A review on phytoconstituents of marine brown algae

Future Journal of Pharmaceutical Sciences - Tập 6 - Trang 1-11 - 2020
Masuma M. Hakim1, Illa C. Patel1
1Department of Life Sciences, Hemchandracharya North Gujarat University, Patan, India

Tóm tắt

From the last few years, the development and discovery of bioactive compounds and their potential properties from marine algae have been enhanced significantly. The coastal area is a huge storehouse for propitious algae. It has been the genuine reality that the consequence of marine algae as a source of different compounds is increasing. Numerous advanced research devices are available for the discovery of synthetic compounds but still many researchers are working on natural bioactive compounds to discover their biological properties, which are useful to society. Marine algae are taking the preponderance of consideration from investigators owing to its phenomenon of biological activity like anti-cancer, anti-viral, cholesterol-reducing, and many more. A variety of compounds are collected from algae with specific purposes as they remain in an extremely ambitious and hard state; this condition is responsible for the synthesis of very particularly effective bioactive compounds. The present article is concentrating on the brown algae of the Gujarat coast, phlorotannins, polyphenol, phytosterol from brown algae, and their various applications. The main importance has been given to the secondary metabolites and various applications of marine brown algae. From this review, it can be concluded that the prominent bioactive compounds from brown algae can cure many serious diseases. Besides, the potential biological activities of a special bioactive compound may represent the interest in the industry of pharmaceuticals, cosmeceutical, and functional foods.

Tài liệu tham khảo

Kolanjinathan K, Ganesh P, Saranraj P (2014) Pharmacological importance of seaweeds: a review. World J Fish Marine Sci 6(1):01–15. https://doi.org/10.5829/idosi.wjfms.2014.06.01.76195 Dawczynski C, Schubert R, Jahreis G (2007) Amino acids, fatty acids, and dietary fibre in edible seaweed products. Food Chem 103:891–899. https://doi.org/10.1016/j.foodchem.2006.09.041 Fleurence J (1999) Seaweed proteins: biochemical, nutritional aspects and potential uses. Trends Food Sci Technol 10:25–28. https://doi.org/10.1016/S0924-2244(99)00015-1 Anantharaman P (2002) Manual on identification of seaweed. All India coordinate project on survey and Inventorization of coastal and marine biodiversity. J Mar Biol Assoc India 29:1–9 Dang TT, Michael CB, Ian A, Christopher JS (2018) Comparison of chemical profile and antioxidant properties of the brown algae. Int J Food Sci Technol 53:174–181. https://doi.org/10.1111/ijfs.13571 Gupta S, Abu-Ghannam N (2011) Bioactive potential and possible health effects of edible brown seaweeds. Trends Food Sci Technol 22:315–326. https://doi.org/10.1016/j.tifs.2011.03.011 Sanchez-Machado DI, López-Cervantes J, López-Hernández J, Paseiro-Losada P (2004) An HPLC method for the quantification of sterols in edible seaweeds. Biomed Chromatogr 18:183–190. https://doi.org/10.1002/bmc.316 Whittaker MH, Frankos VH, Wolterbeek AMP, Waalkens-Berendsen DH (2000) Effects of dietary phytosterols on cholesterol metabolism and atherosclerosis: clinical and experimental evidence. Am J Med 109:600–601. https://doi.org/10.1016/S0002-9343(00)00588-X Pal A, Kamthania MC, Kumar A (2014) Bioactive compounds and properties of seaweeds- a review. OA Lib J 