The Ability of Edible Mushrooms to Act as Biocatalysts: Preparation of Chiral Alcohols Using Basidiomycete Strains

Kohji Ishihara, Yukiko Nishikawa, Mari Kaneko, Anna Kinoshita, Nozomi Kumazawa, Daichi Kobashigawa, Kohei Kuroda, Masashi Osawa, Tatsunori Yamamoto, Nobuyoshi Nakajima, Hiroki Hamada, Noriyoshi Masuoka

Department of Life Science, Okayama University of Science, Okayama, Japan.
Graduate School of Health and Welfare Science, Okayama Prefectiral University, Soja, Japan.
Research Institute of Biotechnology, Fujiwara Techno-Art Co., Ltd. Okayama, Japan.

DOI: 10.4236/aim.2012.22008                

Abstract

To examine the potential ability of edible mushrooms to act as biocatalysts, 19 basidiomycete strains were screened. Modified media (PG, O, and PGO medium) for liquid cultivation of these basidiomycete strains were designed and tested. Wet cells (>10 g) of 4 basidiomycete strains (Pleurotus salmoneostramineus H7, P. salmoneostramineus H13, Ganoderma lucidum NBRC31863, Flammulina velutipes NBRC31862) were harvested from PGO medium for 7 days. The stereoselective reduction of α-keto esters using the 4 strains was tested. It was found that each of these strains had a reducing activity toward 6 aliphatic α-keto esters. In the presence of L-alanine as an additive, the reduction of ethyl 2-oxobutanoate and ethyl 2-oxopentanoete by P. salmoneostramineus H7 produced the corresponding alcohol with a high conversion ratio and with excellent enantiomeric excess (>99% e.e. (R)). Furthermore, ethyl pyruvate, ethyl 2-oxobutanoate, and ethyl 2-oxopentanoate were predominantly reduced to the corresponding (R)-hydroxy ester (>99% e.e.) by G. lucidum. Thus, we found that these edible mushrooms have great potential to be used as biocatalysts for the stereoselective reduction of carbonyl compounds.

Keywords

Basidiomycete; Edible Mushroom; Biocatalyst; Chiral Alcohol

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1]	A. T. Borchers, J. S. Stern, R. M. Hackman, C. L. Keen and M. E. Gershwin, “Mushrooms, Tumors, and Immunity,” Proceedings of the Society for Experimental Biology and Medicine, Vol. 221, No. 4, 1999, pp. 281-293. doi:10.1046/j.1525-1373.1999.d01-86.x
[2]	A. T. Borchers, C. L. Keen and M. E. Gershwin, “Mushrooms, Tumors, and Immunity: An Update,” Experimental Biology and Medicine, Vol. 229, No. 5, 2004, pp. 393-406.
[3]	A. T. Borchers, A. Krishnamurthy, C. L. Keen, F. J. Meyers and M. E. Gershwin, “The Immunobiology of Mushrooms,” Experimental Biology and Medicine, Vol. 233, No. 3, 2008, pp. 259-276. doi:10.3181/0708-MR-227
[4]	R. Kondo and I. Kamei, “Biodegradation of Dioxins and PCBs by Mushroom Fungi,” BioIndustry, Vol. 23, No. 12, 2006, pp. 68-76.
[5]	A. S. Purnomo, T. Mori, I. Kamei, T. Nishii and R. Kondo, “Application of Mushroom Waste Medium from Pleurotus ostreatus for Bioremediation of DDT-Contaminated Soil,” International Biodeterioration and Biodegradation, Vol. 64, No. 5, 2010, pp. 397-402.
[6]	V. A. Edalli and C. M. Kamanavalli, “Removal of Phenolic Compounds by Mushroom Polyphenol Oxidase from Pleurotus Species,” Ecoscan, Vol. 4, No. 1, 2010, pp. 89-92.
[7]	T. Eggen, “Application of Fungal Substrate from Commercial Mushroom Production—Pleurotus ostreatus—for Bioremediation of Creosote Contaminated Soil,” International Biodeterioration and Biodegradation, Vol. 44, No. 2-3, 1999, pp. 117-126. doi:10.1016/S0964-8305(99)00073-6
[8]	K. Ishihara, K. Iwai, H. Yamaguchi, N. Nakajima, K. Nakamura and T. Ohshima, “Stereoselective Reduction of α- and β-Keto Esters with Aerobic Thermophiles, Bacillus Strains,” Bioscience, Biotechnology, and Biochemistry, Vol. 60, No. 11, 1996, pp. 1896-1898. doi:10.1271/bbb.60.1896
[9]	K. Ishihara, M. Nishitani, H. Yamaguchi, N. Nakajima, T. Ohshima and K. Nakamura, “Preparation of Optically Active α-Hydroxy Esters: Stereoselective Reduction of α-Keto Esters Using Thermophilic Actinomycetes,” Journal of Fermentation and Bioengineering, Vol. 84, No. 3, 1997, pp. 268-270. doi:10.1016/S0922-338X(97)82068-5
[10]	K. Ishihara, H. Yamaguchi, H. Hamada, N. Nakajima and K. Nakamura, “Stereocontrolled Reduction of α-Keto Esters with thermophilic Actinomycete, Streptomyces thermocyaneoviolaceus IFO14271,” Journal of Molecular Catalysis B: Enzymatic, Vol. 10, No. 4, 2000, pp. 429-434. doi:10.1016/S1381-1177(99)00115-0
[11]	K. Ishihara, H. Yamaguchi, N. Adachi, H. Hamada and N. Nakajima, “Stereocontrolled Reduction of α- and β-Keto Esters with Micro Green Algae, Chlorella strains,” Bioscience, Biotechnology, and Biochemistry, Vol. 64, No. 10, 2000, pp. 2099-2103. doi:10.1271/bbb.64.2099
[12]	K. Ishihara, N. Nakajima, H. Yamaguchi, H. Hamada and Y. Uchimura, “Stereoselective Reduction of Keto Esters with Marine Micro Algae,” Journal of Molecular Catalysis B: Enzymatic, Vol. 15, No. 1-3, 2001, pp. 101-104. doi:10.1016/S1381-1177(00)00247-2
[13]	K. Ishihara, H. Yamaguchi and N. Nakajima, “Stereoselective Reduction of Keto Esters: Thermophilic Bacteria and Microalgae as New Biocatalysts,” Journal of Molecular Catalysis B: Enzymatic, Vol. 23, No. 2-6, 2003, pp. 171-189. doi:10.1016/S1381-1177(03)00081-X
[14]	K. Ishihara, H. Nagai, K. Takahashi, M. Nishiyama and N. Nakajima, “Stereoselective Reduction of α-Keto Ester and α-Keto Amide with Marine Actinomycetes, Salinispora Strains, as Novel Biocatalysts,” Biochemistry Insights, Vol. 4, 2011, pp. 29-33. doi:10.4137/BCI.S7877
[15]	K. Nakamura, K. Inoue, K. Ushio, S. Oka and A. Ohno, “Stereochemical Control on Yeast Reduction of α-Keto Esters. Reduction by Immobilized Bakers’ Yeast in Hexane,” Journal of Organic Chemistry, Vol. 53, No. 11, 1998, pp. 2589-2593. doi:10.1021/jo00246a035