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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Protein | Definition | Taxonomy |
---|---|---|
Cytosolic phospholipase A2 | A cytosolic phospholipase A2 that is encoded in the genome of cow. [OMA:A4IFJ5, PRO:DNx] | Bos taurus (cattle) |
Diacylglycerol lipase-alpha | A diacylglycerol lipase-alpha that is encoded in the genome of human. [PRO:DNx, UniProtKB:Q9Y4D2] | Homo sapiens (human) |
Diacylglycerol O-acyltransferase 2 | A diacylglycerol O-acyltransferase 2 that is encoded in the genome of human. [PRO:DNx, UniProtKB:Q96PD7] | Homo sapiens (human) |
Diacylglycerol lipase-beta | A diacylglycerol lipase-beta that is encoded in the genome of human. [PRO:DNx, UniProtKB:Q8NCG7] | Homo sapiens (human) |
Cytosolic phospholipase A2 | A cytosolic phospholipase A2 that is encoded in the genome of human. [PRO:DNx, UniProtKB:P47712] | Homo sapiens (human) |
Diacylglycerol O-acyltransferase 1 | A diacylglycerol O-acyltransferase 1 that is encoded in the genome of human. [PRO:DNx, UniProtKB:O75907] | Homo sapiens (human) |
Compound | Definition | Classes | Roles |
---|---|---|---|
cannabinol | Cannabinol: A physiologically inactive constituent of Cannabis sativa L. | dibenzopyran | |
1,6-bis(cyclohexyloximinocarbonyl)hexane | 1,6-bis(cyclohexyloximinocarbonyl)hexane: selective inhibitor of canine platelet diglyceride lipase | carbamate ester; organonitrogen compound | |
ici 204,219 | zafirlukast: a leukotriene D4 receptor antagonist | carbamate ester; indoles; N-sulfonylcarboxamide | anti-asthmatic agent; leukotriene antagonist |
cannabichromene | 1-benzopyran | ||
(6ar-trans)-isomer of tetrahydrocannabivarin 9 | |||
delta(9)-tetrahydrocannabinolic acid | Delta(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 acid | cannabidiolic 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 | |
cannabidiol | cannabidiol : 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 |
orlistat | orlistat : 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 |
arachidonyltrifluoromethane | AACOCF3 : 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 |
amentoflavone | biflavonoid; hydroxyflavone; ring assembly | angiogenesis inhibitor; antiviral agent; cathepsin B inhibitor; P450 inhibitor; plant metabolite | |
cannabigerol | cannabigerol : 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 |
ochnaflavone | ochnaflavone : 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 acid | cannabigerolic 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 | |
efipladib | efipladib: structure in first source | ||
CAY10435 | oxazolopyridine | ||
methyl arachidonylfluorophosphonate | phosphonic ester | ||
pyrrophenone | pyrrophenone: structure in first source | ||
ly2183240 | LY2183240: structure in first source | biphenyls | |
cannabidivarin | cannabidivarin: from Cannabis sativa | monoterpenoid | |
omdm 169 | OMDM 169: has antinociceptive activity; structure in first source | ||
azd3988 | AZD3988: for treatment of obesity and diabetes; structure in first source | ||
a-922500 | aromatic ketone | ||
am 6701 | |||
azd7687 | AZD7687: structure in first source | ||
pf-04620110 | PF-04620110: a DGAT1 inhibitor; structure in first source | ||
pradigastat | |||
pf-06424439 | PF-06424439: an inhibitor of diacylglycerol acyltransferase 2; structure in first source |