Production of allantoin, rabdosiin and rosmarinic acid in callus cultures of the seacoastal plant Mertensia maritima (Boraginaceae)

详细信息    查看全文

• 作者：S. A. Fedoreyev (1)
  Y. V. Inyushkina (2) yulya.in@rambler.ru
  V. P. Bulgakov (24)
  M. V. Veselova (1)
  G. K. Tchernoded (2)
  A. V. Gerasimenko (3)
  Y. N. Zhuravlev (2)
• 关键词：Rabdosiin &#8211 ; Rosmarinic acid &#8211 ; Allantoin &#8211 ; Callus culture &#8211 ; Mertensia maritima
• 刊名：Plant Cell, Tissue and Organ Culture
• 出版年：2012
• 出版时间：July 2012
• 年：2012
• 卷：110
• 期：1
• 页码：183-188
• 全文大小：262.1 KB
• 参考文献：1. Abdelmohsen UR, Ali W, Eom SH, Hentschel U, Roitsch T (2011) Synthesis of distinctly different sets of antimicrobial activities by elicited plant cell suspension cultures. Plant Cell Tiss Organ Cult 106:105–113
  2. Becker LC, Bergfeld WF, Belsito DV, Klaassen CD, Marks JG Jr, Shank RC, Slaga TJ, Snyder PW, Alan Andersen F (2010) Final report of the safety assessment of allantoin and its related complexes. Int J Toxicol 29:84S–97S
  3. Bonfill M, Mangas S, Moyano E, Cusido RM, Palaz贸n J (2011) Production of centellosides and phytosterols in cell suspension cultures of Centella asiatica. Plant Cell Tiss Organ Cult 104:61–67
  4. Boonsnongcheep P, Korsangruang S, Soonthornchareonnon N, Chintapakorn Y, Saralamp P, Prathanturarug S (2010) Growth and isoflavonoid accumulation of Pueraria candollei var. candollei and P. candollei var. mirifica cell suspension cultures. Plant Cell Tiss Organ Cult 2:119–126
  5. Bulgakov VP, Khodakovskaya MV, Labetskaya NV, Tchernoded GK, Zhuravlev YN (1998) The impact of plant rolC oncogene on ginsenoside production by ginseng hairy root cultures. Phytochemistry 49:1929–1934
  6. Bulgakov VP, Inyushkina YV, Fedoreyev SA (2011a) Rosmarinic acid and its derivatives: biotechnology and applications. Crit Rev Biotechnol. doi:10.3109/07388551.2011.596804
  7. Bulgakov VP, Tchernoded GK, Veselova MV, Fedoreyev SA, Muzarok TI, Zhuravlev YN (2011b) Catechin production in cultured cells of Taxus cuspidata and Taxus baccata. Biotechnol Lett 33:1879–1883
  8. Ding S, Jia L, Durandin A, Crean C, Kolbanovskiy A, Shafirovich V, Broyde S, Geacintov NE (2009) Absolute configurations of spiroiminodihydantoin and allantoin stereoisomers: Comparison of computed and measured electronic circular dichroism spectra. Chem Res Toxicol 22:1189–1193
  9. Fedoreyev SA, Veselova MV, Krivoschekova OE, Mischenko NP, Denisenko VA, Dmitrenok PS, Glazunov VP, Bulgakov VP, Tchernoded GK, Zhuravlev YN (2005) Caffeic acid metabolites from Eritrichium sericeum cell cultures. Planta Med 71:446–451
  10. Fedoreyev SA, Bulgakov VP, Grishchenko OV, Veselova MV, Krivoschekova OE, Kulesh NI, Denisenko VA, Tchernoded GK, Zhuravlev YN (2008) Isoflavonoid composition of a callus culture of the relict tree Maackia amurensis Rupr. et Maxim. J Agric Food Chem 56:7023–7031
  11. Filippi SB, Azevedo RA, Sodek L, Mazzafera P (2007) Allantoin has a limited role as nitrogen source in cultured coffee cells. J Plant Physiol 164:544–552
  12. Georgiev MI, Weber J, Maciuk A (2009) Bioprocessing of plant cell cultures for mass production of targeted compounds. Appl Microbiol Biotechnol 83:809–823
  13. Inyushkina YV, Bulgakov VP, Veselova MV, Bryukhanov VM, Zverev YF, Lampatov VV, Azarova OV, Tchernoded GK, Fedoreyev SA, Zhuravlev YN (2007) High rabdosiin and rosmarinic acid production in Eritrichium sericeum callus cultures and the effect of the calli on Masugi-nephritis in rats. Biosci Biotechnol Biochem 71:1286–1293
  14. Irvani N, Solouki M, Omidi M, Zare AR, Shahnazi S (2010) Callus induction and plant regeneration in Dorem ammoniacum D., an endangered medicinal plant. Plant Cell Tiss Organ Cult 100:293–299
  15. Ito H, Miyazaki T, Ono M, Sakurai H (1998) Antiallergic activities of rabdosiin and its related compounds: chemical and biochemical evaluations. Bioorg Med Chem 6:1051–1056
  16. Kahn K, Tipton PA (2000) Kinetics and mechanism of allantoin racemization. Bioorg Chem 27:62–72
