Optimization of Subcritical Water Extraction of Rosmarinic Acid from Perilla (<i>Perilla frutescens</i> L.) Seed Meal and Its Antioxidant Activity

YAN Linlin; WANG Yanhui; ZHANG Jiachan; ZHENG Guangyao

doi:10.13386/j.issn1002-0306.2022080130

Volume 44 Issue 17

Aug. 2023

Turn off MathJax

Article Contents

Abstract

References

Science and Technology of Food Industry > 2023 > 44(17): 176-185. > DOI: 10.13386/j.issn1002-0306.2022080130

YAN Linlin, WANG Yanhui, ZHANG Jiachan, et al. Optimization of Subcritical Water Extraction of Rosmarinic Acid from Perilla (Perilla frutescens L.) Seed Meal and Its Antioxidant Activity[J]. Science and Technology of Food Industry, 2023, 44(17): 176−185. (in Chinese with English abstract). doi: 10.13386/j.issn1002-0306.2022080130.

Citation:

PDF (3915 KB)

Optimization of Subcritical Water Extraction of Rosmarinic Acid from Perilla (Perilla frutescens L.) Seed Meal and Its Antioxidant Activity

1.
Institute of Chemical Industry of Forest Products, CAF, National Engineering Lab. for Biomass Chemical Utilization, Key Lab. of Chemical Engineering of Forest Products, National Forestry and Grassland Administration, Key Lab. of Biomass Energy and Material, Jiangsu Province, Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, Nanjing 210042, China
2.
Beijing Key Lab. of Plant Resource Research and Development, Beijing Technology and Business University, Beijing 100048, China

More Information

Received Date: August 14, 2022
Available Online: July 04, 2023

Graphical Abstract

Abstract

Abstract

Subcritical water extraction (SWE), a green and environmentally friendly extraction technology, was successfully used to extract rosmarinic acid from Perilla seed meal (PSM). Based on the results of single-factor experiments, three-factor and three-level of response surface methodology were used to optimize the extraction parameters of rosmarinic acid in PSM, including extraction temperature (140~180 ℃), extraction time (20~40 min) and solid-liquid ratio (1:30~1:50 g/mL). Meanwhile, the effects of SWE and several conventional extraction methods on the extraction yields of rosmarinic acid and their antioxidant activities (DPPH and ABTS free radical scavenging capacity) of PSM extracts were compared. The results showed that the optimized parameters were as follows: Extraction temperature 163 ℃, extraction time 30 min, and the ratio of solid to liquid 1:41 g/mL. Under these conditions, the extraction yield of rosmarinic acid was 4.91±0.16 mg/g dw, and the free radicals scavenging capacities of DPPH and ABTS were 10.62 and 13.46 mgV_C/g dw, respectively, which were significantly higher than those of several conventional extraction methods. In addition, scanning electron microscope (SEM) showed that the structure of the PSM residues became looser after SWE, which could benefit the extraction of rosmarinic acid.
- subcritical water extraction,
- Perilla seed meal,
- rosmarinic acid,
- response surface methodology,
- antioxidant activities

FullText(HTML)

References (54)

