1,2-diacylglycerol compound, preparation method therefor, and immunomodulator containing same as active ingredient
AssigneeEnzychem Lifesciences Corporation
InventorsKi Young SOHN, Jae Wha KIM, Sun Young YOON, Chang Hyun YOO, Jin Seon JEONG
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Abstract
Disclosed are a novel 1,2-diacylglycerol compound that useful for improving, preventing or treating inflammation-related diseases by inhibiting overexpression of various inflammatory cytokines such as IL-4 and IL-6 or chemokine CXCL8 related to the migration of inflammatory cells, a method for preparing the same, and an immunomodulator containing the same as an active ingredient. The 1,2-diacylglycerol compound is represented by Chemical Formula 2 in the patent specification.
Claims14
A 1,2-diacylglycerol compound represented by following Chemical formula 2,
- in Chemical formula 2, R1 is a fatty acid residue of 8 to 18 carbon atoms, and R3 is a fatty acid residue of 4 to 18 carbon atoms, and R2 is alkyl group of 1 to 3 carbon atoms,
- (R4 is an aliphatic or aromatic hydrocarbon group of 2 to 8 carbon atoms),
- and represents a bonding portion.
A method for preparing 1,2-diacylglycerol compound comprising the steps of:
- reacting a glycidyl chloride and fatty acid (R1-OH, R1 is a fatty acid residue of 8 to 18 carbon atoms) to obtain a compound A, as shown in Reaction 1 below;
- reacting a compound A and R2-OH (R2 is a alkyl group of 1 to 3 carbon atoms,
- (R4 is an aliphatic or aromatic hydrocarbon group of 2 to 8 carbon atoms),
- and represents a bonding portion) to obtain a compound B, as shown in Reaction 2 below;
- and
- reacting a compound B and fatty acid (R3-OH, R3 is a fatty acid residue of 4 to 18 carbon atoms), as shown in Reaction 3 below.
A method for preparing 1,2-diacylglycerol compound comprising the steps of:
- reacting a solketal and fatty acid (R1-OH, R1 is a fatty acid residue of 8 to 18 carbon atoms) to obtain a compound C, and the compound C is subjected to a hydrolysis reaction to obtain compound D, as shown in Reaction 4 below;
- reacting a compound D and R2-OH (R2 is a alkyl group of 1 to 3 carbon atoms,
- (R4 is an aliphatic or aromatic hydrocarbon group of 2 to 8 carbon atoms),
- and represents a bonding portion) to obtain a compound B, as shown in Reaction 5 below;
- reacting a compound B and fatty acid (R3-OH, R3 is a fatty acid residue of 4 to 18 carbon atoms), as shown in Reaction 3 below.
An immunomodulator comprising 1,2-diacylglycerol compound represented by following Chemical formula 2 as an active ingredient,
- in Chemical formula 2, R1 is a fatty acid residue of 8 to 18 carbon atoms, and R3 is a fatty acid residue of 4 to 18 carbon atoms, and R2 is alkyl group of 1 to 3 carbon atoms,
- (R4 is an aliphatic or aromatic hydrocarbon group of 2 to 8 carbon atoms),
- and represents a bonding portion.
A health functional food composition for immunity enhancement, comprising 1,2-diacylglycerol compound represented by following Chemical formula 2 as an active ingredient,
- in Chemical formula 2, R1 is a fatty acid residue of 8 to 18 carbon atoms, and R3 is a fatty acid residue of 4 to 18 carbon atoms, and R2 is alkyl group of 1 to 3 carbon atoms,
- (R4 is an aliphatic or aromatic hydrocarbon group of 2 to 8 carbon atoms),
- and represents a bonding portion.
Dependencies are inferred from the claim text.