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Chronic actinic dermatitis to sesquiterpene lactones: [2+2] photoreaction toward thymidine of (+) and (-) alpha-methylene-hexahydrobenzofuranone with a cis ring junction.

Abstract
(+) and (-) alpha-methylene-hexahydrobenzofuranone derivatives with a stereochemically pure cis ring junction were used as models of sesquiterpene lactones to study their photoreactivity toward thymidine. After 313 nm irradiation of a deoxygenated acetone solution of lactone models and thymidine, six [2+2] photoadducts were isolated for each enantiomer and fully characterized by a combination of NMR experiments. A common syn regioselectivity and exo stereoselectivity were observed for photoadducts. This high photoreactivity of alpha-methylene-gamma-butyrolactone ring toward thymidine could be an explanation of the progressive evolution of allergic contact dermatitis toward chronic actinic dermatitis.
AuthorsSébastien Fuchs, Valérie Berl, Jean-Pierre Lepoittevin
JournalPhotochemistry and photobiology (Photochem Photobiol) 2010 May-Jun Vol. 86 Issue 3 Pg. 545-52 ISSN: 1751-1097 [Electronic] United States
PMID20113426 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
Chemical References
  • Lactones
  • Sesquiterpenes
  • alpha-methylene gamma-butyrolactone
  • 4-Butyrolactone
  • Thymidine
Topics
  • 4-Butyrolactone (analogs & derivatives, chemistry)
  • Dermatitis, Allergic Contact (etiology)
  • Humans
  • Lactones (chemistry)
  • Magnetic Resonance Spectroscopy
  • Photosensitivity Disorders (chemically induced, etiology)
  • Sesquiterpenes (chemistry, radiation effects)
  • Thymidine (chemistry)
  • Ultraviolet Rays (adverse effects)

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