Optimization of Extraction Process, Isolation and Characterization of Mycosporine-Like Amino Acids from Four Species of Marine Red Macroalgaes

HAN Xiu; QIAN Liangliang; CHENG Tongjie; SHEN Yan; DENG Xiaoqun; ZHU Wenxuan; SUN Yingying

doi:10.13386/j.issn1002-0306.2021110358

Volume 43 Issue 18

Sep. 2022

Turn off MathJax

Article Contents

Abstract

References

Science and Technology of Food Industry > 2022 > 43(18): 208-216. > DOI: 10.13386/j.issn1002-0306.2021110358

HAN Xiu, QIAN Liangliang, CHENG Tongjie, et al. Optimization of Extraction Process, Isolation and Characterization of Mycosporine-Like Amino Acids from Four Species of Marine Red Macroalgaes[J]. Science and Technology of Food Industry, 2022, 43(18): 208−216. (in Chinese with English abstract). doi: 10.13386/j.issn1002-0306.2021110358.

Citation:

PDF (3338 KB)

Optimization of Extraction Process, Isolation and Characterization of Mycosporine-Like Amino Acids from Four Species of Marine Red Macroalgaes

1.
Jiangsu Key Laboratory of Marine Biotechnology, Jiangsu Ocean University, Lianyungang 222005, China
2.
Lianyungang Comprehensive Inspection and Testing Center for Quality and Technology, Lianyungang 222006, China

More Information

Received Date: November 29, 2021
Available Online: July 07, 2022

Graphical Abstract

Abstract

Abstract

Marine macroalgae is one of the good sources of mycosporine-like amino acids (MAAs), especially red macroalgae. As a new type of active substances with commercial development prospect, extraction, isolation and characterization of MAAs are far from enough for the application. To obtain the extraction process of MAAs from four species of red macroalgae (Bangia fusco-purpurea, Gelidium amansii, Gracilaria confervoides, and Gracilaria sp.), a series of single-factor and orthogonal experiments were carried out to analyze the effects of extraction temperature, time, times and solid-liquid ratio on the yields of MAAs. The extraction process of MAAs was optimized, and the extracts were isolated and identified. The optimized extraction processes of MAAs were obtained as follows: 45 ℃, 3 h, 4 times, 1:25 g/mL. 45 ℃, 1 h, 4 times, 1:20 g/mL. 45 ℃, 2 h, 3 times, 1:15 g/mL. 40 ℃, 1 h, 3 times, 1:20 g/mL. Four MAAs extracts of red algae were prepared by using the above extraction process, and the yields were 249.3, 197.9, 146.4 and 449.5 mg/g, respectively. All of them showed UV absorption characteristics and color reaction of MAAs in UV spectrum and thin layer chromatography (TLC). Furthermore, MAAs extracts from Bangia fusco-purpurea (or Gracilaria sp.) were isolated by silica gel column chromatography to obtain one fraction H1 (or two fractions J1 and J2). MAAs composition and proportion of these fractions were determined by UV, HPLC and MS, and comparison with existing literatures. H1 included shinorine, palythine and porphyra-334 (the content of these three MAAs was 95.4% of the content of the fraction H1), and palythenic acid (4.6%). Shinorine, palythine, porphyra-334 (96.3% of the fraction J1), and palythenic acid (3.7%) were in J1. And J2 was palythine.
- mycosporine-like amino acids,
- red macroalgae,
- extraction process,
- isolation,
- characterization

FullText(HTML)

References (32)