1:752. https://doi.org/10.4236/oalib.1100752 Wijesinghea JP, You JP (2012) Biological activities and potential industrial applications of fucose rich sulfated polysaccharides and fucoidans isolated from brown seaweeds: a review. Carbohydr Polym 88:13–20. https://doi.org/10.1016/j.carbpol.2011.12.029 Blunt JW, Copp BR, Munro MHG, Northcote PT, Prinsep MR (2018) Marine natural products. Nat Prod Rep 23:26–78. https://doi.org/10.1039/c3np70117d Paula JC, Pedrini AG, Pinheiro MD, Pereira RC, Teixeira VL (2001) Chemical similarity between the brown algae Dictyota cervicornis and D. pardalis (Dictyotales, Phaeophyta). Biochem Syst Ecol 29:425–427. https://doi.org/10.1016/S0305-1978(00)00066-1 PMID: 11182491 Cox S, Gupta S, Abu-Ghannam N (2012) Effect of different rehydration temperatures on the moisture, content of phenolic compounds, antioxidant capacity and textural properties of edible Irish brown seaweed. LWT-Food Sci Technol 47:300–307. https://doi.org/10.1016/j.lwt.2012.01.023 Chakaborty K, Joseph D, Praveen NK (2015) Antioxidant activities and phenolic contents of three red seaweeds (division: Rhodophyta) harvested from the Gulf of Mannar of peninsular India. J Food Sci Technol 52:1924–1935. https://doi.org/10.1007/s13197-013-1189-2 PMID: 25829573 Dixit DC, Reddy CRK, Balar N, Suthar P, Gajaria T, Gadhavi DK (2018) Assessment of the nutritive, biochemical, antioxidant and antibacterial potential of eight tropical macro algae along Kachchh coast, India as human food supplements. J Aquat Food Prod T 27:61–79. https://doi.org/10.1080/10498850.2017.1396274 Cumashi A, Ushakova NA, Preobrazhenskaya ME, D’Incecco A, Piccoli A, Totani L (2007) A comparative study of the anti-inflammatory, anticoagulant, antiangiogenic, and antiadhesive activities of nine different fucoidans from brown seaweeds. Glycobiology 17:541–552. https://doi.org/10.1093/glycob/cwm014 PMID: 17296677 Durig J, Bruhn T, Zurborn KH, Gutensohn K, Bruhn HD, Béress L (1997) Anticoagulant fucoidan fractions from Fucus vesiculosus induce platelet activation in vitro. Thromb Res 85:79–491. https://doi.org/10.1016/S0049-3848(97)00037-6 Generalić Mekinić I, Skroza D, Šimat V, Hamed I, Čagalj M, Popović Perković Z (2019) Phenolic content of brown algae (Pheophyceae) species: extraction, identification, and quantification. Biomolecules 9(6):244. https://doi.org/10.3390/biom9060244 Paul JJP, Devi SDKS (2013) Seasonal variability of Ulva species (green seaweed) in Tirunelveli region, the southeast coast of Tamil Nadu, India. Res J Marine Sci 1(1):14–17 Chakraborty S, Bhattacharya T (2012) Nutrient composition of marine benthic algae found in the Gulf of Kutch coastline, Gujarat, India. J Algal Biomass Util 3(1):32–38 Hoek C, Mann D, Jahns HM, Jahns M (1995) Algae: an introduction to phycology. Cambridge University Press Krishnamurthy V, Joshi HV (1970) A check list of Indian marine algae. Central salt and Marine Chemical Research Institute Bhavnagar, Springer, p 39 Untawale AG, Dhargalkar VK, Agadi VV (1983) A list of marine algae from IndiaNational Institute of Oceanology. Goa. Tech. Rep, p 42 Sahoo D, Sahoo N, Debasish (2001) Seaweeds of India coast. A.P.H Publication, New Delhi, p 283. https://doi.org/10.1007/978-90-481-2488-6 Oza RM, Zaidi S (2001) A revised check-list of Indian marine algae. Central salt and Marine Chemical Research Institute, Bhavnagar, p 296 Venkataraman K, Wafar M (2005) Coastal and marine biodiversity of India. Indian J Marine Sci 34(1):57–75 Jha B, Reddy CRK, Thakur MC, Rao UM (2009) The diversity and distribution