Vibrational spectroscopy for structural characterization of bioactive compounds

Comprehensive Analytical Chemistry

Volumn 65, Issue , 2014, Pages 115-148

  Singh, Keisham S ^a   Majik, Mahesh S ^a   Tilvi, Supriya ^a  

^a NATIONAL INSTITUTE OF OCEANOGRAPHY   (India)

Author keywords

Bioactive compounds; Chitin; Infrared spectroscopy; Marine organisms; Raman spectra; Steroids; Sulfated polysaccharides

Indexed keywords

EID: 84906544393     PISSN: 0166526X     EISSN: None     Source Type: Book Series    
DOI: 10.1016/B978-0-444-63359-0.00006-9     Document Type: Chapter

References (133)

1. Xu F., Yu J., Tesso T., Dowell F., Wang D. Qualitative and quantitative analysis of lignocellulosic biomass using infrared techniques: A mini review. Appl. Energy 2013, 104:801.
2. R.-Saona L.E., Allendorf M.E. Use of FTIR for rapid authentication and detection of adulteration of food. Ann. Rev. Food Sci. Tech. 2011, 2:1.
3. Moros J., Garrigues S., de la Guardia M. Vibrational spectroscopy provides a green tool for multi-component analysis. Trends in Anal. Chem. 2010, 29:578.
4. Maquelin K., Kirschner C., C.-Smith L.-P., van den Braak N., Endtz Ph.H., Naumann D., Puppels G.J. Identification of medically relevant microorganisms by vibrational spectroscopy. J. Microbiol. Methods 2002, 51:255.
5. Grube M., Rutkis R., Gavare M., Lasa Z., Strazdina I., Galinina N., Kalnenieks U. Application of FT-IR Spectroscopy for Fingerprinting of Zymomonas mobilis Respiratory Mutants. Spectroscopy: An International Journal 2012, 27:581.
6. Rösch P., Harz M., Krause M., Petry R., Peschke K.-D., Burkhardt H., Ronneberger O., Schüle A., Schmauz G., Riesenberg R., Wuttig A., Lankers M., Hofer S., Thiele H., Motzkus H.W.J.P. Online monitoring and identification of bioaerosol (OMIB). Biophotonics, Visions for Better Health Care 2006, 596. Wiley-VCH, Weinheim:. J. Popp, M. Strehle (Eds.).
7. Virkler K., Lednev I.K. Raman spectroscopic signature of semen and its potential application to forensic body fluid identification. Forensic Sci. Int. 2009, 193:56-62.
8. Pereira L. Identification of phycocolloids by vibrational spectroscopy. World Seaweed Resources -An authoritative reference system 2006, ETI Information Services Ltd. A.T. Critchley, M. Ohno, D.B. Largo (Eds.).
9. Harz M., Rösch P., Popp J. Vibrational Spectroscopy 22, A Powerful Tool for the Rapid Identification of Microbial Cells at the Single-Cell Level. Cytometry Part A 2009, 75A:104.
10. Creighton J.A. Spectroscopy of Surface 1988, 21. Wiley, New York. R.J. Clark, R.E. Hester (Eds.).
11. Das R.S., Agrawal Y.K. Raman spectroscopy: Recent Advancements, techniques and applications. Vibrational Spectroscopy 2011, 57:163.
12. Matitoli T.A., Hoffmann A., Sockalingum D.G. Application of near-IR Fourier transform resonance spectroscopy to the study of photosynthetic proteins Spectrochim. Acta A 1993, 49:785.
13. Schrader B. Infrared and Raman Spectroscopy. Methods and Applications 1995, VCH, Weinheim. B. Schrader (Ed.).
14. Harrick N.J. Internal Reflection Spectroscopy 1967, John Wiley & Sons Inc., 342.
15. Fuller M.P., Griffiths P.R. Diffuse reflectance measurements by infrared Fourier transform spectrometry. Anal. Chem. 1978, 50:1906.
16. Messerschmidt R.G., Harthcock M.A. Infrared microscopy theory and Applications, United States 1988, Mercel Dekker, New York, NY.
