Monoglycerides from the brown alga Sargassum sagamianum:: Isolation, synthesis, and biological activity

被引:38
作者
Chang, Hyeun Wook [2 ]
Jang, Kyoung Hwa [1 ,3 ]
Lee, Doohyun [1 ]
Kang, Hee Ryong [1 ]
Kim, Tae-Yoon [4 ]
Lee, Bong Ho [5 ]
Choi, Byoung Wook [5 ]
Kim, Sanghee [1 ,3 ]
Shin, Jongheon [1 ,3 ]
机构
[1] Seoul Natl Univ, Coll Pharm, Seoul 151742, South Korea
[2] Youngnam Univ, Coll Pharm, Gyeongsangbuk 712749, South Korea
[3] Seoul Natl Univ, Inst Nat Prod Res, Seoul 151742, South Korea
[4] Catholic Univ Korea, Dept Dermatol, Seoul 137040, South Korea
[5] Hanbat Natl Univ, Dept Biotechnol, Taejon 305719, South Korea
关键词
polyunsaturated fatt acid-derived; monoglycerides; brown alga; 1-octadecatetraenoyl glycerol; synthesis; bioactivity; inhibition of phospholipase A2; inhibition of cyclooxygenase-2;
D O I
10.1016/j.bmcl.2008.05.008
中图分类号
R914 [药物化学];
学科分类号
100701 [药物化学];
摘要
Polyunsaturated fatty acid-derived monoglycerides were characterized from the marine brown alga Sargassum sagamianum, collected from Jeju Island, Korea. A new compound of this structural class was isolated and determined to be 1-octadecatetraenoyl glycerol, by combined spectroscopic methods. Based on the structures and bioactivity of these compounds, a series of monoglycerides were synthesized using glycerol and various fatty acids. Several compounds exhibited moderate to significant inhibition of phospholipase A(2) and cyclooxygenase-2. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3589 / 3592
页数:4
相关论文
共 22 条
[1]
Interfacial enzymology:: The secreted phospholipase A2-paradigm [J].
Berg, OG ;
Gelb, MH ;
Tsai, MD ;
Jain, MK .
CHEMICAL REVIEWS, 2001, 101 (09) :2613-2653
[2]
Marine natural products [J].
Blunt, John W. ;
Copp, Brent R. ;
Hu, Wan-Ping ;
Munro, Murray H. G. ;
Northcote, Peter T. ;
Prinsep, Michele R. .
NATURAL PRODUCT REPORTS, 2007, 24 (01) :31-86
[3]
Secreted phospholipase A2 inhibitors are also potent blockers of binding to the M-type receptor [J].
Boilard, Eric ;
Rouault, Morgane ;
Surrel, Fanny ;
Le Calvez, Catherine ;
Bezzine, Sofiane ;
Singer, Alan ;
Gelb, Michael H. ;
Lambeau, Gerard .
BIOCHEMISTRY, 2006, 45 (44) :13203-13218
[4]
NO-donor COX-2 inhibitors. New nitrooxy-substituted 1,5-diarylimidazoles endowed with COX-2 inhibitory and vasodilator properties [J].
Chegaev, Konstantin ;
Lazzarato, Loretta ;
Tosco, Paolo ;
Cena, Clara ;
Marini, Elisabetta ;
Rolando, Barbara ;
Carrupt, Pierre-Alain ;
Fruttero, Roberta ;
Gasco, Alberto .
JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (07) :1449-1457
[5]
Cyclooxygenase in biology and disease [J].
Dubois, RN ;
Abramson, SB ;
Crofford, L ;
Gupta, RA ;
Simon, LS ;
Van De Putte, LBA ;
Lipsky, PE .
FASEB JOURNAL, 1998, 12 (12) :1063-1073
[6]
Potent inhibitors of lipoprotein-associated phospholipase A2:: Benzaldehyde O-heterocycle-4-carbonyloxime [J].
Jeong, Hyung Jae ;
Park, Yong-Dae ;
Park, Ho-Yong ;
Jeong, Il Yun ;
Jeong, Tae-Sook ;
Lee, Woo Song .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (21) :5576-5579
[7]
A continuous spectrophotometric assay for phospholipase A2 activity [J].
Jiménez, M ;
Cabanes, J ;
Gandía-Herrero, F ;
Escribano, J ;
García-Carmona, F ;
Pérez-Gilabert, M .
ANALYTICAL BIOCHEMISTRY, 2003, 319 (01) :131-137
[8]
Enzymatic synthesis of high-purity structured lipids with caprylic acid at 1,3-positions and polyunsaturated fatty acid at 2-position [J].
Kawashima, A ;
Shimada, Y ;
Yamamoto, M ;
Sugihara, A ;
Nagao, T ;
Komemushi, S ;
Tominaga, Y .
JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY, 2001, 78 (06) :611-616
[9]
Lp-PLA2 inhibitory activities of fatty acid glycerols isolated from Saururus chinensis roots [J].
Lee, WS ;
Kim, MJ ;
Beck, YI ;
Park, YD ;
Jeong, TS .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (15) :3573-3575
[10]
Scaffold of the cyclooxygenase-2 (COX-2) inhibitor carprofen provides Alzheimer γ-secretase modulators [J].
Narlawar, Rajeshwar ;
Perez Revuelta, Blanca I. ;
Haass, Christian ;
Steiner, Harald ;
Schmidt, Boris ;
Baumann, Karlheinz .
JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (26) :7588-7591