Application Notes:
This high purity and well-defined product is ideal as a standard and for biological studies.1 Dihydroceramide is a critical
intermediate in the synthesis of many complex sphingoid bases. Inhibition of dihydroceramide synthesis by some fungal
toxins (such as fumonisin B1) that have a similar structure causes an increase in sphinganine and sphinganine-1-phosphate
and a decrease in other sphingolipids leading to a number of diseases including oesophageal cancer. Dihydroceramide,
synthesized by the acylation of sphinganine, is subsequently converted into ceramide via a desaturase enzyme or into
phytosphingosine via the C4-hydrozylase enzyme2. N-(4-Hydroxyphenyl) retinamide (4-HPR) has been tested as an anticancer
agent. It inhibits the dihydroceramide desaturase enzyme in cells resulting in a high concentration of dihydroceramide
and dihydro-sphingolipids and this is thought to be the cause of the anti-cancer effects.3 Dihydrosphingosine induces cell
death in a number of types of malignant cells.
References:
1. Z. Zakeri et al. “Stereospecific Induction of Apoptosis in U937 Cells by N-Octanoyl-Sphingosine Stereoisomers and N-Octyl-Sphingosine” European
Journal of Biochemistry, vol. 236 pp. 729-737, 1996
2. Y. Mizutani, A. Kihara, and Y. Igarashi “Identifcation of the human sphingolipid C4-hydroxylase, hDES2, and its up-regulation during keratinocyte
differentiation” FEBS Letters, vol. 563 pp. 93-97, 2004
3. W. Zheng “Fenretinide increases dihydroceramide and dihydrosphingolipids due to inhibition of dihydroceramide desaturase” Georgia Institute of
Technology, 2006