Abstract
Purpose
Rice bran acid oil (RBAO) is a free fatty acid-containing byproduct derived from the neutralization step of rice bran oil refinery. It is usually used as a low-value product for animal feed. Given the large amount of bioactive compound, γ-oryzanol, in the RBAO, there is the opportunity to redeploy RBAO as a source for other high-value products. The present study aims to develop a simple alkaline hydrolysis method that could concurrently produce ferulic acid (FA) and phytosterols/triterpene alcohols (PTs) from the γ-oryzanol in the RBAO. The biological activities of FA and PTs were then evaluated for their suitability as cosmetic ingredients.
Methods
The molar ratios of RBAO to KOH and the hydrolysis reaction time were investigated at 80 °C. The hydrolyzed products were chemically characterized by high-performance size-exclusion chromatography and were subsequently purified to remove impurities. The biological activities including sun protection factor, antioxidant activity, tyrosinase inhibition and collagenase activities were evaluated.
Results
The study shows that the RBAO to KOH ratio of 1:15 with 15 min reaction time gave the highest FA yield. The purification procedure resulted in FA and PTs purities of 96.93% and 90.23%, respectively. The FA demonstrated potent cosmetic properties (UV absorption, antioxidant activities, tyrosinase and collagenase inhibitory effects) that compared favorably with that of commercial FA. On the other hand, the PTs showed little activity against 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals.
Conclusion
This work presents a simple, fast and energy-efficient methodology for the simultaneous production of FA and PTs from RBAO. The RBAO-derived FA is suitable for cosmetic applications, while the PTs showed weak inhibitory activity on DPPH radicals.
Graphical Abstract
Similar content being viewed by others
Data Availability
The data will be kept by the authors of this study.
Code Availability
Not applicable.
References
Kim, K.H., Tsao, R., Yang, R., Cui, S.W.: Phenolic acid profiles and antioxidant activities of wheat bran extracts and the effect of hydrolysis conditions. Food Chem. 95(3), 466–473 (2006). https://doi.org/10.1016/j.foodchem.2005.01.032
Kumar, N., Pruthi, V.: Potential applications of ferulic acid from natural sources. Biotechnol. Rep. 4, 86–93 (2014). https://doi.org/10.1016/j.btre.2014.09.002
Tam, L.T., Ha, N.C., Thom, L.T., Zhu, J.Y., Wakisaka, M., Hong, D.D.: Ferulic acid extracted from rice bran as a growth promoter for the microalga Nannochloropsis oculata. J. Appl. Phycol. 33, 37–45 (2021). https://doi.org/10.1007/s10811-020-02166-5
Qian, W., Liu, W., Zhu, D., Cao, Y., Tang, A., Gong, G., Su, H.: Natural skin-whitening compounds for the treatment of melanogenesis (review). Exp. Ther. Med. 20(1), 173–185 (2020). https://doi.org/10.3892/etm.2020.8687
Son, M.J., Rico, C.W., Nam, S.H., Kang, M.Y.: Influence of oryzanol and ferulic acid on the lipid metabolism and antioxidative status in high fat-fed mice. J. Clin. Biochem. Nutr. 46(2), 150–156 (2010). https://doi.org/10.3164/jcbn.09-98
Staniforthet, V., Huang, W.C., Aravindaram, K., Yang, N.S.: Ferulic acid, a phenolic phytochemical, inhibits UVB-induced matrix metalloproteinases in mouse skin via posttranslational mechanisms. J. Nutr. Biochem. 23(5), 443–451 (2012). https://doi.org/10.1016/j.jnutbio.2011.01.009