  17. Krzyzanowska J, Czubacka A, Pecio L, Przybys M, Doroszewska T, Stochmal A, Oleszek W (2012) The effects of jasmonic acid and methyl jasmonate on rosmarinic acid production in Mentha x piperita cell suspension cultures. Plant Cell Tiss Organ Cult 108:73–81
  18. Mosquim PR, Sodek L (1992) Partitioning of nitrogen in soybean fruit explants cultured with glutamine, asparagine or allantoin. Plant Physiol Biochem 30:451–457
  19. Panya A, Laguerre M, Lecomte J, Villeneuve P, Weiss J, McClements DJ, Decker EA (2010) Effects of hitosan and rosmarinate esters on the physical and oxidative stability of liposomes. J Agric Food Chem 58:5679–5684
  20. P茅rez-Fons L, Garz贸n MT, Micol V (2010) Relationship between the antioxidant capacity and effect of rosemary (Rosmarinus officinalis L.) polyphenols on membrane phospholipid order. J Agric Food Chem 58:161–171
  21. Reshetnyak MV, Il’in SG, Utkina NK, Yanovskii AI, Struchkov YT (1988) Crystal and molecular structures of 1,8-diacetyl-3-methyl-DL-allantoin. Chem Nat Compd 24:163–360
  22. Sim玫es-Gurgel C, Cordeiro LS, Castro TC, Callado CH, Albarello N, Mansur E (2011) Establishment of anthocyanin-producing cell suspension cultures of Cleome rosea Vahl ex DC (Capparaceae). Plant Cell Tiss Organ Cult 106:537–545
  23. Thornfeldt C (2005) Cosmeceuticals containing herbs: fact, fiction, and future. Dermatol Surg 31:873–880
  24. Todd CD, Tipton PA, Blevins DG, Piedras P, Pineda M, Polacco JC (2006) Update on ureide degradation in legumes. J Exp Bot 57:5–12
  25. Vit贸ria AP, Mazzafera P (1999) Xanthine degradation and related enzymes activities in leaves and fruits of two coffea species differing in caffeine catabolism. J Agric Food Chem 47:1851–1855
  26. Vost谩lov谩 J, Zdarilov谩 A, Svobodov谩 A (2010) Prunella vulgaris extract and rosmarinic acid prevent UVB-induced DNA damage and oxidative stress in HaCaT keratinocytes. Arch Dermatol Res 302:171–181
  27. Yamamoto H, Yazaki K, Inoue K (2000) Simultaneous analysis of shikimate-derived secondary metabolites in Lithospermum erythrorhizon cell suspension cultures by high-performance liquid chromatography. J Chromatogr B 738:3–15
  28. Yoon KD, Yang M-H, Chin Y-W, Park JH, Kim J (2008) Determination of allantoin in Dioscorea Rhizoma by high performance liquid chromatography using cyano columns. Natur Prod Sci 14:254–259
  29. Jintao Z, Zhigui Z, Ke Y (1992) Studies on the synthesis, structure and properties of 5-ureidoacetolactam. Acta Sci Nat Univ Jil 1:87–89
• 作者单位：1. Pacific Institute of Bioorganic Chemistry, Far East Branch of Russian Academy of Sciences, Vladivostok, 690022 Russia2. Institute of Biology and Soil Science, Far East Branch of Russian Academy of Sciences, 159 Stoletija Str., Vladivostok, 690022 Russia3. Institute of Chemistry, Far East Branch of Russian Academy of Sciences, Vladivostok, 690022 Russia4. Far Eastern Federal University, Vladivostok, 690000 Russia
• 刊物类别：Biomedical and Life Sciences
• 刊物主题：Life Sciences
  Plant Sciences
  Plant Physiology
  
• 出版者：Springer Netherlands
• ISSN：1573-5044

文摘

A callus culture of the extreme halophyte seacoastal plant Mertensia maritima (Boraginaceae) was established from apical shoots of the plant using a modified Murashige and Skoog medium supplemented with 6-benzyladenine (0.5 mg/L) and α-naphthaleneacetic acid (2.0 mg/L). Three main compounds, (−)-R-allantoin, (+)-rabdosiin and rosmarinic acid, were isolated from extracts of M. maritima calli by liquid chromatography and identified by 1H and 13C NMR, UV, ECD and HPLC–MS. Quantitative HPLC analysis showed that the calli produce (+)-rabdosiin (0.14% dry wt), rosmarinic acid (0.74% dry wt) and (−)-R-allantoin (3.7% dry wt). Allantoin was detected in plant cell cultures for the first time. All of these metabolites were also present in lower quantities in different parts of the plant. The presence of rabdosiin and rosmarinic acid, in combination with the skin-conditioning agent (−)-R-allantoin, represents a potentially useful novel composition for skin protection.