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An integrated approach using UHPLC-PDA-HRMS and 2D HSQC NMR for the metabolic profiling of the red alga Laurencia: Dereplication and tracing of natural products
Authors/Creators
- 1. Department of Pharmacognosy and Chemistry of Natural Products, School of Pharmacy, University of Athens, Panepistimiopolis Zografou, Athens 15771, Greece & Institute of Biology, Medicinal Chemistry and Biotechnology, National Hellenic Research Foundation, 48 Vassileos Constantinou Ave., Athens 11635, Greece
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Kokkotou, Katerina, Ioannou, Efstathia, Nomikou, Marianna, Pitterl, Florian, Vonaparti, Ariadni, Siapi, Eleni, Zervou, Maria, Roussis, Vassilios (2014): An integrated approach using UHPLC-PDA-HRMS and 2D HSQC NMR for the metabolic profiling of the red alga Laurencia: Dereplication and tracing of natural products. Phytochemistry 108: 208-219, DOI: 10.1016/j.phytochem.2014.10.007, URL: http://dx.doi.org/10.1016/j.phytochem.2014.10.007
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- urn:lsid:plazi.org:pub:EF614603FFDF7870FFAB0570FFCD713E
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- Figure: 10.5281/zenodo.10490440 (DOI)
- Figure: 10.5281/zenodo.10490444 (DOI)
- Figure: 10.5281/zenodo.10490446 (DOI)
- Figure: 10.5281/zenodo.10490448 (DOI)
References
- ACD/C, 2012. H NMR predictor and DB. Version 12.01. Advanced Chemistry Development Inc, Toronto, ON, Canada. Available online: <www.acdlabs.com>.
- Blunt, J.W., Copp, B.R., Keyzers, R.A., Munro, M.H.G., Prinsep, M.R., 2013. Marine natural products. Nat. Prod. Rep. 30, 237-323, and earlier reviews in this series.
- Boeckman, R.K., Zhang, J., Reeder, M.R., 2002. Synthetic and mechanistic studies of the retro-Claisen rearrangement. 4. An application to the total synthesis of (+)- laurenyne. Org. Lett. 4, 3891-3894.
- Cabrita, M.T., Vale, C., Rauter, A.P., 2010. Halogenated compounds from marine algae. Mar. Drugs 8, 2301-2317.
- Chatter, R., Kladi, M., Tarhouni, S., Maatoug, R., Kharrat, R., Vagias, C., Roussis, V., 2009. Neorogioltriol: a brominated diterpene with analgesic activity from Laurencia glandulifera. Phytochem. Lett. 2, 25-28.
- Cox, P.J., Imre, S., Islimyeli, S., Thomson, R.H., 1982. Obtusallene I, a new halogenated allene from Laurencia obtusa. Tetrahedron Lett. 23, 579-580.
- Davyt, D., Fernandez, R., Suescun, L., Mombru, A.W., Saldana, J., Dominguez, L., Fujii, M.T., Manta, E., 2006. Bisabolanes from the red alga Laurencia scoparia. J. Nat. Prod. 69, 1113-1116.
- De Nys, R., Coll, J.C., Bowden, B.F., 1992. Tropical marine algae. VIII. The structural determination of novel sesquiterpenoid metabolites from the red alga Laurencia majuscula. Aust. J. Chem. 45, 1611-1623.
- Dias, D.A., Urban, S., Roessner, U., 2012. A historical overview of natural products in drug discovery. Metabolites 2, 303-336.
- Elsevier, C.J., Vermeer, P., Gedanken, A., Runge, W., 1985. Synthesis and absolute configurations of halogenoallenes. J. Org. Chem. 50, 364-367.
- Falshaw, C.P., King, T.J., Imre, S., Islimyeli, S., Thomson, R.H., 1980. Laurenyne, a new acetylene from Laurencia obtusa - crystal structure and absolute configuration. Tetrahedron Lett. 21, 4951-4954.