Valério, R., Cadima, M., Crespo, J.G., Brazinha, C.: Extracting ferulic acid from corn fibre using mild alkaline extraction: a pilot scale study. Waste Biomass Valoriz. 13, 287–297 (2022). https://doi.org/10.1007/s12649-021-01514-x
Wang, O., Liu, J., Cheng, Q., Guo, X., Wang, Y., Zhao, L., Zhou, F., Ji, B.: Effects of ferulic acid and γ-oryzanol on high-fat and high-fructose diet-induced metabolic syndrome in rats. PLoS ONE 10(2), e0118135 (2015). https://doi.org/10.1371/journal.pone.0118135
Sharma, M., Khichar, M.K., Agrawal, R.D.: Isolation and identification of phytosterols from Bignonia venusta (L.). Asian J. Pharm. Clin. Res. 10(12), 247–251 (2017). https://doi.org/10.22159/ajpcr.2017.v10i12.21009
Akihisa, T., Kojima, N., Katoh, N., Ichimura, Y., Suzuki, H., Fukatsu, M., Maranz, S., Masters, E.T.: Triterpene alcohol and fatty acid composition of shea nuts from seven African countries. J. Oleo Sci. 59(7), 351–360 (2010). https://doi.org/10.5650/jos.59.351
Doering, T., Holtkötter, O., Schlotmann, K., Jassoy, C., Petersohn, D., Wadle, A., Waldmann-Laue, M.: Cutaneous restructuration by apple seed phytosterols: from DNA chip analysis to morphological alterations. Int. J. Cosmet. Sci. 27(2), 142 (2005). https://doi.org/10.1111/j.1467-2494.2005.00259_1.x
Miras-Moreno, B., Sabater-Jara, A.B., Pedreño, M.A., Almagro, L.: Bioactivity of phytosterols and their production in plant in vitro cultures. J. Agric. Food Chem. 64(38), 7049–7058 (2016). https://doi.org/10.1021/acs.jafc.6b02345
Global Market Insight. Natural ferulic acid market. https://www.gminsights.com/industry-analysis/natural-ferulic-acid-market (2019). Accessed 6 May 2023
Global Market Insight. Phytosterols market. https://www.gminsights.com/industry-analysis/phytosterols-market (2021). Accessed 6 May 2023
Alexandri, M., López-Gómez, J.P., Olszewska-Widdrat, A., Venus, J.: Valorising agro-industrial wastes within the circular bioeconomy concept: the case of defatted rice bran with emphasis on bioconversion strategies. Fermentation 6(2), 42 (2020). https://doi.org/10.3390/fermentation6020042
Expert Market Research. Global rice bran oil market outlook. https://www.expertmarketresearch.com/reports/rice-bran-oil-market#:~:text=The%20global%20rice%20bran%20oil%20market%20attained%20a%20volume%20of,its%20health%20benefits%20among%20consumers (2022). Accessed 16 Dec 2022
Chakrabarti, P.P., Jala, R.C.R.: Chapter 3—Processing technology of rice bran oil. In: Cheong, L.Z., Xu, X. (eds.) Rice bran and rice bran oil, pp. 55–95. AOCS Press, London (2019)
Kadoglidou, K., Kalaitzidis, A., Stavrakoudis, D., Mygdalia, A., Katsantonis, D.: A novel compost for rice cultivation developed by rice industrial by-products to serve circular economy. Agronomy 9(9), 553 (2019). https://doi.org/10.3390/agronomy9090553
Korhonen, J., Honkasalo, A., Seppälä, J.: Circular economy: the concept and its limitations. Ecol. Econ. 143, 37–46 (2018). https://doi.org/10.1016/j.ecolecon.2017.06.041
Meedam, A., Usaku, C., Daisuk, P., Shotipruk, A.: Comparative study on physicochemical hydrolysis methods for glycerides removal from rice bran acid oil for subsequent γ-oryzanol recovery. Biomass Convers. 12, 245–252 (2022). https://doi.org/10.1007/s13399-020-00775-1
Ito, J., Sawada, K., Ogura, Y., Xinyi, F., Rahmania, H., Mohri, T., Kohyama, N., Kwon, E., Eitsuka, T., Hashimoto, H., Kuwahara, S., Miyazawa, T., Nakagawa, K.: Definitive evidence of the presence of 24-methylenecycloartanyl ferulate and 24-methylenecycloartanyl caffeate in barley. Sci. Rep. 9(1), 2572 (2019). https://doi.org/10.1038/s41598-019-48985-6
