Synthetic Dihydrosphingosines

Dihydrosphingosine (sphinganine) is the precursor of dihydroceramide which is then desaturated to form ceramide. It is a critical intermediate in the synthesis of many complex sphingoid bases and ceramide analogs. It has been suggested that dihydrosphingosine may induce cell death in malignant cells.1 Inhibition of dihydroceramide synthesis by some fungal toxins having a similar structure causes an increase in dihydrosphingosine and dihydrosphingosine-1-phosphate and a decrease in other sphingolipids, leading to a number of diseases including oesophageal cancer.2 Dihydrosphingosine has been found to mediate fumonisin (a toxic dihydrosphingosine analog) induced hypotension.3 Yeasts contain mainly the saturated C18 base dihydrosphingosine rather than the unsaturated C18 base sphingosine which is common in animals.

References:

  1. M. Rahmaniyan et al. "Identification of dihydroceramide desaturase as a direct in vitro target for fenretinide" J Biol Chem., Vol. 286(28) pp.24754-64, 2011
  2. L. van der Westhuizen et al. “Sphingoid base levels in humans consuming fumonisin-contaminated maize in rural areas of the former Transkei, South Africa: a cross-sectional study” Food Additives and Contaminants, Vol. 25(11) pp. 1385 – 1391, 2008
  3. Shih-Hsuan Hsiao et al. “Effects of Exogenous Sphinganine, Sphingosine, and Sphingosine-1-Phosphate on Relaxation and Contraction of Porcine Thoracic Aortic and Pulmonary Arterial Rings” Toxicological Sciences, Vol. 86(1) pp. 194-199, 2005