17. Rao C.N.R. Chemical application of Infrared spectroscopy 1963, Acedemic press, New York.
18. Dijkstra R.J., Ariese F., Gooijer C., Brinkman U.A. Raman spectroscopy as a detection method for liquid-separation techniques. Trends Anal. Chem. 2005, 24:304.
19. Pelton J.T., McLean L.R. Spectroscopic Methods for Analysis of Protein Secondary Structure. Anal. Biochem. 2000, 277:167.
20. Jiao G., Yu G., Zhang J., Ewart H.S. Chemical Structures and Bioactivities of Sulfated Polysaccharides from Marine Algae. Mar. Drugs 2011, 9:196.
21. Manzoo E., Ciavatta M.L., Gavagnin M., Mollo E., Guo Y.-W., Cimino G. Isocyanide terpene metabolites of Phyllidiella pustulosa, A Nudibranch from the south China Sea. J. Nat. Prod. 2004, 67:1701.
22. Briggs L., Colebrook L. Infrared spectra of flavonones and flavones. Carbonyl and hydroxyl stretching and CH out-of-plane bending absorption. Spectrochim. Acta 1962, 18:939.
23. Naumann D., Labischinski H., Giesbrecht P. The characterization of microorganisms by Fourier-transform infrared spectroscopy (FT-IR). Modern Techniques for Rapid Microbiological Analysis 1991, 43. VCH Publishers, New York. W.H. Nelson (Ed.).
24. Shahidi F., Arachchi J.K.V., Jeon Y.-J. Food applications of chitin and chitosans. Trends Food Sci. Technol. 1999, 10:37.
25. Martino A.D., Sittinger M., Risbud M.V. Chitosan: A versatile biopolymer for orthopaedic tissue-engineering. Biomaterials 2005, 26:5983.
26. Dutta P.K., Tripathi S., Mehrotra G.K., Dutta J. Perspectives for chitosan based antimicrobial films in food applications. Food Chem. 2009, 114:1173.
27. Rinaudo M. Chitin and chitosan: Properties and application. Prog. Polym. Sci. 2006, 31:603.
28. Kumar M.N.V.R. A review of chitin and chitosan applications. React. Funct. Polym. 2000, 46:1.
29. Kumar M.N.V.R., Muzarelli R.A., Muzarelli C., Sashiwa H., Domb A.J. Chitosan chemistry and pharmaceutical perspectives. Chem. Rev. 2004, 104:6017.
30. Minke R., Blackwell J. The structure of α-chitin. J. Mol. Biol. 1978, 120:167.
31. Jang M.K., Kong B.G., Jeong Y.I., Lee C.H., Nah J.W. Physicochemical characterization of α-chitin, β-chitin and γ-chitin separated from natural resources. J. Polym. Sci. Part A Polym. Chem. 2004, 42:3423.
32. C.-Filho S.P., Britto D.D., Curti E., Abreu F.R., Cardoso M.B., Battisti M.V., Sim P.C., Lavall R.L. Extraction, structures and properties of α- and β-chitin. Quim. Nova 2007, 30:644.
33. Clark G.L., Smith A.F. X-ray diffraction studies of chitin, chitosan and derivatives. J. Phys. Chem. 1937, 40:863.
34. Trombotto S., Ladavière C., Delolme F., Domard A. Chemical preparation and structural characterization of a homogenous series of chitin/chitosan oligomers. Biomacromolecules 2008, 9:1731.
35. Sajomsang W., Ruktanonchai U.R., Gonil P., Nuchuchua O. Mucoadhesive property and biocompatibility of methylated N-aryl chitosan derivatives. Carbohydr. Polym. 2009, 78:945.
36. Urreaga J.M., de la Orden M.U. Chemical interactions and yellowing in chitosan-treated cellulose. Eur. Polym. J. 2006, 42:2606.
37. Kumirska J., Czerwicka M., Kaczyński Z., Bychowska A., Brzozowski K., Thöming J., Stepnowski P. Application of Spectroscopic Methods for Structural Analysis of Chitin and Chitosan. Mar. Drugs 2010, 8:1567.
38. Pearson F.G., Marchessault R.H., Liang C.Y. Infrared spectra of crystalline polysaccharides V. Chitin. J. Polym. Sci. 1960, 13:101.