References

[1]	NADEEM M, IMRAN M, GONDAL A T, et al. Therapeutic potential of rosmarinic acid: a comprehensive review[J]. Applied Sciences,2019,9(15):3139. doi: 10.3390/app9153139
[2]	LUO C, ZOU L, SUN H, et al. A review of the anti-inflammatory effects of rosmarinic acid on inflammatory diseases[J]. Frontiers in Pharmacology,2020,11:153. doi: 10.3389/fphar.2020.00153
[3]	MARCHEV A S, VASILEVA L V, AMIROVA K M, et al. Rosmarinic acid-from bench to valuable applications in food industry[J]. Trends in Food Science & Technology,2021,117:182−193.
[4]	SIK B, HANCZNÉ E L, KAPCSÁNDI V, et al. Conventional and nonconventional extraction techniques for optimal extraction processes of rosmarinic acid from six Lamiaceae plants as determined by HPLC-DAD measurement[J]. Journal of Pharmaceutical and Biomedical Analysis,2020,184:113173. doi: 10.1016/j.jpba.2020.113173
[5]	NGO Y L, LAU C H, CHUA L S. Review on rosmarinic acid extraction, fractionation and its anti-diabetic potential[J]. Food and Chemical Toxicology,2018,121:687−700. doi: 10.1016/j.fct.2018.09.064
[6]	苏平, 王根女, 吴丹, 等. 迷迭香酸的生理活性功能及其来源研究进展[J]. 食品与发酵工业,2008,34(12):135−138. [SU P, WANG G N, WU D, et al. Progress in rosmarinic acid biological activities and its sources[J]. Food and Fermentation Industries,2008,34(12):135−138. SU P, WANG G N, WU D, et al. Progress in rosmarinic acid biological activities and its sources[J]. Food and Fermentation Industries, 2008, 34(12): 135-138.
[7]	程贤, 毕良武, 赵振东, 等. 迷迭香酸的提取纯化及生物活性研究进展[J]. 林产化学与工业,2015,35(4):151−158. [CHENG X, BI L, ZHAO Z D, et al. Research progress on extraction, purification and biological activities of rosmarinic acid[J]. Chemistry and Industry of Forest Products,2015,35(4):151−158. doi: 10.3969/j.issn.0253-2417.2015.04.024 CHENG X, BI L, ZHAO Z D, et al. Research progress on extraction, purification and biological activities of rosmarinic acid[J]. Chemistry and Industry of Forest Products, 2015, 35(4): 151-158. doi: 10.3969/j.issn.0253-2417.2015.04.024
[8]	HA T J, LEE J H, LEE M H, et al. Isolation and identification of phenolic compounds from the seeds of Perilla frutescens (L.) and their inhibitory activities against α-glucosidase and aldose reductase[J]. Food Chemistry,2012,135(3):1397−1403. doi: 10.1016/j.foodchem.2012.05.104
[9]	KIM D H, LEE J H. Comparative evaluation of phenolic phytochemicals from perilla seeds of diverse species and screening for their tyrosinase inhibitory and antioxidant properties[J]. South African Journal of Botany,2019,123:341−350. doi: 10.1016/j.sajb.2019.03.015
[10]	JIANG T, GUO K, LIU L, et al. Integrated transcriptomic and metabolomic data reveal the flavonoid biosynthesis metabolic pathway in Perilla frutescens (L.) leaves[J]. Scientific Reports,2020,10(1):16207. doi: 10.1038/s41598-020-73274-y
[11]	ZHANG H, LI H, ZHANG Z, et al. Optimization of ultrasound assisted extraction of polysaccharides from perilla seed meal by response surface methodology: Characterization and in vitro antioxidant activities[J]. Journal of Food Science,2021,86(2):306−318. doi: 10.1111/1750-3841.15597
[12]	LEE J H, PARK K H, LEE M H, et al. Identification, characterisation, and quantification of phenolic compounds in the antioxidant activity-containing fraction from the seeds of Korean perilla (Perilla frutescens) cultivars[J]. Food Chemistry,2013,136(2):843−852. doi: 10.1016/j.foodchem.2012.08.057
