10.2 Terpenes
10 min read•august 20, 2024
Terpenes are a diverse class of organic compounds found in plants, fungi, and insects. They play crucial roles in medicinal chemistry due to their wide range of biological activities and potential therapeutic applications. Understanding their classification, structure, and biosynthesis is key to harnessing their medicinal properties.
Terpenes are classified based on the number of isoprene units they contain, ranging from to . Their biosynthesis involves complex pathways, including the mevalonate and non-mevalonate routes. Terpenes exhibit various biological functions, serving as defense compounds, signaling molecules, and structural components in nature.
Terpene classification and structure
- Terpenes are a diverse class of organic compounds produced by various plants, fungi, and some insects that play important roles in medicinal chemistry due to their wide range of biological activities and potential therapeutic applications
- The classification and structure of terpenes are based on the number of isoprene units (C5H8) they contain and their structural complexity, which determine their physical, chemical, and biological properties
Isoprene rule for terpene biosynthesis
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- The isoprene rule states that terpenes are formed by the head-to-tail condensation of isoprene units (dimethylallyl pyrophosphate and isopentenyl pyrophosphate) via the mevalonate or non-mevalonate pathways
- This rule explains the structural diversity of terpenes and their classification based on the number of isoprene units they contain (monoterpenes, , , and triterpenes)
- The isoprene rule also helps predict the possible structures and stereochemistry of terpenes based on their biosynthetic origins and enzymatic modifications
Mono-, sesqui-, di-, and triterpenes
- Monoterpenes (C10) are the simplest terpenes, containing two isoprene units, and are commonly found in essential oils (, )
- Sesquiterpenes (C15) consist of three isoprene units and exhibit a wide range of biological activities (, )
- Diterpenes (C20) are composed of four isoprene units and include important compounds like (anticancer) and (antihypertensive)
- Triterpenes (C30) are made up of six isoprene units and have complex structures with multiple rings (, )
Acyclic, monocyclic, and polycyclic terpenes
- Terpenes can also be classified based on their structural complexity and the presence of ring systems
- have an open-chain structure without any rings (myrcene, geraniol)
- contain a single ring system, which can be saturated or unsaturated (menthol, limonene)
- have multiple fused or bridged ring systems, leading to complex three-dimensional structures (camphor, pinene)
Biosynthesis of terpenes
- The biosynthesis of terpenes involves the formation of isoprene units from primary metabolites and their subsequent condensation, cyclization, and modification by various enzymes
- Understanding the biosynthetic pathways of terpenes is crucial for medicinal chemistry, as it enables the production of terpene-based drugs through metabolic engineering and synthetic biology approaches
Mevalonate pathway for terpene synthesis
- The is the primary route for terpene biosynthesis in eukaryotes and some bacteria
- It starts with the condensation of acetyl-CoA units to form 3-hydroxy-3-methylglutaryl-CoA (HMG-CoA), which is then reduced to mevalonate by HMG-CoA reductase
- Mevalonate undergoes a series of phosphorylation and decarboxylation reactions to form isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP), the building blocks of terpenes
Non-mevalonate pathway for terpene synthesis
- The non-mevalonate pathway, also known as the methylerythritol phosphate (MEP) pathway, is an alternative route for terpene biosynthesis found in most bacteria and plant plastids
- It begins with the condensation of pyruvate and glyceraldehyde 3-phosphate to form 1-deoxy-D-xylulose 5-phosphate (DXP), which is then converted to MEP
- The MEP pathway involves a series of enzymatic reactions to produce IPP and DMAPP, which are used for terpene synthesis
Terpene synthases and cyclization reactions
- Terpene synthases are the key enzymes responsible for the condensation of IPP and DMAPP units to form the basic skeletons of terpenes
- These enzymes catalyze the formation of linear terpene precursors (geranyl pyrophosphate, farnesyl pyrophosphate, and geranylgeranyl pyrophosphate) and their subsequent cyclization reactions
- Terpene cyclization involves the formation of carbocation intermediates and their rearrangement, leading to the structural diversity of (monoterpene cyclases, sesquiterpene cyclases, and diterpene cyclases)
Biological functions of terpenes
