Novel terpenoids of the fungus Aspergillus insuetus isolated from the Mediterranean sponge Psammocinia sp. collected along the coast of Israel

Elazar Cohen; Liat Koch; Kathy Myint Thu; Yocheved Rahamim; Yaniv Aluma; Micha Ilan; Oded Yarden; Shmuel Carmeli

doi:10.1016/j.bmc.2011.05.045

Novel terpenoids of the fungus Aspergillus insuetus isolated from the Mediterranean sponge Psammocinia sp. collected along the coast of Israel

Elazar Cohen, Liat Koch, Kathy Myint Thu, Yocheved Rahamim, Yaniv Aluma, Micha Ilan, Oded Yarden, Shmuel Carmeli^*

^*Corresponding author for this work

Department of Plant Pathology and Microbiology

Research output: Contribution to journal › Article › peer-review

70 Scopus citations

Abstract

Three novel meroterpenoids, insuetolides A-C (1-3) and four drimane sesquiterpenes, the new (E)-6-(4′-hydroxy-2′-butenoyl)-strobilactone A (4) and the known 2α, 9α, 11-trihydroxy-6-oxodrim-7-ene (5), strobilactone A (6) and (E,E)-6-(6′,7′-dihydroxy-2′,4′- octadienoyl)-strobilactone A (7), were isolated from the EtOAc extract of the culture medium of the marine-derived fungus Aspergillus insuetus (OY-207), which was isolated from the Mediterranean sponge Psammocinia sp. The structures of the compounds were determined by spectroscopic methods. Insuetolides A-C reveal a new carbon skeleton derived from the cyclization of farnesyl and 3, 5-dimethylorsellinic acid. Compounds 1, 6, and 7 exhibited anti-fungal activity towards Neurospora crassa with MIC values of 140, 242, and 162 μM, respectively; and compounds 3, 4, and 7 exhibited mild cytotoxicity towards MOLT-4 human leukemia cells.

Original language	English
Pages (from-to)	6587-6593
Number of pages	7
Journal	Bioorganic and Medicinal Chemistry
Volume	19
Issue number	22
DOIs	https://doi.org/10.1016/j.bmc.2011.05.045
State	Published - 15 Nov 2011

Bibliographical note

Funding Information:
We thank Noam Tal, The Mass Spectrometry Laboratory of The School of Chemistry, Tel Aviv University, for the mass spectra measurements. This study was supported by the Israel Science Foundation grant ( ISF 996/06 ).

Keywords

Aspergillus insuetus
Drimane sesquiterpens
Marine-derived fungi
Meroteroenoids
Psammocinia sp
Sponge

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.bmc.2011.05.045

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title = "Novel terpenoids of the fungus Aspergillus insuetus isolated from the Mediterranean sponge Psammocinia sp. collected along the coast of Israel",

abstract = "Three novel meroterpenoids, insuetolides A-C (1-3) and four drimane sesquiterpenes, the new (E)-6-(4′-hydroxy-2′-butenoyl)-strobilactone A (4) and the known 2α, 9α, 11-trihydroxy-6-oxodrim-7-ene (5), strobilactone A (6) and (E,E)-6-(6′,7′-dihydroxy-2′,4′- octadienoyl)-strobilactone A (7), were isolated from the EtOAc extract of the culture medium of the marine-derived fungus Aspergillus insuetus (OY-207), which was isolated from the Mediterranean sponge Psammocinia sp. The structures of the compounds were determined by spectroscopic methods. Insuetolides A-C reveal a new carbon skeleton derived from the cyclization of farnesyl and 3, 5-dimethylorsellinic acid. Compounds 1, 6, and 7 exhibited anti-fungal activity towards Neurospora crassa with MIC values of 140, 242, and 162 μM, respectively; and compounds 3, 4, and 7 exhibited mild cytotoxicity towards MOLT-4 human leukemia cells.",

keywords = "Aspergillus insuetus, Drimane sesquiterpens, Marine-derived fungi, Meroteroenoids, Psammocinia sp, Sponge",

author = "Elazar Cohen and Liat Koch and Thu, {Kathy Myint} and Yocheved Rahamim and Yaniv Aluma and Micha Ilan and Oded Yarden and Shmuel Carmeli",

note = "Funding Information: We thank Noam Tal, The Mass Spectrometry Laboratory of The School of Chemistry, Tel Aviv University, for the mass spectra measurements. This study was supported by the Israel Science Foundation grant ( ISF 996/06 ). ",

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doi = "10.1016/j.bmc.2011.05.045",

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AU - Cohen, Elazar

AU - Koch, Liat

AU - Thu, Kathy Myint

AU - Rahamim, Yocheved

AU - Aluma, Yaniv

AU - Ilan, Micha

AU - Yarden, Oded

AU - Carmeli, Shmuel

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KW - Meroteroenoids

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Novel terpenoids of the fungus Aspergillus insuetus isolated from the Mediterranean sponge Psammocinia sp. collected along the coast of Israel

Abstract

Bibliographical note

Keywords

UN SDGs

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