Metabolic products of Aspergillus terreus. IX. Biosynthesis of butyrolactone derivatives isolated from strains IFO 8835 and 4100.

Nitta, Koh‐hei; Fujita, N.; Yoshimura, Takuro; Arai, Kunizo; Yamamoto, Yuzuru

doi:10.1248/cpb.31.1528

Cited by 70 publications

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“…9) These compounds were isolated by column chromatography (Sephadex LH-20, silica gel, and reversed-phase HPLC), wherein fractions were analyzed by TLC and 1 H-NMR. Compounds 3-5, and 7 were identified on the basis of the MS and NMR data as butyrolactone I, 1,3) butyrolactone II, 2,3) butyrolactone IV, 3) and aspernolide B, 5) respectively. All these butenolides were previously isolated from A. terreus.…”

Section: Resultsmentioning

confidence: 99%

“…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.…”

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Butyrolactones from the Fungus Aspergillus terreus BCC 4651

et al. 2010

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NoteAs part of our research program on the utilization of bioresouces in Thailand, we have been screening fungal extracts for in vitro assays inclusive of antimycobacterial and antiplasmodial activities. 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. We report herein the structure elucidation of the new compounds and biological activities of isolated compounds. Results and DiscussionInitial study of the cultures grown in a common liquid medium, Czapek-Dox broth, under shaking resulted in the isolation of the known compounds 3-5, 7, and 8. Further studies revealed that butyrolactone derivatives were efficiently produced when the fungus BCC 4651 was fermented in yeast extract sucrose medium (YES; a sucrose-rich liquid medium) under static conditions. The culture provided with two new compounds 1 and 2 along with 3, 5, 6 and terrein, which is one of the commonly occurring Aspergillus toxins. 9)These compounds were isolated by column chromatography (Sephadex LH-20, silica gel, and reversed-phase HPLC), wherein fractions were analyzed by TLC and 1 H-NMR. Compounds 3-5, and 7 were identified on the basis of the MS and NMR data as butyrolactone I, 1,3) butyrolactone II, 12) Methylation of 6 (MeI, K 2 CO 3 , N,N-dimethylformamide (DMF)) gave the dimethylated derivative 9, which was subsequently converted to the (S)-and (R)-a-methoxy-a-(trifluoromethyl)phenylacetic acid (MTPA) ester derivatives 10a and 10b, respectively. The Dd-values (d S -d R ) of the Mosher esters unambiguously indicated the 8ЉS-configuration (Fig. 1).Butyrolactone VI (1) was isolated as a colorless solid. The molecular formula was determined to be C 24 H 26 O 9 by high resolution-electrospray ionization-mass spectra (HR-ESI-MS). The IR spectrum showed broad and intense absorption bands at n max 3442 (broad) and 1739 cm Ϫ1. The 1 H-and 13 C-NMR spectra were similar to those of other butyrolactone Butyrolactones from the Fungus Aspergillus terreus BCC 4651Rachada HARITAKUN, Pranee RACHTAWEE, Rungtiwa CHANTHAKET, Nattawut BOONYUEN, and Masahiko ISAKA* National Center for Genetic Engineering and Biotechnology; 113 Thailand Science Park, Phaholyothin Road, Klong Luang, Pathumthani 12120, Thailand. Received July 16, 2010; accepted August 3, 2010; published online August 6, 2010 Two new butenolides, butyrolactones VI (1) and VII (2), were isolated together with six known compounds, but...

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Butyrolactones from the Fungus Aspergillus terreus BCC 4651

et al. 2010

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“…africanus IFO8835 [44]. Its biosynthesis in this organism has been elucidated [45] and involves conversion of phenylalanine or tyrosine to methyl phydroxyphenylpyruvate 3.1, two molecules of which are then condensed between positions 2 and 3'. The product 3.2 is lactonised, followed by isoprenylation in the last step, see Fig.…”

Section: Butyrolactone-imentioning

confidence: 99%

Inhibitors of Cyclin-Dependent Kinases as Anti-Cancer Therapeutics

Fischer

Lane²

2000

CMC

141

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Initiation, progression, and completion of the cell cycle are regulated by various cyclin-dependent kinases (CDKs), which are thus critical for cell growth. Tumour development is closely associated with genetic alteration and deregulation of CDKs and their regulators, suggesting that inhibitors of CDKs may be useful anticancer therapeutics. Indeed, early results suggest that transformed and normal cells differ in their requirement for e.g. cyclin/CDK2 and that it may be possible to develop novel antineoplastic agents devoid of the general host toxicity observed with conventional cystostatic drugs. Numerous active-site inhibitors of CDKs have been studied; the main limitation with these ATP antagonists is kinase specificity for CDKs. However, screening of compound collections, as well as rational design based on enzyme-ligand complex crystal structures, are now yielding pre-clinical candidates, particularly certain purine and flavonoid analogues, with impressive potency and selectivity. Natural CDK inhibitors (CKIs), e.g. the tumour suppressor gene products p16 INK4 , p21 WAF1 , and p27 KIP1 , form the starting point for the design of mechanism-based CDK inhibitors. A number of these small proteins have been dissected and inhibitory lead peptides amenable to peptidomimetic development have been identified. Conversion of these peptides into pharmaceutically useful molecules is greatly aided by the recent elucidation of CKI/CDK crystal and solution structures. Additional interaction sites on CDKs being exploited for the purposes of inhibitor design include: phosphorylation/dephosphorylation sites, macromolecular substrate binding site, CKS regulatory subunit binding sites, cyclin-binding site, cellular localisation domain, and destruction box. Finally, progress has recently been made in the application of antisense technology in order to target CDK activity.

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“…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. In addition, the biosynthesis of aspernolides A and B were probably an extension of butyrolactone I by modification of the side chain.…”

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confidence: 99%

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

Qiao

2012

Chem. Pharm. Bull.

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Two new furandiones named asperterone B (1) and C (2) together with four known metabolites (3-6) were isolated from the liquid culture of the endophytic fungus Aspergillus terreus MHL-P22 residing in the fresh leaves of Malus halliana. The structures of the new compounds were elucidated by analysis of their MS, IR, 1D-and 2D-NMR spectra. 1 and 2 showed moderate cytotoxic activities against human colorectal carcinoma SW1116 cells with IC 50 values of 57.5 and 71.0 µM, respectively. The biosynthetic pathway for 1, 2 and their analogues was also postulated and briefly discussed.

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Metabolic products of Aspergillus terreus. IX. Biosynthesis of butyrolactone derivatives isolated from strains IFO 8835 and 4100.

Cited by 70 publications

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Butyrolactones from the Fungus Aspergillus terreus BCC 4651

Butyrolactones from the Fungus Aspergillus terreus BCC 4651

Inhibitors of Cyclin-Dependent Kinases as Anti-Cancer Therapeutics

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

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