Antiviral sulfoquinovosyldiacylglycerols (SQDGs) from the Brazilian brown seaweed Sargassum vulgare

Marine Drugs

Volumn 11, Issue 11, 2013, Pages 4628-4640

  Plouguerné, Erwan ^a   De Souza, Lauro M ^b   Sassaki, Guilherme L ^b   Cavalcanti, Jéssica Figueiredo ^c   Romanos, Maria Teresa Villela ^c   Da Gama, Bernardo A P ^a   Pereira, Renato Crespo ^a   Barreto Bergter, Eliana ^c  

^a FLUMINENSE FEDERAL UNIVERSITY   (Brazil)

^b FEDERAL UNIVERSITY OF PARANÁ   (Brazil)

^c FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

Author keywords

Anti HSV activity; Glycolipids; Palmitic acid; Sargassum vulgare; Sulfoquinovosyldiacylglycerol

Indexed keywords

1 O MARGAROYL 2 O PALMITOYL 3 O (6 SULFOQUINOVOPYRANOSYL)GLYCEROL; 1 O MYRISTOYL 2 O PALMITOYL 3 O (6 SULFOQUINOVOPYRANOSYL)GLYCEROL; 1 O NONADECANOYL 2 O PALMITOYL 3 O (6 SULFOQUINOVOPYRANOSYL)GLYCEROL; 1 O OLEOYL 2 O PALMITOYL 3 O (6 SULFOQUINOVOPYRANOSYL)GLYCEROL; 1 O TRICOSANOYL 2 O MARGAROYL 3 O (6 SULFOQUINOVOPYRANOSYL)GLYCEROL; 1,2 DI O PALMITOYL 3 O (6 SULFOQUINOVOPYRANOSYL)GLYCEROL; ACICLOVIR; ANTIINFECTIVE AGENT; ANTIVIRUS AGENT; SULFOQUINOVOSYLDIGLYCERIDE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIVIRAL ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; COLUMN CHROMATOGRAPHY; CONTROLLED STUDY; DRUG EFFECT; DRUG SCREENING; DRUG STRUCTURE; ELECTROSPRAY MASS SPECTROMETRY; HERPES SIMPLEX VIRUS; LIPID ANALYSIS; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; SARGASSUM; SARGASSUM VULGARE; TANDEM MASS SPECTROMETRY; THIN LAYER CHROMATOGRAPHY; VIRUS IDENTIFICATION;

HERPES; HUMAN HERPESVIRUS 1; SARGASSUM VULGARE; SIMPLEXVIRUS;

ANIMALS; ANTIVIRAL AGENTS; BRAZIL; CELL LINE; CERCOPITHECUS AETHIOPS; GLYCOLIPIDS; HERPESVIRUS 1, HUMAN; HERPESVIRUS 2, HUMAN; LIPIDS; SARGASSUM; SEAWEED; VERO CELLS;

EID: 84889246110     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md11114628     Document Type: Article

References (46)

