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Volatile Bioactive Compounds from Marine Macro-Algae and their Pharmacological Properties


Affiliations
1 Department of Marine Biotechnology, AMET University, Chennai, Tamil Nadu – 603 112, India
 

The present study is aimed at identification of bioactive compounds and their pharmacological properties of four macro-algae (Hydropuntia edulis, Halymenia venusta, Ulva lactuca and Padina gymnospora) from the Hare Island, Tuticorin district of Tamil Nadu, India. The characterization of ethanol extracted compounds was done using GC-MS techniques. The major secondary metabolites such as alkaloids, phenol, saponins, flavonoids, steroids, terpenoids and tannins were recorded from all the algal samples. The numbers of major volatile compounds recorded in the GC-MS analysis are 32, 19, 8 and 14 in H. edulis, H. venusta, U. lactuca and P. gymnospora, respectively. All these identified compounds could be of therapeutic values for many acute and chronic diseases and disorders. These secondary metabolites belong to alkanes, aliphatic amines, aromatics, aldehydes, 1°, 2° amines and ketone groups. Many of these characterized compounds could be used for therapeutic purposes.

Keywords

Bioactive Compounds, Marine Macro-Algae, Pharmacological Properties, Secondary Metabolites, Therapeutic Values.
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  • Mohapatra L, Pati P, Panigrahy R & Bhattamisra S K, Therapeutic health booster: seaweeds against several maladies, Indian J Geo-Mar Sci, 42 (5) (2013) 538-546.
  • Mariya V & Ravindran V S, Biomedical and Pharmacological significance of marine macro - algae-review, Indian J Geo-Mar Sci, 42 (5) (2013) 527-537.
  • Rani S & Usha R, Utilization of seaweeds in enhancing the biochemicals and productivity of Cassia angustifolia Vahl, Indian J Geo-Mar Sci, 4 (2) (2013) 184-188.
  • Vijayaraj R, Sri Kumaran N, Altaff K, Ramadevi S & Sherlin Rosita A, In Silico Pharmacokinetics and Molecular Docking of Novel Bioactive Compound (11-Methoxy-2-Methyltridecane-4-Ol) for Inhibiting Carbohydrates Hydrolyzing Enzyme, J Biol Act Prod Nat, 9 (6) (2019) 445-456.
  • Richards J T, Kern E R, Glasgow L A, Overall J C, Deign E F, et al., Antiviral activity of extracts from marine algae, Antimicrob Agents Chemother, 14 (1) (1978) 24-30.
  • Oumaskour K, Boujaber M, Etahiri S &Assobhei O, Screening of antibacterial and antifungal activities in green and brown algae from the coast of Sidi Bouzid (El Jadida, Morocco), Afri J Biotech, 11 (104) (2012) 16831-16837.
  • Athukorala Y, Lee K W, Kim S K & JeonY J, Anticoagulant activity of marine green and brown algae collected from Jeju Island in Korea, Bioresour Technol, 98 (9) (2007) 1711-1716.
  • Abirami R G & Kowsalya S, Anticancer Activity of Methanolic and Aqueous Extract of Ulva Fasciata in Albino Mice, Int J Pharm Pharm Sci, 4 (2) (2012) 681-684.
  • Boonchum W, Peerapornpisal Y, Kanjanapothi D, Pekkoh J, Amornlerdpison D, et al., Antimicrobial and anti-inflammatory properties of various seaweeds from the gulf of Thailand, Int J Agric Biol, 13 (1) (2011) 100-104.
  • Manisseri M K, Geetha A & Syda R G, Common Seaweeds and Seagrasses of India Herbarium, (Central Marine Fisheries Research Institute, Kochi), Vol 2, 2012, pp. 41. http://eprints.cmfri.org.in/id/eprint/8948
  • Harborne J B, Methods of extraction and isolation, In: Phytochemical methods, 3rd edn, (Chapman & Hall, an imprint of Thomson Science, UK), 1998, pp. 60-66.
  • Aliyu A B, Ibrahim H, Musa A M, Ibrahim M A, Oyewale A O, et al., In vitro evaluation of antioxidant activity of Anisopus mannii NE Br, Afri J Biotech, 9 (16) (2010) 2437-2441.