[13]	TANG W, SUN B, ZHAO Y. Preparative separation and purification of rosmarinic acid from perilla seed meal via combined column chromatography[J]. Journal of Chromatography B,2014,947−948:41−48. doi: 10.1016/j.jchromb.2013.12.007
[14]	ZHOU X J, YAN L L, YIN P P, et al. Structural characterisation and antioxidant activity evaluation of phenolic compounds from cold-pressed Perilla frutescens var. arguta seed flour[J]. Food Chemistry,2014,164:150−157. doi: 10.1016/j.foodchem.2014.05.062
[15]	CHUMPHUKAM O, PINTHA K, KHANAREE C, et al. Potential anti-mutagenicity, antioxidant, and anti-inflammatory capacities of the extract from perilla seed meal[J]. Journal of Food Biochemistry,2018,42(5):e12556. doi: 10.1111/jfbc.12556
[16]	LEE J H, CHO Y S. Assessment of phenolic profiles from various organs in different species of perilla plant (Perilla frutescens (L.) Britt.) and their antioxidant and enzyme inhibitory potential[J]. Industrial Crops and Products,2021,171:113914. doi: 10.1016/j.indcrop.2021.113914
[17]	ZHANG Y, MEI X, ZHANG Q, et al. Protective effect of a rosmarinic acid–rich extract from cold‐pressed Perilla frutescens seed flour on oxidative hepatotoxicity in vitro and in vivo[J]. Journal of Food Biochemistry,2018,42(2):e12492. doi: 10.1111/jfbc.12492
[18]	梅喜刚, 张琦, 李曼娜, 等. 紫苏粕中迷迭香酸的提取与富集工艺研究[J]. 食品工业科技,2017,38(6):250−255. [MEI X G, ZHANG Q, LI M N, et al. Extraction and enrichment of rosmarinic acid from residues of perilla seeds[J]. Science and Technology of Food and Industry,2017,38(6):250−255. MEI X G, ZHANG Q, LI M N, et al. Extraction and enrichment of rosmarinic acid from residues of perilla seeds[J]. Science and Technology of Food and Industry, 2017, 38(6): 250-255.
[19]	YAN L L, ZHENG G Y. Comparing profiles and antioxidant properties of soluble and insoluble phenolics in Perilla frutescens seed flour extracts obtained by different extraction/hydrolysis methods[J]. International Journal of Food Science & Technology,2017,52(11):2497−2504.
[20]	AKOURY E. Isolation and structural elucidation of rosmarinic acid by nuclear magnetic resonance spectroscopy[J]. American Research Journals of Chemistry,2019,2(1):17−23.
[21]	OLIVEIRA G A R, DE OLIVEIRA A E, DA CONCEIÇÃO E C, et al. Multiresponse optimization of an extraction procedure of carnosol and rosmarinic and carnosic acids from rosemary[J]. Food Chemistry,2016,211:465−473. doi: 10.1016/j.foodchem.2016.05.042
[22]	NGUYEN H C, NGUYEN H N, HUANG M Y, et al. Optimization of aqueous enzyme-assisted extraction of rosmarinic acid from rosemary (Rosmarinus officinalis L.) leaves and the antioxidant activity of the extract[J]. Journal of Food Processing and Preservation,2021,45(3):e15221.
[23]	CALEJA C, BARROS L, PRIETO M A, et al. Extraction of rosmarinic acid from Melissa officinalis L. by heat-, microwave-and ultrasound-assisted extraction techniques: A comparative study through response surface analysis[J]. Separation and Purification Technology,2017,186:297−308. doi: 10.1016/j.seppur.2017.06.029
[24]	ZAKARIA S M, KAMAL S M M. Subcritical water extraction of bioactive compounds from plants and algae: Applications in pharmaceutical and food ingredients[J]. Food Engineering Reviews,2016,8:23−34. doi: 10.1007/s12393-015-9119-x
[25]	ZHANG J, WEN C, ZHANG H, et al. Recent advances in the extraction of bioactive compounds with subcritical water: A review[J]. Trends in Food Science & Technology,2020,95:183−195.
