Skip to main content
Log in

Combining UV Irradiation and Alkaline Deacetylation to Obtain Vitamin D- and Chitosan-Enriched Fractions from Shiitake Mushrooms (Lentinula edodes)

  • RESEARCH
  • Published:
Food and Bioprocess Technology Aims and scope Submit manuscript

Abstract

Shiitake mushrooms (Lentinula edodes) contain compounds with hypocholesterolemic and immune-modulatory activities such as ergosterol and chitin that can be partially transformed into vitamin D and chitosan to yield extracts with enhanced bioactivities. A method was optimized to increase vitamin D2 levels by irradiating a non-soluble fraction obtained from shiitake mushrooms during 1 h with UV-light (254 nm) at 50 °C in methanol. After 1 h, almost all of the ergosterol was transformed into vitamin D2. The conversion ratio can be simply adjusted by reducing the irradiation time. A deacetylation treatment with 50% NaOH for 24 h at 95 °C was needed to generate chitosan and other water-soluble lower molecular weight derivatives from chitin. To obtain an extract enriched in both compounds, the defined methods can be combined, but the extracts should be firstly deacetylated and later irradiated. In this order, an extract is obtained containing vitamin D2 (4.65 mg/g) and chitosan (2.83%).

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

Data Availability

Research data are not shared.

Abbreviations

SP:

Shiitake powder

SF:

Soluble fraction

NSF:

Non-soluble fraction

UV:

Ultraviolet

DA:

Deacetylation

References

  • Amjadi, S., Emaminia, S., Nazari, M., Davudian, S. H., Roufegarinejad, L., & Hamishehkar, H. (2019). Application of reinforced ZnO nanoparticle-incorporated gelatin bionanocomposite film with chitosan nanofibre for packaging of chicken fillet and cheese as food models. Food and Bioprocess Technology, 12(7), 1205–1219. https://doi.org/10.1007/s11947-019-02286-y

    Article  CAS  Google Scholar 

  • Ao, T., Kikuta, J., & Ishii, M. (2021). The effects of vitamin D on immune system and inflammatory diseases. In Biomolecules (Vol. 11, Issue 11). MDPI. https://doi.org/10.3390/biom11111624

  • Chen, J., Zhang, M., Mujumdar, A. S., & Phuhongsunge, P. (2022). 4D printing induced by microwave and ultrasound for mushroom mixtures: Efficient conversion of ergosterol into vitamin D2. Food Chemistry, 387. https://doi.org/10.1016/j.foodchem.2022.132840

  • Chien, R. C., Yen, M. T., & Mau, J. L. (2016). Antimicrobial and antitumor activities of chitosan from shiitake stipes, compared to commercial chitosan from crab shells. Carbohydrate Polymers, 138, 259–264. https://doi.org/10.1016/j.carbpol.2015.11.061

    Article  CAS  PubMed  Google Scholar 

  • Chugh, R. M., Mittal, P., MP, N., Arora, T., Bhattacharya, T., Chopra, H., Cavalu, S., & Gautam, R. K. (2022). Fungal mushrooms: A natural compound with therapeutic applications. In Frontiers in Pharmacology (Vol. 13). Frontiers Media S.A. https://doi.org/10.3389/fphar.2022.925387

  • Dai, X., Stanilka, J. M., Rowe, C. A., Esteves, E. A., Nieves, C., Spaiser, S. J., Christman, M. C., Langkamp-Henken, B., & Percival, S. S. (2015). Consuming Lentinula edodes (Shiitake) Mushrooms Daily Improves Human Immunity: A randomized dietary intervention in healthy young adults. Journal of the American College of Nutrition, 34(6), 478–487. https://doi.org/10.1080/07315724.2014.950391

    Article  CAS  PubMed  Google Scholar 

  • de Britto, D., & Campana-Filho, S. P. (2007). Kinetics of the thermal degradation of chitosan. Thermochimica Acta, 465(1–2), 73–82. https://doi.org/10.1016/j.tca.2007.09.008

    Article  CAS  Google Scholar 

  • El-Ramady, H., Abdalla, N., Badgar, K., Llanaj, X., Törős, G., Hajdú, P., Eid, Y., & Prokisch, J. (2022). Edible mushrooms for sustainable and healthy human food: nutritional and medicinal attributes. In Sustainability (Switzerland) (Vol. 14, Issue 9). MDPI. https://doi.org/10.3390/su14094941

