Biologically Active Oxylipins from Enzymatic and Nonenzymatic Routes in Macroalgae

被引:62
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
来源
MARINE DRUGS | 2016年 / 14卷 / 01期
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
  • [1] 2,4-decadienals are produced via (R)-11-HPITE from arachidonic acid in marine green alga Ulva conglobata
    Akakabe, Y
    Matsui, K
    Kajiwara, T
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (17) : 3607 - 3609
  • [2] Enantioselective formation of (R)-9-HPODE and (R)-9-HPOTrE in marine green alga Ulva conglobata
    Akakabe, Y
    Matsui, K
    Kajiwara, T
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (10) : 3171 - 3173
  • [3] Valuable compounds in macroalgae extracts
    Andrade, Paula B.
    Barbosa, Mariana
    Matos, Rui Pedro
    Lopes, Graciliana
    Vinholes, Juliana
    Mouga, Teresa
    Valentao, Patricia
    [J]. FOOD CHEMISTRY, 2013, 138 (2-3) : 1819 - 1828
  • [4] Biosynthesis of oxylipins in non-mammals
    Andreou, Alexandra
    Brodhun, Florian
    Feussner, Ivo
    [J]. PROGRESS IN LIPID RESEARCH, 2009, 48 (3-4) : 148 - 170
  • [5] Hepoxilin B3 and its enzymatically formed derivative trioxilin B3 are incorporated into phospholipids in psoriatic lesions
    Antón, R
    Camacho, M
    Puig, L
    Vila, L
    [J]. JOURNAL OF INVESTIGATIVE DERMATOLOGY, 2002, 118 (01) : 139 - 146
  • [6] Arterburn L.M., 2008, WO Patent, Patent No. [2008/103753 A2, 2008103753]
  • [7] Arterburn L.M., 2011, U.S. Patent, Patent No. [2011/0112191 A1, 20110112191, US 2011/0112191 A1]
  • [8] Nonenzymatic α-Linolenic Acid Derivatives from the Sea: Macroalgae as Novel Sources of Phytoprostanes
    Barbosa, Mariana
    Collado-Gonzalez, Jacinta
    Andrade, Paula B.
    Ferreres, Federico
    Valentao, Patricia
    Galano, Jean-Marie
    Durand, Thierry
    Gil-Izquierdo, Angel
    [J]. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2015, 63 (28) : 6466 - 6474
  • [9] ISOLATION OF 12-(S)-HEPE FROM THE RED MARINE ALGA MURRAYELLA-PERICLADOS AND REVISION OF STRUCTURE OF AN ACYCLIC ICOSANOID FROM LAURENCIA-HYBRIDA - IMPLICATIONS TO THE BIOSYNTHESIS OF THE MARINE PROSTANOID HYBRIDALACTONE
    BERNART, M
    GERWICK, WH
    [J]. TETRAHEDRON LETTERS, 1988, 29 (17) : 2015 - 2018
  • [10] UNPRECEDENTED OXYLIPINS FROM THE MARINE GREEN-ALGA ACROSIPHONIA-COALITA
    BERNART, MW
    WHATLEY, GG
    GERWICK, WH
    [J]. JOURNAL OF NATURAL PRODUCTS, 1993, 56 (02): : 245 - 259