- Terpenes play diverse biological roles in the organisms that produce them, serving as defense compounds, signaling molecules, and structural components
- Understanding the biological functions of terpenes is essential for medicinal chemistry, as it provides insights into their potential therapeutic applications and guides the development of terpene-based drugs
Terpenes in plant defense mechanisms
- Many plants produce terpenes as part of their chemical defense against herbivores, pathogens, and environmental stresses
- Monoterpenes and sesquiterpenes often act as volatile repellents or toxins that deter feeding by insects and mammals (pyrethrins, azadirachtin)
- Diterpenes and triterpenes can serve as phytoalexins, antimicrobial compounds that are synthesized in response to pathogen attack (momilactones, phytosterols)
Terpenes as insect attractants and repellents
- Some terpenes function as insect pheromones, chemical signals that mediate communication within a species (bark beetle aggregation pheromones)
- Other terpenes act as kairomones, chemical cues that attract natural enemies of herbivores, such as predators and parasitoids (E-β-farnesene)
- Certain terpenes, like citronellal and geraniol, are used as insect repellents in personal care products and pest control formulations
Terpenes in microbial interactions
- Terpenes produced by microorganisms, such as bacteria and fungi, play important roles in their ecological interactions and survival strategies
- Some microbial terpenes act as quorum sensing molecules, regulating gene expression and coordinating population behavior (farnesol in Candida albicans)
- Terpenes can also mediate symbiotic relationships between microbes and their hosts, such as in the case of rhizobial bacteria and legume plants (hopanoids)
Medicinal properties of terpenes
- Terpenes exhibit a wide range of medicinal properties, making them valuable lead compounds for drug discovery and development
- The therapeutic potential of terpenes is attributed to their diverse chemical structures and ability to interact with various biological targets
Anti-inflammatory and analgesic terpenes
- Several terpenes have been shown to possess anti-inflammatory and analgesic activities, making them potential candidates for the treatment of chronic inflammatory diseases and pain management
- Monoterpenes like menthol and limonene inhibit pro-inflammatory cytokines and reduce pain sensitivity by interacting with transient receptor potential (TRP) channels
- Triterpenes such as boswellic acids and celastrol have potent anti-inflammatory effects by modulating NF-κB and MAPK signaling pathways
Antimicrobial and antiviral terpenes
- Many terpenes exhibit antimicrobial and antiviral properties, offering new strategies for combating drug-resistant pathogens and emerging viral diseases
- Monoterpenes like thymol and carvacrol disrupt bacterial cell membranes and inhibit essential enzymes, showing broad-spectrum antibacterial activity
- Sesquiterpenes such as artemisinin and parthenolide have potent antimalarial and antiviral effects, targeting specific metabolic pathways in the pathogens
Anticancer and chemopreventive terpenes
- Terpenes have shown promising anticancer and chemopreventive activities, acting through various mechanisms such as inducing apoptosis, inhibiting cell proliferation, and modulating oncogenic signaling pathways
- Diterpenes like taxol and andrographolide are widely used in cancer chemotherapy, targeting microtubule dynamics and inducing cell cycle arrest
- Triterpenes such as betulinic acid and ginsenosides have demonstrated chemopreventive effects by inducing phase II detoxification enzymes and modulating epigenetic factors
Terpenes in essential oils
- Essential oils are complex mixtures of volatile terpenes and other aromatic compounds obtained from plants, which have been used for centuries in traditional medicine, , and cosmetics
- The composition and biological activities of essential oils are largely determined by the types and proportions of terpenes they contain
Monoterpenes in essential oils
- Monoterpenes are the most abundant constituents of essential oils, contributing to their characteristic odors and therapeutic properties
- Common monoterpenes found in essential oils include limonene (citrus oils), menthol (peppermint oil), and linalool (lavender oil)
- Monoterpene-rich essential oils are used for their antimicrobial, anti-inflammatory, and anxiolytic effects, as well as their pleasant aromas
Sesquiterpenes in essential oils
- Sesquiterpenes are another important class of terpenes found in essential oils, often contributing to their complex fragrances and biological activities
- Examples of sesquiterpenes in essential oils include β-caryophyllene (clove oil), farnesol (rose oil), and chamazulene (chamomile oil)
