Skip to main content
. Author manuscript; available in PMC: 2017 Jan 1.
Published in final edited form as: Chem Phys Lipids. 2015 Sep 25;194:110–116. doi: 10.1016/j.chemphyslip.2015.09.007

Table 1.

The ability of ceramide and various analogs to permeabilize the outer membrane of isolated rat liver mitochondria and rat erythrocytes, and inhibit the enzymatic activity of cytochrome oxidase. The first compound (#1) is the natural stereoisomer.

(#) Name Type of change MOM Permeabilization relative to C16-ceramidea Erythrocyte Lysis (%)a mean±S.D. Oxidase Inhibition
(1) (2S,3R,4E) C16-ceramide stereo-chemistry 1 <2 No
(2) (2R,3S,4E) C16-ceramide 0.16±0.04** 18 ± 0.1*** No
(3) (2S,3S,4E) C16-ceramide 0.80±0.09* 32 ± 2** No
(4) (2S,3R,4E) C16-ceramine amide linkage N/D 48 ± 2*** Yes
(5) (2S,3R,4E) C16-urea-ceramide 2.29±0.07*** 52 ± 2*** No
(6) (2S,3R,4E) N-methyl-C16-ceramide 0.21±0.04* <2 No
(7) (2S,3R,4E) 1-O-methyl-C16-ceramide hydroxyl groups 0.0*** <2 No
(8) (2S,3R,4E) 3-O-methyl-C16-ceramide 1.1±0.15 66 ± 7** No
(9) (2S,3R) C16-dh-ceramideb double bond 0.0**** <2 No
(10) (2S,3R,4R) C16-phytoceramide 2.3±0.5* 24 ± 1*** No
(11) (2S,3R) C16-4,5-deh-ceramideb 1.2±0.2 48 ± 2*** No
(12) (2S,3R,4E) C16-(4,5-allene)-ceramide 3.0±0.26* 69 ± 1*** No
(13) (2S,3R,15E) C16-dh*-ceramideb 3.8±0.59*** 57 ± 5** No
(14) (2S,3R,4E) C10-ceramide acyl chains 6.6±0.26*** 87 ± 0.5*** No
(15) (2S,3R,4E) 13C/C16-ceramide 6.1±0.27*** 43 ± 2*** No
(16) (2S,3R,4E) C6-NBD-ceramide N/D 13 ± 5*c Yes
(17) (2S,3R,4E) C18:1-ceramide N/D 42 ± 3** Yes
a

Statistical significance was determined using the Student's t test and the P values are as follows:

*

<.05

**

<.01

***

<.001; values are given as mean ± SE of at least 3 experiments

b

dh is dihydro; deh is dehydro/triple bond.

c

The dose of the analog was 10 times less than for the rest.

N/D: not done.