References

[1]	ORFANOUDAKI M, HARTMANN A, KARSTEN U, et al. Chemical profiling of mycosporine-like amino acids in twenty-three red algal species[J]. Journal of Phycology,2019,55(2):393−403. doi: 10.1111/jpy.12827
[2]	SUN Y Y, ZHANG N S, ZHOU J, et al. Distribution, contents, and types of mycosporine-like amino acids (MAAs) in marine macroalgae and a database for MAAs based on these characteristics[J]. Marine Drugs,2020,18(1):43−66. doi: 10.3390/md18010043
[3]	ATHUKORALA Y, TRANG S, KWOK C, et al. Antiproliferative and antioxidant activities and mycosporine-like amino acid profiles of wild-harvested and cultivated edible Canadian marine red macroalgae[J]. Molecules,2016,21(1):1−17.
[4]	牛美英. 麒麟菜中类菌孢素氨基酸(MAAs)的提取、纯化、鉴定及抗氧化活性研究[D]. 青岛: 中国海洋大学, 2014. NIU M Y. The study on the isolation, purification, identification andantioxidant activity of mycosporine-like amino acids (MAAs) in Eucheuma[D]. Qingdao: Ocean University of China, 2014.
[5]	LAMARE M D, LESSER M P, BARKER M F, et al. Variation in sunscreen compounds (mycosporine-like amino acids) for marine species along a gradient of ultraviolet radiation transmission within doubtful sound, New Zealand[J]. New Zealand Journal of Marine and Freshwater Research,2004,38(5):775−793. doi: 10.1080/00288330.2004.9517277
[6]	HOYER K, KARSTEN U, SAWALL T, et al. Photoprotective substances in Antarctic macroalgae and their variation with respect to depth distribution, different tissues and developmental stages[J]. Marine Ecology Progress Series,2001,211:117−129. doi: 10.3354/meps211117
[7]	ORFANOUDAKI M, HARTMANN A, MILADINOVIC H, et al. Bostrychines A~F, six novel mycosporine-like amino-acids and a novel betaine from the red alga Bostrychia scorpioides[J]. Marine Drugs,2019,17(6):356−371. doi: 10.3390/md17060356
[8]	AGUILERA J, BISCHOF K, KARSTEN U, et al. Seasonal variation in ecophysiological patterns in macroalgae from an Arctic fjord. II. pigment accumulation and biochemical aefence systems against high light stress[J]. Marine Biology,2002,140:1087−1095. doi: 10.1007/s00227-002-0792-y
[9]	KORBEE N, HUOVINEN P, FIGUEROA F L, et al. Availability of ammonium influences photosynthesis and the accumulation of mycosporine-like amino acids in two Porphyra species (Bangiales, Rhodophyta)[J]. Marine Biology,2005,146:645−654. doi: 10.1007/s00227-004-1484-6
[10]	GUIHENEUF F, GIETL A, STENGEL D B. Temporal and spatial variability of mycosporine-like amino acids and pigments in three edible red seaweeds from western Ireland[J]. Journal of Applied Phycology,2018,30:2573−2586. doi: 10.1007/s10811-018-1436-z
[11]	BRIANI B, SISSINI M N, LUCENA L A, et al. The influence of environmental features in the content of mycosporine-like amino acids in red marine algae along the Brazilian coast[J]. Journal of Phycology,2018,54(3):380−390. doi: 10.1111/jpy.12640
[12]	HARTMANN A, MURAUER A, GANZERA M. Quantitative analysis of mycosporine-like amino acids in marine algae by capillary electrophoresis with diode-array detection[J]. Journal of Pharmaceutical and Biomedical Analysis,2017,138:153−157. doi: 10.1016/j.jpba.2017.01.053
[13]	CHUANG L F, CHOU H N, SUNG P J. Porphyra-334 isolated from the marine algae Bangia atropurpurea: Conformational performance for energy conversion[J]. Marine Drugs,2014,12(9):4732−4740. doi: 10.3390/md12094732
[14]	张婉. 海萝藻中类菌胞素氨基酸的提取与抗氧化保湿特性研究[D]. 上海: 上海海洋大学, 2016. ZHANG W. Study on extraction, antioxidation and moisturizing activities of MAAs from Gloiopeltis furcata[D]. Shanghai: Shanghai Ocean University, 2016.
[15]	孙颖颖, 杨子轩, 周静, 等. 大型海藻类菌孢素氨基酸提取工艺及定性检测研究[J]. 食品科技,2021,46(3):205−211. [SUN Y Y, YANG Z X, ZHOU J, et al. Extraction process and a qualitative detection method of mycosporine-like amino acids from six species of marine macroalgae[J]. Food Science and Technology,2021,46(3):205−211. doi: 10.13684/j.cnki.spkj.2021.03.034 SUN Y Y, YANG Z X, ZHOU J, et al. Extraction process and a qualitative detection method of Mycosporine-like amino acids from six species of marine macroalgae[J]. Food Science and Technology, 2021, 46(3): 205-211. doi: 10.13684/j.cnki.spkj.2021.03.034