  • Fukushima-Sakuno, E. (2020). Bioactive small secondary metabolites from the mushrooms Lentinula edodes and Flammulina velutipes. In Journal of Antibiotics, 73(10), 687–696. Springer Nature. https://doi.org/10.1038/s41429-020-0354-x

  • Gil-Ramírez, A., Aldars-García, L., Palanisamy, M., Jiverdeanu, R. M., Ruiz-Rodríguez, A., Marín, F. R., Reglero, G., & Soler-Rivas, C. (2013). Sterol enriched fractions obtained from Agaricus bisporus fruiting bodies and by-products by compressed fluid technologies (PLE and SFE). Innovative Food Science and Emerging Technologies, 18, 101–107. https://doi.org/10.1016/j.ifset.2013.01.007

    Article  CAS  Google Scholar 

  • Grady, L. T., & Thakker, K. D. (1980). Stability of solid drugs: Degradation of ergocalciferol (vitamin D2) and cholecalciferol (vitamin D3) at high humidities and elevated temperatures. Journal of Pharmaceutical Sciences, 69(9), 1099–1102. https://doi.org/10.1002/jps.2600690932

    Article  CAS  PubMed  Google Scholar 

  • Janoušek, J., Pilařová, V., Macáková, K., Nomura, A., Veiga-Matos, J., Silva, D. D. da, Remião, F., Saso, L., Malá-Ládová, K., Malý, J., Nováková, L., & Mladěnka, P. (2022). Vitamin D: Sources, physiological role, biokinetics, deficiency, therapeutic use, toxicity, and overview of analytical methods for detection of vitamin D and its metabolites. Critical Reviews in Clinical Laboratory Sciences, 1–38. https://doi.org/10.1080/10408363.2022.2070595

  • John Kasongo, K., Tubadi, D. J., Bampole, L. D., Kaniki, T. A., Kanda, N. J. M., & Lukumu, M. E. (2020). Extraction and characterization of chitin and chitosan from Termitomyces titanicus. SN Applied Sciences, 2(3). https://doi.org/10.1007/s42452-020-2186-5

  • Ko, J. A., Lee, B. H., Lee, J. S., & Park, H. J. (2008). Effect of UV-B exposure on the concentration of vitamin D2 in sliced shiitake mushroom (Lentinus edodes) and white button mushroom (Agaricus bisporus). Journal of Agricultural and Food Chemistry, 56(10), 3671–3674. https://doi.org/10.1021/jf073398s

    Article  CAS  PubMed  Google Scholar 

  • Lago, M. A., Sendón, R., de Quirós, A.R.-B., Sanches-Silva, A., Costa, H. S., Sánchez-Machado, D. I., Valdez, H. S., Angulo, I., Aurrekoetxea, G. P., Torrieri, E., López-Cervantes, J., & Paseiro, P. (2014). Preparation and characterization of antimicrobial films based on chitosan for active food packaging applications. Food and Bioprocess Technology, 7(10), 2932–2941. https://doi.org/10.1007/s11947-014-1276-z

    Article  CAS  Google Scholar 

  • Lee, G. S., Byun, H. S., Yoon, K. H., Lee, J. S., Choi, K. C., & Jeung, E. B. (2009). Dietary calcium and vitamin D2 supplementation with enhanced Lentinula edodes improves osteoporosis-like symptoms and induces duodenal and renal active calcium transport gene expression in mice. European Journal of Nutrition, 48(2), 75–83. https://doi.org/10.1007/s00394-008-0763-2

    Article  CAS  PubMed  Google Scholar 

  • Li, S., He, Y., Lin, S., Hao, L., Ye, Y., Lv, L., Sun, Z., Fan, H., Shi, Z., Li, J., Feng, R., Na, L., Wang, Y., Li, Y., & Sun, C. (2016). Increase of circulating cholesterol in vitamin D deficiency is linked to reduced vitamin D receptor activity via the Insig-2/SREBP-2 pathway. Molecular Nutrition and Food Research, 60(4), 798–809. https://doi.org/10.1002/mnfr.201500425