- Gerssen, A., Mulder, P.P.J., de Boer, J., 2011. Screening of lipophilic marine toxins in shellfish and algae: development of a library using liquid chromatography coupled to orbitrap mass spectrometry. Anal. Chim. Acta 685, 176-185.
- Gonzalez, A.G., Martin, J.D., Martin, V.S., Norte, M., Perez, R., Ruana, J.Z., Drexler, S.A., Clardy, J., 1982. Non-terpenoid C15 metabolites from the red seaweed Laurencia pinnatifida. Tetrahedron 38, 1009-1014.
- Goulitquer, S., Potin, P., Tonon, T., 2012. Mass spectrometry-based metabolomics to elucidate functions in marine organisms and ecosystems. Mar. Drugs 10, 849- 880.
- Guella, G., Mancinci, I., Oztunc, A., Pietra, F., 2000. Conformational bias in macrocyclic ethers and observation of high solvolytic reactivity at a masked furfuryl (=2-furylmethyl) C-atom. Helv. Chim. Acta 83, 336-348.
- Gutierrez-Cepeda, A., Fernandez, J.J., Gil, L.V., Lopez-Rodriguez, M., Norte, M., Souto, M.L., 2011. Non-terpenoid C15 acetogenins from Laurencia marilzae. J. Nat. Prod. 74, 441-448.
- Howard, B.M., Fenical, W., 1976. 10-Bromo- α -chamigrene. Tetrahedron Lett. 17, 2519-2520.
- Irie, T., Suzuki, M., Kurosawa, E., Masamune, T., 1970. Laurinterol, debromolaurinterol and isolaurinterol, constituents of Laurencia intermedia Yamada. Tetrahedron 26, 3271-3277.
- Kamada, T., Vairappan, C.S., 2012. A new bromoallene-producing chemical type of the red alga Laurencia nangii Masuda. Molecules 17, 2119-2125.
- Kato, Y., Okada, S., Atobe, K., Endo, T., Matsubara, F., Oguma, T., Haraguchi, K., 2009. Simultaneous determination by APCI-LC/MS/MS of hydroxylated and methoxylated polybrominated diphenyl ethers found in marine biota. Anal. Chem. 81, 5942-5948.
- Kladi, M., Ntountaniotis, D., Zervou, M., Vagias, C., Ioannou, E., Roussis, V., 2014. Glandulaurencianols A-C, brominated diterpenes from the red alga, Laurencia glandulifera and the sea hare Aplysia punctata. Tetrahedron Lett. 552, 2835- 2837.
- Kladi, M., Vagias, C., Papazafiri, P., Furnari, G., Serio, D., Roussis, V., 2007. New sesquiterpenes from the red alga Laurencia microcladia. Tetrahedron 63, 7606- 7611.
- Konig, G.M., Wright, A.D., 1994. New C15 acetogenins and sesquiterpenes from the red alga Laurencia sp. cf. L. gracilis. J. Nat. Prod. 57, 477-485.
- Konig, G.M., Wright, A.D., Sticher, O., Angerhofer, C.K., Pezzuto, J.M., 1994. Biological activities of selected marine natural products. Planta Med. 60, 532-537.
- Kostiainen, R., Kauppila, T.J., 2009. Effect of eluent on the ionization process in liquid chromatography-mass spectrometry. J. Chromatogr. A 1216, 685-699.
- Lang, G., Mayhudin, N.A., Mitova, M.I., Sun, L., van der Sar, S., Blunt, J.W., Cole, A.L.J., Ellis, G., Laatsch, H., Munro, M.H.G., 2008. Evolving trends in the dereplication of natural product extracts: new methodology for rapid, small-scale investigation of natural product extracts. J. Nat. Prod. 71, 1595-1599.
- Lowe, G., 1965. The absolute configuration of allenes. J. Chem. Soc., Chem. Commun., 411-413.
