Butyrolactones from Aspergillus terreus.

Abstract

In the process development of lovastatin using Aspergillus terreus DRCC 152 in solid state fermentation, we have isolated a new butyrolactone-IV (3) along with the previously reported butyrolactone-I (1) and butyrolactone-II (2) produced under submerged conditions. The structure of compound 3 has been characterized as 3-hydroxy-5-[2-(1-hydroxy-1-methylethyl)-2(R)-2,3-dihydro-benzo[b]furan- 5 ylmethyl]-4-(4-hydroxyphenyl)-5-methoxycarbonyl-(5R)-2,5-dihydro-2 -furanone on the basis of spectroscopic studies. The absolute stereochemistry has been determined by single crystal X-ray diffraction studies. The cytotoxic and antibacterial activities of these compounds were determined.

Butyrolactone and Cycloheptanetrione from Mangrove-Associated Fungus <i>Aspergillus terreus</i>

“…1) Some different types of metabolites have been subsequently isolated from A. terreus strains. [2][3][4][5][6][7][8] Among these, some sesquiterpene lactone and butyrolactone compounds have exhibited potent acetylcholinesterase inhibition activity and cyclin-dependent kinases inhibition activity. 4,7) In our continuing search for new anti-tumor compounds from marine fungi, A. terreus was isolated from mangrove-associated marine sediments collected in Guangxi Zhuang Autonomous Region of China.…”

Butyrolactones from the Fungus Aspergillus terreus BCC 4651

“…An extract from Aspergillus terreus BCC 4651 exhibited moderate activity against Mycobacterium tuberculosis H37Ra (minimum inhibitory concentration (MIC) 25 mg/ml) and the 1 H-NMR spectrum of the extract showed a unique profile, therefore, we selected the strain for large scale fermentation and chemical investigation. This study led to the isolation of two new butenolides, butyrolactones VI (1) and VII (2), together with the known compounds, butylolactone I (3), 1) butyrolactone II (4), 2) butyrolactone IV (5), 3) butyrolactone V (6), 4) and aspernolide B (7). 5) A known diketopiperazine, bisdethiodi(methylthio)-acetylaranotin (8), [6][7][8] was also isolated as an antimycobacterial constituent of the culture extract.…”

Furandiones from an Endophytic <i>Aspergillus terreus</i> Residing in <i>Malus halliana</i>

“…Because of the structural similarity of furandiones 1 and 2 with butenolides such as butyrolactone I-IV, 15,16) aspernolides A and B, 17) which were also isolated form A. terreus, the biosynthetic pathway for the two furandiones was probably similar with those of butenolides. The reported feeding experiments on the biosynthesis of xenofuranones A and B 18) and butyrolactone I 19) have shown that these butenolide derivatives were produced via condensation of α-ketocarboxylic acids such as phenylpyruvic acid and p-hydroxyphenylpyruvic acid.…”