Abstract
The structure elucidation of new secondary metabolites derived from marine and terrestrial sources is frequently a challenging task. The hurdles include the ability to isolate stable secondary metabolites of sufficient purity that are often present in <0.5 % of the dry weight of the sample. This usually involves a minimum of several chromatographic purification steps. The second issue is the stability of the compound isolated. It must always be assumed when dealing with the isolation of natural products that the compound may rapidly degrade during and/or after the isolation, due to sensitivity to light, air oxidation, and/or temperature. In this way, precautions need to be taken, as much as possible to avoid any such chemical inter-conversions and/or degradations. Immediately after purification, the next step is to rapidly acquire all analytical spectroscopic data in order to complete the characterization of the isolated secondary metabolite(s), prior to any possible decomposition. The final hurdle in this multiple step process, especially in the acquisition of the NMR spectroscopic and other analytical data (mass spectra, infrared and ultra-violet spectra, optical rotation, etc.), is to assemble the structural moieties/units in an effort to complete the structure elucidation. Often ambiguity with the elucidation of the final structure remains when structural fragments identified are difficult to piece together on the basis of the HMBC NMR correlations or when the relative configuration cannot be unequivocally identified on the basis of NOE NMR enhancements observed. Herein, we describe the methodology used to carry out the structure elucidation of a new C16 chamigrene, cycloelatanene A (5) which was isolated from the southern Australian marine alga Laurencia elata (Rhodomelaceae). The general approach and principles used in the structure determination of this compound can be applied to the structure elucidation of other small molecular weight compounds derived from either natural or synthetic sources.
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsReferences
Erickson KL, Scheuer PJ (1983) Marine Natural Products: Chemical and Biological Perspectives. New York: Academic Press
König GM, Wright AD (1997) Laurencia rigida: chemical investigations of its antifouling dichloromethane extract. J Nat Prod 60:967–970
Sims JJ, Fenical W (1972) Marine natural products III. Johnstonol, an unusual halogenated epoxide from the red alga Laurencia Johnstonii. Tett Lett 3:195–198
Nai-Yun J, Xiao-Ming L, Ke L, Bin-Gui W (2007) Laurendecumallenes A-B and laurendecumenynes A-B, halogenated nonterpenoid C15-acetogenins from the marine red alga Laurencia decumbens. J Nat Prod 70:1499–1502
Suzuki M, Takahashi Y, Matsuo Y, Masuda M (1996) Pannosallene, a brominated C15 nonterpenoid from Laurencia pannosa. Phytochemistry 41:1101–1103
Francisco MEY, Erickson KL (2001) Ma’iliohydrin, a cytotoxic chamigrene dibromhydrin from a Philippine Laurencia species. J Nat Prod 64:790–791
Kikuchi H, Suzuki T, Suzuki M, Kurosawa E (1985) A new chamigrene-type bromo diether from the red alga Laurencia nipponica Yamada. Bull Chem Soc Jpn 58:2437–2438
Dias DA, Urban S (2011) Phytochemical studies of the southern Australian marine alga, Laurencia elata. Phytochemistry 72:2081–2089
Fronczek F (1989) Redetermination of the absolute configuration of deoxyprepacifenol, from the Mediterranean red alga, Laurencia majuscula. Acta Crystallogr Sect C Cryst Struct Commun 45:1102–1104
Watanabe K, Umeda K, Miyakado M (1989) Isolation and identification of three insecticidal principles from the red alga Laurencia nipponica Yamada. Agric Biol Chem 53:2513–2515
Suzuki T, Kurosawa E (1979) New bromo acetal from the marine alga, Laurencia nipponica Yamada. Chem Lett (3):301–304
Kimura J, Kamada N, Tsujimoto Y (1999) Fourteen chamigrene derivatives from a red alga, Laurencia nidifica. Bull Chem Soc Jpn 72:289–292
Kurata K, Suzuki T, Suzuki M, Kurosawa E, Furusaki A, Matsumoto T (1983) Constituents of marine plants 53. Laureacetal-D and -E, two new secochamigrene derivatives from the red alga Laurencia nipponica Yamada. Chem Lett (4):557–560
Suzuki M, Segawa M, Suzuki T, Kurosawa E (1985) Structures of two new halochamigrene derivatives from the red alga Laurencia nipponica Yamada. Bull Chem Soc Jpn 58:2435–2436
Jongaramruong J, Blackman AJ, Skelton BW, White AH (2002) Chemical relationships between the sea hare Aplysia parvula and the red seaweed Laurencia filiformis from Tasmania. Aust J Chem 55:275–280
San-Martín A, Darias J, Soto H, Contreras C, Herrera JS, Rovirosa J (1997) A new C15 acetogenin from the marine alga Laurencia claviformis. J Nat Prod 10:303–311
Ojika M, Shizuri Y, Yamada K (1982) A halogenated chamigrane epoxide and six related halogen-containing sesquiterpenes from the red alga Laurencia okamurai. Phytochemistry 21:2410–2411
Kurata K, Suzuki T, Suzuki M, Kurosawa E, Furusaki A, Matsumoto T (1983) Constituents of marine plants 52. Laurenical, a novel sesquiterpene α,β-unsaturated aldehyde from the red alga Laurencia Nipponica Yamada. Chem Lett (3):299–300
Acknowledgments
We gratefully acknowledge Mr Robert Brkljaca for his assistance in producing and processing the NMR figures that appear in this chapter.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2013 Springer Science+Business Media, LLC
About this protocol
Cite this protocol
Urban, S., Dias, D.A. (2013). NMR Spectroscopy: Structure Elucidation of Cycloelatanene A: A Natural Product Case Study. In: Roessner, U., Dias, D. (eds) Metabolomics Tools for Natural Product Discovery. Methods in Molecular Biology, vol 1055. Humana Press, Totowa, NJ. https://doi.org/10.1007/978-1-62703-577-4_8
Download citation
DOI: https://doi.org/10.1007/978-1-62703-577-4_8
Published:
Publisher Name: Humana Press, Totowa, NJ
Print ISBN: 978-1-62703-576-7
Online ISBN: 978-1-62703-577-4
eBook Packages: Springer Protocols