39. 13CNMR, FT-IR and FT-Raman spectroscopy. Carbohydr. Polym. 1992, 17:97.
40. Baskar D., Kumar T.S.S. Effect of deacetylation time on the preparation, properties and swelling behavior of chitosan films. Carbohydr. Polym. 2009, 78:767.
41. Rinaudo M. Chitin and chitosan: Properties and application. Prog. Polym. Sci. 2006, 31:603.
42. Kasaai M.R. Various Methods for Determination of the Degree of N-Acetylation of Chitin, Chitosan: A Review. J. Agric. Food Chem. 2009, 57:1667.
43. Sabnis S., Block L.H. Improved infrared spectroscopic method for the analysis of degree of N-deacetylation. Polym. Bull. 1997, 39:67.
44. Silva S.S., Menezes S.M.C., Garcia R.B. Synthesis and characterization of polyurethane-g-chitosan. Eur. Polym. J. 2003, 39:1515.
45. Becker C.F., Guimarães J.A., Mourão P.A.S., Verli H. Conformation of sulfated galactan and sulfated fucan in aqueous solutions: implications to their anticoagulant activities. J. Mol. Graph. Mod. 2007, 26:391.
46. F.-Tischer P.C.S., Talarico L.B., Noseda M.D., Guimarães S.M.P.B., Duarte M.E.R. Chemical structure and antiviral activity of carrageenans from Meristiella gelidium againstherpes simplex and dengue virus. Carbohydrate Polymers 2006, 63:459.
47. Souza M.C.R., Marques C.T., Dore C.M.G., Silva F.R.F., Rocha H.A.O., Leite E.L. Antioxidant activities of sulfated polysaccharides from brown and red seaweeds. J. Appl. Phycol. 2007, 19:153.
48. Koyanagi S., Tanigawa N., Nakagawa H., Soeda S., Shimeno H. Over sulfation of fucoidan enhances its anti-angiogenic and antitumor activities. Biochem. Pharmacol. 2003, 65:173.
49. Costa L.S., Fidelis G.P., Cordeiro S.L., Oliveira R.M., Sabry D.A., Camara B.G., Nobre L.T.D.B., Costa M.S.S.P., A.-Lima J., Farias E.H.C., Leite E.L., Rocha H.A.O. Biomed. Pharmacother. 2010, 64:21.
50. Souza B.W.S., Cerqueira M.A., Bourbon A.I., Pinheiro A.C., Martins J.T., Teixeira J.A., Manuel A., Coimbra B., António A. Vicente Chemical characterization and antioxidant activity of sulfated polysaccharide from the red seaweed Gracilaria birdiae. Food Hydrocolloid 2007, 27:287.
51. Chopin T., Kerin B.F., Mazerolle R. Phycocolloid chemistry as a taxonomic indicator of phylogeny in the Gigartinales, Rhodophyceae: a review and current developments using Fourier transform infrared diffuse reflectance spectroscopy. Phycol. Res. 1999, 47:167.
52. L. Pereira, S. F. Gheda, P. J. A. R.-Claro, Analysis by vibrational spectroscopy of seaweed polysaccharides with potential use in food, pharmaceutical, and cosmetic industries, Int. J. Carbohy Chem. doi:10.1155/2013/537202.
53. Aneiros A., Garateix A. Bioactive peptides from marine sources: pharmacological and isolation procedures. J. Chromatgr. B 2004, 803:41.
54. Ibrahim S.R.M., E.-Ebel R.A., Mohamed G.A., Youssef D.T.A., Wray V., Proksch P., Callyaerin G. A new cytotoxic cyclic peptide from the marine sponge Callyspongia aerizusa. ARKIVOC 2008, 164.
55. Barth A. The infrared absorption of amino acid side chains. Prog. Biophys Mol. Bio. 2000, 74:141.
56. Kasai T., Furukawa K., Sakamura S. Infrared and mass spectra of α- amino acid amides. J. Fac. Agr. Hokkaido Univ. 1979, 59:279.
