Page last updated: 2024-10-24

monoacylglycerol biosynthetic process

Definition

Target type: biologicalprocess

The chemical reactions and pathways resulting in the formation of monoacylglycerol, any ester of glycerol in which any one of its hydroxyl groups has been acylated with a fatty acid, the other being non-esterified. [ISBN:0198506732]

Monoacylglycerol biosynthesis is a crucial metabolic pathway involved in the synthesis of monoacylglycerols (MAGs), which are simple lipids composed of a glycerol backbone and a single fatty acid chain. MAGs serve as essential building blocks for various lipids, including diacylglycerols (DAGs) and triacylglycerols (TAGs), the primary energy storage molecules in organisms. The biosynthesis of MAGs primarily occurs via two main pathways:

**1. Glycerol-3-phosphate pathway:**
a. **Glycerol-3-phosphate acyltransferase (GPAT)** catalyzes the first committed step in this pathway. It attaches a fatty acid to the sn-1 position of glycerol-3-phosphate, forming lysophosphatidic acid (LPA).
b. **LPA acyltransferase (LPAAT)** then adds a second fatty acid to the sn-2 position of LPA, yielding phosphatidic acid (PA).
c. **Phosphatidic acid phosphatase (PAP)** removes the phosphate group from PA, generating diacylglycerol (DAG).
d. **Diacylglycerol lipase (DAG lipase)** hydrolyzes DAG, producing MAG and a free fatty acid.

**2. Acylglycerol pathway:**
a. This pathway utilizes free glycerol as a starting material.
b. **Glycerol kinase (GK)** phosphorylates glycerol, forming glycerol-3-phosphate.
c. **Glycerol-3-phosphate acyltransferase (GPAT)** then adds a fatty acid to glycerol-3-phosphate, initiating the pathway similar to the glycerol-3-phosphate pathway.

**Regulation of Monoacylglycerol Biosynthesis:**
a. The activity of enzymes involved in MAG biosynthesis is tightly regulated by various factors, including substrate availability, hormonal signals, and cellular energy status.
b. For example, GPAT activity is stimulated by insulin and inhibited by glucagon, reflecting the role of MAG biosynthesis in energy storage.

**Biological Significance of Monoacylglycerol Biosynthesis:**
a. **Lipid metabolism:** MAGs are crucial intermediates in the biosynthesis of other lipids, such as DAGs and TAGs.
b. **Signaling:** MAGs can act as signaling molecules, modulating cellular processes like cell growth, differentiation, and inflammation.
c. **Membrane structure:** MAGs contribute to the formation of cell membranes, particularly in the endoplasmic reticulum.
d. **Energy storage:** TAGs, which are derived from MAGs, serve as the primary energy storage molecules in organisms.

In summary, monoacylglycerol biosynthesis is a complex and highly regulated pathway that plays a critical role in lipid metabolism, cellular signaling, and energy storage. The production of MAGs is essential for the synthesis of other vital lipids, ensuring the proper function of various cellular processes.'
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Proteins (6)

ProteinDefinitionTaxonomy
Cytosolic phospholipase A2 A cytosolic phospholipase A2 that is encoded in the genome of cow. [OMA:A4IFJ5, PRO:DNx]Bos taurus (cattle)
Diacylglycerol lipase-alphaA diacylglycerol lipase-alpha that is encoded in the genome of human. [PRO:DNx, UniProtKB:Q9Y4D2]Homo sapiens (human)
Diacylglycerol O-acyltransferase 2A diacylglycerol O-acyltransferase 2 that is encoded in the genome of human. [PRO:DNx, UniProtKB:Q96PD7]Homo sapiens (human)
Diacylglycerol lipase-betaA diacylglycerol lipase-beta that is encoded in the genome of human. [PRO:DNx, UniProtKB:Q8NCG7]Homo sapiens (human)
Cytosolic phospholipase A2A cytosolic phospholipase A2 that is encoded in the genome of human. [PRO:DNx, UniProtKB:P47712]Homo sapiens (human)
Diacylglycerol O-acyltransferase 1A diacylglycerol O-acyltransferase 1 that is encoded in the genome of human. [PRO:DNx, UniProtKB:O75907]Homo sapiens (human)

Compounds (28)

