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Biosynthesis of Vanillin via Ferulic Acid in Vanilla planifolia

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† Graduate School of Life and Environmental Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8572, Japan
§ Institute of Nutrition Sciences, Kagawa Nutrition University, Sakado, Saitama 350-0288, Japan
*Author to whom correspondence should be addressed (telephone +81-29-853-4933; fax +81-29-853-4605; e-mail [email protected]).
‡Present address: Yuki Research Center, Bayer CropScience K.K., Yuki, Ibaraki 307-0001, Japan.
Cite this: J. Agric. Food Chem. 2009, 57, 21, 9956–9961
Publication Date (Web):October 9, 2009
https://doi.org/10.1021/jf901204m
Copyright © 2009 American Chemical Society
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Abstract

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14C-Labeled phenylalanine, 4-coumaric acid, 4-hydroxybenzaldehyde, 4-hydroxybenzyl alcohol, ferulic acid, and methionine were applied to disks of green vanilla pods 3 and 6 months after pollination (immature and mature pods), and the conversion of these compounds to vanillin or glucovanillin was investigated. In mature green vanilla pods, radioactivities of 11, 15, 29, and 24% from 14C-labeled phenylalanine, 4-coumaric acid, ferulic acid, and methionine, respectively, were incorporated into glucovanillin within 24 h. In the incorporation processes of methionine and phenylalanine into glucovanillin, some of the 14C labels were also trapped by the unlabeled ferulic acid. However, 14C-labeled 4-hydroxybenzaldehyde and 4-hydroxybenzyl alcohol were not converted to glucovanillin. On the other hand, in immature green vanilla pods radioactivities of the above six compounds were not incorporated into glucovanillin. Although 4-coumaric acid, ferulic acid, 4-hydroxybenzaldehyde, and 4-hydroxybenzyl alcohol were converted to the respective glucose esters or glucosides and vanillin was converted to glucovanillin, their conversions were believed to be from the detoxication of the aglycones. These results suggest that the biosynthetic pathway for vanillin is 4-coumaric acid → → ferulic acid → → vanillin → glucovanillin in mature vanilla pods.

