Absolute Configuration of Mycosporine-Like Amino Acids, Their Wound Healing Properties and In Vitro Anti-Aging Effects

被引:35
作者
Orfanoudaki, Maria [1 ]
Hartmann, Anja [1 ]
Alilou, Mostafa [1 ]
Gelbrich, Thomas [2 ]
Planchenault, Patricia [3 ]
Derbre, Severine [3 ]
Schinkovitz, Andreas [3 ]
Richomme, Pascal [3 ]
Hensel, Andreas [4 ]
Ganzera, Markus [1 ]
机构
[1] Univ Innsbruck, Inst Pharm, Pharmacognosy, Innrain 80-82, A-6020 Innsbruck, Austria
[2] Univ Innsbruck, Inst Pharm, Pharmaceut Technol, Innrain 52c, A-6020 Innsbruck, Austria
[3] Univ Angers, SONAS, SFR QUASAV, EA921,Dept Pharm,Fac Hlth Sci, 16 Bd Daviers, F-49045 Angers, France
[4] Univ Munster, Inst Pharmaceut Biol & Phytochem, Corrensstr 48, D-48149 Munster, Germany
基金
奥地利科学基金会;
关键词
mycosporine-like amino acids; stereochemistry; X-ray crystallography; ECD; anti-aging; wound healing; MOLECULAR-STRUCTURE; PORPHYRA-334; BIOSYNTHESIS; INHIBITION; ANTIOXIDANT; DERIVATIVES; PROTECTION; CRYSTAL; AGES;
D O I
10.3390/md18010035
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Mycosporine-like amino acids (MAAs) are water-soluble metabolites, reported to exhibit strong UV-absorbing properties. They have been found in a wide range of marine organisms, especially those that are exposed to extreme levels of sunlight, to protect them against solar radiation. In the present study, the absolute configuration of 14 mycosporine-like-amino acids was determined by combining the results of electronic circular dichroism (ECD) experiments and that of advanced Marfey's method using LC-MS. The crystal structure of a shinorine hydrate was determined from single crystal X-ray diffraction data and its absolute configuration was established from anomalous-dispersion effects. Furthermore, the anti-aging and wound-healing properties of these metabolites were evaluated in three different assays namely the inhibition of collagenase, inhibition of advanced glycation end products (AGEs) and wound healing assay (scratch assay).
引用
收藏
页数:16
相关论文
共 48 条
[1]   Bio-Guided Isolation of Methanol-Soluble Metabolites of Common Spruce (Picea abies) Bark by-Products and Investigation of Their Dermo-Cosmetic Properties [J].
Angelis, Apostolis ;
Hubert, Jane ;
Aligiannis, Nektarios ;
Michalea, Rozalia ;
Abedini, Amin ;
Nuzillard, Jean-Marc ;
Gangloff, Sophie C. ;
Skaltsounis, Alexios-Leandros ;
Renault, Jean-Hugues .
MOLECULES, 2016, 21 (11)
[2]   Advanced glycation inhibition and protection against endothelial dysfunction induced by coumarins and procyanidins from Mammea neurophylla [J].
Bach Tai Dang ;
Geny, Charlotte ;
Blanchard, Patricia ;
Rouger, Caroline ;
Tonnerre, Pierre ;
Charreau, Beatrice ;
Rakolomalala, Gilbertine ;
Randriamboavonjy, Joseph Iharinjaka ;
Loirand, Gervaise ;
Pacaud, Pierre ;
Litaudon, Marc ;
Richomme, Pascal ;
Seraphin, Denis ;
Derbre, Severine .
FITOTERAPIA, 2014, 96 :65-75
[3]   Evaluation of the wound healing potential of Wedelia trilobata (L.) leaves [J].
Balekar, Neelam ;
Katkam, Nadpi Gangadhar ;
Nakpheng, Titpawan ;
Jehtae, Kholeeyoh ;
Srichana, Teerapol .
JOURNAL OF ETHNOPHARMACOLOGY, 2012, 141 (03) :817-824
[4]   The Genetic and Molecular Basis for Sunscreen Biosynthesis in Cyanobacteria [J].
Balskus, Emily P. ;
Walsh, Christopher T. .
SCIENCE, 2010, 329 (5999) :1653-1656
[5]   Chemical Composition, Antioxidant and Anti-AGEs Activities of a French Poplar Type Propolis [J].
Boisard, Severine ;
Le Ray, Anne-Marie ;
Gatto, Julia ;
Aumond, Marie-Christine ;
Blanchard, Patricia ;
Derbre, Severine ;
Flurin, Catherine ;
Richomme, Pascal .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2014, 62 (06) :1344-1351
[6]   Mycosporine-Like Amino Acids Promote Wound Healing through Focal Adhesion Kinase (FAK) and Mitogen-Activated Protein Kinases (MAP Kinases) Signaling Pathway in Keratinocytes [J].
Choi, Yun-Hee ;
Yang, Dong Joo ;
Kulkarni, Atul ;
Moh, Sang Hyun ;
Kim, Ki Woo .
MARINE DRUGS, 2015, 13 (12) :7055-7066
[7]   Mycosporine-Like Amino Acids: Potential Health and Beauty Ingredients [J].
Chrapusta, Ewelina ;
Kaminski, Ariel ;
Duchnik, Kornelia ;
Bober, Beata ;
Adamski, Michal ;
Bialczyk, Jan .
MARINE DRUGS, 2017, 15 (10)
[8]   BIOSYNTHESIS OF MYCOSPORINES - MYCOSPORINE GLUTAMINOL IN TRICHOTHECIUM-ROSEUM [J].
FAVREBONVIN, J ;
BERNILLON, J ;
SALIN, N ;
ARPIN, N .
PHYTOCHEMISTRY, 1987, 26 (09) :2509-2514
[9]   A nonempirical method using LC/MS for determination of the absolute configuration of constituent amino acids in a peptide: Combination of Marfey's method with mass spectrometry and its practical application [J].
Fujii, K ;
Ikai, Y ;
Oka, H ;
Suzuki, M ;
Harada, K .
ANALYTICAL CHEMISTRY, 1997, 69 (24) :5146-5151
[10]   CRYSTAL AND MOLECULAR-STRUCTURE OF PALYTHINE TRIHYDRATE [J].
FURUSAKI, A ;
MATSUMOTO, T ;
TSUJINO, I ;
SEKIKAWA, I .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1980, 53 (02) :319-323