57. Linder R., Nispel M., Haber T., Kleinermanns K. Gas-phase FT-IR spectra of natural amino acids. Chem. Phys. Lett. 2005, 409:260.
58. L.-Vien D., Colthup N.B., Fateley W.G., Grasselli J.G. The Handbook of Infrared and Raman Characteristic Frequencies of Organic Molecules 1991, Academic Press Inc., San Diego.
59. Ellepola S.W., Choi S.-M., Phillips D.L., Ma C.-Y. Raman spectroscopic study of rice globulin. J. Cereal Sci. 2006, 43:85.
60. L.-Chan E.C.Y., Nakai S., Hirotsuka M. Protein Structure-Function Relationships in Foods 1994, Blackie Academic, London. R.Y. Yada, R.L. Jackson, L.L. Smith (Eds.).
61. Friedberg F., O'Dell M.S. Infrared spectra of some DNP-α-amino acids. Can. J. Chem. 1959, 37:1469.
62. Koegel R.J., Greenstein G.P., Winitz M., Birnbaum S.M., McCallum R.A. Studies on Diastereoisomeric α-Amino Acids and Corresponding α-Hydroxy Acids. V. Infrared Spectra. J. Am. Chem. Soc. 1955, 77:5708.
63. Moore W.H., Krimm S. Vibrational analysis of peptides, polypeptides and proteins, β-poly(L-alanine) and β-Poly(L-alanylglycine). Biopolymers 1976, 15:2465.
64. Elliott A., Ambrose E.J. Structure of synthetic polypeptides. Nature 1950, 165:921.
65. Krimm S., Bandekar J. Vibrational spectroscopy and conformation of peptides, polypeptides, and proteins. Adv. Protein Chem. 1986, 38:181.
66. Colthup N.B., Daly L.H., Wiberley S.E. Introduction to Infrared and Raman Spectroscopy 1975, Academic Press, New York. 2nd Edition.
67. Kong J., Yu S. Fourier transform infrared spectroscopic analysis of protein secondary structures. Acta Biochimica et Biophysica Sinica 2007, 39:549.
68. Pelton J.T., McLean L.R. Spectroscopic Methods for Analysis of Protein Secondary Structure. Ana. Biochem. 2000, 277:167.
69. Tamm L.K., Tatulian S.A. Infrared Spectroscopy of Proteins and Peptides in Lipid Bilayers. Q. Rev. Biophys. 1997, 30:365.
70. Jackson M., Mantsch H.H. The use and misuse of FTIR Spectroscopy in the Determination of Protein Structure. Crit. Rev. Biochem. Mol 1995, 30:95.
71. Maiti N.C., Apetri M.M., Zagorski M.G., Carey P.R., Anderson V.E. Raman Spectroscopic Characterization of Secondary Structure in Natively Unfolded Proteins: α-Synuclein. J. Am. Chem. Soc. 2004, 126:2399.
72. Miura T., Suzuki K., Kohata N., Takeuchi H. Metal binding modes of Alzheimer's amyloid beta-peptide in insoluble aggregates and soluble complexes, Biochemistry Metal binding modes of Alzheimer's amyloid beta-peptide in insoluble aggregates and soluble complexes. Biochemistry 2000, 39:7024.
73. Chen M.C., Lord R.C. Laser-excited Raman spectroscopy of biomolecules. VI. Polypeptides as conformational models. J. Am. Chem. Soc. 1974, 96:4750.
74. Sane S.U., Cramer S.M., Przybycien T.M. Holistic approach to protein secondary structure characterization using amide I band Raman spectroscopy. Anal. Biochem. 1999, 269:255.
75. Honzatko R.B., Williams R.W. Raman spectroscopy of avidin: secondary structure, disulfide conformation, and the environment of tyrosine. Biochemistry 1982, 21:6201.
76. Lambert J.B., Keske R.G., Charat R.E., Jovanovich A.P. The conformational rivalry between the nonbonding electron pair and the proton on nitrogen. J. Am. Chem. Soc. 1967, 89:3761.
77. Braekman J.C., Daloze P., Abreu P.M.D., Leopardi C.P., Germain G., Meerssche M.V. A Novel type of Bis-quinolizidine alkaloids from the sponge Petrosia Seriata. Tetrahedron Lett. 1982, 23:4277.
