Brominated polyunsaturated lipids with protein tyrosine phosphatase-1B inhibitory activity from Chinese marine sponge Xestospongia testudinaria

A new brominated polyunsaturated lipid, methyl (E,E)-14,14-dibromo-4,6,13-tetradecatrienoate (1), along with three known related analogues (2–4), were isolated from the Et2O-soluble portion of the acetone extract of Chinese marine sponge Xestospongia testudinaria treated with diazomethane. The structure of the new compound was elucidated by detailed spectroscopic analysis and by comparison with literature data. Compound 3 exhibited significant inhibitory activity against protein tyrosine phosphatase 1B (PTP1B), a key target for the treatment of type II diabetes and obesity, with an IC50 value of 5.30 ± 0.61 μM, when compared to the positive control oleanolic acid (IC50 = 2.39 ± 0.26 μM).

[1]  O. Taglialatela‐Scafati,et al.  Brominated polyunsaturated lipids from the Chinese sponge Xestospongia testudinaria as a new class of pancreatic lipase inhibitors. , 2014, European journal of medicinal chemistry.

[2]  N. Matsuura,et al.  Stimulators of adipogenesis from the marine sponge Xestospongia testudinaria , 2013 .

[3]  Zhenzhong Wang,et al.  A concise synthesis of xestospongic acid methyl ester with pancreatic lipase inhibitory activity , 2013, Journal of Asian natural products research.

[4]  M. Bourguet-Kondracki,et al.  Antifouling 26,27-cyclosterols from the Vietnamese marine sponge Xestospongia testudinaria. , 2013, Journal of natural products.

[5]  Cheng-Shi Jiang,et al.  Natural products possessing protein tyrosine phosphatase 1B (PTP1B) inhibitory activity found in the last decades , 2012, Acta Pharmacologica Sinica.

[6]  Yonghong Liu,et al.  Brominated aliphatic hydrocarbons and sterols from the sponge Xestospongia testudinaria with their bioactivities. , 2011, Chemistry and physics of lipids.

[7]  P. Proksch,et al.  Xestospongienols A–L, Brominated Acetylenic Acids from the Chinese Marine Sponge Xestospongia testudinaria , 2011 .

[8]  P. Proksch,et al.  Brominated polyunsaturated lipids and their stereochemistry from the Chinese marine sponge Xestospongia testudinaria , 2011 .

[9]  Bin Yang,et al.  Chemical and Biological Aspects of Marine Sponges of the Genus Xestospongia , 2010, Chemistry & biodiversity.

[10]  A. Combs Recent advances in the discovery of competitive protein tyrosine phosphatase 1B inhibitors for the treatment of diabetes, obesity, and cancer. , 2010, Journal of medicinal chemistry.

[11]  M. Tremblay,et al.  Lipidyl pseudopteranes A-F: isolation, biomimetic synthesis, and PTP1B inhibitory activity of a new class of pseudopteranoids from the Gorgonian Pseudopterogorgia acerosa. , 2008, Journal of natural products.

[12]  Sheng Zhang,et al.  PTP1B as a drug target: recent developments in PTP1B inhibitor discovery. , 2007, Drug discovery today.

[13]  F. Nan,et al.  O-methyl nakafuran-8 lactone, a new sesquiterpenoid from a hainan marine sponge Dysidea sp. , 2006, Journal of Asian natural products research.

[14]  Jiwu Chen,et al.  Discovery of novel inhibitor of human leukocyte common antigen-related phosphatase. , 2005, Biochimica et biophysica acta.

[15]  J. Kusari,et al.  Protein-tyrosine phosphatase-1B acts as a negative regulator of insulin signal transduction , 1998, Molecular and Cellular Biochemistry.

[16]  Butler,et al.  Isolation of xestosterol esters of brominated acetylenic fatty acids from the marine sponge xestospongia testudinaria , 1999, Journal of natural products.

[17]  Cimino,et al.  Further Petroformynes from Both Atlantic and Mediterranean Populations of the Sponge Petrosia ficiformis , 1998, Journal of natural products.

[18]  E. Delong,et al.  Brominated acetylenic fatty acids from Xestospongia sp., a marine spongebacteria association , 1995 .

[19]  M. Gavagnin,et al.  Further Structural Studies on the Petroformynes , 1995 .

[20]  S. Matsunaga,et al.  Antifungal Brominated C18 Acetylenic Acids from the Marine Sponge, Petrosia volcano Hoshino , 1993 .

[21]  M. Bourguet-Kondracki,et al.  Bioactive bromopolyacetylenes from the marine sponge Xestospongia testudinaria , 1992 .

[22]  D. Tucker,et al.  Further Acetylenic Acids from the Marine Sponge Xestospongia testudinaria , 1991 .

[23]  D. Tucker,et al.  A brominated bisacetylenic acid from the marine sponge Xestospongia testudinaria , 1985 .