Premium
Characterization of skin‐surface lipids from the monkey ( Macaca fascicularis )
Author(s) -
NishimakiMogami Tomoko,
Minegishi Kenichiro,
Takahashi Atushi,
Kawasaki Yasushi,
Kurokawa Yuji,
Uchiyama Mitsuru
Publication year - 1988
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/bf02536207
Subject(s) - chemistry , sterol , fatty acid , wax , gas chromatography , long chain , alkane , chromatography , diol , stereochemistry , organic chemistry , biochemistry , cholesterol , hydrocarbon , polymer science
Skin‐surface lipids from the monkey Macaca fascicularis are composed of sterol esters (38%), cholesterol (4%) and two types of wax diesters, identified as Type II (IIa and IIb, 17% and 40%, respectively). Type IIa contained diesters of 1,2‐alkanediols esterified with two molecules of long‐chain (C 14 −C 34 ) fatty acids having straight and branched chains. In the diesters IIa, fatty acids shorter than C 19 predominated in position 1, and fatty acids longer than C 20 predominated in position 2. Type IIb contained diesters of 1,2‐alkanediols esterified with C 4 and C 5 branched‐chain fatty acids (predominantly isovaleric acid) at position 1 and long‐chain (C 14 −C 27 ) acids, having straight and branched chains, at position 2. The shortchain acids were converted to 2‐nitrophenylhydrazides and analyzed by high‐performance liquid chromatography (HPLC). Ammonia chemical ionization (CI)‐gas chromatography (GC)‐mass spectrometry (MS) resolved the intact diesters IIb into 12 peaks corresponding to molecular weights ranging from 597 to 748, and showed that the molecular species, such as C 21 −C 16 −C 5 (diol, fatty acid in position 2, fatty acid in position 1), C 22 −C 16 −C 5 and C 23 −C 16 −C 5 , were prevalent. The fatty acids from both diesters were mostly (>98%) saturated. The 1,2‐alkanediols from both diesters consisted of C 16 −C 26 saturated straight‐ and branched‐chain components. The acyl groups of sterol esters contained 86% C 14 −C 34 branched‐chain acids. The unsaturated fatty acids (5.4%) belonged to a straight‐chain monoenoic series having extremely long chains (C 18 −C 34 ). The branched‐chain structures in the fatty acids and diols were iso and anteiso. These results show the species‐specific profile for the skin‐surface lipid synthesis.