[26]	LI W, FAN Y, ZHANG S, et al. Extraction of rosmarinic acid from Perilla seeds using green protic ionic liquids[J]. Microchemical Journal,2021,170:106667. doi: 10.1016/j.microc.2021.106667
[27]	TANG B, BI W, TIAN M, et al. Application of ionic liquid for extraction and separation of bioactive compounds from plants[J]. Journal of Chromatography B,2012,904:1−21. doi: 10.1016/j.jchromb.2012.07.020
[28]	ALSHAMMARI O A O, ALMULGABSAGHER G A A, RYDER K S, et al. Effect of solute polarity on extraction efficiency using deep eutectic solvents[J]. Green Chemistry,2021,23:5097−5105. doi: 10.1039/D1GC01747K
[29]	CHENG Y, XUE F, YU S, et al. Subcritical water extraction of natural products[J]. Molecules,2021,26(13):4004. doi: 10.3390/molecules26134004
[30]	陈劲, 傅菊惠, 张建会, 等. 亚临界水技术的应用研究进展[J]. 分子科学学报,2021,37(5):443−452. [CHEN J, FU J H, ZHANG J H, et al. Application of subcritical water technology[J]. Journal of Molecular Science,2021,37(5):443−452. CHEN J, FU J H, ZHANG J H, et al. Application of subcritical water technology[J]. Journal of Molecular Science, 2021, 37(5): 443-452.
[31]	白雪, 赵梦娜, 岳小湘, 等. 亚临界水提取植物源生物活性物质的研究进展[J]. 食品工业科技,2022,43(4):470−477. [BAI X, ZHAO M N, XUE X X, et al. Research progress in subcritical water extraction of bioactive substances from plants[J]. Science and Technology of Food and Industry,2022,43(4):470−477. doi: 10.13386/j.issn1002-0306.2021030298 BAI X, ZHAO M N, XUE X X, et al. Research progress in subcritical water extraction of bioactive substances from plants[J]. Science and Technology of Food and Industry, 2022, 43(4): 470-477. doi: 10.13386/j.issn1002-0306.2021030298
[32]	PINTO D, VIEIRA E F, PEIXOTO A F, et al. Optimizing the extraction of phenolic antioxidants from chestnut shells by subcritical water extraction using response surface methodology[J]. Food Chemistry,2021,334:127521. doi: 10.1016/j.foodchem.2020.127521
[33]	KIM D S, LIM S B. Kinetic study of subcritical water extraction of flavonoids from Citrus unshiu peel[J]. Separation and Purification Technology,2020,250:117259. doi: 10.1016/j.seppur.2020.117259
[34]	CVETANOVIĆ A, ŠVARC-GAJIĆ J, ZEKOVIĆ Z, et al. Subcritical water extraction as a cutting edge technology for the extraction of bioactive compounds from chamomile: Influence of pressure on chemical composition and bioactivity of extracts[J]. Food Chemistry,2018,266:389−396. doi: 10.1016/j.foodchem.2018.06.037
[35]	ZHANG J, WEN C, CHEN M, et al. Antioxidant activities of Sagittaria sagittifolia L. polysaccharides with subcritical water extraction[J]. International Journal of Biological Macromolecules,2019,134:172−179. doi: 10.1016/j.ijbiomac.2019.05.047
[36]	ŠVARC-GAJIĆ J, MORAIS S, DELERUE-MATOS C, et al. Valorization potential of oilseed cakes by subcritical water extraction[J]. Applied Science,2020,10(24):8815. doi: 10.3390/app10248815
[37]	SHI F, JIANG Z B, XU J, et al. Optimized extraction of phenolic antioxidants from red pitaya (Hylocereus polyrhizus) seeds by subcritical water extraction using response surface methodology[J]. Journal of Food Measurement and Characterization,2022,16:2240−2258. doi: 10.1007/s11694-021-01212-1
[38]	WANG Y, YE Y, WANG L, et al. Antioxidant activity and subcritical water extraction of anthocyanin from raspberry process optimization by response surface methodology[J]. Food Bioscience, 2021, 44(Part A): 101394.