Lerma-García, M.J., Herrero-Martínez, J.M., Simó-Alfonso, E.F., Mendonça, C.R.B., Ramis-Ramos, G.: Composition, industrial processing and applications of rice bran γ-oryzanol. Food Chem. 115(2), 389–404 (2009). https://doi.org/10.1016/j.foodchem.2009.01.063
Sombutsuwan, P., Nakornsadet, A., Aryusuk, K., Akepratumchai, S., Jeyashoke, N., Lilitchan, S., Krisnangkura, K.: Recovery of γ-oryzanol from rice bran acid oil by an acid-base extraction method with the assistance of response surface methodology. J. Oleo Sci. 67(11), 1405–1415 (2018). https://doi.org/10.5650/jos.ess18073
Zullaikah, S., Melwita, E., Ju, Y.H.: Isolation of oryzanol from crude rice bran oil. Bioresour. Technol. 100(1), 299–302 (2009). https://doi.org/10.1016/j.biortech.2008.06.008
Ou, S., Luo, Y., Xue, F., Huang, C., Zhang, N., Liu, Z.: Seperation and purification of ferulic acid in alkaline-hydrolysate from sugarcane bagasse by activated charcoal adsorption/anion macroporous resin exchange chromatography. J. Food Eng. 78(4), 1298–1304 (2007). https://doi.org/10.1016/j.jfoodeng.2005.12.037
Truong, H.T., Van Do, M., Huynh, L.D., Nguyen, L.T., Do, A.T., Le, T.T.X., Duong, H.P., Takenaka, N., Imamura, K., Maeda, Y.: Ultrasound-assisted, base-catalyzed, homogeneous reaction for ferulic acid production from γ-oryzanol. J. Chem. 2018, 3132747 (2018). https://doi.org/10.1155/2018/3132747
Gadalkar, S.M., Rathod, V.K.: Pre-treatment of ferulic acid esterases immobilized on MNPs to enhance the extraction of ferulic acid from defatted rice bran in presence of ultrasound. Biocatal. Agric. Biotechnol. 10, 342–351 (2017). https://doi.org/10.1016/j.bcab.2017.03.016
Truong, H.T., Van, M.D., Huynh, L.D., Nguyen, L.T., Tuan, A.D., Thanh, T.L.X., Phuoc, H.D., Takenaka, N., Imamura, K., Maeda, Y.: A method for ferulic acid production from rice bran oil soapstock using a homogenous system. Appl. Sci. 7(8), 796 (2017). https://doi.org/10.3390/app7080796
Taniguchi, H., Nomura, E., Tsuno, T., Minami, S., Kato, K., Hayashi, C.: US Patent 5,288,902, 1994
Blanchard, C.O., Sutterlin, W.R., Long, R.A.: WIPO (PCT) Patent WO2021/138549 A1, 2021
Pojjanapornpun, S., Jiruttisakul, A., Chumsantea, S., Sombutsuwan, P., Nakornsadet, A., Krisnangkura, K., Aryusuk, K.: Effect of mobile phase composition on the separation of neutral lipids, γ-oryzanol and its saponified compounds on a 100-Å Phenogel column. In: The 3rd International Conference on Advanced Research in Applied Science and Engineering, Oxford, 2–4 July 2021. https://doi.org/10.33422/3rd.raseconf.2021.07.01
Petrović, M., Jovanović, M., Lević, S., Nedović, V., Mitić-Ćulafić, D., Semren, T.Ž., Veljović, S.: Valorization potential of Plantago major L. solid waste remaining after industrial tincture production: insight into the chemical composition and bioactive properties. Waste Biomass Valoriz. 13, 1639–1651 (2022). https://doi.org/10.1007/s12649-021-01608-6
Era, B., Floris, S., Sogos, V., Porcedda, C., Piras, A., Medda, R., Fais, A., Pintus, F.: Anti-aging potential of extracts from Washingtonia filifera seeds. Plants 10(1), 151 (2021). https://doi.org/10.3390/plants10010151
Rumiyati, Jayasena, V., James, A.P.: Total phenolic and phytosterol compounds and the radical scavenging activity of germinated Australian sweet lupin flour. Plant Foods Hum. Nutr. 68(4), 352–357 (2013). https://doi.org/10.1007/s11130-013-0377-6
