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Polybrominated diphenyl ethers from the marine organisms Lendenfeldia dendyi and Sinularia dura with anti-MRSa activity

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Abstract

Bioassay-guided fractionation of the marine sponge Lendenfeldia dendyi and the soft coral Sinularia dura resulted in the isolation of five polybrominated diphenyl ethers (1–5). The structures of the isolated compounds were determined using spectroscopic methods (1D and 2D NMR) and HRMS analyses. The absolute structures of compounds 1 and 2 were confirmed by X-ray analysis. Antimicrobial testing of the isolated compounds along with the acetylated derivative of compound 2 (2a) indicated that they displayed a significant and selective activity against methicillin-resistant Staphylococcus aureus (MRSa) with IC50 values of <0.04–1.18 µM. The antimalarial and antileishmanial activities of the isolated compounds were also evaluated.

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References

  • Aceret TL, Coll JC, Uchio Y, Sammarco PW (1998) Antimicrobial activity of the diterpenes flexibilide and sinulariolide derived from Sinularia flexibilis Quoy and Gaimard 1833 (Coelenterata: Alcyonacea, Octocorallia). Comp Biochem Physiol Part C Pharmacol Toxicol Endocrinol 120(1):121–126

    Article  CAS  Google Scholar 

  • Alvi K, Crew Ph (1992) Homoscalarane sesterterpenes from Lendenfeldia frondosa. J Nat Prod 55:859–865

    Article  CAS  PubMed  Google Scholar 

  • Chill L, Rudi A, Aknin M, Loya Sh, Hizi A, Kashman Y (2004) New sesterterpenes from Madagascan Lendenfeldia sponges. Tetrahedron 60:10619–10626

    Article  CAS  Google Scholar 

  • Franzblau SG, Witzig RS, McLaughlin JC, Torres P, Madico G, Hernandez A, Degnan MT, Cook MB, Quenzer VK, Ferguson RM, Gilman RH (1998) Rapid, low-technology MIC determination with clinical Mycobacterium tuberculosis isolates by using the microplate Alamar Blue assay. J Clin Microbiol 36:362–366

    CAS  PubMed Central  PubMed  Google Scholar 

  • Handayani D, Edrada RA, Proksch P, Wray V, Witte L, Van Soest RW, Soedarsono A (1997) Four new bioactive polybrominated diphenyl ethers of the sponge Dysidea herbacea from West Sumatra, Indonesia. J Nat Prod 60(12):1313–1316

    Article  CAS  PubMed  Google Scholar 

  • Hanif N, Tanaka J, Setiawan A, Trianto A, de Voogd NJ, Murni A, Tanaka C, Higa T (2007) Polybrominated diphenyl ethers from the Indonesian sponge Lamellodysidea Herbacea. J Nat Prod 70(3):432–435

    Article  CAS  PubMed  Google Scholar 

  • Kazlauskas R, Murphy P, Wells R (1982) Five new C26 tetracyclic terpenes from a sponge (Lendenfeldia sp.). Aust J Chem 35:51–59

    Article  CAS  Google Scholar 

  • Kurata K, Amiya T (1980) Bis (2,3,6-tribromo-4,5-dihydroxybenzyl) ether from the red alga, Symphyocladia latiuscula. Phytochemistry 19(1):141–142

    Article  CAS  Google Scholar 

  • Liu H, Namikoshi M, Meguro S, Nagai H, Kobayashi H, Yao X (2004) Isolation and characterization of polybrominated diphenyl ethers as inhibitors of microtubule assembly from the marine sponge Phyllospongia dendyi collected at Palau. J Nat Prod 67(3):472–474

    Article  CAS  PubMed  Google Scholar 

  • Ma GY, Khan SI, Jacob MR, Tekwani BL, Li ZQ, Pasco DS, Walker LA, Khan LA (2004) Antimicrobial and antileishmanial activities of hypocrellins A and B. Antimicrob Agents Chemother 48:4450–4452

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  • Makler MT, Hinrichs DJ (1993) Measurement of the lactate-dehydrogenase activity of Plasmodium falciparum as an assessment of parasitemia. Am J Trop Med Hyg 48:205–210

    CAS  PubMed  Google Scholar 

  • Mustafa J, Khan SI, Ma GY, Walker LA, Khan IA (2004) Synthesis and anticancer activities of fatty acid analogs of podophyllotoxin. Lipids 39:167–172

    Article  CAS  PubMed  Google Scholar 

  • Radhika P, Rao PR, Archana J, Rao NK (2005) Anti-inflammatory activity of a new sphingosine derivative and cembrenoid diterpene (lobohedleolide) isolated from marine soft corals of Sinularia crassa Tixier-Durivault and Lobophytum species of the Andaman and Nicobar Islands. Biol Pharm Bull 28(7):1311–1313

    Article  CAS  PubMed  Google Scholar 

  • Radwan MM, Manly SP, Ross SA (2007) Two new sulfated Sterols from the marine sponge Lendenfeldia dendyi. Nat Prod Commun 2(9):901–904