  • Solanki R, Gupta A, Tripathy A, Soni D & Jana G K, Pharmacognostic, phytochemical and physiochemical studies of Atrocarpus hetrophyllus leaf (Moracae), J Nat Prod Plant Resour, 1 (4) (2011) 20-26.
  • Mandal P, Sinha S P & Mandal N C, Antimicrobial activity of Saponins from Acacia auriculiformis, Fitoterapia, 76 (5) (2005) 462-565.
  • Kolodziej H, Kayser O, Radtke O A, Kiderlen A F & Koch E, Pharmacological profile of extracts of Pelargonium sidoides and their constituents, Phytomedicine, 10 (2003) 18-24.
  • Boge T C, Himes R H, Vander Velde D G & Georg G I, The effect of the aromatic rings of taxol on biological activity and solution conformation: synthesis and evaluation of saturated taxol and taxotere analogs, J Med Chem, 37 (20) (1994) 3337-3343.
  • Viu E, Zapata A, Capdevila J L, Fossom L H, Skolnick P, et al., Glycine site antagonists and partial agonists inhibit N-methyl-D-aspartate receptor-mediated [3H] arachidonic acid release in cerebellar granule cells, J Pharmacol Exp Ther, 285 (2) (1998) 527-532.
  • Pânzariu A T, Apotrosoaei M, Vasincu I M, Drăgan M, Constantin S, et al., Synthesis and biological evaluation of new 1, 3-thiazolidine-4-one derivatives of nitro-l-arginine methyl ester, Chem Cent J, 10 (1) (2016) p. 6.
  • Gregory J S, Bonfiglio M F, Dasta J F, Reilley T E, Townsend M C, et al., Experience with phenylephrine as a component of the pharmacologic support of septic shock, Crit Care Medi, 19 (11) (1991) 1395-1400.
  • Armstrong J & Hunt D E, In vitro antimicrobial activity of actinobolin applied to tooth surfaces, J Period Res, 8 (6) (1973) 404-405.
  • Tweedie D J, Erikson J M & Prough R A, Metabolism of hydrazine anti-cancer agents, Pharm Therap, 34 (1) (1987) 111-127.
  • Kim H M, Shim I S, Baek Y W, Han H J, Kim P J, et al., Investigation of disinfectants for foot-and-mouth disease in the Republic of Korea, J Infect Public Health, 6 (5) (2013) 331-338.
  • Sivajothi V & Dakappa S S, In vitro and in silico antidiabetic activity of pyran ester derivative isolated from Tragiacannabina, Asi Pac J Tro Biomed, 4 (2014) S455-S459.
  • O'Callaghan C N, Anticancer Agents: VIII. Synthesis of Substituted Benzopyranom-[2, 3-d] Pyrimidines from 3-Carbamoyl-2-Iminochromens, In: Proceedings of the Royal Irish Academy, Section B: Bio, Geo Chemi Sci, 1973, pp. 291-297.
  • Idan S A, Al-Marzoqi A H & Hameed I H, Spectral analysis and anti-bacterial activity of methanolic fruit extract of Citrullus Colocynthis using Gas Chromatography- Mass-Spectrometry, Afr J Biotechn, 14 (46) (2015) 3131-3158.
  • Chee D N A, Rodis M L, Saat N, Ngaini Z & Halim A N A, Synthesis and Antibacterial Study Of Organotin(Iv) Complexes Containing Hydrazinopyridine Ligand, Malaysian J Anal Sci, 21 (5) (2017) 1143 - 1150.
  • Ghorab M M, Alqasoumi S I, Abdel-Kader M S & Alsaid M S, Utility of L-Norephedrine in the semisynthesis of novel thiourea and thiazolidine derivatives as a new class of anticancer agents, Acta Pol Pharm, 71 (2014) 615-623.
  • Xuan T D, Minh T N & Khanh T D, Isolation and biological activities of 3-hydroxy-4 (1H)-pyridone, J Pla Intera, 11 (1) (2016) 94-100.
  • Xu G P, Wang H B & Wu Z L, Efficient bioreductive production of (S)-N-Boc-3-hydroxypiperidine using ketoreductase ChKRED03, Pro Biochem, 51 (7) (2016) 881-885.
  • Guo L, Wu J Z, Han T, Cao T, Rahman K, et al., Chemical composition, antifungal and antitumor properties of ether extracts of Scapania Verrucosa Heeg and its endophytic fungus Chaetomium fusiforme, Molecules, 13 (9) (2008) 2114–2125.
  • Rajini A, Nookaraju M, Reddy I A K & Venkatathri N, Synthesis, characterization, antimicrobial and cytotoxicity studies of a novel titanium dodecylamino phosphate, J Saudi Chem Soc, 21 (2017) S77-S85.
  • Wei S, Quanquan Q, Peiyuan L, Xiaolin L, Qi X, et al., Synthesis, Characterization, and Anticancer Activity of a Series of Ketone-N4-Substituted Thiosemicarbazones and Their Ruthenium(II) Arene Complexes, Inorg Chem, 52 (21) (2013) 12440–12449.