- Sesquiterpene-containing essential oils are valued for their anti-inflammatory, antispasmodic, and skin-healing properties
Terpene composition and variability
- The terpene composition of essential oils can vary significantly depending on factors such as plant species, geographical origin, harvest time, and extraction methods
- This variability can influence the biological activities and therapeutic potential of essential oils, making standardization and quality control important considerations
- Advances in analytical techniques like - (GC-MS) have enabled the detailed characterization of terpene profiles in essential oils, facilitating their medicinal use and research
Extraction and isolation of terpenes
- The extraction and isolation of terpenes from plant materials is a critical step in their medicinal use and research, as it determines the purity, yield, and biological activity of the obtained compounds
- Various methods are employed for terpene extraction and isolation, each with its advantages and limitations
Steam distillation of terpenes
- Steam distillation is the most common method for extracting volatile terpenes from plant materials, particularly for essential oil production
- In this process, steam is passed through the plant material, causing the volatile terpenes to evaporate and condense in a cooling system
- Steam distillation is suitable for extracting monoterpenes and sesquiterpenes, but may degrade heat-sensitive compounds and produce artifacts
Solvent extraction of terpenes
- Solvent extraction involves the use of organic solvents (hexane, ethanol, or supercritical CO2) to dissolve and extract terpenes from plant materials
- This method is more efficient than steam distillation for extracting higher molecular weight terpenes (diterpenes and triterpenes) and thermolabile compounds
- Solvent extraction requires the removal of the solvent after extraction, which can be achieved by evaporation, distillation, or chromatographic techniques
Chromatographic techniques for terpene isolation
- Chromatographic techniques are used for the purification and isolation of individual terpenes from crude extracts or essential oils
- Column chromatography, using silica gel or other adsorbents, is commonly employed for the fractionation of terpene mixtures based on their polarity and molecular size
- High-performance liquid chromatography (HPLC) and gas chromatography (GC) are powerful tools for the separation and quantification of terpenes, often coupled with mass spectrometry (MS) for structural elucidation
Terpene derivatives and analogs
- Terpene derivatives and analogs are synthetic or semisynthetic compounds that are structurally related to naturally occurring terpenes but have been modified to improve their pharmacological properties or bioavailability
- The development of terpene derivatives and analogs is a key strategy in medicinal chemistry for optimizing the therapeutic potential of terpenes and overcoming their limitations
Semisynthetic terpene derivatives
- Semisynthetic terpene derivatives are obtained by chemically modifying naturally occurring terpenes to introduce new functional groups or alter their structural features
- Examples of semisynthetic terpene derivatives include artemether (antimalarial) and taxotere (anticancer), which are derived from artemisinin and taxol, respectively
- Semisynthesis allows for the optimization of terpene structures for improved potency, selectivity, and pharmacokinetic properties
Terpene-based drug discovery and development
- Terpenes serve as valuable lead compounds for drug discovery and development, inspiring the design of novel therapeutic agents with improved efficacy and safety profiles
- Medicinal chemists use terpene scaffolds as starting points for the synthesis of diverse libraries of analogs, which are then screened for their biological activities and structure-activity relationships (SARs)
- Successful examples of terpene-based drugs include the antihypertensive drug losartan (derived from oleanolic acid) and the antibiotic tiacumicin B (derived from a macrolide terpene)
Structure-activity relationships of terpenes
- Understanding the structure-activity relationships (SARs) of terpenes is crucial for the rational design of terpene-based drugs and the optimization of their pharmacological properties
- SAR studies involve the systematic modification of terpene structures and the evaluation of their biological activities, enabling the identification of key structural features responsible for their therapeutic effects
- Techniques such as quantitative structure-activity relationship (QSAR) modeling and molecular docking are used to predict the biological activities of terpene analogs and guide the design of new derivatives
Terpenes in traditional medicine
