Photochemical Studies of the Tridachiahydropyrones in Seawater

Abstract

Sea water is a strong absorber of UV-B radiation. We hypothesized that the photochemical product distribution of a restricted family of marine-derived polypropionates may be affected by attenuation of UV in the natural habitat. Laboratory scale experiments support this hypothesis, indicating that dissolved organic materials (DOM) may play a decisive role in the distribution of photoproducts in marine animals lacking the protection of a shell.

Key words

mollusc - tridachiahydropyrone - UV radiation - DOM - sea water

References and Notes

• 1 Davies-Coleman MT. Garson MJ. Nat. Prod. Rep.  1998,  15:  477 
• 2 Wahidullah S. Guo Y.-W. Fakhr I. Mollo E. In Molluscs: From Chemo-ecological Study to Biotechnological Application   Cimino G. Gavagnin M. Springer; Berlin Heidelberg: 2006.  p.175-192  
• 3 Faulkner DJ. Ghiselin MT. Mar. Ecol. Prog. Ser.  1983,  13:  295 
• 4 Faulkner DJ. Ecological Roles of Marine Natural Products   Paul VJ. Comstock Publishing Associates; Itheca NY: 1992.  p.19-163  
• 5a Trench RK. Greene R. Bystrom B. J. Cell Biol.  1969,  42:  404-417  
• 5b Trench RK. Trench M. Muscatine L. Biol. Bull.  1972,  142:  335 
• 6 Ireland C. Faulkner DJ. Clardy J. J. Am. Chem. Soc.  1979,  101:  1275 
• 7 Ireland C. Faulkner DJ. Tetrahedron (Suppl.)  1981,  37:  223 
• 8 Dawe RD. Wright JLC. Tetrahedron Lett.  1986,  27:  2559 
• 9a Zuidema DR. Jones PB. J. Nat. Prod.  2005,  68:  481 
• 9b Jones PB. Zuidema DR. J. Photochem. Photobiol., B  2006,  83:  137 
• 10a Manzo E. Ciavatta ML. Gavagnin M. Mollo E. Wahidulla S. Cimino G. Tetrahedron Lett.  2005,  46:  465 
• 10b Cueto M. D’Croz LD. Maté JL. Aurelio S.-M. Darias J. Org. Lett.  2005,  7:  415 
• 11 Gavagnin M. Mollo E. Cimino G. Ortea J. Tetrahedron Lett.  1996,  37:  4259 
• 12 Fu X. Hong EP. Schmitz FJ. Tetrahedron  2000,  56:  8989 
• 13 Ireland C. Scheuer P. Science  1979,  205:  922 
• 15 Sharma P. Griffiths N. Moses JE. Org. Lett.  2008,  10:  4025 
• 16 Sharma P. Lygo B. Williams L. Moses JE. J. Am. Chem. Soc.  2009,  131:  5966 
• 17 Whitehead RF. De-Mora S. Issues in Environmental Science and Technology, No. 14   The Royal Society of Chemistry; London: 2000. 
• 18 Bricaud A. Morel A. Prieur L. Limnol. Oceanogr.  1981,  27:  43 
• 19 Hedges J. Humic Substances and Their Role in the Environment   Frimmel F. Christman R. Wiley; New York: 1988.  p.45 
• 20 Vilariño T. Fiol S. Brandariz I. Herrero R. Sastre de Vicente ME. J. Chem. Res., Synop.  1997,  222 

14

The digestive diverticula flank the dorsal surface of the animal.

21

Sea water was collected from the west coast of Wales in May 2009 and was used within three days.

22

UV transmission for borosilicate glass λ >280 nm. 125 W medium pressure lamp produces predominantly 365-366 nm radiation with smaller levels in the UV region at 254, 265, 270, 289, 297, 302, 313 and 334 nm.