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

82 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 ).

UN SDGs

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

SDG 3 Good Health and Well-being

Keywords

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

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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

N1 - 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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N2 - 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.

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KW - Drimane sesquiterpens

KW - Marine-derived fungi

KW - Meroteroenoids

KW - Psammocinia sp

KW - Sponge

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ER -

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

Abstract

Bibliographical note

UN SDGs

Keywords

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