  • Bass P D, Gubler D A, Judd T C & Williams R M, Mitomycinoid alkaloids: mechanism of action, biosynthesis, total syntheses, and synthetic approaches, Chem Revi, 113 (8) (2013) 6816-6863.
  • Efimova M A, Ivanov A V, GaffarovKh Z & Moskvichev O V, Immunobiological Properties of Reovirus Type I, Russ Agric Sci, 40 (2) (2014) 153–156.
  • Alarcón B, Lacal J C, Fernández-Sousa J & Carrasco L, Screening for new compounds with antiherpes activity, Antiviral Res, 4 (5) (1984) 231-244.
  • Mochizuki A, Nakamoto Y, Naito H, Uoto K & Ohta T, Design, synthesis, and biological activity of piperidine diamine derivatives as factor Xa inhibitor, Bioorg Med Chem Lett, 18 (2) (2008) 782-787.
  • Ishiwata S, Itoh K, Yamaguchi T, Ishida N & Mizugaki M, Comparison of serum and urinary levels of modified nucleoside, 1- methyladenosine, in cancer patients using a monoclonal antibody based inhibition ELISA Tohoku, J Exp Med, 176 (1) (1995) 61-8.
  • Cheng Y, Xie G, Chen T, Qiu Y, Zou X, et al., Distinct urinary metabolic profile of human colorectal cancer, J Proteome Res, 11 (2) (2012) 1354-63.
  • Ahmed S A, Ahmed O M & Elgendy H S, Novel Synthesis of Purine Analogues and Thieno [2, 3-b] pyridine derivatives with anticancer and antioxidant activity, J Pharm Res, 8 (9) (2014) 1303-1313.
  • Kim S H, Bartholomew D G, Allen L B, Robins R K & Revankar G R, Imidazo [1,2-a]-s-triazine nucleosides, Synthesis and antiviral activity of the N-bridgehead guanine, guanosine, and guanosine monophosphate analogues of imidazo[1,2-a]-s-triazine, J Med Chem, 21 (9) (1978) 883-889.
  • Javid S, Chaudhari S K, Munir I, Amjad M S, Akbar K F, et al., Plant Metabolites and Pharmacological Activities of Leptadenia Pyrotechnica (Forssk.) Decne, Nat Bioact Compd, (2019) 551-560.
  • Kolodziej H, Traditionally used Pelargonium species: Chemistry and biological activity of umckaloabo extracts and their constituents, Curr Topics Phytochem, 3 (2000) 77-93.
  • Maleki M, Karimi G, Tafaghodi M, Raftari S & Nahidi Y, Comparison of intralesional two percent zinc sulfate and glucantime injection in treatment of acute cutaneous leishmaniasis, Indian J Dermat, 57 (2) (2012) 118–122.
  • Mishra R, Jha K K, Kumar S & Tomer I, Synthesis, properties and biological activity of thiophene: A review, Der Pharma Chemica, 3 (4) (2011) 38-54.
  • Naito H, Ohsuki S, Sugimori M, Atsumi R, Minami M, et al., Synthesis and antitumor activity of novel pyrimidinylpyrazole derivatives. II. Optimization of the phenylpiperazine moiety of 1-[5-methyl-1-(2-pyrimidinyl)-4-pyrazolyl]-3-phenylpiperazinyl-1-trans-propenes, Chem Pharma Bull, 50 (4) (2002) 453-462.
  • Lucchini JJ, Corre J & Cremieux A, Antibacterial activity of phenolic compounds and aromatic alcohols, Res Microbiol, 141 (4) (1990) 499-510.
  • Liu T, Dong X, Xue N, Wu R, He Q, et al., Synthesis and biological evaluation of 3, 4-diaryl-5-aminoisoxazole derivatives, Bioorganic Med Chem, 17 (17) (2009) 6279-6285.
  • La Verne D, Harry R, Peter U, Nwangwu T, Holcslaw, et al., Partial synthesis of 6'-hydroxycinchonine and its antiarrhythmic activity in mice, J Med Chem, 22 (8) (1979) 1014–1016.
  • Özkay Y, Işıkdağ İ, İncesu Z & Akalın G, Synthesis of 2-substituted-N-[4-(1-methyl-4, 5-diphenyl-1H-imidazole-2-yl) phenyl] acetamide derivatives and evaluation of their anticancer activity, Euro J Med Chem, 45 (8) (2010) 3320-3328.
  • Wright H B, Dunnigan D A & Biermacher U, Hypocholesteremic Agents. I. Pyridyl Carbinols, J Med Chem, 7 (1) (1964) 113-115.
  • Kazemi M, Phenolic profile, antioxidant capacity and anti-inflammatory activity of Anethumgraveolens L. essential oil, Nat Prod Res, 29 (6) (2015) 551-553.