[16]	金宁宁. 江蓠中类菌胞素氨基酸（MAAs）分离纯化及应用研究[D]. 青岛: 中国海洋大学, 2012. JIN N N. Study on the isolation, purification and application of mycosporine-like amino acids (MAAs) in Gracilaria changii[D]. Qingdao: Ocean University of China, 2012.
[17]	张苗苗. 紫菜中类菌孢素氨基酸（MAAs）制备工艺的研究[D]. 青岛: 中国海洋大学, 2015. ZHANG M M. The preparation techniques of mycosporine-like amino acid from Porphyra yezoensis[D]. Qingdao: Ocean University of China, 2015.
[18]	丁兰平, 黄冰心, 谢艳齐. 中国大型海藻的研究现状及其存在的问题[J]. 生物多样性,2011,19(6):798−804. [DING L P, HUANG B X, XIE Y Q. Advances and problems with the study of marine macroalgae of China seas[J]. Biodiversity Science,2011,19(6):798−804. DING L P, HUANG B X, XIE Y Q. Advances and problems with the study of marine macroalgae of China seas[J]. Biodiversity Science, 2011, 19(6): 798-804.
[19]	国家卫生和计划生育委员会. GB 5009.3-2016食品安全国家标准, 食品中水分的测定[S]. 北京: 中国标准出版社, 2016. China's National Health and Family Planning Commission. GB 5009.3-2016 National Food Safety Standard. Determination of moisture in foods[S]. Beijing: China Standards Press, 2016.
[20]	国家卫生和计划生育委员会. GB 5009.5-2016食品安全国家标准, 食品中蛋白质的测定[S]. 北京: 中国标准出版社, 2016. China's National Health and Family Planning Commission. GB 5009.5-2016 National Food Safety Standard. Determination of protein in foods[S]. Beijing: China Standards Press, 2016.
[21]	国家卫生和计划生育委员会. GB 5009.6-2016食品安全国家标准食品中脂肪的测定[S]. 北京: 中国标准出版社, 2016. China's National Health and Family Planning Commission. GB 5009.6-2016 National food safety standard. Determination of fat in foods[S]. Beijing: China Standards Press, 2016.
[22]	国家卫生和计划生育委员会. GB 5009.4-2016食品安全国家标准食品中灰分的测定[S]. 北京: 中国标准出版社, 2016. China's National Health and Family Planning Commission. GB 5009.4-2016 National food safety standard. Determination of ash in foods[S]. Beijing: China Standards Press, 2016.
[23]	李峰. 大型海藻角叉菜活性成分的研究[D]. 大连: 大连海洋大学, 2019. LI F. Study on the active constituents of macroalgae Chondrus ocellatus Holemes[D]. Dalian: Dalian Ocean University, 2019.
[24]	ZHANG Z, TASHIRO Y, MATSUKAWA S, et al. Influence of pH and temperature on the ultraviolet-absorbing properties of porphyra-334[J]. Fisheries Science,2005,71(6):1382−1384. doi: 10.1111/j.1444-2906.2005.01106.x
[25]	ELIPE M V S. Advantages and disadvantages of nuclear magnetic resonance spectroscopy as a hyphenated technique[J]. Analytica Chimica Acata,2003,497(1):1−25.
[26]	应锐, 张朝辉, 段筱杉, 等. 紫菜中类菌孢素氨基酸纯化工艺的优化及其抗紫外辐射作用研究[J]. 海洋科学,2017,41(2):71−80. [YING R, ZHANG C H, DUAN X S, et al. Optimization of purification process of mycosporine-like amino acid from Porphyra haitanensis and study on its antiultraviolet activity[J]. Marine Science,2017,41(2):71−80. doi: 10.11759/hykx20160811002 YING R, ZHANG C H, DUAN X S, et al. Optimization of purification process of mycosporine-like amino acid from Porphyra haitanensis and study on its antiultraviolet activity[J]. Marine Science, 2017, 41(2): 71-80. doi: 10.11759/hykx20160811002
[27]	贺庆梅. 海藻中紫外线吸收物质的制备与特性的研究[D]. 青岛: 中国海洋大学, 2008. HE Q M. Study on preparation and character of UV-absorbing compound in seaweeds[D]. Qingdao: Ocean University of China, 2008.
[28]	LEE M H, KIM Y K, YOON N Y, et al. Study on UV absorption materials derived from red algae Gloiopeltis fucatas and Mazzaella sp. in Russia[J]. Fish Aquat Sci,2012,15(4):361−363.
[29]	CHAVES-PENA P, CODA F D L, FIGUEROA F L, et al. Quantitative and qualitative HPLC analysis of mycosporine-like amino acids extracted in distilled water for cosmetical uses in four Rhodophyta[J]. Marine Drugs,2019,18(1):27−40. doi: 10.3390/md18010027
[30]	HARTMANN A, BECKER K, KARSTEN U, et al. Analysis of mycosporine-like amino acids in selected algae and cyanobacteria by hydrophilic interaction liquid chromatography and a novel MAA from the red alga Catenella repens[J]. Marine Drugs,2015,13(10):6291−6305. doi: 10.3390/md13106291
[31]	BEDOUX G, HARDOUIN K, MARTY C, et al. Chemical characterization and photoprotective activity measurement of extracts from the red macroalga Solieria chordalis[J]. Botanica Marina,2014,57(4):291−301. doi: 10.1515/bot-2013-0118
[32]	PLACK P A, FRASER N W, GRANT P T, et al. Gadusol, an enolic derivative of cyclohexane-1, 3-dione present in the roes of cod and other marine fish. Isolation, properties and occurrence compared with ascorbic acid[J]. Biochemical Journal,1981,199(3):741−747. doi: 10.1042/bj1990741

