Abstract
This study determined the composition of the monosaccharide, 3, 6-anhydrogalactose (AnGal), in red algae and explored the potential whitening activity of the extract. Using gas chromatography–mass spectrometry (GC–MS), the AnGal composition of six different species of red seaweed (Porphyra haitanensis, Gracilaria chouae, Gracilaria blodgettii, Gracilaria lemaneiformis, Eucheuma galetinae, and Gelidium amansii) was successfully analyzed, revealing molar ratios ranging from 1.0:1.0 to 1.0:3.1 of AnGal and galactose (Gal), respectively. Employing the tyrosinase inhibition assay, the skin-whitening effect of AnGal red seaweed polysaccharides was determined. Polysaccharides from P. haitanensis, G. chouae, and G. blodgettii as well as their degradation products showed higher tyrosinase inhibitory activity (inhibition rates 24.2–26.8%). These results suggest that the GC–MS approach could conveniently be used in quality control or for the quantitative determination of AnGal and Gal in red seaweed polysaccharides as well as exploring their potential application in cosmetic and functional food products. The findings here exhibited that red seaweed polysaccharides and their degradation products were potential ingredients for cosmeceutical industries.
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References
Chen H, Wang F, Mao H, Yan X (2014) Degraded λ-carrageenan activates NF-κB and AP-1 pathways in macrophages and enhances LPS-induced TNF-α secretion through AP-1. Biochim Biophys Acta 1840 7:2162–2170. https://doi.org/10.1016/j.bbagen.2014.03.011
Cheong KL, Wu DT, Zhao J, Li SP (2015) A rapid and accurate method for the quantitative estimation of natural polysaccharides and their fractions using high performance size exclusion chromatography coupled with multi-angle laser light scattering and refractive index detector. J Chromatogr A 1400:98–106. https://doi.org/10.1016/j.chroma.2015.04.054
Cheong KL, Qiu HM, Du H, Liu Y, Khan BM (2018) Oligosaccharides derived m red seaweed: production, properties, and potential health and cosmetic applications. Molecules 23(10):2451. https://doi.org/10.3390/molecules23102451
Cui M, Wu J, Wang S, Shu H, Zhang M, Liu K, Liu K (2019) Characterization and anti-inflammatory effects of sulfated polysaccharide from the red seaweed Gelidium pacificum Okamura. Int J Biol Macromol 129:377–385. https://doi.org/10.1016/j.ijbiomac.2019.02.043
Hridya H, Amrita A, Sankari M, George Priya Doss C, Gopalakrishnan M, Gopalakrishnan C, Siva R (2015) Inhibitory effect of brazilein on tyrosinase and melanin synthesis: kinetics and in silico approach. Int J Biol Macromol 81:228–234. https://doi.org/10.1016/j.ijbiomac.2015.07.064
Jesumani V, Du H, Pei P, Zheng C, Cheong KL, Huang N (2019) Unravelling property of polysaccharides from Sargassum sp. as an anti-wrinkle and skin whitening property. Int J Biol Macromol 140:216–224. https://doi.org/10.1016/j.ijbiomac.2019.08.027
Jiang Z, Yu G, Liang Y, Song T, Zhu Y, Ni H, Yamaguchi K, Oda T (2019) Inhibitory effects of a sulfated polysaccharide isolated from edible red alga Bangia fusco-purpurea on α-amylase and α-glucosidase. Biosci Biotechnol Biochem 83(11):2065–2074. https://doi.org/10.1080/09168451.2019.1634515
Khan BM, Qiu HM, Wang XF, Liu ZY, Zhang JY, Guo YJ, Chen WZ, Liu Y, Cheong KL (2019) Physicochemical characterization of Gracilaria chouae sulfated polysaccharides and their antioxidant potential. Int J Biol Macromol 134:255–261. https://doi.org/10.1016/j.ijbiomac.2019.05.055
Khan BM, Qiu HM, Xu SY, Liu Y, Cheong KL (2020) Physicochemical characterization and antioxidant activity of sulphated polysaccharides derived from Porphyra haitanensis. Int J Biol Macromol 145:1155–1161. https://doi.org/10.1016/j.ijbiomac.2019.10.040
Kim JH, Yun EJ, Yu S, Kim KH, Kang NJ (2017) Different levels of skin whitening activity among 3,6-anhydro-L-galactose, agarooligosaccharides, and neoagarooligosaccharides. Mar Drugs 15(10):321. https://doi.org/10.3390/md15100321
Kim JH, Lee JE, Kim KH, Kang NJ (2018) Beneficial effects of marine algal-derived carbohydrates for skin health. Mar Drugs 16(11):459. https://doi.org/10.3390/md16110459
Kravchenko AO, Byankina Barabanova AO, Glazunov VP, Yakovleva IM, Yermak IM (2018) Seasonal variations in a polysaccharide composition of Far Eastern red seaweed Ahnfeltiopsis flabelliformis (Phyllophoraceae). J Appl Phycol 30(1):535–545. https://doi.org/10.1007/s10811-017-1262-8
Navarro DA, Stortz CA (2003) Determination of the configuration of 3,6-anhydrogalactose and cyclizable α-galactose 6-sulfate units in red seaweed galactans. Carbohydr Res 338(20):2111–2118. https://doi.org/10.1016/S0008-6215(03)00345-8
Ruocco N, Costantini S, Guariniello S, Costantini M (2016) Polysaccharides from the marine environment with pharmacological, cosmeceutical and nutraceutical potential. Molecules 21(5):551. https://doi.org/10.3390/molecules21050551