78. Singh K.S., Das B., Naik C.G. Quinolizidines alkaloids: Petrosin and xestospongins from the sponge Oceanapia sp. J. Chem. Sci. 2011, 123:601.
79. Venkateswaralu Y., Reddy V.R. Bis-1-Oxaquinolizidines from the sponge Haliclona Exigua. J. Nat. Prod. 1984, 57:1283.
80. Goud T.V., Ready N.R., Ram T.S., Venkateswarlu Y. Anti-HIV Active Petrosins from the Marine Sponge Petrosia similis. Biol. Pharm. Bull. 2003, 26:1498.
81. K. Y. Orabi, K. A. El Sayed, M. T. Hamann, D. C. Dunbar, Mansour S. A.- Said, T. Higa, M. Kelly, Araguspongines K and L, New Bioactive Bis-1-oxaquinolizidine N-Oxide Alkaloids from Red Sea Specimens of Xestospongia exigua, J. Nat. prod. 65 (2002) 1782.
82. Kobayashi M., Kawazoe K., Kitagawa I. Aragupetrosine A. New vasodilative macrocyclic quinolizidine alkaloid from Okinawan marine sponge Xestospongia sp. Tetrahedron Lett. 1989, 30:4149.
83. Bohlmann F. Zur konfigurationsbestimmung von chinolizin Derivaten. Angew Chem. 1957, 69:641.
84. Tourwe D., Vanbinst G. Carbon-13 Nuclear Magnectic Resonance Spectroscopy of Quinolizidine Derivatives. Heterocycle 1978, 2:507.
85. Parameswaran P.S., Naik C.G., Kamat S.Y. Renieramycins H and I, two novel alkaloids from the sponge Haliclona Cribricutis Dendy. Ind. J. Chem. 1998, 37B:1258.
86. Gross H., König G.M. Terpenoids from marine organisms: unique structures and their pharmacological potential. Phytochem. Rev. 2005, 5:115.
87. Sung P.-J., Chiang M.Y., Tsai W.-T., Su J.-H., Su Y.-M., Wu Y.-C. Chlorinated briarane-type diterpenoids from the gorgonian coral Ellisella robusta (Ellisellidae). Tetrahedron 2007, 63:12860.
88. Iwashima M., Matsumoto Y., Takenaka Y., Iguchi K., Yamori T. New Marine Diterpenoids from the Okinawan Soft Coral Clavularia koellikeri. J. Nat. Prod. 2002, 65:1441.
89. Singh K.S., Kaminsky W., Rodrigues C., Naik C.G. Structural studies and antimicrobial properties of norcembrane diterpenoid from an Indian soft coral Sinularia inelegans Tixier-Durivault. J. Chem. Sci. 2009, 121:1041.
90. Briton G., Armit G.M., Lau S.Y.M., Patel A.K., Shone C.C. Carotenoproteins. Carotenoids Chemistry and Biochemistry 1981, 32:237.
91. Nomura T., Kikuchi M., Kubodera A., Kawakami Y. Proton-donative antioxidant activity of fucoxanthin with 1,1-diphenyl-2-picrylhydrazyl (DPPH). Biochem. Mol. Bio. Intl. 1997, 42:361.
92. Wang H., Fu Z.-M., Han C.-C. The Potential Applications of Marine Bioactives against Diabetes and Obesity. Am. J. Mar. Sci. 2014, 2:1.
93. Peng J., Yuan J.-P., Wu C.-F., Wang J.-H. Fucoxanthin, a Marine Carotenoid Present in Brown Seaweeds and Diatoms: Metabolism and Bioactivities Relevant to Human Health. Mar. Drugs 2011, 9:1806.
94. Khanafari A., Saberi A., Azar M., Vosooghi Gh., Jamili Sh., Sabbaghzadeh B. Extraction of Astaxanthin esters from shrimp waste by chemical and microbial methods. J. Environ health Sc. Eng. 2007, 4:93.
95. G. Rajauria, N. A.-Ghannam, Isolation and partial characterization of bioactive fucoxanthin from Himanthalia elongata brown sea weed: A TLC-based approach, Int. J. Anal. Chem. doi:10.1155/2013/802573.