- Terpenes have been used in traditional medicine systems for centuries, often as part of complex herbal preparations or essential oils
- The medicinal properties of terpenes in traditional medicine have inspired modern research into their therapeutic potential and mechanisms of action
Terpenes in Ayurvedic medicine
- Ayurvedic medicine, the traditional medical system of India, employs numerous terpene-containing plants for the treatment of various ailments
- Examples of terpenes used in Ayurvedic medicine include limonene (from Citrus spp.), β-caryophyllene (from Syzygium aromaticum), and withanolides (from Withania somnifera)
- Ayurvedic formulations containing terpenes are used for their anti-inflammatory, immunomodulatory, and adaptogenic properties
Terpenes in Traditional Chinese Medicine
- Traditional Chinese Medicine (TCM) has a long history of using terpene-rich plants and essential oils for the prevention and treatment of diseases
- Terpenes such as artemisinin (from Artemisia annua), ginkgolides (from Ginkgo biloba), and ginsenosides (from Panax ginseng) are important components of TCM formulas
- TCM practitioners use terpene-containing herbs for their antimicrobial, cardiovascular, and neuroprotective effects, often in combination with other herbs based on the principles of TCM theory
Terpenes in other traditional medical systems
- Terpenes are also used in other traditional medical systems around the world, such as traditional African medicine, Native American medicine, and Islamic medicine
- Examples include the use of eucalyptol (from Eucalyptus spp.) in traditional African medicine for respiratory disorders, and the use of thymol (from Thymus vulgaris) in Islamic medicine for its antimicrobial properties
- The study of terpenes in traditional medicine can provide valuable insights into their therapeutic potential and guide the development of new terpene-based drugs
Safety and toxicity of terpenes
- While many terpenes have demonstrated therapeutic benefits, it is important to consider their safety and potential toxicity when developing terpene-based drugs or using them in medicinal applications
- The safety and toxicity of terpenes can vary depending on factors such as dose, route of administration, and individual susceptibility
Terpene-drug interactions and contraindications
- Terpenes can interact with other drugs, leading to potential adverse effects or altered pharmacological responses
- Some terpenes, such as grapefruit juice furanocoumarins, are known to inhibit cytochrome P450 enzymes, which can increase the bioavailability and toxicity of certain drugs (statins, calcium channel blockers)
- Terpenes may also have contraindications for certain medical conditions or populations, such as pregnancy, lactation, or specific allergies
Allergic reactions and sensitization to terpenes
- Some individuals may develop allergic reactions or sensitization to specific terpenes, particularly when exposed to high concentrations or prolonged use
- Terpenes such as limonene and linalool are known to cause contact dermatitis in susceptible individuals, especially when oxidized or degraded
- Proper patch testing and labeling of terpene-containing products can help identify and prevent allergic reactions
Toxicological studies on terpenes
- Toxicological studies are essential for evaluating the safety and potential adverse effects of terpenes before
Key Terms to Review (29)
Acyclic terpenes: Acyclic terpenes are a type of terpene that do not have a cyclic structure, meaning they are open-chain compounds. These compounds are formed from isoprene units, which are the building blocks of terpenes, and can vary in length and complexity. Acyclic terpenes play significant roles in various biological processes and are commonly found in nature, contributing to the scent of many plants and serving as precursors to more complex terpenes.
Anti-inflammatory properties: Anti-inflammatory properties refer to the ability of certain compounds to reduce inflammation, which is the body's response to injury or infection. This can help alleviate symptoms associated with various health conditions, making it an important focus in medicinal chemistry. These properties are especially significant in the study of natural compounds found in plants, where they can modulate inflammatory pathways and provide therapeutic benefits.
Antimicrobial activity: Antimicrobial activity refers to the ability of a substance to inhibit the growth of or kill microorganisms, such as bacteria, viruses, fungi, and parasites. This property is crucial in medicinal chemistry for developing drugs and compounds that can effectively combat infections and diseases caused by these pathogens. Certain natural compounds, including terpenes and flavonoids, exhibit antimicrobial activity, making them valuable in the search for new therapeutic agents.
