α-Glucosidase Inhibitors from the Marine-Derived Fungus Aspergillus flavipes HN4-13.

Three new butenolide derivatives, flavipesolides A-C (1-3), along with 13 known compounds (4-13, aspulvinone Q, monochlorosulochrin, and dihydrogeodin), were isolated from the marine-derived Aspergillus flavipes HN4-13 from a Lianyungang coastal sediment sample. The structures were elucidated by spectroscopic evidence. Compounds 4-6 and 9 were noncompetitive α-glucosidase inhibitors with Ki/IC50 values of 0.43/34, 2.1/37, 0.79/19, and 2.8/90 μM, respectively. Compounds 1-3, 8, 10, and 13 are mixed α-glucosidase inhibitors with Ki/IC50 values of (2.5, 19)/44, (3.4, 14)/57, (9.2, 4.7)/95, (6.3, 5.5)/55, (1.4, 0.60)/9.9, and (2.5, 7.2)/33 μM, respectively (IC50 101 μM for acarbose and 79 μM for 1-deoxynojirimycin).

[1]  J. Hao,et al.  New α-glucosidase inhibitors from marine algae-derived Streptomyces sp. OUCMDZ-3434 , 2016, Scientific Reports.

[2]  Haifeng Wang,et al.  Polyketide butenolide, diphenyl ether, and benzophenone derivatives from the fungus Aspergillus flavipes PJ03-11. , 2016, Bioorganic & medicinal chemistry letters.

[3]  Xue-Qiong Yang,et al.  Anti-phytopathogen, multi-target acetylcholinesterase inhibitory and antioxidant activities of metabolites from endophytic Chaetomium globosum , 2016, Natural product research.

[4]  Desheng Liu,et al.  Diphenyl derivatives from coastal saline soil fungus Aspergillus iizukae , 2014, Archives of Pharmacal Research.

[5]  Xiao‐Ming Li,et al.  New butenolide derivatives from the marine-derived fungus Paecilomyces variotii with DPPH radical scavenging activity , 2015 .

[6]  W. Dong,et al.  Butyrolactones from the Endophytic Fungus Aspergillus versicolor and their Anti-Tobacco Mosaic Virus Activity , 2015 .

[7]  T. Zhu,et al.  Structures and antiviral activities of butyrolactone derivatives isolated from Aspergillus terreus MXH-23 , 2014, Journal of Ocean University of China.

[8]  M. Kołaczkowski,et al.  Fungal ABC transporter-associated activity of isoflavonoids from the root extract of Dalea formosa. , 2013, Journal of natural products.

[9]  Hyun Ju Lee,et al.  An expedient synthesis of 3-arylmethylbutenolides from α-methylene-γ-butyrolactones: a useful synthetic application of palladium-catalyzed chelation-controlled oxidative arylation protocol , 2013 .

[10]  Tonghan Zhu,et al.  New Marine Natural Products of Microbial Origin from 2010 to 2013 , 2013 .

[11]  S. Nam,et al.  Antibacterial butenolides from the Korean tunicate Pseudodistoma antinboja. , 2012, Journal of natural products.

[12]  N. Nakajima,et al.  Isolation of a new phlorotannin, a potent inhibitor of carbohydrate-hydrolyzing enzymes, from the brown alga Sargassum patens. , 2012, Journal of agricultural and food chemistry.

[13]  N. Boonyuen,et al.  Butyrolactones from the fungus Aspergillus terreus BCC 4651. , 2010, Chemical & pharmaceutical bulletin.

[14]  K. Hong,et al.  Cyclic tripeptides from the halotolerant fungus Aspergillus sclerotiorum PT06-1. , 2010, Journal of natural products.

[15]  P. Stephens,et al.  Determination of the absolute configurations of pharmacological natural products via density functional theory calculations of vibrational circular dichroism: the new cytotoxic iridoid prismatomerin. , 2007, The Journal of organic chemistry.

[16]  T. Tsuji,et al.  Identification and Preliminary SAR Studies of (+)-Geodin as a Glucose Uptake Stimulator for Rat Adipocytes , 2005, The Journal of Antibiotics.

[17]  K. Sivasithamparam,et al.  New chlorinated diphenyl ethers from an Aspergillus species. , 2002, Journal of natural products.

[18]  F. Pietra.  Secondary metabolites from marine microorganisms: bacteria, protozoa, algae and fungi. Achievements and prospects. , 1997, Natural product reports.

[19]  T. Mosmann.  Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. , 1983, Journal of immunological methods.

[20]  K. Arai,et al.  Metabolic Products of Aspergillus terreus. IX. Biosynthesis of Butyrolactone Derivatives isolated from Strains IFO 8835 and 4100 , 1983 .

[21]  Yuzuru Yamamoto,et al.  Studies on the Metabolic Products of Aspergillus terreus. III. Metabolites of the Strain IFO 8835. (1) , 1976 .

[22]  S. Natori,et al.  Structures of Osoic Acids and Related Compounds, Metabolites of Oospora sulphurea-ochracea v. BEYMA. , 1962 .