What are lipids and what are their primary biological functions?

Lipids are a diverse group of organic compounds that encompass fats, waxes, sterols, fat-soluble vitamins, and phospholipids, among others. Their key biological functions include storing energy, participating in cell signaling, and serving as structural components of cell membranes. This broad category of molecules plays a vital role in many biological processes.

What are the main applications of lipids in industry?

Lipids find significant applications in various industries, notably the cosmetic and food industries. They are also increasingly utilized in the field of nanotechnology, highlighting their versatility beyond biological roles.

What are the two fundamental biochemical subunits that give rise to biological lipids?

Biological lipids originate from two distinct biochemical subunits: ketoacyl groups and isoprene groups. These building blocks are condensed through specific biochemical pathways to form the wide array of lipid molecules found in nature.

According to the LIPID MAPS consortium, what are the eight major categories of lipids?

The LIPID MAPS consortium classifies lipids into eight major categories: fatty acyls, glycerolipids, glycerophospholipids, sphingolipids, and polyketides (all derived from ketoacyl subunits), along with sterol lipids and prenol lipids (derived from isoprene subunits).

How did Henri Braconnot classify lipids in 1815?

In 1815, Henri Braconnot classified lipids into two main categories: 'suifs,' which referred to solid greases or tallow, and 'huiles,' which referred to fluid oils. This early classification laid groundwork for future lipid studies.

What contribution did Michel Eugène Chevreul make to lipid classification in 1823?

Michel Eugène Chevreul expanded upon earlier classifications in 1823 by developing a more detailed system. His categories included oils, greases, tallow, waxes, resins, balsams, and volatile or essential oils.

Who synthesized the first synthetic triglyceride, and what was it?

The first synthetic triglyceride was tributyrin, reported by Théophile-Jules Pelouze in 1844. He created it by reacting butyric acid with glycerin in the presence of concentrated sulfuric acid.

What role did William Prout identify for fats in human and animal nutrition?

In 1827, William Prout recognized fats as a crucial nutrient for humans and animals, alongside proteins and carbohydrates. This highlighted the dietary importance of lipids beyond just their physical properties.

What were Theodore Gobley's and Johann Ludwig Wilhelm Thudichum's contributions to understanding phospholipids?

Theodore Gobley discovered phospholipids in mammalian brain and hen eggs in 1847, naming them 'lecithins.' Later, Thudichum identified phospholipids like cephalin and sphingomyelin, as well as glycolipids like cerebroside, in the human brain.

How was the term 'lipid' introduced and defined?

The term 'lipide' was introduced in 1923 by French pharmacologist Gabriel Bertrand, derived from the Greek word 'lipos' meaning 'fat.' Bertrand's definition expanded the concept to include not only traditional fats but also more complex 'lipoids.' The term was later anglicized to 'lipid'.

What are fatty acyls, and how are they synthesized?

Fatty acyls are a diverse group of molecules, essentially fatty acids and their derivatives, synthesized through a process called fatty acid synthesis. This process involves elongating an acetyl-CoA primer with malonyl-CoA or methylmalonyl-CoA groups.

Describe the structure and properties of fatty acids.

Fatty acids consist of a hydrocarbon chain with a carboxylic acid group at one end. This structure gives them a polar, hydrophilic head and a nonpolar, hydrophobic tail, making them amphiphilic. The hydrocarbon chain can range from four to 24 carbons and may be saturated or unsaturated.

How does the presence of double bonds affect the configuration and properties of fatty acids?

Double bonds in fatty acids can exist in either cis or trans configurations. Cis-double bonds cause the fatty acid chain to bend, which increases membrane fluidity, especially when multiple cis-double bonds are present, as seen in linolenic acid. Most naturally occurring fatty acids have the cis configuration.

What are glycerolipids, and what is their primary role?

Glycerolipids are compounds based on mono-, di-, or tri-substituted glycerols. The most common type is triglycerides, which are triesters of glycerol and fatty acids. Triglycerides serve as the main form of stored fat in animal tissues, acting as a crucial energy reserve.

What are glycosylglycerols, and where are they found?

Glycosylglycerols are subclasses of glycerolipids characterized by sugar residues attached to glycerol via a glycosidic linkage. Examples include digalactosyldiacylglycerols found in plant membranes and seminolipid found in mammalian sperm cells.