    Article  CAS  PubMed  Google Scholar 

  • Li, X., Xing, R., Xu, C., Liu, S., Qin, Y., Li, K., Yu, H., & Li, P. (2021). Immunostimulatory effect of chitosan and quaternary chitosan: A review of potential vaccine adjuvants. Carbohydrate Polymers, 264(April), 118050. https://doi.org/10.1016/j.carbpol.2021.118050

  • Mattila, P., Lampi, A. M., Ronkainen, R., Toivo, J., & Piironen, V. (2002). Sterol and vitamin D2 contents in some wild and cultivated mushrooms. Food Chemistry, 76, 293–298. https://doi.org/10.1016/S0308-8146(01)00275-8

    Article  CAS  Google Scholar 

  • Morales, D., Gil-Ramirez, A., Smiderle, F. R., Piris, A. J., Ruiz-Rodriguez, A., & Soler-Rivas, C. (2017). Vitamin D-enriched extracts obtained from shiitake mushrooms (Lentinula edodes) by supercritical fluid extraction and UV-irradiation. Innovative Food Science and Emerging Technologies, 41, 330–336. https://doi.org/10.1016/j.ifset.2017.04.008

    Article  CAS  Google Scholar 

  • Morales, D., Piris, A. J., Ruiz-Rodriguez, A., Prodanov, M., & Soler-Rivas, C. (2018a). Extraction of bioactive compounds against cardiovascular diseases from Lentinula edodes using a sequential extraction method. Biotechnology Progress, 34(3), 746–755. https://doi.org/10.1002/btpr.2616

    Article  CAS  PubMed  Google Scholar 

  • Morales, D., Shetty, S. A., López-Plaza, B., Gómez-Candela, C., Smidt, H., Marín, F. R., & Soler-Rivas, C. (2021). Modulation of human intestinal microbiota in a clinical trial by consumption of a β-d-glucan-enriched extract obtained from Lentinula edodes. European Journal of Nutrition, 60(6), 3249–3265. https://doi.org/10.1007/s00394-021-02504-4

    Article  CAS  PubMed  Google Scholar 

  • Morales, D., Smiderle, F. R., Piris, A. J., Soler-Rivas, C., & Prodanov, M. (2019a). Production of a β-D-glucan-rich extract from Shiitake mushrooms (Lentinula edodes) by an extraction/microfiltration/reverse osmosis (nanofiltration) process. Innovative Food Science and Emerging Technologies, 51, 80–90. https://doi.org/10.1016/j.ifset.2018.04.003

    Article  CAS  Google Scholar 

  • Morales, D., Smiderle, F. R., Villalva, M., Abreu, H., Rico, C., Santoyo, S., Iacomini, M., & Soler-Rivas, C. (2019b). Testing the effect of combining innovative extraction technologies on the biological activities of obtained β-glucan-enriched fractions from Lentinula edodes. Journal of Functional Foods, 60. https://doi.org/10.1016/j.jff.2019.103446

  • Morales, D., Tabernero, M., Largo, C., Polo, G., Piris, A. J., & Soler-Rivas, C. (2018b). Effect of traditional and modern culinary processing, bioaccessibility, biosafety and bioavailability of eritadenine, a hypocholesterolemic compound from edible mushrooms. Food and Function, 9(12), 6360–6368. https://doi.org/10.1039/c8fo01704b

    Article  CAS  PubMed  Google Scholar 

  • Morales, D., Tejedor-Calvo, E., Jurado-Chivato, N., Polo, G., Tabernero, M., Ruiz-Rodríguez, A., Largo, C., & Soler-Rivas, C. (2019c). In vitro and in vivo testing of the hypocholesterolemic activity of ergosterol- and β-glucan-enriched extracts obtained from shiitake mushrooms (Lentinula edodes). Food and Function, 10(11), 7325–7332. https://doi.org/10.1039/c9fo01744e

    Article  CAS  PubMed  Google Scholar 

  • Moumita, S., & Das, B. (2022). Assessment of the prebiotic potential and bioactive components of common edible mushrooms in India and formulation of synbiotic microcapsules. LWT, 156. https://doi.org/10.1016/j.lwt.2021.113050

  • Palanisamy, M., Aldars-García, L., Gil-Ramírez, A., Ruiz-Rodríguez, A., Marín, F. R., Reglero, G., & Soler-Rivas, C. (2014). Pressurized water extraction of β-glucan enriched fractions with bile acids-binding capacities obtained from edible mushrooms. Biotechnology Progress, 30(2), 391–400. https://doi.org/10.1002/btpr.1865

    Article  CAS  PubMed  Google Scholar 

  • Rementeria, A., Ezkurra, P., Hernando, F., Ponton, J., Sevilla, M. J., & Cisterna, R. (1991). Chitin assay to estimate the growth of Candida albicans in organs of infected mice. In Journal of Medical and Veterinary Mycology (Vol. 29).

