Structure and cytotoxicity of arnamial and related fungal sesquiterpene aryl esters

Mathias Misiek; Jessica Williams; Kathrin Schmich; Wolfgang Hüttel; Irmgard Merfort; Christine E. Salomon; Courtney C. Aldrich; Dirk Hoffmeister

doi:10.1021/np900314p

Structure and cytotoxicity of arnamial and related fungal sesquiterpene aryl esters

Mathias Misiek, Jessica Williams, Kathrin Schmich, Wolfgang Hüttel, Irmgard Merfort, Christine E. Salomon, Courtney C. Aldrich, Dirk Hoffmeister

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Abstract

We report on the structure elucidation of arnamial, a new Δ^2,4-protoilludane everninate ester from the fungus Armillaria mellea, and on the apoptotic activity of arnamial as well as the cytotoxic activity of structurally related compounds on selected human cancer cells. Arnamial showed cytotoxicity against Jurkat T cells, MCF-7 breast adenocarcinoma, CCRFCEM lymphoblastic leukemia, and HCT-116 colorectal carcinoma cells at IC₅₀ ) 3.9, 15.4, 8.9, and 10.7 μM, respectively, and the related aryl ester melledonal C showed cytotoxic activity against CCRF-CEM cells (IC₅₀ ) 14.75 μM). [1,2-13C₂]Acetate feeding supports a polyketide origin of the orsellinic acid moiety of arnamial.

Original language	English (US)
Pages (from-to)	1888-1891
Number of pages	4
Journal	Journal of Natural Products
Volume	72
Issue number	10
DOIs	https://doi.org/10.1021/np900314p
State	Published - Oct 23 2009

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title = "Structure and cytotoxicity of arnamial and related fungal sesquiterpene aryl esters",

abstract = "We report on the structure elucidation of arnamial, a new Δ2,4-protoilludane everninate ester from the fungus Armillaria mellea, and on the apoptotic activity of arnamial as well as the cytotoxic activity of structurally related compounds on selected human cancer cells. Arnamial showed cytotoxicity against Jurkat T cells, MCF-7 breast adenocarcinoma, CCRFCEM lymphoblastic leukemia, and HCT-116 colorectal carcinoma cells at IC50 ) 3.9, 15.4, 8.9, and 10.7 μM, respectively, and the related aryl ester melledonal C showed cytotoxic activity against CCRF-CEM cells (IC50 ) 14.75 μM). [1,2-13C2]Acetate feeding supports a polyketide origin of the orsellinic acid moiety of arnamial.",

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AU - Misiek, Mathias

AU - Williams, Jessica

AU - Schmich, Kathrin

AU - Hüttel, Wolfgang

AU - Merfort, Irmgard

AU - Salomon, Christine E.

AU - Aldrich, Courtney C.

AU - Hoffmeister, Dirk

PY - 2009/10/23

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N2 - We report on the structure elucidation of arnamial, a new Δ2,4-protoilludane everninate ester from the fungus Armillaria mellea, and on the apoptotic activity of arnamial as well as the cytotoxic activity of structurally related compounds on selected human cancer cells. Arnamial showed cytotoxicity against Jurkat T cells, MCF-7 breast adenocarcinoma, CCRFCEM lymphoblastic leukemia, and HCT-116 colorectal carcinoma cells at IC50 ) 3.9, 15.4, 8.9, and 10.7 μM, respectively, and the related aryl ester melledonal C showed cytotoxic activity against CCRF-CEM cells (IC50 ) 14.75 μM). [1,2-13C2]Acetate feeding supports a polyketide origin of the orsellinic acid moiety of arnamial.

AB - We report on the structure elucidation of arnamial, a new Δ2,4-protoilludane everninate ester from the fungus Armillaria mellea, and on the apoptotic activity of arnamial as well as the cytotoxic activity of structurally related compounds on selected human cancer cells. Arnamial showed cytotoxicity against Jurkat T cells, MCF-7 breast adenocarcinoma, CCRFCEM lymphoblastic leukemia, and HCT-116 colorectal carcinoma cells at IC50 ) 3.9, 15.4, 8.9, and 10.7 μM, respectively, and the related aryl ester melledonal C showed cytotoxic activity against CCRF-CEM cells (IC50 ) 14.75 μM). [1,2-13C2]Acetate feeding supports a polyketide origin of the orsellinic acid moiety of arnamial.

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Structure and cytotoxicity of arnamial and related fungal sesquiterpene aryl esters

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