Aromatherapy: Aromatherapy is a holistic healing practice that utilizes essential oils extracted from plants to promote physical and emotional well-being. By harnessing the therapeutic properties of these oils, aromatherapy aims to enhance overall health, alleviate stress, and improve mood through inhalation or topical application.
Artemisinin: Artemisinin is a potent antimalarial compound derived from the sweet wormwood plant, Artemisia annua. This natural product has gained significant importance in medicine due to its effectiveness against malaria, especially in treating multidrug-resistant strains of the parasite Plasmodium falciparum. Its discovery and subsequent use have revolutionized malaria treatment protocols and continue to play a critical role in global health efforts.
Betulinic acid: Betulinic acid is a pentacyclic triterpenoid compound derived from the bark of the birch tree. It is recognized for its potential therapeutic properties, including anti-cancer and anti-inflammatory effects, linking it closely to the broader category of terpenes which are known for their diverse biological activities and structural complexity.
Bisabolol: Bisabolol is a natural monocyclic sesquiterpene alcohol primarily derived from the essential oil of the Candeia tree and is known for its soothing, anti-inflammatory, and antimicrobial properties. It plays an important role in the cosmetic and pharmaceutical industries, as it enhances the efficacy of various formulations while providing a pleasant scent.
Cyclic terpenes: Cyclic terpenes are a class of terpenes characterized by their ring structures, which can vary in size and complexity. These compounds are derived from isoprene units and can be found in many natural sources, playing significant roles in the scent and flavor of plants, as well as in their defense mechanisms. The cyclic nature of these compounds contributes to their unique chemical properties and biological activities.
Diterpenes: Diterpenes are a class of chemical compounds made up of four isoprene units, which gives them a backbone of 20 carbon atoms. These compounds play a significant role in the chemistry of many plants, often contributing to their aroma and medicinal properties. Diterpenes are known for their diverse biological activities and can be found in various natural sources, including essential oils and resins.
FDA Regulations: FDA regulations are the rules set by the U.S. Food and Drug Administration to ensure the safety, efficacy, and security of drugs, biologics, medical devices, and food products. These regulations govern everything from clinical trials to manufacturing processes, aiming to protect public health and facilitate the approval of new therapies and treatments.
Forskolin: Forskolin is a natural compound derived from the roots of the Coleus forskohlii plant, belonging to the mint family. It is known for its ability to activate adenylate cyclase, an enzyme that increases levels of cyclic AMP (cAMP) in cells, influencing various physiological processes. Forskolin's connection to medicinal chemistry stems from its potential therapeutic uses, including weight loss, heart health, and as a potential treatment for glaucoma.
Functionalization: Functionalization refers to the process of introducing new functional groups or modifying existing ones on a molecule, which can significantly alter its chemical properties and biological activity. This process is crucial in the synthesis and design of various organic compounds, especially in drug development, where specific functional groups can enhance therapeutic effects or reduce toxicity.
Gas chromatography: Gas chromatography is a technique used to separate and analyze compounds that can be vaporized without decomposition. It involves the movement of a sample mixture through a column that is coated with a stationary phase, where components of the mixture interact differently with this phase, leading to separation. This method is particularly useful for analyzing volatile organic compounds, including terpenes found in essential oils and plants.
GRAS Status: GRAS status stands for 'Generally Recognized As Safe' and refers to a designation by the FDA that certain substances added to food are considered safe by qualified experts. This designation allows specific substances, including certain natural compounds, to be used in food products without the need for pre-market approval. GRAS status is crucial in the context of food safety and regulation, especially when discussing compounds derived from natural sources like terpenes, which are often used in flavoring and fragrance.
Isoprene Unit: The isoprene unit is a five-carbon building block, specifically 2-methyl-1,3-butadiene, that serves as the fundamental structural component of terpenes and terpenoids. This unit's significance lies in its ability to polymerize and combine in various ways, leading to the vast diversity of terpene structures found in nature, which are essential for a variety of biological functions.
Limonene: Limonene is a cyclic monoterpene that is primarily found in the rinds of citrus fruits like oranges and lemons. This colorless liquid has a strong citrus aroma and is well-known for its role in flavoring and fragrance applications, as well as for its potential health benefits and industrial uses. Limonene is classified as a terpene, a significant category of compounds derived from plants, which contribute to the characteristic scents and flavors in various essential oils.