CompoundDefinitionClassesRoles
cannabinolCannabinol: A physiologically inactive constituent of Cannabis sativa L.dibenzopyran
1,6-bis(cyclohexyloximinocarbonyl)hexane1,6-bis(cyclohexyloximinocarbonyl)hexane: selective inhibitor of canine platelet diglyceride lipasecarbamate ester;
organonitrogen compound
ici 204,219zafirlukast: a leukotriene D4 receptor antagonistcarbamate ester;
indoles;
N-sulfonylcarboxamide
anti-asthmatic agent;
leukotriene antagonist
cannabichromene1-benzopyran
(6ar-trans)-isomer of tetrahydrocannabivarin 9
delta(9)-tetrahydrocannabinolic acidDelta(9)-tetrahydrocannabinolic acid : A diterpenoid that is 6a,7,8,10a-tetrahydro-6H-benzo[c]chromene substituted at position 1 by a hydroxy group, positions 6, 6 and 9 by methyl groups and at position 3 by a pentyl group. A biosynthetic precursor to Delta(9)-tetrahydrocannabinol, the principal psychoactive constituent of the cannabis plant.benzochromene;
diterpenoid;
hydroxy monocarboxylic acid;
phytocannabinoid;
polyketide
anti-inflammatory agent;
biomarker;
metabolite;
neuroprotective agent
cannabidiolic acidcannabidiolic acid : A dihydroxybenzoic acid that is olivetolic acid in which the hydrogen at position 3 is substituted by a 3-p-mentha-1,8-dien-3-yl (limonene) group.

cannabidiolic acid: structure
dihydroxybenzoic acid;
phytocannabinoid;
polyketide;
resorcinols
cannabidiolcannabidiol : An cannabinoid that is cyclohexene which is substituted by a methyl group at position 1, a 2,6-dihydroxy-4-pentylphenyl group at position 3, and a prop-1-en-2-yl group at position 4.

Cannabidiol: Compound isolated from Cannabis sativa extract.
olefinic compound;
phytocannabinoid;
resorcinols
antimicrobial agent;
plant metabolite
orlistatorlistat : A carboxylic ester resulting from the formal condensation of the carboxy group of N-formyl-L-leucine with the hydroxy group of (3S,4S)-3-hexyl-4-[(2S)-2-hydroxytridecyl]oxetan-2-one. A pancreatic lipase inhibitor, it is used as an anti-obesity drug.

Orlistat: A lactone derivative of LEUCINE that acts as a pancreatic lipase inhibitor to limit the absorption of dietary fat; it is used in the management of obesity.
beta-lactone;
carboxylic ester;
formamides;
L-leucine derivative
anti-obesity agent;
bacterial metabolite;
EC 2.3.1.85 (fatty acid synthase) inhibitor;
EC 3.1.1.3 (triacylglycerol lipase) inhibitor
arachidonyltrifluoromethaneAACOCF3 : A fatty acid derivative that is arachidonic acid in which the OH part of the carboxy group has been replaced by a trifluoromethyl group

arachidonyltrifluoromethane: structure given in first source; inhibits 85-kDa phospholipase A2
fatty acid derivative;
ketone;
olefinic compound;
organofluorine compound
EC 3.1.1.4 (phospholipase A2) inhibitor
amentoflavonebiflavonoid;
hydroxyflavone;
ring assembly
angiogenesis inhibitor;
antiviral agent;
cathepsin B inhibitor;
P450 inhibitor;
plant metabolite
cannabigerolcannabigerol : A member of the class of resorcinols that is resorcinol which is substituted by a (2E)-3,7-dimethylocta-2,6-dien-1-yl group at position 2 and by a pentyl group at position 5. It is a natural product found in Cannabis sativa and Helichrysum species.

cannabigerol: RN given refers to (E)-isomer; structure given in first source
phytocannabinoid;
resorcinols
anti-inflammatory agent;
antibacterial agent;
antioxidant;
appetite enhancer;
cannabinoid receptor agonist;
neuroprotective agent;
plant metabolite
ochnaflavoneochnaflavone : A biflavonoid with an ether linkage between the B-rings of the apigenin and luteolin subunits. It has been isolated from several members of the Ochnaceae plant family.

ochnaflavone: from Lonicera japonica; structure given in first source
aromatic ether;
biflavonoid;
hydroxyflavone
anti-inflammatory agent;
antiatherogenic agent;
antibacterial agent;
EC 3.1.1.4 (phospholipase A2) inhibitor;
leukotriene antagonist;
plant metabolite
cannabigerolic acidcannabigerolic acid : A dihydroxybenzoic acid that is olivetolic acid in which the hydrogen at position 3 is substituted by a geranyl group. A biosynthetic precursor to Delta(9)-tetrahydrocannabinol, the principal psychoactive constituent of the cannabis plant.

cannabigerolic acid: structure in first source
dihydroxybenzoic acid;
diterpenoid;
phytocannabinoid;
polyketide;
resorcinols
efipladibefipladib: structure in first source
CAY10435oxazolopyridine
methyl arachidonylfluorophosphonatephosphonic ester
pyrrophenonepyrrophenone: structure in first source
ly2183240LY2183240: structure in first sourcebiphenyls
cannabidivarincannabidivarin: from Cannabis sativamonoterpenoid
omdm 169OMDM 169: has antinociceptive activity; structure in first source
azd3988AZD3988: for treatment of obesity and diabetes; structure in first source
a-922500aromatic ketone
am 6701
azd7687AZD7687: structure in first source
pf-04620110PF-04620110: a DGAT1 inhibitor; structure in first source
pradigastat
pf-06424439PF-06424439: an inhibitor of diacylglycerol acyltransferase 2; structure in first source