Whangsomnuek, N., Mungmai, L., Mengamphan, K., Amornlerdpison, D.: Bioactive compounds of aqueous extracts of flower and leaf of Etlingera elatior (Jack) R.M.Sm. for cosmetic application. Maejo Int. J. Sci. Technol. 13, 196–208 (2019)
Alam, N., Yoon, K.N., Lee, K.R., Shin, P.G., Cheong, J.C., Yoo, Y.B., Shim, M.J., Lee, M.W., Lee, U.Y., Lee, T.S.: Antioxidant activities and tyrosinase inhibitory effects of different extracts from Pleurotus ostreatus fruiting bodies. Mycobiology 38, 295–301 (2010)
Zakiah, K., Anwar, E., Nurhayati, T.: In-vitro evaluation of antioxidant activity and anti-collagenase activity of Thalassia hempricii as a potent ingredients for anti-wrinkle cosmetics. Pharmacogn. J. 10(4), 778–782 (2018). https://doi.org/10.5530/pj.2018.4.131
Paiva, L.B.D., Goldbeck, R., Santos, W.D., Squina, F.M.: Ferulic acid and derivatives: molecules with potential application in the pharmaceutical field. Braz. J. Pharm. Sci. 49(3), 395–411 (2013). https://doi.org/10.1590/S1984-82502013000300002
Peres, D.D.A., Sarruf, F.D., de Oliveira, C.A., Velasco, M.V.R., Baby, A.R.: Ferulic acid photoprotective properties in association with UV filters: multifunctional sunscreen with improved SPF and UVA-PF. J. Photochem. Photobiol. B Biol. 185, 46–49 (2018). https://doi.org/10.1016/j.jphotobiol.2018.05.026
Surendran, G., McAteer, M., Zanchelli, P., Dhimitruka, I.: Assessment of hydroxycinnamic acids potential for use as multifunctional active ingredients in sunscreens, via a comparative UV spectroscopy analysis. J. Chem. Pharm. Res. 11, 37–44 (2019)
Mancuso, C., Santangelo, R.: Ferulic acid: pharmacological and toxicological aspects. Food Chem. Toxicol. 65, 185–195 (2014). https://doi.org/10.1016/j.fct.2013.12.024
Zduńska, K., Dana, A., Kolodziejczak, A., Rotsztejn, H.: Antioxidant properties of ferulic acid and its possible application. Skin Pharmacol. Physiol. 31(6), 332–336 (2018). https://doi.org/10.1159/000491755
Hatice, B.: The effects of free radicals on aging process. Curr. Trends Biomed. Eng. Biosci. 13(5), 555871 (2018). https://doi.org/10.19080/CTBEB.2018.13.555871
Costa, R., Santos, L.: Delivery systems for cosmetics—from manufacturing to the skin of natural antioxidants. Powder Technol. 322, 402–416 (2017). https://doi.org/10.1016/j.powtec.2017.07.086
Naidoo, K., Birch-Machin, M.A.: Oxidative stress and ageing: the influence of environmental pollution, sunlight and diet on skin. Cosmetics 4(1), 4 (2017). https://doi.org/10.3390/cosmetics4010004
Xu, Z., Godber, J.S.: Antioxidant activities of major components of γ-oryzanol from rice bran using a linoleic acid model. J. Am. Oil Chem. Soc. 78, 645–649 (2001). https://doi.org/10.1007/s11746-001-0320-1
Takahashi, T., Miyazawa, M.: Tyrosinase inhibitory activities of cinnamic acid analogues. Pharmazie 65(12), 913–918 (2010). https://doi.org/10.1691/ph.2010.0654
Miao, Z., Kayahara, H., Tadasa, K.: Synthesis and biological activities of ferulic acid–amino acid derivatives. Biosci. Biotechnol. Biochem. 61(3), 527–529 (1997). https://doi.org/10.1271/bbb.61.527
Strzępek-Gomółka, M., Gaweł-Beben, K., Angelis, A., Antosiewicz, B., Sakipova, Z., Kozhanova, K., Głowniak, K., Kukula-Koch, W.: Identification of mushroom and murine tyrosinase inhibitors from Achillea biebersteinii Afan. extract. Molecules 26(4), 964 (2021). https://doi.org/10.3390/molecules26040964
Maruyama, H., Kawakami, F., Lwin, T.T., Imai, M., Shamsa, F.: Biochemical characterization of ferulic acid and caffeic acid which effectively inhibit melanin synthesis via different mechanisms in B16 melanoma cells. Biol. Pharm. Bull. 41(5), 806–810 (2018). https://doi.org/10.1248/bpb.b17-00892