Supplements (0)

Cited By

Cited by

Periodical cited type(7)

1.	高瑞萍，刘松林，吴振. UV-C联合热处理对橙汁品质特性的影响. 食品工业科技. 2022(09): 79-86 . 本站查看
2.	石岩，魏锋，马双成. 枸橼药用研究进展. 中国药物警戒. 2022(05): 574-578 .
3.	李灵，熊芸，张钰瑶，杜奎，李明章，高平，谢玥. 响应面法优化猕猴桃类胡萝卜素提取工艺. 四川大学学报(自然科学版). 2022(05): 162-168 .
4.	陈慧聪，焦烨磊，王伟隆，黄旭雄. 基于UPLC对卤虫体内类胡萝卜素检测方法的建立. 天津科技大学学报. 2022(06): 9-17 .
5.	何香凝，刘娜，王园，王瑞芳，安晓萍，齐景伟. 酶解玉米芯木聚糖的超声辅助提取工艺及抗氧化活性. 食品工业. 2021(05): 1-5 .
6.	田童瑶，何东青，高溥，谢旭东，李选晋，李艳，张华峰，张颖. 蔬菜染色再生纸制作的科普实验. 大学化学. 2021(10): 218-226 .
7.	鞠玉旋，谢倩，陈清西. 石仙桃总黄酮提取工艺优化及抗氧化活性分析. 园艺与种苗. 2021(11): 15-20+27 .