NMR-spectroscopic screening of spider venom reveals sulfated nucleosides as major components for the brown recluse and related species

Proceedings of the National Academy of Sciences of the United States of America

Volumn 105, Issue 38, 2008, Pages 14283-14287

  Schroeder, Frank C ^a,b   Taggi, Andrew E ^b,e   Gronquist, Matthew ^c   Malik, Rabia U ^b   Grant, Jacqualine B ^d   Eisner, Thomas ^b   Meinwald, Jerrold ^b  

^a United States Department of Agriculture Agricultural Research Service and Boyce Thompson Institute for Plant Research   (United States)

^b Department of Obstetrics Gynecology   (United States)

^c STATE UNIVERSITY OF NEW YORK AT FREDONIA   (United States)

^d MICHIGAN TECHNOLOGICAL UNIVERSITY   (United States)

^e DUPONT COMPANY   (United States)

Author keywords

Chemical prospecting; Loxosceles; Metabolomics; Natural products; Neurotoxins

Indexed keywords

NEUROTOXIN; SPIDER VENOM;

ARTICLE; CONTROLLED STUDY; ELECTROSPRAY MASS SPECTROMETRY; HETERONUCLEAR MULTIPLE BOND CORRELATION; HETERONUCLEAR MULTIPLE QUANTUM COHERENCE; METABOLOMICS; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEAR OVERHAUSER EFFECT; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

ANIMALS; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; NUCLEOSIDES; PHOSPHORIC DIESTER HYDROLASES; SPECIES SPECIFICITY; SPIDER VENOMS; SPIDERS; SULFATES;

ARANEAE; LOXOSCELES; LOXOSCELES RECLUSA;

EID: 55749084225     PISSN: 00278424     EISSN: 10916490     Source Type: Journal    
DOI: 10.1073/pnas.0806840105     Document Type: Article

References (23)

1. Cobas JC, Groves P, Martin-Pastor M, De Capua A (2005) New applications, processing methods and pulse sequences using diffusion NMR. Curr Anal Chem 1:289-305.
2. Halouska S, Powers R (2006) Negative impact of noise on the principal component analysis of NMR data. J Magn Res 178:88-95.
3. Dossey AT, Walse SS, Rocca JR, Edison AS (2006) Single-insect NMR: A new tool to probe chemical biodiversity. Am Chem Soc Chem Biol 1:511-514.
4. Zhang F, Dossey AT, Zachariah C, Edison AS, Bruschweiler R (2007) Strategy for automated analysis of dynamic metabolic mixtures by NMR. Application to an insect venom. Anal Chem 79:7748-7752.
5. Taggi AE, Meinwald J, Schroeder FC (2004) A new approach to natural products discovery exemplified by the identification of sulfated nucleosides in spider venom. J Am Chem Soc 126:10364-10369.
6. McCormick J, et al. (1999) Structure and total synthesis of HF-7, a neuroactive glyconucleoside disulfate from the funnel-web spider Hololena curta. J Am Chem Soc 121:5661-5665.
7. McCormick KD, Meinwald J (1993) Neurotoxic acylpolyamines from spider venoms. J Chem Ecol 19:2411-2451.
8. Schulz S (1997) The chemistry of spider toxins and spider silk. Angew Chem Int Ed Engl 36:314-326.
9. Platnick NI (1997) Advances in Spider Taxonomy 1992-1995 with Redescriptions 1940-1980 (Am Mus of Nat Hist, New York).
10. Platnick NI (2007) The World Spider Catalog, ver 7.5 (Am Mus of Nat Hist, New York), http://research.amnh.org/entomology/spiders/catalog/index. html.
11. Ovtchinnikov SV (1841) The nominotypical spider subgenus Coelotes. Tethys. Entomol Res 2: 35-48.
12. Chesnov S, Bigler L, Hesse M (2000) The spider Paracoelotes birulai: Detection and structure elucidation of new acylpolyamines by on-line coupled HPLC-APCI-MS and HPLC-APCI-MS/MS. Helv Chim Acta 83:3295-3305.
13. Gertsch WJ, Mulaik S (1940) The spiders of Texas. Bull Am Mus Nat Hist 77:307-340.
14. Gertsch WJ, Ennik F (1983) The spider genus Loxosceles in North America, and the West Indies (Araneae, Loxoscelidae). Bull Am Mus Nat Hist 175:264-360.
15. Vetter RS, Visscher PK (1998) Bites and stings of medically important venomous arthropods. Int J Dermatol 37:481-496.
16. Lacey ME, Subramanian R, Olson DL, Webb AG, Sweedler JV (1999) High-resolution NMR spectroscopy of sample volumes from 1 nl to 10 μl. Chem Rev 99:3133-3152.
17. Schroeder FC, et al. (2007) Differential analysis of two-dimensional NMR spectra: New natural products from a pilot-scale fungal extract library. Angew Chem Int Ed 46:901-904.
18. Grant JB, Land B (2002) Transcutaneous amphibian stimulator (TAS): A device for the collection of amphibian skin secretions. Herpetol Rev 33:38-41.
19. Norment BR, Smith OE (1968) Effect of Loxosceles reclusa Gertsch and Mulaik venom against hemocytes of Acheta domesticus (Linnaeus). Toxicon 7:141-144.
20. Tzouros M, Chesnov S, Bienz S, Hesse M, Bigler L (2005) New linear polyamine derivatives in spider venoms. Toxicon 46:350-354.
21. Jasys VJ, et al. (1990) Isolation, structure elucidation, and synthesis of novel hydroxylamine-containing polyamines from the venom of the Agelenopsis aperta spider. J Am Chem Soc 112:6696-6704.
22. Quistad GB, Lam WW, Casida JE (1993) Identification of bis(agmatine)oxalamide invenom from the primitive hunting spider, Plectreurys tristis (Simon). Toxicon 31:920-924.
23. Yamaji N, et al. (2004) Structure and enantioselective synthesis of polyamine toxin MG30 from the venom of the spider Macrothele gigas. Tetrahedron Lett 45:5371-5373.