  • Kumar P, Chandak N, Kaushik P, Sharma C, Kaushik D, et al., Benzenesulfonamide bearing pyrazolylpyrazolines: synthesis and evaluation as anti-inflammatory–antimicrobial agents, Med Chem Res, 23 (2) (2014) 882-895.
  • Giri R S, Thaker H M, Giordano T, Williams J, Rogers D, et al., Design, synthesis and characterization of novel 2-(2, 4-disubstituted-thiazole-5-yl)-3-aryl-3H-quinazoline-4-one derivatives as inhibitors of NF-κB and AP-1 mediated transcription activation and as potential anti-inflammatory agents, Euro J Med Chem, 44 (5) (2009) 2184-2189.
  • Bergaoui A, Boughalleb N, Ben Jannet H, Harzallah-Shiric F, El Mahjoub M, et al., Chemical composition and antifungal activity of volatiles from three Opuntia species growing in Tunisia, Pak J Biol Sci, 10 (15) (2007) 2485-2489.
  • Cuzzocrea S, Chatterjee P K, Mazzon E, Dugo L, Serraino I, et al., Pyrrolidine dithiocarbamate attenuates the development of acute and chronic inflammation, British J Pharma, 135 (2) (2002) 496-510.
  • Stangel M, Moharregh-Khiabani D, Linker R A & Gold R, Fumaric acid and its esters in the treatment of multiple sclerosis: studies and effects, Nervenarzt, 79 (2) (2008) 212-217.
  • Bernini R, Barontini M, Cis V, Carastro I, Tofani D, et al., Synthesis and Evaluation of the Antioxidant Activity of Lipophilic Phenethyl Trifluoroacetate Esters by In Vitro ABTS, DPPH and in Cell- Culture DCF Assays, Molecules, 23 (1) (2018) p. E208.
  • Kendziorek M, Paszkowski A & Zagdańska B, Biochemical characterization and kinetic properties of alanine aminotransferase homologues partially purified from wheat (Triticum aestivum L.), Phytochemistry, 82 (2012) 7-14.
  • Hadizadeh F, Ebrahimzadeh M A, Hosseinzadeh H, Motamed-Shariaty V, Salami S et al., Antidepressant and antioxidant activities of some 2-benzoxazolinone derivatives as Bupropion analogues, Pharmacologyonline, 1 (2009) 331-335.
  • Zhang X, Lei P, Sun T, Jin X, Yang X, et al., Design, Synthesis, and Fungicidal Activity of Novel Thiosemicarbazide Derivatives Containing Piperidine Fragments, Molecules, 22 (12) (2017) p. 2085.
  • Pantelić N, Stanojković T P, Zmejkovski B B, Sabo T J & Kaluđerović G N, In vitro anticancer activity of gold (III) complexes with some esters of (S, S)-ethylenediamine-N, N′-di-2-propanoic acid, Eur J Med Chem, 90 (2015) 766-774.
  • Jain N K, Kulkarni S K & Singh A, Modulation of NSAID-induced antinociceptive and anti-inflammatory effects by α2-adrenoceptor agonists with gastroprotective effects, Life Sci, 70 (24) (2002) 2857-2869.
  • Kamata R, Nakajima D & Shiraishi F, Agonistic effects of diverse xenobiotics on the constitutive androstane receptor as detected in a recombinant yeast-cell assay, In Vitro Toxicol, 46 (2018) 335-349.
  • Manirarora J N, Parnell S A, Hu Y H, Kosiewicz M M & Alard P, NOD dendritic cells stimulated with Lactobacilli preferentially produce IL-10 versus IL-12 and decrease diabetes incidence, Clin Dev Immunol, 2011 (2011) p. 630187.
  • Van Vugt-Lussenburg B M, Van der Lee R B, Man H Y, Middelhof I, Brouwer A, et al., Incorporation of metabolic enzymes to improve predictivity of reporter gene assay results for estrogenic and anti-androgenic activity, Reprodu Toxic, 75 (2018) 40-48.
  • Saludes J P, Garson M J, Franzblau S G & Aguinaldo A M, Antitubercular constituents from the hexane fraction of Morinda citrifolia Linn. (Rubiaceae), Phytother Res, 16 (7) (2002) 683-685.
  • Srinivasan G V, Sharanappa P, Leela N K, Sadashiva C T & Vijayan K K, Chemical composition and antimicrobial activity of the essential oil of Leea indica (Burm. f.) Merr. Flowers, Nat Prod Radiance, 8 (5) (2009) 488-493.
  • Chang Y, Lathrop R, Bohm E, Gander-Meisterernst I, Greger R, et al., Medicament for the treatment of viral skin and tumour diseases, United States Patent (US9770406), 2017, p. 1.