What are glycerophospholipids, and why are they important in cell membranes?

Glycerophospholipids, commonly known as phospholipids, are vital components of cell membranes in eukaryotes and bacteria. Their amphipathic nature allows them to form the lipid bilayer, which separates the cell's interior from the external environment. They are also involved in metabolism and cell signaling.

What are some examples of glycerophospholipids and their functions?

Common glycerophospholipids found in biological membranes include phosphatidylcholine, phosphatidylethanolamine, and phosphatidylserine. Some, like phosphatidylinositols and phosphatidic acids, also function as or are precursors to membrane-derived second messengers involved in cell signaling.

What is the defining structural feature of sphingolipids?

Sphingolipids are characterized by a backbone structure derived from a sphingoid base, which is synthesized from the amino acid serine and a fatty acyl CoA. This backbone is then converted into various complex lipids like ceramides, phosphosphingolipids, and glycosphingolipids.

What are ceramides, and what types of fatty acids are typically found in them?

Ceramides are a major subclass of sphingoid base derivatives. They consist of a sphingoid base linked to a fatty acid via an amide bond. The fatty acids in ceramides are usually saturated or monounsaturated, with chain lengths typically ranging from 16 to 26 carbons.

What are the major phosphosphingolipids found in mammals and insects?

In mammals, the primary phosphosphingolipids are sphingomyelins (ceramide phosphocholines). In contrast, insects predominantly contain ceramide phosphoethanolamines.

What are glycosphingolipids, and what are some examples?

Glycosphingolipids are a diverse group of lipids composed of one or more sugar residues attached via a glycosidic bond to a sphingoid base. Examples include simple and complex forms like cerebrosides and gangliosides.

What are sterols, and what is their common structural feature?

Sterols are a class of lipids characterized by a specific fused four-ring core structure. A key feature is the substitution of one hydrogen atom with a hydroxyl group, typically at position 3 of the carbon chain. Cholesterol is a well-known example.

What are some examples of sterols and their roles in different organisms?

Cholesterol is a major sterol in animal cell membranes. Plants have phytosterols like beta-sitosterol and stigmasterol, while fungi primarily use ergosterol in their cell membranes. Bile acids are oxidized derivatives of cholesterol in mammals.

How are steroids classified based on their carbon atom count, and what are some examples?

Steroids are classified by their carbon atom count. C18 steroids include estrogens, C19 steroids include androgens like testosterone, and C21 steroids include progestogens, glucocorticoids, and mineralocorticoids. Secosteroids, like vitamin D, involve a cleaved ring structure.

What are prenol lipids, and what are their precursors?

Prenol lipids are synthesized from five-carbon unit precursors, isopentenyl diphosphate and dimethylallyl diphosphate, primarily produced via the mevalonic acid pathway. These lipids are built by the successive addition of these C5 units.

What are some biologically important prenol lipids and their functions?

Carotenoids, which are simple isoprenoids, function as antioxidants and are precursors to vitamin A. Vitamins E and K, along with ubiquinones, are examples of quinones and hydroquinones that contain an isoprenoid tail attached to a quinonoid core.

What are saccharolipids, and what is a common example?

Saccharolipids are lipids where fatty acids are attached to a sugar backbone, forming structures compatible with membrane bilayers. A prominent example is Lipid A, a component of lipopolysaccharides in Gram-negative bacteria, which consists of acylated glucosamine units.

How are polyketides synthesized, and what are some of their applications?

Polyketides are synthesized by the polymerization of acetyl and propionyl subunits using enzymes similar to fatty acid synthases. They are diverse secondary metabolites found in various organisms and include many important antimicrobial, antiparasitic, and anticancer agents like erythromycins and epothilones.

What is the primary structural component of eukaryotic cell membranes?

Glycerophospholipids are the main structural components of biological membranes, including the plasma membrane and intracellular organelle membranes in eukaryotic cells. These amphipathic molecules form the characteristic lipid bilayer.

Besides glycerophospholipids, what other lipids are significant components of biological membranes?

In addition to glycerophospholipids, biological membranes also contain other lipid components. Sphingomyelin and sterols, such as cholesterol in animal cell membranes, are also found and contribute to membrane structure and function.

What are galactosyldiacylglycerols and sulfoquinovosyldiacylglycerol, and where are they important?