96. de Oliveira V.E., Castro H.V., Edwards H.G.M., de Oliveira L.F.C. Carotenes and carotenoids in natural biological samples: a Raman spectroscopic analysis. J. Raman Spectrosc. 2010, 6:642.
97. Withnall R., Chowdhry B.Z., Silver J., Edwards H.G.M., de Oliveira L.F.C. Raman spectra of carotenoids in natural products, Spectrochim. Acta A 2003, 10:2207.
98. Schulz H., Baranska M., Baranski R. potential of NIR-FT-Raman spectroscopies in natural carotenoids analysis. Biopolymers 2005, 77:212.
99. Heneczkowski M., Kopacz M., Nowak D., KuzD́nair A. Infrared spectrum analysis of some flavonoids. Drug Res. 2001, 58:415.
100. Kokilam G., Vasuki S., Sajitha N. Biochemical composition, alginic acid yield and antioxidant activity of brown seaweeds from Mandapam region, Gulf of Mannar. J App. Pharm Sci. 2013, 3:99.
101. Briggs L., Colebrook L. Infrared spectra of flavanones and flavones. Carbonyl and hydroxyl stretching and CH out-of-plane bending absorption, Spectrochim. Acta 1962, 18:939.
102. Cornard J.-P., Barbillat J., Merlin J.-C. Performance of a versatile multichannel microprobe in Raman, fluorescence, and absorption measurements. Microbeam Anal. 1994, 3:13.
103. Merlin J.-C., Statoua A., Cornard J.-P., - Idrissi M.S., Brouillard R. Resonance Raman spectroscopic studies of anthocyanins and anthocanidins in aqueous solution. Phytochemistry 1994, 35:227.
104. Merlin J.-C., Cornard J.P. Vibrational analysis of hydroxyflavylium derivatives by IR, Fourier transform Raman and resonace Raman and resonance Raman spectroscopies, Spectrochim. Acta A 1994, 50:703.
105. F. Siebert, P. Hildebrandt, Vibrational Spectroscopy in Life Science (1st edition), Wiley VCH, ISBN 978-3527405060, ISA (2007).
106. Sheu J.H., Wang G.H., Sung P.J., Chiu Y.H., Duh C.Y. Cytotoxic Sterols from the Formosan Brown Alga Turbinariaornata. Planta Med. 1997, 63:571.
107. Wachter G.A., Franzblau S.G., Montenegro G., Hoffmann J.J., Maiese W.M., Timmermann B.N. Inhibition of Mycobacterium Tuberculosis Growth by Saringosterol from Lessonianigrescens. J. Nat. Prod. 2001, 64:1463.
108. Boul A.D., Blunt J.W., Browne J.W., Kumar V., Meakins G.D., Pinhey J.T., Thomas V.E. Microbiological Hydroxylation of Steroids. Part II. Structural information and infrared spectrometry: carbonyl, preturbed methylene and hydroxyl vibrations of Steroidal Ketones and Alcohols. J. Chem. Soc. C 1971, 1130.
109. Holly S., Jalsovszky G., Egyed O. Infrared Intensities of Pregn-4-ene-3,20-dione Derivatives. J. Mol. Struct. 1980, 60:139.
110. Jones R.N., Humphries P., Herling F., Dobriner K. Steroid Metabolism. XII. Determination of the structure of the side chains of C-21 steroids by Infrared Spectrometry. J. Am. Chem. Soc. 1952, 74:2820.
111. Cui E.-J., Park H.-J., Park H., Chung I.-S., Kim J.-Y., Yeon S.-W., Baek N. Isolation of Sterols from Cowpea (Vignasinensis) Seeds and Their Promotion Activity on HO-1. J. Korean Soc. Appl. Biol. Chem. 2011, 54:362.
112. Aruldhas G., Jalsovszky G., Holly S. Infrared Absorption Intensities of Steroids. Acta Chim. Acad. Sei. Hung. 1980, 104:117.
