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 that have a similar structure causes an increase in dihydrosphingosine and dihydrosphingosine-1-phosphate and a decrease in other sphingolipids. This leads 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:

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
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
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