Galactosyldiacylglycerols and sulfoquinovosyldiacylglycerol are lipids that lack a phosphate group. They are important components of the membranes in chloroplasts and related organelles in plants and algae, and are among the most abundant lipids in photosynthetic tissues.

How do phospholipids self-organize in an aqueous environment?

Due to their amphipathic nature, phospholipids self-organize in water through the hydrophobic effect. Their polar heads face the water, while their hydrophobic tails cluster together, forming structures like micelles, liposomes, or lipid bilayers.

What is the significance of lipid bilayer formation in the origin of life?

The ability of lipids to form self-organized structures like protocell membranes is considered a key step in models of abiogenesis, the process by which life is thought to have originated from non-living matter.

What is the role of triglycerides in energy storage?

Triglycerides are a primary form of energy storage in both animals and plants, found in adipose tissue. Their complete oxidation yields significantly more energy per gram (about 38 kJ/g or 9 kcal/g) compared to carbohydrates and proteins (about 17 kJ/g or 4 kcal/g).

How is lipid signaling involved in cellular communication?

Lipid signaling is a vital aspect of cell communication. Specific lipids act as signaling molecules or cellular messengers, often by activating G protein-coupled or nuclear receptors, influencing processes like calcium mobilization, cell growth, and apoptosis.

What are some examples of lipids that function as signaling molecules?

Examples of lipids involved in signaling include sphingosine-1-phosphate (a sphingolipid regulating calcium and cell growth), diacylglycerol and phosphatidylinositol phosphates (involved in protein kinase C activation), and prostaglandins (eicosanoids involved in inflammation).

What are the functions of the fat-soluble vitamins A, D, E, and K?

The fat-soluble vitamins A, D, E, and K are isoprene-based lipids that function as essential nutrients. They are stored in the liver and fatty tissues and have diverse roles in the body, though the specific roles are not detailed in this text.

What is the role of acyl-carnitines in fatty acid metabolism?

Acyl-carnitines are involved in the transport of fatty acids into and out of mitochondria. This transport is crucial for the process of beta-oxidation, where fatty acids are broken down to produce energy.

What are polyprenols and their phosphorylated derivatives involved in?

Polyprenols and their phosphorylated derivatives play important transport roles, specifically in the transfer of oligosaccharides across membranes. They are involved in glycosylation reactions, polysaccharide biosynthesis, and protein glycosylation.

What are cardiolipins, and where are they found in high concentrations?

Cardiolipins are a subclass of glycerophospholipids characterized by four acyl chains and three glycerol groups. They are particularly abundant in the inner mitochondrial membrane and are thought to activate enzymes involved in oxidative phosphorylation.

What are the major dietary lipids consumed by humans and animals?

The primary dietary lipids for humans and other animals are triglycerides, sterols, and membrane phospholipids obtained from both plant and animal sources.

Why are linoleic acid and alpha-linolenic acid considered essential fatty acids?

Linoleic acid (an omega-6 fatty acid) and alpha-linolenic acid (an omega-3 fatty acid) are essential fatty acids because humans and other mammals cannot synthesize them from simpler precursors. They must be obtained through the diet.

Where are linoleic acid and alpha-linolenic acid commonly found in the diet?

Linoleic acid is abundant in many vegetable oils like safflower, sunflower, and corn oil. Alpha-linolenic acid is found in green leafy plants, seeds, nuts, and legumes, notably flax, rapeseed, walnuts, and soy.

What are the health benefits associated with omega-3 fatty acids?

Studies suggest positive health benefits from consuming omega-3 fatty acids, particularly longer-chain variants like eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) found in fish oil. These benefits are linked to infant development, cancer prevention, cardiovascular health, and mental well-being.

What is the established health risk associated with trans fats?

Consumption of trans fats, often found in partially hydrogenated vegetable oils, is well-established as a risk factor for cardiovascular disease. Improper cooking methods that overheat lipids can also inadvertently create trans fats.

What is beta-oxidation, and where does it occur?

Beta-oxidation is the metabolic process where fatty acids are broken down into acetyl-CoA. This process primarily occurs within the mitochondria or peroxisomes of cells and is a key step in generating energy from fats.

How is excess dietary carbohydrate converted in animals?