of seaweeds of Gujarat coast. Springer Science and Business Media B. V, New York, p 215 Ragan MA, Glombitza KW (1986) Phlorotannins, brown algal polyphenols. Progr Phycol Res 4:129–241 Kim J, Um M, Yang H, Kim I, Lee C, Kim Y, Yoon M, Kim Y, Kim J, Cho S (2016) Method development and validation for dieckol in the standardization of phlorotannins preparations. Fish Aquatic Sci 19:1–6. https://doi.org/10.1186/s41240-016-0003-2 Koivikko R, Loponen J, Pihlaja K, Jormalainen V (2007) High-performance liquid chromatographic analysis of phlorotannins from the brown alga Fucus vesiculosus. Phytochem Anal 18:326–332. https://doi.org/10.1002/pca.986 PMID: 17623367 Saravana PS, Getachew AT, Cho YJ, Choi JH, Park YB, Woo HC, Chun BS (2017) Influence of co-solvents on fucoxanthin and phlorotannin recovery from brown seaweed using supercritical CO2. J Supercrit Fluids 120:295–303. https://doi.org/10.1016/j.supflu.2016.05.037 SanchezCamargo AP, Montero L, Cifuentes A, Herrero M, Ibáñez E (2016) Application of Hansen solubility approach for the subcritical and supercritical selective extraction of phlorotannins from Cystoseira abies-marina. RSC Adv 6:94884–94895. https://doi.org/10.1039/C6RA16862K Okada Y, Ishimaru A, Suzuki R, Okuyama T (2004) A new phloroglucinol derivative from the brown alga Eisenia bicyclis: potential for the effective treatment of diabetic complications. J Nat Prod 67:103–105. https://doi.org/10.1021/np030323j PMID: 14738398 Wijesekara I, Yoon NY, Kim SK (2010) Phlorotannins from Ecklonia cava (Phaeophyceae): biological activities and potential health benefits. BioFactors 36(6):408–414. https://doi.org/10.1002/biof.114 PMID: 20803523 Young MH, Jong SB, Jin WH, Nam HL (2007) Isolation of a new phlorotannin, fucodiphlorethol G, from a brown alga Ecklonia cava. Bull Kor Chem Soc 28:1595–1597. https://doi.org/10.5012/bkcs.2007.28.9.1595 Yoon NY, Chung HY, Kim HR, Choi JS (2008) Acetyl- and butyryl-cholinesterase inhibitory activities of sterols and phlorotannins from Ecklonia stolonifera. Fisheries Sci 74:200. https://doi.org/10.1111/j.1444-2906.2007.01511.x Shibata T, Yamaguchi K, Nagayama K, Kawaguchi S, Nakamura T (2012) Inhibitory activity of brown algal phlorotannins against glycosidases from the viscera of the turban shell Turbo cornutus. Eur J Phycol 37:493–500. https://doi.org/10.1017/S0967026202003918 Nagayama K, Shibata T, Fujimoto K, Honjo T, Nakamura T (2003) Algicidal effect of phlorotannins from the brown alga Ecklonia kurome on red tide microalgae. Aquaculture 218:601–611. https://doi.org/10.1016/S0044-8486(02)00255-7 Jung HA, Hyun SK, Kim HR, Choi JS (2006) Angiotensin converting enzyme I inhibitory activity of phlorotannins from Ecklonia stolonifera. Fisheries Sci 72:1292–1299. https://doi.org/10.1111/j.1444-2906.2006.01288.x Joe MJ, Kim SN, Choi HY, Shin WS, Park GM, Kang DW, Kim YK (2006) The inhibitory effects of eckol and dieckol from Ecklonia stolonifera on the expression of matrix metalloproteinase-1 in human dermal fibroblasts. Biol Pharm Bull 29:1735–1739. https://doi.org/10.1248/bpb.29.1735 PMID: 16880634 Sugiura Y, Matsuda K, Yamada Y, Nishikawa M, Shoiya K, Katsuzaki H, Imai K, Amano H (2006) Isolation of a new anti-allergic phlorotannin, phlorofucofuroeckol-b, from an edible brown alga Eisenia arborea. Biosci. Biotechnol. Biochem 70(11):2807–2811. https://doi.org/10.1271/bbb.60417 Koch M, Gregson RP (1984) Brominated phlorethols and nonhalogenated phlorotannins from the brown alga Cystophora congesta. Phytochemistry 