  • Roncero-Ramos, I., & Delgado-Andrade, C. (2017). The beneficial role of edible mushrooms in human health. In Current Opinion in Food Science (Vol. 14, pp. 122–128). Elsevier Ltd. https://doi.org/10.1016/j.cofs.2017.04.002

  • Savin, S., Craciunescu, O., Oancea, A., Ilie, D., Ciucan, T., Antohi, L. S., Toma, A., Nicolescu, A., Deleanu, C., & Oancea, F. (2020). Antioxidant, cytotoxic and antimicrobial activity of chitosan preparations extracted from Ganoderma lucidum mushroom. Chemistry and Biodiversity, 17(7). https://doi.org/10.1002/cbdv.202000175

  • Silva, I. M. V., Machado, F., Moreno, M. J., Nunes, C., Coimbra, M. A., & Coreta-Gomes, F. (2021). Polysaccharide structures and their hypocholesterolemic potential. In Molecules (Vol. 26, Issue 15). MDPI AG. https://doi.org/10.3390/molecules26154559

  • Smiderle, F. R., Morales, D., Gil-Ramírez, A., de Jesus, L. I., Gilbert-López, B., Iacomini, M., & Soler-Rivas, C. (2017). Evaluation of microwave-assisted and pressurized liquid extractions to obtain β-D-glucans from mushrooms. Carbohydrate Polymers, 156, 165–174. https://doi.org/10.1016/j.carbpol.2016.09.029

    Article  CAS  PubMed  Google Scholar 

  • Taofiq, O., Corrêa, R. C. G., Barros, L., Prieto, M. A., Bracht, A., Peralta, R. M., González-Paramás, A. M., Barreiro, M. F., & Ferreira, I. C. F. R. (2019). A comparative study between conventional and non-conventional extraction techniques for the recovery of ergosterol from Agaricus blazei Murrill. Food Research International, 125. https://doi.org/10.1016/j.foodres.2019.108541

  • Taofiq, O., Fernandes, Â., Barros, L., Barreiro, M. F., & Ferreira, I. C. F. R. (2017). UV-irradiated mushrooms as a source of vitamin D2: A review. In Trends in Food Science and Technology (Vol. 70, pp. 82–94). Elsevier Ltd. https://doi.org/10.1016/j.tifs.2017.10.008

  • Teichmann, A., Dutta, P. C., Staffas, A., & Jägerstad, M. (2007). Sterol and vitamin D2 concentrations in cultivated and wild grown mushrooms: Effects of UV irradiation. LWT - Food Science and Technology, 40(5), 815–822. https://doi.org/10.1016/j.lwt.2006.04.003

    Article  CAS  Google Scholar 

  • Tejedor-Calvo, E., Morales, D., Marco, P., Venturini, M. E., Blanco, D., & Soler-Rivas, C. (2019). Effects of combining electron-beam or gamma irradiation treatments with further storage under modified atmospheres on the bioactive compounds of Tuber melanosporum truffles. Postharvest Biology and Technology, 155, 149–155. https://doi.org/10.1016/j.postharvbio.2019.05.022

    Article  CAS  Google Scholar 

  • Vallespir, F., Crescenzo, L., Rodríguez, Ó., Marra, F., & Simal, S. (2019). Intensification of low-temperature drying of mushroom by means of power ultrasound: Effects on drying kinetics and quality parameters. Food and Bioprocess Technology. https://doi.org/10.1007/s11947-019-02263-5

    Article  Google Scholar 

  • Viacava, G. E., Cenci, M. P., & Ansorena, M. R. (2022). Effect of chitosan edible coatings incorporated with free or microencapsulated thyme essential oil on quality characteristics of fresh-cut carrot slices. Food and Bioprocess Technology, 15(4), 768–784. https://doi.org/10.1007/s11947-022-02783-7