When there is an oversupply of dietary carbohydrate, animals convert the excess into triglycerides through a process called lipogenesis. This involves synthesizing fatty acids from acetyl-CoA and esterifying them.

What is the difference between fatty acid synthesis in animals versus plants and bacteria?

In animals and fungi, fatty acid synthesis reactions are carried out by a single multifunctional protein. In contrast, plants and bacteria utilize separate enzymes for each step in the fatty acid biosynthesis pathway.

What is the process of desaturation in fatty acid synthesis?

Desaturation is a reaction that introduces a double bond into a fatty acyl chain, converting saturated fatty acids into unsaturated ones. For example, stearic acid is desaturated to oleic acid by stearoyl-CoA desaturase-1 in humans.

What are the two main pathways for producing isoprene precursors in different organisms?

Animals and archaea primarily use the mevalonate pathway to produce isoprene precursors from acetyl-CoA. Plants and bacteria, however, utilize the non-mevalonate pathway, which uses pyruvate and glyceraldehyde 3-phosphate as substrates.

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What are Lipids?

Definition and Solubility

Lipids constitute a broad group of organic compounds, encompassing fats, waxes, sterols, fat-soluble vitamins (A, D, E, K), monoglycerides, diglycerides, phospholipids, and others. They are broadly defined as hydrophobic or amphiphilic small molecules. This amphiphilic nature allows certain lipids to self-assemble into structures like vesicles or membranes in aqueous environments.

Biological Roles

The primary functions of lipids include energy storage, acting as signaling molecules, and serving as structural components of cell membranes. Their diverse roles are fundamental to cellular structure and biological processes.

Industrial Applications

Beyond their biological significance, lipids find applications in various industries, including the cosmetic industry, the food industry, and advanced fields like nanotechnology, highlighting their versatility.

Historical Context

Early Classifications

The scientific understanding of lipids evolved over centuries. In 1815, Henri Braconnot categorized lipids into solid greases (suifs) and fluid oils (huiles). Michel Eugène Chevreul later refined this in 1823, including waxes, resins, and essential oils.

Synthesis and Nomenclature

Significant advancements occurred with the synthesis of triglycerides by Thophile-Jules Pelouze (1844) and Marcellin Berthelot. The term "lipide" was introduced by Gabriel Bertrand in 1923, encompassing not only fats but also more complex molecules, a term later anglicized to "lipid."

Nutritional Recognition

William Prout, in 1827, recognized fats as a crucial nutrient for humans and animals, alongside proteins and carbohydrates, establishing their importance in dietary science.

Lipid Categories

Fatty Acyls

These are fatty acids and their derivatives, characterized by a hydrocarbon chain with polar and nonpolar ends. They can be saturated or unsaturated, with cis or trans isomers affecting molecular configuration. Examples include eicosanoids like prostaglandins and leukotrienes.

Structure: Hydrocarbon chain with a carboxylic acid group.
Properties: Amphipathic, soluble in nonpolar solvents.
Variations: Saturated, unsaturated (cis/trans isomers), chain length.
Key Derivatives: Eicosanoids (prostaglandins, leukotrienes), fatty esters, fatty amides (e.g., anandamide).

Glycerolipids

Composed of mono-, di-, and tri-substituted glycerols. The most common are triglycerides (triesters of glycerol), which form the bulk of storage fat. Glycosylglycerols, linked to sugars, are found in plant membranes.

Core Structure: Glycerol backbone.
Main Type: Triglycerides (energy storage).
Other Types: Glycosylglycerols (e.g., digalactosyldiacylglycerols in plants).

Glycerophospholipids

Also known as phospholipids, these are major structural components of cell membranes. They are amphipathic, with a phosphate ester linkage to a head group. Examples include phosphatidylcholine (PC), phosphatidylethanolamine (PE), and phosphatidylserine (PS), crucial for membrane integrity and signaling.

Key Feature: Phosphate group linked to glycerol.
Membrane Role: Primary structural component of lipid bilayers.
Examples: Phosphatidylcholine (PC), Phosphatidylethanolamine (PE), Phosphatidylserine (PS), Phosphatidylinositol (PI).
Variations: Plasmalogens (ether linkage), alkyl-linked forms.

