Abstract
Nonenzymatic conversion of Chl a to Chl d was performed for the first time by dilute hydrogen peroxide (H2O2) in aqueous acetone (acetone/dilute H2O2 = 10/1, v/v) at 303 K in the dark. The conversion was observed within five minutes incubation when 0.3% H2O2 was used. The Chl d production yield reached to the maximum, ca. 0.41%, at the incubation time of 5 min. The Chl a to Chl d conversion was also observed when 3% H2O2 and 0.03% H2O2 were used, but the maximum yields were much lower, 0.05% and 0.16%, respectively. The converted Chl d was then gradually degraded probably due to the strong oxidation power of H2O2. Our findings indicate that Chl d is apt to be produced as one of the degradation products of Chl a in nature.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Akiyama M, Miyashita H, Watanabe T, Kise H, Miyachi S, Kobayashi M (2001) Detection of Chlorophyll d′ and Pheophytin a in a Chlorophyll d-Dominating Oxygenic Photosynthetic Prokaryote Acaryochloris Marina. Anal Sci 17: 205–208
Hynninen PH, Kaartinen V, Kolehmainen E (2010) Horseradish Peroxidase-Catalyzed Oxidation of Chlorophyll a with Hydrogen Peroxide Characterization of the Products and Mechanism of the Reaction. Biochimica et Biophysica Acta 1797: 531–542
Holt AS (1961) Further Evidence of the Relation between 2-Desvinyl-2-Formyl-Chlorophyll a and Chlorophyll d. Can. J. Botany. 39: 327–331
Holt AS, Morley HV (1959) A Proposed Structurefor Chlorophyll d. Can. J. Chem. 37: 507–514
Kashiyama Y, Miyashita H, Ohkubo S, Ogawa NO, Chikaraishi Y, Takano Y, Suga H, Toyofuku T, Nomaki H, Kitazato H, Nagata T, Ohkouchi N (2008) Evidence of Global Chlorophyll d. Science 321: 658
Itoh S, Okada N, Ohashi S, Nakazato M, Iwamoto K, Shiraiwa Y, Miyashita H, Kobayashi M (2009) Novel Conversion of Chlorophyll a into Chlorophyll d Catalyzed by Extracts of Vegetables and Fruits. Phycologia 48: 49–50
Kobayashi M, Watanabe S, Gotoh T, Koizumi H, Itoh Y, Akiyama M, Shiraiwa Y, Tsuchiya T, Miyashita H, Mimuro M, Yamashita T, Watanabe T (2005) Minor but Key Chlorophylls in Photosystem II. Photosynth Res 84: 201–207
Koizumi H, Itoh Y, Hosoda S, Akiyama M, Hoshino T, Shiraiwa Y, Kobayashi M (2005) Serendipitous Discovery of Chl d Formation from Chl a with Papain. Sci Tech Adv Material 6: 551–557
Manning WM, Strain HH (1943) Chlorophyll d, a Green Pigment of the Red Algae. J Biol Chem 151:1–19
Mironov AF (1996) Synthesis and Properties of New Chlorin and Bacteriochlorin Photosensitizers. Proc SPIE 2625: 23–32
Mironov AF, Kozyrev AN, Perepyolkin PY (1994) New Sensitizers for Diagnosis and Photodynamic Therapy of Malignant Tissues. Proc SPIE 2078: 186–192
Mironov AF, Ruziev RD, Lebedeva VS (2004) Synthesis and Chemical Transformations of N-Hydroxy-and N-Hydroxyalkylcycloimides of Chlorin p6. Russian J Bioorganic Chemistry 30: 466–476
Miyashita H, Ikemoto H, Kurano N, Adachi K, Chihara M, Miyachi S (1996) Chlorophyll d As a Major Pigment. Nature 383: 402
Ohashi S, Miyashita H, Okada N, Iemura T, Watanabe T, Kobayashi M (2008) Unique Photosystems in Acaryochloris Marina. Photosynth. Res. 98: 141–149
Ohashi S, Iemura T, Okada N, Itoh S, Furukawa H, Okuda M, Ohnishi-Kameyama M, Ogawa T, Miyashita H, Watanabe T, Itoh S, Oh-oka H, Inoue K, Kobayashi M (2010) An Overview on Chlorophylls and Quinones in the Photosystem I-Type Reaction Centers. Photosynth. Res. 104: 305–319
Okada N, Itoh S, Nakazato M, Miyashita H, Ohashi S, Kobayashi M (2009) Effective Hydrolysis of Chlorophyll a to Yield Chlorophyllide a by Papain in Aqueous Acetone. Current Topics in Plant Biology 10: 47–52
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
Copyright information
© 2013 Zhejiang University Press, Hangzhou and Springer-Verlag Berlin Heidelberg
About this paper
Cite this paper
Aoki, K. et al. (2013). Nonenzymatic Formation of Chl d from Chl a with Hydrogen Peroxide. In: Photosynthesis Research for Food, Fuel and the Future. Advanced Topics in Science and Technology in China. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-32034-7_172
Download citation
DOI: https://doi.org/10.1007/978-3-642-32034-7_172
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-32033-0
Online ISBN: 978-3-642-32034-7
eBook Packages: Biomedical and Life SciencesBiomedical and Life Sciences (R0)