Eun, C.H., Kang, M.S., Kim, I.J.: Elastase/collagenase inhibition compositions of Citrus unshiu and its association with phenolic content and anti-oxidant activity. Appl. Sci. 10(14), 4838 (2020). https://doi.org/10.3390/app10144838
Laronha, H., Caldeira, J.: Structure and function of human matrix metalloproteinases. Cells 9(5), 1076 (2020). https://doi.org/10.3390/cells9051076
Utami, S., Sachrowardi, Q.R., Damayanti, N.A., Wardhana, A., Syarif, I., Nafik, S., Arrahman, B.C., Kusuma, H.S.W., Widowati, W.: Antioxidants, anticollagenase and antielastase potentials of ethanolic extract of ripe sesoot (Garcinia picrorrhiza Miq.) fruit as antiaging. J. Herbmed Pharmacol. 7(2), 88–93 (2018). https://doi.org/10.15171/jhp.2018.15
Kusano, A., Seyama, Y., Nagai, M., Shibano, M., Kusano, G.: Effects of fukinolic acid and cimicifugic acids from Cimicifuga species on collagenolytic activity. Biol. Pharm. Bull. 24(10), 1198–1201 (2001). https://doi.org/10.1248/bpb.24.1198
Bin Sayeed, M.S., Karim, S.M.R., Sharmin, T., Morshed, M.M.: Critical analysis on characterization, systemic effect, and therapeutic potential of beta-sitosterol: a plant-derived orphan phytosterol. Medicines 3(4), 29 (2016). https://doi.org/10.3390/medicines3040029
Zhang, J., Abe, M., Akihisa, T.: Anti-inflammatory and other bioactivities of triterpene esters in shea butter. Acc. Mater. Surf. Res. 2, 127–136 (2017)
Fraterrigo Garofalo, S., Tommasi, T., Fino, D.: A short review of green extraction technologies for rice bran oil. Biomass Convers. Biorefin. 11, 569–587 (2021). https://doi.org/10.1007/s13399-020-00846-3
Sahini, M.G., Mutegoa, E.: Extraction, phytochemistry, nutritional, and therapeutical potentials of rice bran oil: a review. Phytomed. Plus 3(2), 100453 (2023). https://doi.org/10.1016/j.phyplu.2023.100453
Acknowledgements
The authors would like to thank Surin Bran Oil Co., Ltd. (Surin, Thailand) for supplying rice bran acid oil.
Funding
The work was financial supported by King Mongkut’s University of Technology Thonburi (KMUTT) through the Basic Research Fund: for the fiscal year 2024, the KMUTT Research Center of Excellence Project to Lipid Technology Research Group and the KMUTT Postdoctoral Fellowship to Nattawut Whangsomnuek.
Author information
Authors and Affiliations
Contributions
NW contributed with data curation, investigation, methodology, writing—original draft. PS contributed with methodology and discussion. AN contributed with methodology and validation, DA contributed with review, methodology and discussion. LM contributed with review and discussion. KA contributed with conceptualization, project administration, supervision, funding acquisition, resources, writing—review & editing. All the authors read and approved the final manuscript.
Corresponding author
Ethics declarations
Conflict of Interest
The authors declare no conflict of interest.
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.
About this article
Cite this article
Whangsomnuek, N., Sombutsuwan, P., Nakornsadet, A. et al. Valorization of Industrial Byproduct-Rice Bran Acid Oil: Direct Extraction and Evaluation of Ferulic Acid and Phytosterols/Triterpene Alcohols for Cosmetic Applications. Waste Biomass Valor 15, 3017–3029 (2024). https://doi.org/10.1007/s12649-023-02357-4
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12649-023-02357-4