  • Jehoshua K, Berry E, Avraham Y, Najajreh Y, Saidian M, et al., Compounds and methods of treating obesity, United States Patent (US2011178151), 2011, p. 1.
  • Chung E Y, Byun Y H, Shin E J, Chung H S, Lee Y H, et al., Antibacterial effects of vulgarone B from Artemisia iwayomogi alone and in combination with oxacillin, Arch Pharm Res, 32 (12) (2009) 1711-1719.
  • Perestrelo R, Silva C L, Rodrigues F, Caldeira M & Câmara J S, A powerful approach to explore the potential of medicinal plants as a natural source of odor and antioxidant compounds, J Food Sci Technol, 53 (1) (2016) 132-144.
  • Toppo E, Darvin S S, Esakkimuthu S, Stalin A, Balakrishna K, et al., Antihyperlipidemic and hepatoprotective effects of Gardenin A in cellular and high fat diet fed rodent models, Chem Biol Interact, 269 (2017) 9-17.
  • Ismail A M, In L L, Tasyriq M, Syamsir D R, Awang K, et al., Extra virgin olive oil potentiates the effects of aromatase inhibitors via glutathione depletion in estrogen receptor-positive human breast cancer (MCF-7) cells, Food Chem Toxicol, 62 (2013) 817-824.
  • Jeong S O, Son Y, Lee J H, Cheong Y, Park S H, et al., Resveratrol analog piceatannol restores the palmitic acid - induced impairment of insulin signaling and production of endothelial nitric oxide via activation of anti-inflammatory and antioxidativeheme oxygenase-1 in human endothelial cells, Mol Med Rep, 12 (1) (2015) 937-944.
  • Sharma K R, Seenivasagan T, Rao A N, Ganesan K, Agrawal O P, et al., Mediation of oviposition responses in the malaria mosquito Anopheles stephensi Liston by certain fatty acid esters, Parasitol Res, 104 (2) (2009) 281-286.
  • Sestraş R E, Jäntschi L & Bolboacă S D, Poisson parameters of antimicrobial activity: A quantitative structure-activity approach, Int J Mol Sci, 13 (4) (2012) 5207-5229.
  • Kharchenko O V, Kharitonenko A I, Vovk A I, Babiĭ L V, Khil'chevskiĭ A N, et al., Inhibiting properties of stable nitroxyl radicals in reactions of linoleic acid and linoleyl alcohol oxidation catalyzed by 5-lipoxygenase, Ukr Biokhim Zh, 77 (1) (1999) 52-57.
  • Musini A, Rao J P & Giri A, Phytochemicals of Salacia oblonga responsible for free radical scavenging and antiproliferative activity against breast cancer cell lines (MDA-MB-231), Physiol Mol Biol Plants, 21 (4) (2015) 583-590.
  • Bouabdallah S, Sghaier R M, Selmi S, Khlifi D, Laouini D, et al., Current approaches and challenges for chemical characterization of inhibitory effect against cancer cell line isolated from Gokshur extract, J Chromatogr B Analyt Technol Biomed Life Sci, 1026 (2016) 279-285.
  • Lee J H, Kim Y G, Kim C J, Lee J C, Cho M H, et al., Indole-3-acetaldehyde from Rhodococcus sp. BFI 332 inhibits Escherichia coli O157: H7 biofilm formation, Appl Microbiol Biotechnol, 96 (4) (2012) 1071-1078.
  • Cyril R, Lakshmanan R & Thiyagarajan A, In vitro bioactivity and phytochemical analysis of two marine macro-algae, J Coast Life Med, 5 (10) (2017) 427-432.
  • Dhevika S & Deivasigamani B, Phytochemical profiling and GC-MS analysis of Caulerpa racemosa, Res J Life Sci Bioinfor Pharma Chem Sci, 4 (5) (2018) 155 – 165.
  • Sujatha R, Siva D & Nawas P, Screening of phytochemical profile and antibacterial activity of various solvent extracts of marine algae Sargassum swartzii, World Sci News, 115 (2019) 27-40.
  • Ravi S, Banu V H & Nawas P M A, Profiling of phytochemical, antioxidant properties and antimicrobial activity of marine red seaweed Jania rubens, Pharma Inno J, 8 (4) (2019) 445-452.
  • Gwladys S, Vania R P, Klervi L L, Sara M, Fabienne G, et al., Marine green macroalgae: a source of natural compounds with mineralogenic and antioxidant activities, J Appl Phys, 29 (1) (2017) 575-584.