23:2633–2637. https://doi.org/10.1016/S0031-9422(00)84115-1 Gaurav R, Barry F, Nissreen AG (2016) Identification and characterization of phenolic antioxidant compounds from Brown Irish seaweed Himanthalia elongata using LC-DAD-ESI-MS/M. Innov Food Sci Emerg Technol 37:261–268. https://doi.org/10.1016/j.ifset.2016.02.005 Heo SJ, Hwang JY, Choi I, Han JS, Kim HJ, Jeon YJ (2009) Diphlorethohydroxycarmalol isolated from Ishige okamurae, a brown algae, a potent -glucosidase and -amylase inhibitor, alleviates postprandial hyperglycemia in diabetic mice. Eur J Pharmacol 615:252–256. https://doi.org/10.1007/s10811-008-9320-x Afsaneh Y, Alireza G, Ladan D (2016) Chemical constituents and biological activities of two Iranian Cystoseira species. Res Pharm Sci 11(4):311–317. https://doi.org/10.4103/1735-5362.189307 PMID: 27651811 Ferreres F, Lopes G, Gil-Izquierdo A, Andrade BC, Sousa Mouga T, Valentão P (2012) Phlorotannin extracts from fucales characterized by HPLC-DAD-ESI-MSn: approaches to hyaluronidase inhibitory capacity and antioxidant properties. Mar Drugs 10:2766–2781. https://doi.org/10.3390/2Fmd10122766 PMID: 23222802 Piironen V, Toivo J, Puupponen-Pimia R, Lampi AM (2003) Plant sterols in vegetables, fruits and berries. J Sci Food Agric 83:330–337. https://doi.org/10.1002/jsfa.1316 Lagarda MJ, Garcia-Llatas G, Farre R (2006) Analysis of phytosterols in foods. J Pharm Biomed Anal 41:1486–1496. https://doi.org/10.1016/j.jpba.2006.02.052 Abidi SL (2001) Chromatographic analysis of plant sterols in foods and vegetable oils. J Chromatogr 935:173–201. https://doi.org/10.1016/S0021-9673(01)00946-3 PMID:11762774 Rocco A, Fanali S (2009) Analysis of phytosterols in extra-virgin olive oil by nano-liquid chromatography. J Chromatogr A 1216:7173–7178. https://doi.org/10.1016/j.chroma.2009.03.081 PMID:19386314 Gihan AS, Essam AS (2014) Terpenes and sterols composition of marine Brown algae Padina pavonica (Dictyotales) and Hormophysa triquetra (Fucales). Int JPharma Phyto Res 6(4):894–900 Murugan K, Iyer VV (2014) Antioxidant activity and gas chromatographic-mass spectrometric analysis of extracts of the marine algae, Caulerpa peltata and Padina Gymnospora. Indian J Pharm Sci 76(6):548–552. https://doi.org/10.4103/0250-474X.147242 PMID:25593390 Caamal FE, Moo PR, Freile PY, Robledo D (2014) Cytotoxic and antiproliferative constituents from Dictyota ciliolata, Padina sanctae-crucis and Turbinaria tricostata. Pharm Biol 27:1–5. https://doi.org/10.3109/13880209.2014.886273 PMID: 24863279 Ayyad SE, Sowellim SZ, El-Hosini MS, Abo-Atia A (2003) The structural determination of a new steroidal metabolite from the brown alga Sargassum asperifolium. Zeitschrift fur Naturforschung C. J Biosci 58:333–336. https://doi.org/10.1515/znc-2003-5-607 Xiao HX, Zhi QY, Gong KL (2013) Preparation of phytosterols and phytol from edible marine algae by microwave-assisted extraction and high-speed counter-current chromatography. Sep Purif Technol 104:284–289. https://doi.org/10.1016/j.seppur.2012.11.032 Bouzidi N, Viano Y, Ortalo MA, Seridi H, Alliche Z, Daghbouche Y, Culioli G, Hattab M (2014) Sterols from the brown alga Cystoseira foeniculacea: degradation of fucosterol into saringosterol epimers. Arab J Chem:553. https://doi.org/10.1016/j.arabjc.2014.11.004 Aires A (2017) Phenolics in foods: extraction, analysis and measurements. In phenolic compounds-natural sources, importance and applicationsIn Tech pp, pp 61–88. https://doi.org/10.5772/66889 Yajing L, Xiaoting F, Delin D, Xiaoyong L, Jiachao X, Xin G (2017) Extraction and