Seedevi P, Moovendhan M, Viramani S, Shanmugam A (2017) Bioactive potential and structural chracterization of sulfated polysaccharide from seaweed (Gracilaria corticata). Carbohydr Polym 155:516–524. https://doi.org/10.1016/j.carbpol.2016.09.011
Shanura Fernando IP, Asanka Sanjeewa KK, Samarakoon KW, Kim H-S, Gunasekara UKDSS, Park Y-J, Abeytunga DTU, Lee WW, Jeon Y-J (2018) The potential of fucoidans from Chnoospora minima and Sargassum polycystum in cosmetics: antioxidant, anti-inflammatory, skin-whitening, and antiwrinkle activities. J Appl Phycol 30(6):3223–3232. https://doi.org/10.1007/s10811-018-1415-4
Souza BWS, Cerqueira MA, Bourbon AI, Pinheiro AC, Martins JT, Teixeira JA, Coimbra MA, Vicente AA (2012) Chemical characterization and antioxidant activity of sulfated polysaccharide from the red seaweed Gracilaria birdiae. Food Hydrocolloid 27(2):287–292. https://doi.org/10.1016/j.foodhyd.2011.10.005
Sudharsan S, Giji S, Seedevi P, Vairamani S, Shanmugam A (2018) Isolation, characterization and bioactive potential of sulfated galactans from Spyridia hypnoides (Bory) Papenfuss. Int J Biol Macromol 109:589–597. https://doi.org/10.1016/j.ijbiomac.2017.12.097
Thomas NV, Kim SK (2013) Beneficial effects of marine algal compounds in cosmeceuticals. Mar Drugs 11(12):146–164
Wang P, Zhao X, Lv Y, Li M, Liu X, Li G, Yu G (2012) Structural and compositional characteristics of hybrid carrageenans from red algal Chondracanthus chamissoi. Carbohydr Polym 89(3):914–919. https://doi.org/10.1016/j.carbpol.2012.04.034
Wijesekara I, Pangestuti R, Kim SK (2011) Biological activities and potential health benefits of sulfated polysaccharides derived from marine algal. Carbohydr Polym 84(1):14–21. https://doi.org/10.1016/j.carbpol.2010.10.062
Xu SY, Huang X, Cheong KL (2017) Recent advances in marine algal polysaccharides: isolation, structure, and activities. Mar Drugs 15(12):388. https://doi.org/10.3390/md15120388
Xu SY, Kan J, Hu Z, Liu Y, Du H, Pang GC, Cheong KL (2018a) Quantification of neoagaro-oligosaccharide production through enzymatic hydrolysis and its anti-oxidant activities. Molecules 23(6):1354. https://doi.org/10.3390/molecules23061354
Xu SY, Liu JP, Huang X, Du LP, Shi FL, Dong R, Huang XT, Zheng K, Liu Y, Cheong KL (2018b) Ultrasonic-microwave assisted extraction, characterization and biological activity of pectin from jackfruit peel. LWT 90:577–582. https://doi.org/10.1016/j.lwt.2018.01.007
Xu SY, Aweya JJ, Li N, Deng R-Y, Chen W-Y, Tang J, Cheong K-L (2019) Microbial catabolism of Porphyra haitanensis polysaccharides by human gut microbiota. Food Chem 289:177–186. https://doi.org/10.1016/j.foodchem.2019.03.050
Yaphe W, Arsenault GP (1965) Improved resorcinol reagent for the determination of fructose, and of 3,6-anhydrogalactose in polysaccharides. Anal Biochem 13(1):143–148. https://doi.org/10.1016/0003-2697(65)90128-4
Yemm EW, Willis AJ (1954) The estimation of carbohydrates in plant extracts by anthrone. Biochem J 57(3):508–514. https://doi.org/10.1042/bj0570508
Yu G, Hu Y, Yang B, Zhao X, Wang P, Ji G, Wu J, Guan H (2010) Extraction, isolation and structural characterization of polysaccharides from a red alga Gloiopeltis furcata. J Ocean Univ 9(2):193–197. https://doi.org/10.1007/s11802-010-0193-7
Yun EJ, Choi IG, Kim KH (2015) Red macroalgal as a sustainable resource for bio-based products. Trends Biotechnol 33(5):247–249. https://doi.org/10.1016/j.tibtech.2015.02.006
Zhang X, Aweya JJ, Huang ZX, Kang ZY, Bai ZH, Li KH, He XT, Liu Y, Chen XQ, Cheong KL (2020) In vitro fermentation of Gracilaria lemaneiformis sulfated polysaccharides and its agaro-oligosaccharides by human fecal inocula and its impact on microbiota. Carbohydr Polym 234:115894. https://doi.org/10.1016/j.carbpol.2020.115894
Zheng LX, Chen XQ, Cheong KL (2020) Current trends in marine algae polysaccharides: The digestive tract, microbial catabolism, and prebiotic potential. Int J Biol Macromol 151:344–354. https://doi.org/10.1016/j.ijbiomac.2020.02.168
Acknowledgements
We are grateful to Jude Juventus Aweya for his guidance, corrections and contributions to the grammar and sentence structure of the paper This research was financially supported by grants from the National Natural Science Foundation of China (31901692); Natural Science Foundation of Guangdong Province, China (2018A030310151); Department of Education of Guangdong Province with the Teaching Reform Project (2018JGXM44).
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KLC and XQC conceived and designed the experiments. XTX, XZ, and XTX performed the experiment and wrote the manuscript. All authors revised the paper and contributed reagents/materials/analysis tools. All authors reviewed and approved the final manuscript.
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Xie, XT., Zhang, X., Liu, Y. et al. Quantification of 3,6-anhydro-galactose in red seaweed polysaccharides and their potential skin-whitening activity. 3 Biotech 10, 189 (2020). https://doi.org/10.1007/s13205-020-02175-8
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DOI: https://doi.org/10.1007/s13205-020-02175-8