Long-chain sphingoid bases

Stevens VL, Nimkar S, Jamison WC, Liotta DC, Merrill AJJr (1990) Characteristics of the growth inhibition and cytotoxidty of long-chain (sphingoid) bases for Chinese hamster ovary cells evidence for an involvement of protein kinase C. Bio-chim Biophys Acta 1051 37-45... 

Long chain sphingoid base Polar head group... 

Wakita, H., Nishimura, K., and Takigawa, M., Composition of free long-chain (sphingoid) bases in stratum corneum of normal and pathologic human skin conditions, J. Invest. Dermatol., 99, 617,... 

Figure 1 The structural feature common to all sphingolipids is a long-chain sphingoid base. Sphingoid bases are 2-amino-1,3-diols that bear an aliphatic chain. The chain length varies from about 14 to 24 carbon atoms, and the extent of unsaturation, hydroxylation, and methyl-branching in the chain also varies. 1, (2S,3/ ,4f)-sphingosine 2, (2S,3/ )-dihydrosphingosine 3, (2S,3S,4/ )-phytosphingosine 4, 4f,6f-sphingadiene.

MerriU AH Jr, Nimkar S, Menaldino D, Hannun YA, Loomis C, BeU RM, Tyagi SR, Lambeth JD, Stevens VL, et al. Structural requirements for long-chain (sphingoid) base inhibition of protein kinase C in vitro and for the cellular effects of these compounds. Biochemistry 1989 28 3138-3145. 

Merrill, A.H., Jr., Wang, E., and Mullins, R.E. Kinetics of long-chain (sphingoid) base biosynthesis in intact LM cells effects of varying the extracellular concentrations of serine and fatty acid precursors of this pathway. Biochemistry, 11, 1988, 340-345. 

A modest fragment ion at [M-l-Alk-429] corresponding to the loss of the long-chain sphingoid base as a terminal conjugated diene from the [M-i-Alk-(200-t-Alk)]+ ion, which can be used to determine the structure of the sphingoid base of the molecule and then derive the constituent of the FA amide. 

The one resulting from the loss of an 18 0-fatty acyl substituent as a ketene. (The presence of this fragment ion is useful for the identification of the FA substituents in the IPC species and therefore unambiguous elucidating the structure of long-chain sphingoid base.)... 

Two fragment ions arising from fatty acyl and long-chain sphingoid base (e.g., the ions at miz 308 and 236 are generated from dl6 l-18 0 species [23]). 

Stevens, V. L., Winton, E. F., Smith, E. E., Owens, N. E., Kinkade, J. M., and Merrill, A. F., 1989, Differential effects of long chain (sphingoid) bases on the monocytic differentiation of human leukemia (HL-60) cells induced by phorbol esters, la,25-dihydroxyvitamin D3 or ganglioside GM3, Cancer Res. 49 3229-3234. 

Sphingolipids are important constituents of cell membranes in animals, plants, fungi and some bacteria (78). Some important long-chain sphingoid bases are shown in Figure 3. 

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