Sphingolipids

Characterized by a sphingoid base backbone, synthesized from serine. They include ceramides, phosphosphingolipids (like sphingomyelin), and glycosphingolipids (cerebrosides, gangliosides), which are important in nerve tissue and cell recognition.

Core Structure: Sphingoid base (e.g., sphingosine).
Key Derivatives: Ceramides, Sphingomyelins, Cerebrosides, Gangliosides.
Significance: Abundant in neural tissues, involved in cell signaling and recognition.

Sterols

Sterols, like cholesterol, are steroids with a hydroxyl group. They are vital membrane components in animals and precursors to hormones and bile acids. Plant phytosterols and fungal ergosterol are also significant sterols.

Core Structure: Fused four-ring steroid nucleus.
Key Example: Cholesterol (membrane fluidity regulator in animals).
Other Roles: Precursors to steroid hormones (estrogen, testosterone), bile acids, Vitamin D.
Plant/Fungal: Phytosterols, Ergosterol.

Prenols

Synthesized from isoprene units, prenols include terpenes and isoprenoids. Carotenoids (antioxidants, Vitamin A precursors) and vitamins E and K are important examples. They are involved in various biological processes and form the basis of steroid biosynthesis.

Building Blocks: Isoprene units (C5).
Examples: Carotenoids, Vitamins E & K, Ubiquinones.
Biosynthesis: Precursors to steroids, terpenes.

Saccharolipids

Lipids where fatty acids are attached to a sugar backbone, rather than glycerol. A key example is Lipid A, a component of lipopolysaccharides in Gram-negative bacteria, essential for their cell wall structure.

Structure: Fatty acids linked to a sugar moiety.
Key Example: Lipid A (component of bacterial lipopolysaccharides).

Polyketides

Synthesized from acetyl and propionyl subunits, polyketides are a diverse class of natural products. Many possess significant biological activity, serving as antibiotics (e.g., erythromycins, tetracyclines) and anticancer agents (e.g., epothilones).

Synthesis: Polymerization of acetyl-CoA and propionyl-CoA.
Diversity: Wide range of structures and biological activities.
Applications: Antibiotics, anticancer agents, antifungals.
Examples: Erythromycin, Tetracycline, Avermectin, Epothilone.

Biological Functions

Membrane Structure

Lipids, particularly glycerophospholipids and sterols, form the fundamental structure of biological membranes. Their amphipathic nature drives the formation of lipid bilayers, creating cellular compartments and regulating transport across membranes. Plant thylakoid membranes exhibit unique lipid compositions, yet maintain bilayer integrity.

Energy Storage

Triglycerides are the primary form of stored energy in animals and plants. They yield significantly more energy per gram upon oxidation (approx. 38 kJ/g) compared to carbohydrates or proteins (approx. 17 kJ/g), making them highly efficient fuel reserves, crucial for organisms like migratory birds.

Signaling Molecules

Lipids play critical roles in cell signaling. Molecules like sphingosine-1-phosphate, diacylglycerol, phosphatidylinositol phosphates, and steroid hormones act as messengers, regulating cellular processes such as growth, apoptosis, inflammation, and immune responses.

Sphingosine-1-phosphate: Regulates calcium mobilization, cell growth, apoptosis.
Diacylglycerol (DAG) & Phosphatidylinositol Phosphates (PIPs): Involved in calcium-mediated signaling and protein kinase C activation.
Prostaglandins: Eicosanoids involved in inflammation and immunity.
Steroid Hormones: Regulate reproduction, metabolism, blood pressure.
Phosphatidylserine: Signals for phagocytosis of apoptotic cells.

Other Roles

Fat-soluble vitamins (A, D, E, K) are essential isoprene-based lipids with diverse functions. Acyl-carnitines facilitate fatty acid transport into mitochondria for energy production. Cardiolipins, abundant in mitochondria, activate enzymes involved in oxidative phosphorylation.

Metabolism

Biosynthesis

Excess dietary carbohydrates are converted to triglycerides via lipogenesis. Fatty acid synthesis involves enzymes like fatty acid synthases, which polymerize acetyl-CoA units. Unsaturated fatty acids are synthesized via desaturation reactions. Terpenes and isoprenoids are synthesized via the mevalonate or non-mevalonate pathways.