    CAS  Google Scholar 

  • Radwan MM, Manly SP, El-Sayed KA, Wali VB, Sylvester PW, Awate B, Shah G, Ross SA (2008) Sinulodurins A and B, antiproliferative and anti-invasive diterpenes from the soft coral Sinularia dura. J Nat Prod 71(8):1468–1471

    Article  CAS  PubMed  Google Scholar 

  • Rudi A, Shmul G, Benayahu Y, Kashman Y (2006) Sinularectin, a new diterpenoid from the soft coral Sinularia erecta. Tetrahedron Lett 47(17):2937–2939

    Article  CAS  Google Scholar 

  • Samoylenko V, Jacob MR, Khan SI, Zhao J, Tekwani BL, Midiwo JO, Walker LA, Muhammad I (2009) Antimicrobial, antiparasitic and cytotoxic spermine alkaloids from Albizia schimperiana. Nat Prod Commun 4:791–796

    CAS  PubMed Central  PubMed  Google Scholar 

  • Sera Y, Adachi K, Shizuri Y (1999) A new epidioxy sterol as an antifouling substance from a Palauan marine sponge, Lendenfeldia chondrodes. J Nat Prod 62:152–154

    Article  CAS  PubMed  Google Scholar 

  • Stessman C, Ebel R, Corvino A, Crew Ph (2002) Employing dereplication and gradient 1D NMR methods to rapidly characterize sponge-derived sesterterpenes. J Nat Prod 65:1183–1186

    Article  CAS  PubMed  Google Scholar 

  • Takaki H, Koganemaru R, Iwakawa Y, Higuchi R, Miyamoto T (2003) Inhibitory effect of Norditerpenes on LPS-Induced TNF-α production from the Okinawan soft coral, Sinularia sp. Biol Pharm Bull 26(3):380–382

    Article  CAS  PubMed  Google Scholar 

  • Tseng YJ, Ahmed AF, Dai CF, Chiang MY, Sheu JH (2005) Sinulochmodins A-C, three novel terpenoids from the soft coral Sinularia lochmodes. Org Lett 7(17):3813–3816

    Article  CAS  PubMed  Google Scholar 

  • Weber JT (2005) Community-associated methicillin-resistant Staphylococcus aureus. Clin Infect Dis 41(Supplement 4):S269–S272

    Article  CAS  PubMed  Google Scholar 

  • Weber JT, Courvalin P (2005) An emptying quiver: antimicrobial drugs and resistance. Emerg Infect Dis 11(6):791–793

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  • Yamada K, Ujiie T, Yoshida K, Miyamoto T, Higuchi R (1997) Sinulobatins A-D, new amphilectane-type diterpenoids from the Japanese soft coral Sinularia nanolobata. Tetrahedron 53(13):4569–4578

    Article  CAS  Google Scholar 

  • Zhang CX, Yan SJ, Zhang GW, Lu WG, Su JY, Zeng LM, Lian YJ (2005) Cytotoxic diterpenoids from the soft coral Sinularia microclavata. J Nat Prod 68(7):1087–1089

    Article  CAS  PubMed  Google Scholar 

  • Zhang H, Skildum A, Stromquist E, Rose-Hellekant T, Chang LC (2008) Bioactive polybrominated diphenyl ethers from the marine sponge Dysidea sp. J Nat Prod 71(2):262–264

    Article  CAS  PubMed  Google Scholar 

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Acknowledgments

We are grateful to Dr. Bharathi Avula, Dr. Shabana Khan, Surendra Jain, and Ms. Marsha Wright, National Center for Natural Products Research for assistance with the HRESIMS, cytotoxicity, and antimicrobial assays. The authors also acknowledge the US Department of Agriculture, Agriculture Research Services Specific Cooperation Agreement No. 58-6408-7-012 and the NIH, NIAID, Division of AIDS, Grant No. AI 27094, for partial support of this work.

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Authors and Affiliations

  1. National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS, 38677, USA

    Mohamed M. Radwan, Amira S. Wanas, Melissa R. Jacob & Samir A. Ross

  2. Department of Chemistry, College of Science, Louisiana State University, Baton Rouge, LA, 70803, USA

    Frank R. Fronczek

  3. Department of Biomolecular Sciences, National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS, 38677, USA

    Samir A. Ross

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  1. Mohamed M. Radwan
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  2. Amira S. Wanas
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  3. Frank R. Fronczek
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  4. Melissa R. Jacob
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  5. Samir A. Ross
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Correspondence to Samir A. Ross.

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Radwan, M.M., Wanas, A.S., Fronczek, F.R. et al. Polybrominated diphenyl ethers from the marine organisms Lendenfeldia dendyi and Sinularia dura with anti-MRSa activity. Med Chem Res 24, 3398–3404 (2015). https://doi.org/10.1007/s00044-015-1386-9

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  • DOI: https://doi.org/10.1007/s00044-015-1386-9

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