1. Vo, T.; Ngo, D.; Ta, Q. V.; Kim, S. Marine organisms as a therapeutic source against herpes simplex virus infection. Eur. J. Pharm. Sci. 2011, 44, 11-20.
2. Brady, R.C.; Bernstein, D.I. Treatment of herpes simplex virus infections. Antiviral. Res. 2004, 61, 73-81.
3. Celum, C.L. The interaction between herpes simplex virus and human immunodeficiency virus. Herpes 2004, 11, 36A-45A.
4. Bacon, T.H.; Levin, M.J.; Leary, J.J.; Sarisky, R.T.; Sutton, D. Herpes simplex virus resistance to acyclovir and penciclovir after two decades of antiviral therapy. Clin. Microbiol. Rev. 2003, 16, 114-128.
5. Morfin, F.; Thouvenot, D. Herpes simplex virus resistance to antiviral drugs. J. Clin. Virol. 2003, 26, 29-37.
6. Maschek, J.A.; Baker, B.J. The chemistry of algal secondary metabolism. In Algal Chemical Ecology; Amsler, C.D., Ed.; Springer-Verlag: Berlin, Germany, 2008; pp. 1-24.
7. Chakraborty, S.; Ghosh, U. Oceans: A store house of drugs - a review. J. Pharm. Res. 2010, 3, 1293-1296.
8. Blunt, J.W.; Copp, B.R.; Keyzers, R.A.; Munro, M.H.G.; Prinsep, M.R. Marine natural products. Nat. Prod. Rep. 2012, 29, 144-222.
9. Kim, S.K.; Karadeniz, F. Anti-HIV activity of extracts and compounds from marine algae. Adv. Food. Nutr. Res. 2011, 64, 255-265.
10. Saha, S.; Navid, M.H.; Bandyopadhyay, S.S.; Schnitzler, P.; Ray, B. Sulfated polysaccharides from Laminaria angustata: Structural features and in vitro antiviral activities. Carbohydr. Polym. 2012, 87, 123-130.
11. Bandyopadhyay, S.S.; Navid, M.H.; Ghosh, T.; Schnitzler, P.; Ray, B. Structural features and in vitro antiviral activities of sulfated polysaccharides from Sphacelaria indica. Phytochemistry 2011, 72, 276-283.
12. Cardozo, F.T.; Camelini, C.M.; Mascarello, A.; Rossi, M.J.; Nunes, R.J.; Barardi, C.R.; de Mendonça, M.M.; Simões, C.M. Antiherpetic activity of a sulfated polysaccharide from Agaricus brasiliensis mycelia. Antivir. Res. 2011, 92, 108-114.
13. Adhikari, U.; Mateu, C.G.; Chattopadhyay, K.; Pujol, C.A.; Damonte, E.B.; Ray, B. Structure and antiviral activity of sulfated fucans from Stoechospermum marginatum. Phytochemistry 2006, 67, 2474-2482.
14. de Souza, L.M.; Sassaki, G.L.; Romanos, M.T.; Barreto-Bergter, E. Structural characterization and anti-HSV-1 and HSV-2 activity of glycolipids from the marine algae Osmundaria obtusiloba isolated from Southeastern Brazilian coast. Mar. Drugs 2012, 10, 918-931.
15. Kind, T.; Meissen, J.K.; Yang, D.W.; Nocito, F.; Vaniya, A.; Cheng, Y.S.; VanderGheynst, J.S.; Fiehn, O. Qualitative analysis of algal secretions with multiple mass spectrometric platforms. J. Chromagraph. A 2012, 1244, 139-147.
16. Packter, N.M. Lipids in plants and microbes: By J L Harwood and N J Russel. pp 162. George Allen & Unwin, London. 1984. Biochem. Educ. 1985, 13, 94-94.
17. Morimoto, T.; Murakami, N.; Nagatsu, A.; Sakakibara, J. Studies on glycolipids VII. Isolation of two new sulfoquinovosyl diacylglycerols from green alga Chlorella vulgaris. Chem. Pharm. Bull. 1993, 41, 1545-1548.
18. Gustafson, K.R.; Cardellina, J.H.; Fuller, R.W.; Weislow, O.S.; Kiser, R.F.; Snader, K.M.; Patterson, G.M.L.; Boyd, M.R. AIDS-antiviral sulfolipids from cyanobacteria (Blue-Green Algae). J. Natl. Cancer Inst. 1989, 81, 1254-1258.
19. Kikuchi, H.; Tsukitani, Y.; Manda, T.; Fujii, T.; Nakanishi, H.; Kobayashi, M.; Kitagawa, I. Marine Natural Products. X. Pharmacologically active glycolipids from the Okinawan marine sponge Phyllospongia foliascens (PALLAS). Chem. Pharm. Bull. 1982, 30, 3544-3547.
20. Chirasuwan, N.; Chaiklahan, R.; Kittakoop, P.; Chanasattru, W.; Ruengjitchatchawalya, M.; Tanticharoen, M.; Bunnag, B. Anti HSV-1 activity of sulphoquinovosyl diacylglycerol isolated from Spirulina platensis . Scienceasia 2009, 35, 137-141.
21. Wang, H.; Li, Y.L.; Shen, W.Z.; Rui, W.; Ma, X.J.; Cen, Y.Z. Antiviral activity of a sulfoquinovosyldiacylglycerol (SQDG) compound isolated from the green alga Caulerpla racemosa. Bot. Mar. 2007, 50, 185-190.
22. Khotimchenko, S.V. Distribution of glyceroglycolipids in marine algae and grasses. Chem. Nat. Compd. 2002, 38, 223-229.
23. Barreto-Bergter, E.; Sassaki, G.L.; Souza, L.M. Structural analysis of fungal cerebrosides. Front. Microbiol. 2011, 2, 1-11.
