Lyngbyastatins 8-10, elastase inhibitors with cyclic depsipeptide scaffolds isolated from the marine cyanobacterium Lyngbya semiplena

Marine Drugs

Volumn 7, Issue 4, 2009, Pages 528-538

  Kwan, Jason C ^a   Taori, Kanchan ^a   Paul, Valerie J ^b   Luesch, Hendrik ^a  

^a UNIVERSITY OF FLORIDA   (United States)

^b SMITHSONIAN MARINE STATION   (United States)

Author keywords

Cyanobacteria; Cyclic depsipeptides; Elastase inhibitors; Lyngbya semiplena; Lyngbyastatins

Indexed keywords

CYCLODEPSIPEPTIDE; ELASTASE INHIBITOR; LYNGBYASTATIN 10; LYNGBYASTATIN 8; LYNGBYASTATIN 9; PANCREATIC ELASTASE; SCAFFOLD PROTEIN; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; CONTROLLED STUDY; CYANOBACTERIUM; DRUG DEGRADATION; DRUG IDENTIFICATION; DRUG INHIBITION; DRUG ISOLATION; DRUG STRUCTURE; ENZYME INHIBITION; FRAGMENTATION REACTION; GUAM; IC 50; LYNGBYA SEMIPLENA; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE;

CYANOBACTERIA; LYNGBYA SEMIPLENA; SUS;

EID: 75149193409     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md7040528     Document Type: Article

References (26)

1. Tan, L.T. Bioactive natural products from marine cyanobacteria for drug discovery. Phytochemistry 2007, 68, 954-979.
2. Kwan, J.C.; Rocca, J.R.; Abboud, K.A.; Paul, V.J.; Luesch, H. Total structure determination of grassypeptolide, a new marine cytotoxin. Org. Lett. 2008, 10, 789-792.
3. Luesch, H.; Yoshida, W.Y.; Moore, R.E.; Paul, V.J.; Corbett, T.H. Total structure determination of apratoxin A, a potent novel cytotoxin from the marine cyanobacterium Lyngbya majuscula. J. Am. Chem. Soc. 2001, 123, 5418-5423.
4. Taori, K.; Paul, V.J.; Luesch, H. Structure and activity of largazole, a potent antiproliferative agent from the Floridian marine cyanobacterium Symploca sp. J. Am. Chem. Soc. 2008, 130, 1806-1807.
5. Kwan, J.C.; Eksioglu, E.A.; Liu, C.; Paul, V.J.; Luesch, H. Grassystatins A-C from marine cyanobacteria, potent cathepsin E inhibitors that reduce antigen presentation. J. Med. Chem. 2009, 52, 5732-5747.
6. Matthew, S.; Ross, C.; Rocca, J.R.; Paul, V.J.; Luesch, H. Lyngbyastatin 4, a dolastatin 13 analogue with elastase and chymotrypsin inhibitory activity from the marine cyanobacterium Lyngbya confervoides. J. Nat. Prod. 2007, 70, 124-127.
7. Taori, K.; Matthew, S.; Rocca, J.R.; Paul, V.J.; Luesch, H. Lyngbyastatins 5-7, potent elastase inhibitors from Floridian marine cyanobacteria, Lyngbya spp. J. Nat. Prod. 2007, 70, 1593-1600.
8. Yamaki, H.; Sitachitta, N.; Sano, T.; Kaya, K. Two new chymotrypsin inhibitors isolated from the cyanobacterium Microcystis aeruginosa NIES-88. J. Nat. Prod. 2005, 68, 14-18.
9. Ploutno, A.; Shoshan, M.; Carmeli, S. Three novel protease inhibitors from a natural bloom of the cyanobacterium Microcystis aeruginosa. J. Nat. Prod. 2002, 65, 973-978.
10. Itou, Y.; Ishida, K.; Shin, H. J.; Murakami, M. Oscillapeptins A to F, serine protease inhibitors from the three strains of Oscillatoria agardhii. Tetrahedron 1999, 55, 6871-6882.
11. Nakanishi, I.; Kinoshita, T.; Sato, A.; Tada, T. Structure of porcine pancreatic elastase complexed with FR901277, a novel macrocyclic inhibitor of elastases, at 1.6 Å resolution. Biopolymers 2000, 53, 434-445.
12. Matern, U.; Schleberger, C.; Jelakovic, S.; Weckesser, J.; Schulz, G.E. Binding structure of elastase inhibitor scyptolin A. Chem. Biol. 2003, 10, 997-1001.
13. Lee, A.Y.; Smitka, T.A.; Bonjouklian, R.; Clardy, J. Atomic structure of the trypsin-A90720A complex: a unified approach to structure and function. Chem. Biol. 1994, 1, 113-117.
14. Taori, K.; Paul, V.J.; Luesch, H. Kempopeptins A and B, serine protease inhibitors with different selectivity profiles from a marine cyanobacterium, Lyngbya sp. J. Nat. Prod. 2008, 71, 1625-1629.
15. Tremblay, G.M.; Janelle, M.F.; Bourbonnais, Y. Anti-inflammatory activity of neutrophil elastase inhibitors. Curr. Opin. Investig. Drugs 2003, 4, 556-565.
16. von Elert, E.; Oberer, L.; Merkel, P.; Huhn, T.; Blom, J.F. Cyanopeptolin 954, a chlorinecontaining cymotrypsin inhibitor of Microcystis aeruginosa NIVA Cya 43. J. Nat. Prod. 2005, 68, 1324-1327.
17. Mayumi, T.; Kato, H.; Kawasaki, Y.; Harada, K.-I. Formation of diagnostic product ions from cyanobacterial cyclic peptides by the two-bond fission mechanism using ion trap liquid chromatography/multi-stage mass spectrometry. Rapid Commun. Mass Spectom. 2007, 21, 1025-1033.
18. Claridge, T.D.W. High-Resolution NMR Techniques in Organic Chemistry; Elsevier: San Diego, CA, USA, 1999.
19. 13C NMR spectra of complex organic molecules. Curr. Org. Chem. 2001, 5, 253-263.
20. C,H n > 3) in HMBC spectra. Nat. Prod. Commun. 2008, 3, 445-450.
21. Marfey, P. Determination of D-amino acids. II. Use of a bifunctional reagent, 1,5-difluoro-2,4-dinitrobenzene. Carlsberg Res. Commun. 1984, 49, 591-596.
22. Brey, W.W.; Edison, A.S.; Nast, R.E.; Rocca, J.R.; Saha, S.; Withers, R.S. Design, construction, and validation of a 1-mm triple-resonance high-temperature-superconducting probe for NMR. J. Magn. Reson. 2006, 179, 290-293.
23. Matthew, S.; Ross, C.; Paul, V.J.; Luesch, H. Pompanopeptins A and B, new cyclic peptides from the marine cyanobacterium Lyngbya confervoides. Tetrahedron 2008, 64, 4081-4089.
24. Unable to obtain IR due to lack of sample.
25. The retention time of N-Me-D-Tyr-L-FDLA was deduced from that of its enantiomer, N-Me-L-Tyr-D-FDLA.
26. The retention time of N-Me-3′-Br-D-Tyr-L- FDLA was deduced from that of its enantiomer N-Me-3′-Br-L- Tyr-D-FDLA.