identification of phlorotannins from the brown alga, Sargassum fusiforme. Mar Drugs 15:49. https://doi.org/10.3390/md15020049 PMID: 28230766 Cruces E, Rojas Y, Ramire KE, Atala C, Lopez-Alarcon LE, Gomez I (2016) Comparison of different techniques for the preservation and extraction of phlorotannins in the kelp Lessonia spicata (Phaeophyceae): assays of DPPH, ORAC-PGR, and ORAC-FL as testing methods. J Appl Phycol 28:573–580. https://doi.org/10.1007/s10811-015-0602-9 Sanjeewa KA, Kim EA, Son KT, Jeon YJ (2016) Bioactive properties and potentials cosmeceutical applications of phlorotannins isolated from brown seaweeds: a review. J Photochem Photobiol B 162:100–105. https://doi.org/10.1016/j.jphotobiol.2016.06.027 Li YX, Wijesekara I, Li Y, Kim SK (2011) Phlorotannins as bioactive agents from brown algae. Process Biochem 46(12):2219–2224. https://doi.org/10.1016/j.procbio.2011.09.015 Thomas NV, Kim SK (2011) Potential pharmacological applications of polyphenolic derivates from marine brown algae. 32:325–335. https://doi.org/10.1016/j.etap.2011.09.004 Sudha G, Balasundaram A (2018) Analysis of bioactive compounds in Padina pavonica using HPLC, UV-VIS and FTIR techniques. J Pharmacog Phytochem 7(3):3192–3195 Rajamani K, Somasundaram ST (2018) Polyphenols from brown alga, Padina boergesenii (Allendar & Kraft) decelerates renal cancer growth involving cell cycle arrest and induction of apoptosis in renal carcinoma cells. Environ Toxicol:1–8. https://doi.org/10.1002/tox.22619 Sabeena KH, Jacobsen C (2013) Phenolic compounds and antioxidant activities of selected species of seaweeds from Danish coast. Food Chem 138:1670–1681. https://doi.org/10.1016/j.foodchem.2012.10.078 PMID: 23411297 El Gamal AA (2010) Biological importance of marine algae. Saudi Pharmaceut J 18(1):1–25. https://doi.org/10.1016/j.jsps.2009.12.001 Capon RI, Barrow RA, Rochfort S, Jobling M, Skene C, Larcey E, Gill IH, Friedel T, Wadsworth D (1998) Marine nematodes: tetrahydrofuran from a southern australian brown alga.Notheia Anomala. Tetrahdron 54:2227–2242 Bennamara A, Abourrichi A, Berrada M, M’hamed C, Chaib N, Boudouma M, Garneau XF (1999) Methoxybifur-carenone: an antifungal and antibacterial meroditerpenoid from the brown alga Cystoseira tamariscifolia. Phytochemistry 52:37–40 Kim YC, An RB, Yoon NY, Nam TJ, Choi JS (2005) Hepatoprotective constituents of the edible brown alga Ecklonia stolonifera on tacrine-induced cytotoxicity in hep G2 cells. Arch Pharm Res 28(12):1376 Lee YS, Shin KH, Kim BK, Lee S (2004) Anti-diabetic activities of fucosterol from Pelvetia siliquosa. Arch Pharm Res 27(11):1120–1122 Suzuki M, Yamada H, Kurata K (2002) Dictyterpenoids a and B, two novel Diterpenoids with feeding-deterrent activity from the Brown alga Dilophus o kamurae. J Nat Prod 65(2):121–125. https://doi.org/10.1021/np010234b Sugiura Y, Matsuda K, Yamada Y, Nishikawa M, Shioya K, Katsuzaki H (2007) Anti-allergic phlorotannins from the edible brown alga, Eisenia Arborea. Food Sci Technol Res 13:54–60 Jung HA, Hyun SK, Kim HR, Choi JS (2006) Angiotensin-converting enzyme I inhibitory activity of phlorotannins from Ecklonia stolonifera. Fish Sci 72(6):1292–1299. https://doi.org/10.1111/j.1444-2906.2006.01288.x Waghmode AV, Khilare CJ (2018) RP-HPLC profile of major phenolics from brown marine macro algae. J Appl Pharm 10(2):1–5. https://doi.org/10.4172/1920-4159.1000262 Natrah FMI, Harah M, Japar Sidik B, Izzatul NS, Syahidah A (2015) Antibacterial activites of selected seaweed and seagrass from Port Dickson coastal water