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  • Volatile Bioactive Compounds from Marine Macro-Algae and their Pharmacological Properties

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Authors

R Vijayaraj
Department of Marine Biotechnology, AMET University, Chennai, Tamil Nadu – 603 112, India
K Altaff
Department of Marine Biotechnology, AMET University, Chennai, Tamil Nadu – 603 112, India
N Sri Kumaran
Department of Marine Biotechnology, AMET University, Chennai, Tamil Nadu – 603 112, India
Swarnakala
Department of Marine Biotechnology, AMET University, Chennai, Tamil Nadu – 603 112, India

Abstract


The present study is aimed at identification of bioactive compounds and their pharmacological properties of four macro-algae (Hydropuntia edulis, Halymenia venusta, Ulva lactuca and Padina gymnospora) from the Hare Island, Tuticorin district of Tamil Nadu, India. The characterization of ethanol extracted compounds was done using GC-MS techniques. The major secondary metabolites such as alkaloids, phenol, saponins, flavonoids, steroids, terpenoids and tannins were recorded from all the algal samples. The numbers of major volatile compounds recorded in the GC-MS analysis are 32, 19, 8 and 14 in H. edulis, H. venusta, U. lactuca and P. gymnospora, respectively. All these identified compounds could be of therapeutic values for many acute and chronic diseases and disorders. These secondary metabolites belong to alkanes, aliphatic amines, aromatics, aldehydes, 1°, 2° amines and ketone groups. Many of these characterized compounds could be used for therapeutic purposes.

Keywords


Bioactive Compounds, Marine Macro-Algae, Pharmacological Properties, Secondary Metabolites, Therapeutic Values.

References