[39]	DZAH C S, DUAN Y, ZHANG H, et al. Ultrasound-, subcritical water-and ultrasound assisted subcritical water-derived Tartary buckwheat polyphenols show superior antioxidant activity and cytotoxicity in human liver carcinoma cells[J]. Food Research International,2020,137:109598. doi: 10.1016/j.foodres.2020.109598
[40]	闫林林, 郑光耀, 韦朝宽. 响应面法优化石榴叶总酚的亚临界水提取工艺[J]. 食品工业科技,2017,38(19):184−190. [YAN L L, ZHENG G Y, WEI C K. Optimization of subcritical water extraction for total phenolics from pomegranate (Punica granatum L.) leaves by response surface methodology[J]. Science and Technology of Food and Industry,2017,38(19):184−190. doi: 10.13386/j.issn1002-0306.2017.19.034 YAN L L, ZHENG G Y, WEI C K. Optimization of subcritical water extraction for total phenolics from pomegranate (Punica granatum L. ) leaves by response surface methodology[J]. Science and Technology of Food and Industry, 2017, 38(19): 184-190. doi: 10.13386/j.issn1002-0306.2017.19.034
[41]	张榕欣, 邱英莲, 邓金兰, 等. 超声波辅助双酶法制备黑豆多肽的工艺优化及其抗氧化活性研究[J]. 饲料研究,2022,45(13):79−82. [ZHANG R X, QIU Y L, DENG J L, et al. Ultrasound-assisted double-enzyme method for preparing process optimization of black soybean peptides and study on its antioxidant activity[J]. Feed Research,2022,45(13):79−82. doi: 10.13557/j.cnki.issn1002-2813.2022.13.018 ZHANG R X, QIU Y L, DENG J L, et al. Ultrasound-assisted double-enzyme method for preparing process optimization of black soybean peptides and study on its antioxidant activity[J]. Feed Research, 2022, 45(13): 79-82. doi: 10.13557/j.cnki.issn1002-2813.2022.13.018
[42]	AHMADIAN-KOUCHAKSARAIE Z, NIAZMAND R, NAJAFI M N. Optimization of the subcritical water extraction of phenolic antioxidants from Crocus sativus petals of saffron industry residues: Box-Behnken design and principal component analysis[J]. Innovative Food Science & Emerging Technologies,2016,36:234−244.
[43]	闫拯, 王乐, 袁施彬. 响应面法优化提取紫苏籽饼粕迷迭香酸及其抗氧化能力研究[J]. 西华师范大学学报(自然科学版),2017,38(2):134−140. [YAN Z, WANG L, YUAN S B. A study on the extraction of rosmarinic acid from Perilla seed meal and its antioxidant capacity[J]. Journal of China West Normal University (Natural Sciences),2017,38(2):134−140. YAN Z, WANG L, YUAN S B. A study on the extraction of rosmarinic acid from Perilla seed meal and its antioxidant capacity[J]. Journal of China West Normal University (Natural Sciences), 2017, 38(2): 134-140.
[44]	VLADIĆ J, JAKOVLJEVIĆ M, MOLNAR M, et al. Valorization of Yarrow (Achillea millefolium L.) by-product through application of subcritical water extraction[J]. Molecules,2020,25(8):1878. doi: 10.3390/molecules25081878
[45]	汪泽, 崔丽虹, 唐冰, 等. 响应面法优化菠萝叶纤维多酚提取工艺[J]. 食品工业科技,2017,38(1):219−223. [WANG Z, CUI L H, TANG B, et al. Optimization of extraction process for polyphenols from pineapple leaves fiber by response surface methodology[J]. Science and Technology of Food and Industry,2017,38(1):219−223. doi: 10.13386/j.issn1002-0306.2017.01.034 WANG Z, CUI L H, TANG B, et al. Optimization of extraction process for polyphenols from pineapple leaves fiber by response surface methodology[J]. Science and Technology of Food and Industry, 2017, 38(1): 219-223. doi: 10.13386/j.issn1002-0306.2017.01.034
[46]	PAVLIĆ B, VIDOVIĆ S, VLADIĆ J, et al. Subcritical water extraction of sage (Salvia officinalis L.) by-products—process optimization by response surface methodology[J]. The Journal of Supercritical Fluids,2016,116:36−45. doi: 10.1016/j.supflu.2016.04.005