against different aquaculture pathogens. Sains Malaysiana 44(9):1269–1273. https://doi.org/10.17576/jsm-2015-4409-08 Senthilkumar K, Manivasagan P, Venkatesan J, Kim SK (2013) Brown seaweed fucoidan: biological activity and apoptosis, growth signaling mechanism in cancer. Int J Biol Macromol 60:366–374. https://doi.org/10.1016/j.ijbiomac.2013.06.030 PMID: 23817097 Kang Y, Zhi JW, Dongsheng X, Xue S, Wenge Y, Xiaodong Z, Nianjun X (2017) Characterization and potential antitumor activity of polysaccharide from Gracilariopsis lemaneiformis. Drugs 15:100. https://doi.org/10.3390/2Fmd15040100 PMID: 28353631 Corona G, Coman MM, Spencer JPE, Rowland I (2014) Digested and fermented seaweed phlorotannins reduce DNA damage and inhibit growth of HT-29 colon cancer cells. Proc Nutr Soc 73:31. https://doi.org/10.1017/S0029665114000457 Antunes EM, Anthonia FA, Maynard TC, Jameel F, Michael GK, Catherine EV, Denver TH, John JB, Denzil RB (2011) Identification and in vitro anti-esophageal cancer activity of a series of halogenated monoterpenes isolated from the south African seaweeds Plocamium suhrii and Plocamium cornutum. Phytochemistry 72:769–772. https://doi.org/10.1016/j.phytochem.2011.02.003 PMID:121392811 Nishide E, Uchida H (2003) Effects of Ulva powder on the ingestion and excretion of cholesterol in rats. In: Chapman ARO, Anderson RJ, Vreeland VJ, Davison IR (eds) Proceedings of the 17th international seaweed symposium. Oxford University Press, Oxford, pp 165–168 Crockett SL, Wenzig EM, Kunert O, Bauer R (2008) Anti-inflammatory phloroglucinol derivatives from Hypericum empetrifolium. Phytochem Lett 1:37–43. https://doi.org/10.1016/2Fj.phytol.2007.12.003 PMID: 21151761 Daikonya A, Katsuki S, Wu JB, Kitanaka S (2002) Anti-allergic agents from natural sources (4): anti-allergic activity of new phloroglucinol derivatives from Mallotus philippensis (Euphorbiaceae). Chem Pharm Bull(Tokyo) 50:1566–1569. https://doi.org/10.1248/cpb.50.1566 PMID:12499591 Kim MM, Kim SK (2010) Effect of phloroglucinol on oxidative stress and inflammation. Food Chem Toxicol 48:2925–2933. https://doi.org/10.1016/j.fct.2010.07.029 PMID: 20667461 Boopathy N, Kathiresan K (2010) Anticancer drugs from marine flora: an overview. J Oncol 2010:18. https://doi.org/10.1155/2010/214186 Vo TS, Kim SK (2010) Potential anti-HIV agents from marine resources: an overview. Mar Drugs 8:2871–2892. https://doi.org/10.3390/md8122871 PMID: 21339954 Wang W, Wang SX, Guan HS (2012) The antiviral activities and mechanisms of marine polysaccharides: an overview. Mar Drugs 10:2795–2816. https://doi.org/10.3390/md10122795 PMID: 23235354 Jose GM, Anitha R, Muraleedhara K (2015) Antioxidant and antimitotic activities of sulfated polysaccharide from marine brown algae Padina tetrastromatica. J Phytology 7:39–51. https://doi.org/10.19071/jp.2015.v7.2921 Kang SM, Kim KN, Lee SH, Ahn G, Cha SH, Kim AD, Yang XD, Kang MC, Jeon YJ (2011) Anti-inflammatory activity of polysaccharide purified from AMG-assistant extract of Ecklonia cava in LPS-stimulated RAW264.7 macrophages. Carbohydr Polym 85:80–85. https://doi.org/10.1016/j.carbpol.2011.01.052 Li DY, Xu RY, Zhou WZ, Sheng XB, Yang AY, Cheng JL (2002) Effects of fucoidan extracted from brown seaweed on lipid peroxidation in mice. Acta Nutrimenta Sinica 24:389–392. https://doi.org/10.3390/md17100591 Parveen S, Nadumane VK (2020) Anti-angiogenesis and apoptogenic potential of the brown marine alga, Chnoospora minima. Future J Pharmaceutical Sci 6(1):1–14. https://doi.org/10.1186/s43094-020-00039-9