001