TY - JOUR
T1 - Novel terpenoids of the fungus Aspergillus insuetus isolated from the Mediterranean sponge Psammocinia sp. collected along the coast of Israel
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 ).
PY - 2011/11/15
Y1 - 2011/11/15
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.
AB - 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.
KW - Aspergillus insuetus
KW - Drimane sesquiterpens
KW - Marine-derived fungi
KW - Meroteroenoids
KW - Psammocinia sp
KW - Sponge
UR - http://www.scopus.com/inward/record.url?scp=80055022317&partnerID=8YFLogxK
U2 - 10.1016/j.bmc.2011.05.045
DO - 10.1016/j.bmc.2011.05.045
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AN - SCOPUS:80055022317
SN - 0968-0896
VL - 19
SP - 6587
EP - 6593
JO - Bioorganic and Medicinal Chemistry
JF - Bioorganic and Medicinal Chemistry
IS - 22
ER -