24. Folch, J.; Lees, M.; Sloane-Stanley, G.H. A simple method for the isolation and purification of total lipids from animal tissues. J. Biol. Chem. 1957, 226, 497-509.
25. Zianni, R.; Bianco, G.; Lelario, F.; Losito, I.; Palmisano, F.; Cataldi, T.R.I. Fatty acid neutral losses observed in tandem mass spectrometry with collision-induced dissociation allows regiochemical assignment of sulfoquinovosyl-diacylglycerols. J. Mass Spectrom. 2013, 48, 205-215.
26. Sassaki, G.L.; Gorin, P.A.J.; Tischer, C.A.; Iacomini, M. Sulfonoglycolipids from the lichenized basidiomycete Dictyonema glabratum: Isolation, NMR, and ESI-MS approaches. Glycobiology 2001, 11, 345-351.
27. Souza, L.M.; Iacomini, M.; Gorin, P.A.J.; Sari, R.S.; Haddad, M.A.; Sassaki, G.L. Glyco- and sphingophosphonolipids from the medusa Phyllorhiza punctata: NMR and ESI-MS/MS fingerprints. Chem. Phys. Lipids 2007, 145, 85-96.
28. Tsai, C.J.; Pan, B.S. Identification of sulfoglycolipid bioactivities and characteristic fatty acids of marine macroalgae. J. Agric. Food Chem. 2012, 60, 8404-8410.
29. Al-Fadhli, A.; Wahidulla, S.; D'Souza, L. Glycolipids from the red alga Chondria armata (Kutz.) Okamura. Glycobiology 2006, 16, 902-915.
30. Fusetani, N.; Hashimoto, Y. Structures of two water-soluble hemolysins isolated from green alga Ulva pertus . Agric. Biol. Chem. 1975, 39, 2021-2025.
31. Araki, S.; Sakurai, T.; Oohusa, T.; Kayama, M.; Sato, N. Characterization of sulphonoquinovosyl diacylglycerol from marine red alga. Plant Cell Physiol. 1989, 30, 775-781.
32. Son, W.B. Glycolipids from Gracilaria verrucosa. Phytochemistry 1990, 29, 307-309.
33. Siddantha, A.K.; Ramvat, B.K.; Chauvan, V.D.; Achari, B.; Dutta, P.K.; Pakrashi, S.C. Sulphoglycolipid from the green alga Enteromorpha flexuosa (Wulf). J. Agric. Bot. Mar. 1991, 34, 365-367.
34. Logvinov, S.V.; Denisenko, V.A.; Dmitrenok, P.S.; Moiseenko, O.P. Sulfoquinovosyldiacylglycerins from Scaphechinus mirabilis. Chem. Nat. Compd. 2012, 48, 175-179.
35. Harada, H.; Yamashita, U.; Kurihara, H.; Fukushi, E.; Kawabata, J.; Kamei, Y. Antitumor activity of palmitic acid found as a selective cytotoxic substance in a marine red alga. Anticancer Res. 2002, 22, 2587-2590.
36. Kabara, J.J.; Swieczkowski, D.M.; Truant, J.P.; Conley, A.J.; Truant, J.P. Fatty-acids and derivatives as antimicrobial agents. Antimicrob. Agents Chemother. 1972, 2, 23-28.
37. Santoyo, S.; Jaime, L.; Plaza, M.; Herrero, M.; Rodriguez-Meizoso, I.; Ibañez, E.; Reglero, G. Antiviral compounds obtained from microalgae commonly used as carotenoid sources. J. Appl. Phycol. 2012, 24, 731-741.
38. Lee, D.Y.; Lin, X.; Paskaleva, E.E.; Liu, Y.; Puttamadappa, S.S.; Thornber, C.; Drake, J.R.; Habulin, M.; Shekhtman, A.; Canki, M. Palmitic acid is a novel CD4 fusion inhibitor that blocks HIV entry and infection. AIDS Res. Hum. Retrovir. 2009, 25, 1231-1241.
39. Spear, P.G. Herpes simplex virus: Receptors and ligands for cell entry. Cell Microbiol. 2004, 6, 401-410.
40. Wang, W.; Wang, S.X.; Guan, H.S. The antiviral activities and mechanisms of marine polysaccharides: An Overview. Mar. Drugs 2012, 10, 2795-2816.
41. Neyts, J.; Snoeck, R.; Schols, D.; Balzarini, J.; Esko, J.D.; Van Schepdael, A.; De Clercq, E. Sulfated polymers inhibit the interaction of human cytomegalovirus with cell surface heparan sulfate. Virology 1992, 189, 48-58.
42. Skipski, V.P. Thin layer chromatography of neutral glycolipids. Methods Enzymol. 1975, 35, 396-425.
43. Markoulatos, P.; Georgopoulou, A.; Siafakas, N.; Plakokefalos, E.; Tzanakaki, G.; Kourea-Kremastinou, J. Laboratory diagnosis of common herpesvirus infections of the central nervous system by a multiplex PCR assay. J. Clin. Microbiol. 2001, 39, 4426-4432.
44. Borenfreund, E.; Puerner, J.A. Toxicity determined in vitro by morphological alterations and neutral red absorption. Toxicol. Lett. 1985, 24, 119-124.
45. Reed, L.J.; Muench, H. A simple method of estimating 50 per cent end-points. Am. J. Hyg. 1938, 27, 493-497.
46. Nishimura, T.; Toku, K.; Fukuyasu, H. Antiviral compounds. XII. Antiviral activity aminohydrazones of alkoxyphenyl substituted carbonyl compounds against influenza virus in eggs and mice. Kitasato Arch. Exp. Med. 1977, 50, 39-46.