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  4. Hsin-Yi Lo, Chia-Cheng Li, Hui-Man Cheng, I-Chen Liu, Tin-Yun Ho, Chien-Yun Hsiang. Ferulic acid altered IL-17A/IL-17RA interaction and protected against imiquimod-induced psoriasis-like skin injury in mice. Food and Chemical Toxicology 2019, 129 , 365-375. https://doi.org/10.1016/j.fct.2019.04.060
  5. Jin Zhao, Haixiong Xia, Tingyu Yu, Lu Jin, Xuehua Li, Yinghui Zhang, Liping Shu, Lingwen Zeng, Zhixu He, . A colorimetric assay for vanillin detection by determination of the luminescence of o-toluidine condensates. PLOS ONE 2018, 13 (4) , e0194010. https://doi.org/10.1371/journal.pone.0194010
  6. Nethaji J Gallage, Kirsten Jørgensen, Christian Janfelt, Agnieszka J Z Nielsen, Thomas Naake, Eryk Duński, Lene Dalsten, Michel Grisoni, Birger Lindberg Møller. The Intracellular Localization of the Vanillin Biosynthetic Machinery in Pods of Vanilla planifolia. Plant and Cell Physiology 2018, 59 (2) , 304-318. https://doi.org/10.1093/pcp/pcx185
  7. Nethaji J. Gallage, Birger Lindberg Møller. Vanilla: The Most Popular Flavour. 2018,,, 3-24. https://doi.org/10.1007/978-3-319-67903-7_1
  8. , , . Biotechnology of Natural Products. 2018,,https://doi.org/10.1007/978-3-319-67903-7
  9. Osamu Negishi, Yukiko Negishi. Phenylpropanoid 2,3-dioxygenase involved in the cleavage of the ferulic acid side chain to form vanillin and glyoxylic acid in Vanilla planifolia. Bioscience, Biotechnology, and Biochemistry 2017, 81 (9) , 1732-1740. https://doi.org/10.1080/09168451.2017.1353402
  10. Hailian Yang, Jaime Barros-Rios, Galina Kourteva, Xiaolan Rao, Fang Chen, Hui Shen, Chenggang Liu, Andrzej Podstolski, Faith Belanger, Daphna Havkin-Frenkel, Richard A. Dixon. A re-evaluation of the final step of vanillin biosynthesis in the orchid Vanilla planifolia. Phytochemistry 2017, 139 , 33-46. https://doi.org/10.1016/j.phytochem.2017.04.003
  11. Anish Kundu. Vanillin biosynthetic pathways in plants. Planta 2017, 245 (6) , 1069-1078. https://doi.org/10.1007/s00425-017-2684-x
  12. Matthias Wüst. Biosynthesis of Plant-Derived Odorants. 2017,,, 9-10. https://doi.org/10.1007/978-3-319-26932-0_2
  13. . Springer Handbook of Odor. 2017,,https://doi.org/10.1007/978-3-319-26932-0
  14. Atsushi Shigeto, Erinna Nindi Nurasti, Anton Sugiarto, Makoto Togawa, Kenji Kumazawa. The Influence of Harvest Maturity on the Aroma Quality of Vanilla. NIPPON SHOKUHIN KAGAKU KOGAKU KAISHI 2017, 64 (10) , 502-506. https://doi.org/10.3136/nskkk.64.502
  15. Ludger Wessjohann, Anne-Katrin Bauer, Martin Dippe, Jakob Ley, Torsten Geißler. Biocatalytic Synthesis of Natural Products by O -Methyltransferases. 2016,,, 121-146. https://doi.org/10.1002/9783527677122.ch7
  16. , , , . Applied Biocatalysis: From Fundamental Science to Industrial Applications. 2016,,https://doi.org/10.1002/9783527677122
  17. Peng Chen, Lei Yan, Zhengrong Wu, Suyue Li, Zhongtian Bai, Xiaojuan Yan, Ningbo Wang, Ning Liang, Hongyu Li. A microbial transformation using Bacillus subtilis B7-S to produce natural vanillin from ferulic acid. Scientific Reports 2016, 6 (1) https://doi.org/10.1038/srep20400
  18. Igor Jerković, Zvonimir Marijanović, Piotr M. Kuś, Carlo I. G. Tuberoso. Comprehensive Study of Mediterranean (Croatian) Propolis Peculiarity: Headspace, Volatiles, Anti- Varroa -Treatment Residue, Phenolics, and Antioxidant Properties. Chemistry & Biodiversity 2016, 13 (2) , 210-218. https://doi.org/10.1002/cbdv.201500053
  19. Atsushi Shigeto, Shoko Hachisuka, Kenji Kumazawa. Characterization of Potent Odorants in Three Different Cultivars (Madagascar, Comoro and Tahiti) of Vanilla Bean by Aroma Extract Dilution Analysis (AEDA). Food Science and Technology Research 2016, 22 (6) , 811-816. https://doi.org/10.3136/fstr.22.811
  20. Ting Zhang, Juan Chen, Xiaofeng Jia, . Identification of the Key Fields and Their Key Technical Points of Oncology by Patent Analysis. PLOS ONE 2015, 10 (11) , e0143573. https://doi.org/10.1371/journal.pone.0143573
  21. Ulrich Krings, Vida Esparan, Ralf G. Berger. The taste enhancer divanillin: a review on sources and enzymatic generation. Flavour and Fragrance Journal 2015, 30 (5) , 362-365. https://doi.org/10.1002/ffj.3251
  22. Vida Esparan, Ulrich Krings, Marlene Struch, Ralf Berger. A Three-Enzyme-System to Degrade Curcumin to Natural Vanillin. Molecules 2015, 20 (4) , 6640-6653. https://doi.org/10.3390/molecules20046640
  23. Jordan E. Bisanz, Jean M. Macklaim, Gregory B. Gloor, Gregor Reid. Bacterial metatranscriptome analysis of a probiotic yogurt using an RNA-Seq approach. International Dairy Journal 2014, 39 (2) , 284-292. https://doi.org/10.1016/j.idairyj.2014.07.010
  24. Osamu Negishi, Yukiko Negishi. Biosynthesis of Vanillin. 2014,,, 205-209. https://doi.org/10.1016/B978-0-12-398549-1.00039-8
  25. . Flavour Science. 2014,,https://doi.org/
  26. Christelle Lemus, Apostolis Angelis, Maria Halabalaki, Alexios Leandros Skaltsounis. γ-Oryzanol. 2014,,, 409-430. https://doi.org/10.1016/B978-0-12-401716-0.00032-5
  27. . Wheat and Rice in Disease Prevention and Health. 2014,,https://doi.org/
  28. Helena Maruenda, Maria del Lujan Vico, J. Ethan Householder, John P. Janovec, Cristhian Cañari, Angelica Naka, Ana E. Gonzalez. Exploration of Vanilla pompona from the Peruvian Amazon as a potential source of vanilla essence: Quantification of phenolics by HPLC-DAD. Food Chemistry 2013, 138 (1) , 161-167. https://doi.org/10.1016/j.foodchem.2012.10.037
  29. Jianfeng Jin, Isabel W. C. E. Arends, Ulf Hanefeld. Addition of Water to CC Bonds and its Elimination. 2012,,, 467-501. https://doi.org/10.1002/9783527639861.ch11
  30. , , . Enzyme Catalysis in Organic Synthesis. 2012,,https://doi.org/10.1002/9783527639861
  31. Denys J. Charles. Vanilla. 2012,,, 581-587. https://doi.org/10.1007/978-1-4614-4310-0_56
  32. Denys J. Charles. Antioxidant Properties of Spices, Herbs and Other Sources. 2013,,https://doi.org/10.1007/978-1-4614-4310-0
  33. . Bibliography. 2011,,, 211-244. https://doi.org/10.1201/b11443-16
  34. Simon Cotton. Every Molecule Tells a Story. 2011,,https://doi.org/10.1201/b11443
  35. Yimin Zhu, John Ralph. Stereoselective synthesis of 1-O-β-feruloyl and 1-O-β-sinapoyl glucopyranoses. Tetrahedron Letters 2011, 52 (29) , 3729-3731. https://doi.org/10.1016/j.tetlet.2011.05.038
  36. Jianfeng Jin, Ulf Hanefeld. The selective addition of water to CC bonds; enzymes are the best chemists. Chemical Communications 2011, 47 (9) , 2502. https://doi.org/10.1039/c0cc04153j
  37. Tony Lionel Palama, Isabelle Fock, Young Hae Choi, Robert Verpoorte, Hippolyte Kodja. Biological variation of Vanilla planifolia leaf metabolome. Phytochemistry 2010, 71 (5-6) , 567-573. https://doi.org/10.1016/j.phytochem.2009.12.011
  38. Alessio Innocenti, S. Beyza Öztürk Sarıkaya, İlhami Gülçin, Claudiu T. Supuran. Carbonic anhydrase inhibitors. Inhibition of mammalian isoforms I–XIV with a series of natural product polyphenols and phenolic acids. Bioorganic & Medicinal Chemistry 2010, 18 (6) , 2159-2164. https://doi.org/10.1016/j.bmc.2010.01.076

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