New Butyrolactone From a Marine-Derived Fungus Aspergillus Sp

Abstract

Four compounds that belong to two structure types, namely dibenzylbutyrolactone and sesterterpenoids, were obtained from the extract of the strain Aspergillus sp. (2P-22), isolated from a marine sponge, Cliona chilensis. Among them, compound 1 was identified as new, namely butylrolactone-VI. The structures of these compounds were characterized on the basis of spectroscopic data. Biological activities of these fungal metabolites, are described.

γ-Butyrolactones from Aspergillus Species: Structures, Biosynthesis, and Biological Activities

“…Additionally, 1 exhibited weak cytotoxicity towards HL-60 (Caucasian promyelocytic leukemia) with an IC 50 value of 57.5 µM compared with ribavirin (IC 50 100.8 µM) and etoposide (0.042 µM) using the MTT assay [15]. It is noteworthy that 1 and 7 showed significant inhibition of the growth of crown gall tumors on potato discs with inhibition 46% and 64%, respectively, suggesting in vivo antitumor activity for both compounds [16].…”

“…Biogenetically, they are derived from oxidative deamination of amino acids, such as tyrosine and phenyl alanine [1,[11][12]. -Butyrolactones have attracted much attention for their cytotoxic [13][14][15][16], anti-malarial [17], anti-H1N1 [15], anti-cholinesterase [18], antimicrobial [1,[15][16]18], and antioxidant [19] activities, and as lipooxygenase and cyclin-dependent kinase inhibitors [15,19,[20][21][22][23]. Furthermore, from the viewpoint of synthetic organic chemistry, the -butyrolactones are interesting targets to test novel synthetic strategies.…”

Chilean benthic species identified as a new source of antibiotic substances

“…One identifies four seaweeds species as the producer of secondary metabolites that protect them from mussel's attachment (Pansch et al, 2009). Meanwhile, the other study describes a fungus isolated from the marine sponge Cliona chilensis, with the ability to produce antimicrobial and antitumor compounds (San-Martin et al, 2011). Therefore, the present report aims to increase the knowledge about Chilean benthic marine organisms as a natural source of bioactive compounds, especially in northern Chile.…”

Anti-inflammatory butenolide derivatives from the coral-derived fungus Aspergillus terreus and structure revisions of aspernolides D and G, butyrolactone VI and 4′,8′′-diacetoxy butyrolactone VI

“…On reviewing the literature, the pivotal 13 C NMR data for aspernolide D 10 [d C 30.5 (CH 2 , C-7 00 ) 89.1 (CH, C-8 00 ), and 72.4 (C, C-9 00 )] and butyrolactone VI 11 [d C 31.0 (CH 2 , C-7 00 ) 69.6 (CH, C-8 00 ), and 77.2 (C, C-9 00 )] showed close resemblances to those of compounds 5 and 7 (Table 2), respectively, which inspired us to investigate the regular 13 C NMR data of C-7 00 , C-8 00 , and C-9 00 in the 1-(2-hydroxyphenyl)-3-methylbutane-2,3-diol, 2-(2,3dihydrobenzofuran-2-yl)propan-2-ol, and 2,2-dimethylchroman-3-ol motifs for the butenolide derivatives. Take 1, 5, and 7 for examples (Table 2), their chemical shis at C-7 00 showed no obviously diagnostic differences; however, the chemical shis at C-8 00 and C-9 00 showed apparent differences [d C 81.2 (C-8 00 ) and 74.0 (C-9 00 ) for 1; d C 90.4 (C-8 00 ) and 72.5 (C-9 00 ) for 5; d C 70.4 (C-8 00 ) and 78.0 (C-9 00 ) for 7], corresponding to the predicted 13 C NMR data via "C + H NMR Predictor and DB" within the ACD/Labs soware suite, which was regarded as a powerful and useful tool to predict the chemical shis of a given input structure and resolve constitutional structure revisions.…”