Fatty Acid Synthesis: Acetyl-CoA polymerization; occurs via multifunctional proteins (animals/fungi) or separate enzymes (plants/bacteria).
Unsaturated Fatty Acids: Introduced by desaturase enzymes; essential fatty acids (linoleic, alpha-linolenic) must be dietary.
Triglyceride Synthesis: Esterification of fatty acids to glycerol-3-phosphate or diacylglycerol in the endoplasmic reticulum.
Isoprenoid Synthesis: Via mevalonate pathway (animals/archaea) or non-mevalonate pathway (plants/bacteria) from acetyl-CoA or pyruvate/G3P, respectively.
Steroid Biosynthesis: Isoprene units assemble into squalene, then lanosterol, leading to cholesterol and other steroids.

Degradation

Beta-oxidation is the primary process for breaking down fatty acids in mitochondria or peroxisomes. This process removes two-carbon fragments as acetyl-CoA, which then enters the citric acid cycle for ATP production. The complete oxidation of palmitate yields approximately 106 ATP molecules.

Process: Sequential removal of two-carbon units from fatty acids.
Location: Mitochondria and peroxisomes.
Products: Acetyl-CoA, NADH, FADH2.
Energy Yield: Acetyl-CoA enters the citric acid cycle and electron transport chain for ATP synthesis.
Example Yield: Palmitate (16 carbons) yields ~106 ATP.

Nutrition and Health

Essential Fatty Acids

Dietary fat is necessary for absorbing fat-soluble vitamins. Essential fatty acids, like linoleic acid (omega-6) and alpha-linolenic acid (omega-3), cannot be synthesized by mammals and must be obtained from the diet. Fish oils are rich in longer-chain omega-3 fatty acids, linked to numerous health benefits.

Trans Fats and Health

Consumption of trans fats, often found in partially hydrogenated oils, is a recognized risk factor for cardiovascular disease. Improper cooking methods can also convert beneficial fats into trans fats.

Dietary Fat Intake

Current research suggests that the total amount of dietary fat is not strongly linked to weight gain or disease, contrary to earlier beliefs. Studies indicate that the quality and type of fats consumed are more critical for health outcomes than the overall percentage of calories from fat.

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References

Comptes rendus hebdomadaires des sÃ©ances de l'AcadÃ©mie des Sciences, Paris, 1853, 36, 27; Annales de Chimie et de Physique 1854, 41, 216

A full list of references for this article are available at the Lipid Wikipedia page

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This is not professional advice. The information provided on this website is not a substitute for professional scientific, biochemical, or nutritional consultation. Always refer to official scientific literature and consult with qualified professionals for specific needs.

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Lipids: The Molecular Architects of Life

💡 Dive in with Flashcard Learning! 💡

What are Lipids? ℹ️

💧 Definition and Solubility

🔬 Biological Roles

🏭 Industrial Applications

Historical Context ⏳

📜 Early Classifications

🧪 Synthesis and Nomenclature

🍎 Nutritional Recognition

Lipid Categories 📦

🔗 Fatty Acyls

🌿 Glycerolipids

🧠 Glycerophospholipids

🕸️ Sphingolipids

🌟 Sterols

🌳 Prenols

🦠 Saccharolipids

💊 Polyketides

Biological Functions ⚙️

🏠 Membrane Structure

⚡ Energy Storage

💬 Signaling Molecules

💡 Other Roles

Metabolism 🔄

🏗️ Biosynthesis

⬇️ Degradation

Nutrition and Health 🍎

✅ Essential Fatty Acids

⚠️ Trans Fats and Health

⚖️ Dietary Fat Intake

Related Topics 🔗

📚 Further Exploration

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📜 Important Notice

Dive in with Flashcard Learning!

What are Lipids?

Definition and Solubility

Biological Roles

Industrial Applications

Historical Context

Early Classifications

Synthesis and Nomenclature

Nutritional Recognition

Lipid Categories

Fatty Acyls

Glycerolipids

Glycerophospholipids

Sphingolipids

Sterols

Prenols

Saccharolipids

Polyketides

Biological Functions

Membrane Structure

Energy Storage

Signaling Molecules

Other Roles

Metabolism

Biosynthesis

Degradation

Nutrition and Health

Essential Fatty Acids

Trans Fats and Health

Dietary Fat Intake

Related Topics

Further Exploration

Teacher's Corner

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References

Feedback & Support

Disclaimer

Important Notice