- Lyakhova, E.G., Kalinovsky, A.I., Dmitrenok, A.S., Kolesnikova, S.A., Fedorov, S.N., Vaskovsky, V.E., Stonik, V.A., 2006. Structures and absolute stereochemistry of nipponallene and neonipponallene, new brominated allenes from the red alga Laurencia nipponica. Tetrahedron Lett. 47, 6549-6552.
- Manzo, E., Ciavatta, M.L., Gavagnin, M., Puliti, R., Mollo, E., Guo, Y.W., Mattia, C.A., Mazzarella, L., Cimino, G., 2005. Structure and absolute stereochemistry of novel C15 halogenated acetogenins from the anaspidean mollusc Aplysia dactylomela. Tetrahedron 61, 7456-7460.
- MarinLit Database, 2013. Department of Chemistry, University of Canterbury. Available online: <http://www.chem.canterbury.ac.nz/marinlit/marinlit. shtml>.
- Mihopoulos, N., Vagias, C., Mikros, E., Scoullos, M., Roussis, V., 2001. Prevezols A and B: new brominated diterpenes from the red alga Laurencia obtusa. Tetrahedron Lett. 42, 3749-3752.
- Motti, C.A., Freckelton, M.L., Tapiolas, D.M., Willis, R.H., 2009. FTICR-MS and LC-UV/ MS-SPE-NMR applications for the rapid dereplication of a crude extract from the sponge Ianthella flabelliformis. J. Nat. Prod. 72, 290-294.
- Oztunc, A., Imre, S., Lotter, H., Wagner, H., 1991. Two C15 bromoallenes from the red alga Laurencia obtusa. Phytochemistry 30, 255-257.
- Palaniveloo, K., Vairappan, C.S., 2014. Chemical relationship between red algae genus Laurencia and sea hare (Aplysia dactylomela Rang) in the North Borneo Island. J. Appl. Phycol. 26, 1199-1205.
- Schripsema, J., 2010. Application of NMR in plant metabolomics: techniques, problems and prospects. Phytochem. Anal. 21, 14-21.
- Simpson, J.H., 2012. Organic Structure Determination using 2-D NMR Spectroscopy, a Problem-based Approach. Academic Press, Elsevier, pp. 124-168.
- Stallard, M.O., Faulkner, D.J., 1974. Chemical constituents of digestive gland of sea hare Aplysia californica. II. Chemical transformations. Comp. Biochem. Physiol. 49, 37-41.
- Stout, E.P., Kubanek, J., 2010. Marine macroalgal natural products. In: Moore, B., Crews, P. (Eds.), Comprehensive Natural Products. II: Chemistry and Biology, vol. 2. Elsevier Ltd, Kidlington, pp. 52-53.
- Suzuki, M., Furusaki, A., Kurosawa, E., 1979. The absolute configurations of halogenated chamigrene derivatives from the marine alga, Laurencia glandulifera Kutzing. Tetrahedron 35, 823-831.
- Suzuki, T., Suzuki, M., Kurosawa, E., 1975. α -Bromocuparene and α - isobromocuparene, new bromo compounds from Laurencia species. Tetrahedron Lett. 16, 3057-3058.
- ToxID, 2009. Version 2.1.2. Thermo Fisher Scientific Inc. Available online: <www.thermoscientific.com>.
- Wolf, D., Siems, K., 2007. Burning the hay to find the needle data mining strategies in natural product dereplication. Chimia 61, 339-345.
- Wolfender, J.L., Marti, G., Queiroz, E.F., 2010. Advances in techniques for profiling crude extracts and for the rapid identification of natural products: dereplication, quality control and metabolomics. Curr. Org. Chem. 14, 1808- 1832.
- XcaliburTM, 2009. Version 2.1. Thermo Fisher Scientific Inc., Available online: <www.thermoscientific.com>.
- Yuliana, N.D., Khatib, A., Choi, Y.H., Verpoorte, R., 2011. Metabolomics for bioactivity assessment of natural products. Phytother. Res. 25, 157-169.