113. K.- Suhadolc T. IR-spectra of Amides of Steroidal Alkaloids with Lactic acid. Experientia 1983, 39:259.
114. Smith A.M., Eddy C.R. High Resolution Infrared Spectra of Steroids in the Carbon-hydrogen Stretching Region. Anal. Chem. 1959, 31:1539.
115. D'Auria M.V., Minale L., Ricco R. Polyoxygenated Steroids of Marine Origin. Chem. Rev. 1993, 93:1839.
116. Khanavi M., Gheidarloo R., Sadati N., Ardekani M.S., Nabavi S.M., Tavajohi S., Ostad S.N. Cytotoxicity of Fucosterol Containing Fraction of Marine Algae against Breast and Colon Carcinoma Cell Line. Phcog. Mag. 2012, 8:60.
117. Lee S., Lee Y.S., Jung S.H., Kang S.S., Shin K.H. Anti-oxidant Activities of Fucosterol from the Marine Algae Pelvetiasiliqusa. Arch. Pharm. Res. 2003, 26:719.
118. Khanavi M., Nabavi M., Sadati N., Ardekani M.S., Sohrabipour J., Nabavi S.M. Cytotoxic Activity of Some Marine Brown Algae Against Cancer Cell Lines. Biol. Res. 2010, 43:31.
119. Bouzidi N., Daghbouche Y., Hattab M., Aliche Z., Culioli G., Piovetti L., Garrigues S., Guardia M. Determination of Total Sterols in Brown Algae by Fourier Transform Infrared Spectroscopy. Anal. Chim. Acta 2008, 616:185.
120. Schrader B., Steigner E. "Modern methods of steroid analysis" 1973, Academic Press, New York, Chapter 9, 231. E. Heftmann (Ed.).
121. Hider R.C., Kong X. Chemistry and Biology of Siderophores. Nat. Prod. Rep. 2010, 27:637.
122. Csaky T. On Estimation of Bound Hydroxylamine in Biological Materials. Acta Chem. Scandca. 1948, 2:450.
123. Arnow E.L. Colorimetric Determination of the Component of 3,4-Dihydroxyphenylalanine-tyrosine Mixtures. J. Biol. Chem 1937, 118:531.
124. Supanekar S.V., Sorty A.M., Raut A.A. Catecholate siderophores produced by Klebsiellapneumoniae isolated from Rhizosphere of Saccharumofficinarum L. Int. J. Sci. Res. 2013, 2:423.
125. Actis A.L., Fish W., Crosa J.H., Kellerman K., Ellenberger S.R., Hauser F.M., Loehr J.S. Characterization of anguibactin, a novel siderophore from Vibrio anguillarum 775 (pJM1). J. Bact. 1986, 167:57.
126. Tank N., Rajendran N., Patel B., Saraf M. Evaluation and Biochemical Characterization of a Distinctive Pyoverdin from a Pseudomonas isolated from Chickpea Rhizosphere. Braz. J. Microbiol. 2012, 639.
127. Sajjan S. Purification and physiochemical characterization of melanin pigment from Klebsiella sp. GSK,. J. Microbiol. Biotechnol. 2010, 20:1513.
128. Nicolaus R.A., Piattelli M. Progress in the chemistry of natural black pigments. Rend. Acad. Sc. Fis. Mat. 1965, 32:83.
129. Geng J., Yuan P., Shao C., Yu S.B., Zhou B., Zhou P. X. D. Chen Bacterial melanin interacts with double stranded DNA with high affinity and may inhibit cell metabolism in vivo. Arch. Microbiol. 2010, 321:192.
130. Blois M.S. The melanins: their synthesis and structure. Photochem. Photobiol. Rev. 1978, 3:115.
131. Jones D. Ultrastructure and composition of the cell-walls of Sclerotinia sclerotiorum. Trans. Br. Mycol. Soc. 1970, 54:351.
132. Russell J.D., Jones D., Vaughan D., Fraser A.R. A prelimimary study of fungal melanin by infrared spectroscopy. Geoderma 1980, 24:207.
133. Tarangini K., Mishra S. Production, Characterization and Analysis of Melanin from Isolated Marine Pseudomonas sp. using vegetable waste. Res. J. Engineering Sci. 2013, 2:40.