    Article  CAS  Google Scholar 

  • Wang, C. Y. (2020). A review on the potential reuse of functional polysaccharides extracted from the by-products of mushroom processing. In Food and Bioprocess Technology, 13(2), 217–228. Springer. https://doi.org/10.1007/s11947-020-02403-2

  • Wasikiewicz, J. M., Yoshii, F., Nagasawa, N., Wach, R. A., & Mitomo, H. (2005). Degradation of chitosan and sodium alginate by gamma radiation, sonochemical and ultraviolet methods. Radiation Physics and Chemistry, 73(5), 287–295. https://doi.org/10.1016/j.radphyschem.2004.09.021

    Article  CAS  Google Scholar 

  • Wittig, M., Krings, U., & Berger, R. G. (2013). Single-run analysis of vitamin D photoproducts in oyster mushroom (Pleurotus ostreatus) after UV-B treatment. Journal of Food Composition and Analysis, 31(2), 266–274. https://doi.org/10.1016/j.jfca.2013.05.017

    Article  CAS  Google Scholar 

  • Won, D. J., Kim, S. Y., Jang, C. H., Lee, J. S., Ko, J. A., & Park, H. J. (2018). Optimization of UV irradiation conditions for the vitamin D2-fortified shiitake mushroom (Lentinula edodes) using response surface methodology. Food Science and Biotechnology, 27(2), 417–424. https://doi.org/10.1007/s10068-017-0266-0

    Article  CAS  PubMed  Google Scholar 

  • Wong, J. H., Ng, T. B., Chan, H. H. L., Liu, Q., Man, G. C. W., Zhang, C. Z., Guan, S., Ng, C. C. W., Fang, E. F., Wang, H., Liu, F., Ye, X., Rolka, K., Naude, R., Zhao, S., Sha, O., Li, C., & Xia, L. (2020). Mushroom extracts and compounds with suppressive action on breast cancer: Evidence from studies using cultured cancer cells, tumor-bearing animals, and clinical trials. Applied Microbiology and Biotechnology, 104(11), 4675–4703. https://doi.org/10.1007/s00253-020-10476-4

    Article  CAS  PubMed  Google Scholar 

  • Wu, T., Zivanovic, S., Draughon, F. A., & Sams, C. E. (2004). Chitin and chitosan-value-added products from mushroom waste. Journal of Agricultural and Food Chemistry, 52(26), 7905–7910. https://doi.org/10.1021/jf0492565

    Article  CAS  PubMed  Google Scholar 

  • Zhang, Z., Zhao, L., Qu, H., Zhou, H., Yang, H., & Chen, H. (2022). Physicochemical characterization, adsorption function and prebiotic effect of chitin-glucan complex from mushroom Coprinus comatus. International Journal of Biological Macromolecules, 206, 255–263. https://doi.org/10.1016/j.ijbiomac.2022.02.152

    Article  CAS  PubMed  Google Scholar 

Download references

Funding

This research was supported by the national R + D program from the Spanish Ministry of Science and Innovation (project AGL2014-56211-R) and the regional program from the Community of Madrid, Spain (S2013/ABI-2728). D. M. received from the Spanish Ministry of Science and Innovation a Juan de la Cierva Formación scholarship (FJC2020-044585-I).

Author information

Authors and Affiliations

Authors

Contributions

Diego Morales: investigation, methodology, formal analysis, writing of the original draft and figures; Adriana Jiménez Piris: investigation and methodology; Alejandro Ruiz-Rodríguez: supervision and data curation; Cristina Soler-Rivas: supervision, validation, data curation, funding acquisition, writing and reviewing.

Corresponding author

Correspondence to Diego Morales.

Ethics declarations

Conflict of Interest

The authors declare no competing interests.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Morales, D., Piris, A.J., Ruiz-Rodríguez, A. et al. Combining UV Irradiation and Alkaline Deacetylation to Obtain Vitamin D- and Chitosan-Enriched Fractions from Shiitake Mushrooms (Lentinula edodes). Food Bioprocess Technol 16, 1303–1311 (2023). https://doi.org/10.1007/s11947-023-02998-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11947-023-02998-2

Keywords

Navigation