[47]	邹建国, 刘飞, 刘燕燕, 等. 响应面法优化微波辅助提取枳壳中总黄酮工艺[J]. 食品科学,2012,33(2):24−28. [ZOU J G, LIU F, LIU Y Y, et al. Optimization of microwave-assisted extraction of total flavonoids from Fructus Aurantii immaturus by response surface methodology[J]. Food Science,2012,33(2):24−28. ZOU J G, LIU F, LIU Y Y, et al. Optimization of microwave-assisted extraction of total flavonoids from Fructus Aurantii Immaturus by response surface methodology[J]. Food Science, 2012, 33(2): 24-28.
[48]	杨豪, 刘晓雪, 苏海冉, 等. 响应面法优化辣木叶蛋白提取工艺及凝集活性研究[J]. 食品工业科技,2022,43(6):150−157. [YANG H, LIU X X, SU H R, et al. Optimization of extraction process and agglutination activity of Moringa oleifera leaf protein by response surface methodology[J]. Science and Technology of Food and Industry,2022,43(6):150−157. doi: 10.13386/j.issn1002-0306.2021060045 YANG H, LIU X X, SU H R, et al. Optimization of extraction process and agglutination activity of Moringa oleifera leaf protein by response surface methodology[J]. Science and Technology of Food and Industry, 2022, 43(6): 150-157. doi: 10.13386/j.issn1002-0306.2021060045
[49]	罗蓉, 蔡旭, 薛宏坤, 等. 响应面法优化超声辅助低共熔溶剂提取山楂总黄酮工艺[J]. 食品工业科技,2022,43(22):229−237. [LUO R, CAI X, XUE H K, et al. Optimization of ultrasonic-assisted deep eutectic solvent extraction of flavonoids Crataegus pinnatifida using response surface methodology[J]. Science and Technology of Food and Industry,2022,43(22):229−237. doi: 10.13386/j.issn1002-0306.2022010235 LUO R, CAI X, XUE H K, et al. Optimization of ultrasonic-assisted deep eutectic solvent extraction of flavonoids Crataegus pinnatifida using response surface methodology[J]. Science and Technology of Food and Industry, 2022, 43(22): 229-237. doi: 10.13386/j.issn1002-0306.2022010235
[50]	张玥莉, 孙仁弟. 响应面法优化紫苏子中迷迭香酸超声提取工艺的研究[J]. 上海医药,2017,38(7):78−78. [ZHANG Y L, SUN R D. Optimization of the ultrasonic extraction of rosmarinic acid from Perillae fructus by response surface method[J]. Shanghai Medical & Pharmaceutical Journal,2017,38(7):78−78. ZHANG Y L, SUN R D. Optimization of the ultrasonic extraction of rosmarinic acid from Perillae fructus by response surface method[J]. Shanghai Medical & Pharmaceutical Journal, 2017, 38(7): 78-78.
[51]	任志清, 李会珍, 张志军, 等. 不同品种紫苏叶迷迭香酸的提取及其生物活性[J]. 现代食品科技,2021,37(1):92−100. [REN Z Q, LI H Z, ZHANG Z J, et al. Extraction of rosmarinic acid from different varieties of Perilla leaves and its biological activity[J]. Modern Food Science and Technology,2021,37(1):92−100. doi: 10.13982/j.mfst.1673-9078.2021.01.0649 REN Z Q, LI H Z, ZHANG Z J, et al. Extraction of rosmarinic acid from different varieties of Perilla leaves and its biological activity[J]. Modern Food Science and Technology, 2021, 37(1): 92-100. doi: 10.13982/j.mfst.1673-9078.2021.01.0649
[52]	PARK J S, HAN J M, SURENDHIRAN D, et al. Physicochemical and biofunctional properties of Sargassum thunbergii extracts obtained from subcritical water extraction and conventional solvent extraction[J]. The Journal of Supercritical Fluids,2022,182:105535. doi: 10.1016/j.supflu.2022.105535
[53]	KIAMAHALLEH M V, NAJAFPOUR-DARZI G, RAHIMNEJAD M, et al. High performance curcumin subcritical water extraction from turmeric (Curcuma longa L.)[J]. Journal of Chromatography B,2016,1022:191−198. doi: 10.1016/j.jchromb.2016.04.021
[54]	CHENG Y, LIU W, GAO Q, et al. Enhanced extraction of bioactive components of 3, 29–dibenzoylkarounidiol and polysaccharides from Semen richonsanthis using subcritical water technology[J]. Chemistry Select,2019,4(46):13689−13694.