Biologically Active Oxylipins from Enzymatic and Nonenzymatic Routes in Macroalgae

被引:63
作者
Barbosa, Mariana [1 ]
Valentao, Patricia [1 ]
Andrade, Paula B. [1 ]
机构
[1] Univ Porto, Fac Pharm, Dept Chem, REQUIMTE LAQV,Lab Pharmacognosy, Rua Jorge Viterbo Ferreira 228, P-4050313 Oporto, Portugal
关键词
oxylipins; macroalgae; phytoprostanes; biosynthesis; bioactivity; ALGA GRACILARIOPSIS-LEMANEIFORMIS; INDUCED OXIDATIVE STRESS; HYDROXY FATTY-ACIDS; MARINE RED ALGA; ARACHIDONIC-ACID; LAURENCIA-HYBRIDA; INNATE IMMUNITY; BROWN-ALGAE; PPAR-GAMMA; DEFENSE;
D O I
10.3390/md14010023
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Marine algae are rich and heterogeneous sources of great chemical diversity, among which oxylipins are a well-recognized class of natural products. Algal oxylipins comprise an assortment of oxygenated, halogenated, and unsaturated functional groups and also several carbocycles, varying in ring size and position in lipid chain. Besides the discovery of structurally diverse oxylipins in macroalgae, research has recently deciphered the role of some of these metabolites in the defense and innate immunity of photosynthetic marine organisms. This review is an attempt to comprehensively cover the available literature on the chemistry, biosynthesis, ecology, and potential bioactivity of oxylipins from marine macroalgae. For a better understanding, enzymatic and nonenzymatic routes were separated; however, both processes often occur concomitantly and may influence each other, even producing structurally related molecules.
引用
收藏
页数:26
相关论文
共 136 条
[81]   Oxylipin formation in Nostoc punctiforme (PCC73102) [J].
Lang, Imke ;
Feussner, Ivo .
PHYTOCHEMISTRY, 2007, 68 (08) :1120-1127
[82]   Phospholipases and galactolipases trigger oxylipin-mediated wound-activated defence in the red alga Gracilaria chilensis against epiphytes [J].
Lion, U ;
Wiesemeier, T ;
Weinberger, F ;
Beltrán, J ;
Flores, V ;
Faugeron, S ;
Correa, J ;
Pohnert, G .
CHEMBIOCHEM, 2006, 7 (03) :457-462
[83]  
Liu Qing Yan, 1994, Molecular Marine Biology and Biotechnology, V3, P206
[84]   B1-phytoprostanes trigger plant defense and detoxification responses [J].
Loeffler, C ;
Berger, S ;
Guy, A ;
Durand, T ;
Bringmann, G ;
Dreyer, M ;
von Rad, U ;
Durner, J ;
Mueller, MJ .
PLANT PHYSIOLOGY, 2005, 137 (01) :328-340
[85]   PTILODENE, A NOVEL ICOSANOID INHIBITOR OF 5-LIPOXYGENASE AND NA+/K+ ATPASE FROM THE RED MARINE ALGA PTILOTA-FILICINA J AGARDH [J].
LOPEZ, A ;
GERWICK, WH .
TETRAHEDRON LETTERS, 1988, 29 (13) :1505-1506
[86]   2 NEW ICOSAPENTAENOIC ACIDS FROM THE TEMPERATE RED SEAWEED PTILOTA-FILICINA AGARDH,J. [J].
LOPEZ, A ;
GERWICK, WH .
LIPIDS, 1987, 22 (03) :190-194
[87]   Peyssonenynes A and B, novel enediyne oxylipins with DNA methyl transferase inhibitory activity from the red marine alga Peyssonnelia caulifera [J].
McPhail, KL ;
France, D ;
Cornell-Kennon, S ;
Gerwick, WH .
JOURNAL OF NATURAL PRODUCTS, 2004, 67 (06) :1010-1013
[88]   Nonenzymatic oxygenated metabolites of α-linolenic acid B1- and L1-phytoprostanes protect immature neurons from oxidant injury and promote differentiation of oligodendrocyte progenitors through PPAR-γ activation [J].
Minghetti, Luisa ;
Salvi, Rachele ;
Salvatori, Maria Lavinia ;
Ajmone-Cat, Maria Antonietta ;
De Nuccio, Chiara ;
Visentin, Sergio ;
Bultel-Ponce, Valerie ;
Oger, Camille ;
Guy, Alexandre ;
Galano, Jean-Marie ;
Greco, Anita ;
Bernardo, Antonietta ;
Durand, Thierry .
FREE RADICAL BIOLOGY AND MEDICINE, 2014, 73 :41-50
[89]   DISCOVERY OF 12-(S)-HYDROXY-5,8,10,14-ICOSATETRAENOIC ACID [12-(S)-HETE] IN THE TROPICAL RED ALGA PLATYSIPHONIA-MINIATA [J].
MOGHADDAM, MF ;
GERWICK, WH ;
BALLANTINE, DL .
PROSTAGLANDINS, 1989, 37 (02) :303-308
[90]  
MOGHADDAM MF, 1990, J BIOL CHEM, V265, P6126