Mass Spectrometry: Mass spectrometry is an analytical technique used to measure the mass-to-charge ratio of ions, allowing for the identification and quantification of molecules in a sample. This method is essential in various fields for characterizing chemical compounds, analyzing biomolecules, and determining molecular structures, making it invaluable in early drug development, chemical property assessments, and exploring complex mixtures such as natural products.
Menthol: Menthol is a cyclic monoterpene alcohol that is derived from mint oils, particularly peppermint. Its characteristic minty flavor and aroma make it a popular additive in various products such as candies, cosmetics, and medicinal formulations. Menthol's cooling sensation is attributed to its ability to activate the TRPM8 receptor, which plays a crucial role in the perception of cold.
Methylerythritol phosphate pathway: The methylerythritol phosphate (MEP) pathway is a crucial metabolic route used by many bacteria and some plants to synthesize isoprenoids, which are vital for various biological functions. This pathway is an alternative to the mevalonate pathway, primarily found in animals and fungi, and it begins with the conversion of pyruvate and glyceraldehyde-3-phosphate into methylerythritol phosphate, leading to the production of key precursors for terpenes and other important biomolecules.
Mevalonate pathway: The mevalonate pathway is a crucial metabolic pathway that synthesizes isoprenoids, including cholesterol, terpenes, and steroid hormones. It begins with acetyl-CoA and leads to the production of mevalonate, which is then converted into various isoprenoid compounds essential for numerous biological functions. This pathway is particularly important for the biosynthesis of terpenes and plays a role in the formation of alkaloids through further biochemical transformations.
Monocyclic Terpenes: Monocyclic terpenes are a class of organic compounds characterized by a single cyclic structure composed of isoprene units, which are fundamental building blocks of terpenes. These compounds typically consist of a ring structure containing five carbon atoms and may include various functional groups, influencing their chemical properties and biological activities. Monocyclic terpenes are commonly found in essential oils and contribute to the aromatic qualities of many plants.
Monoterpenes: Monoterpenes are a class of organic compounds composed of two isoprene units, resulting in a molecular formula of C10H16. They are widely found in nature, especially in essential oils of various plants, contributing to their aroma and flavor. Monoterpenes are known for their diverse biological activities, including antimicrobial and anti-inflammatory properties, making them significant in both pharmacology and the fragrance industry.
Oleanolic acid: Oleanolic acid is a natural triterpenoid compound found in various plants, notably in the leaves of the olive tree and many other medicinal herbs. This compound is structurally related to other terpenes and has garnered attention for its potential health benefits, including anti-inflammatory, antioxidant, and hepatoprotective properties, making it significant in the study of natural products and their therapeutic applications.
Oxidation: Oxidation refers to a chemical process where a molecule, atom, or ion loses electrons, resulting in an increase in oxidation state. This process is essential in various biological reactions, especially in metabolism, where it plays a crucial role in transforming substances into more hydrophilic forms that can be easily excreted from the body. Additionally, oxidation is fundamental in the activity of specific enzymes, particularly in the metabolism of drugs and natural compounds.
Phytotherapy: Phytotherapy is the use of plant-derived substances for therapeutic purposes to treat or prevent diseases. It involves utilizing the natural properties of plants, including their bioactive compounds, to promote health and well-being. Phytotherapy can encompass a wide range of applications, from herbal medicine to dietary supplements, making it an essential aspect of alternative and complementary medicine.
Polycyclic terpenes: Polycyclic terpenes are a class of organic compounds characterized by multiple interconnected cyclic structures, derived from the natural product class known as terpenes. These compounds play significant roles in the chemical landscape of various organisms, contributing to biological functions and interactions, and are often noted for their complex architectures and diverse pharmacological properties.
Sesquiterpenes: Sesquiterpenes are a class of terpenes that consist of three isoprene units, leading to a molecular formula of C15H24. These compounds play important roles in the plant kingdom, often contributing to the aroma and flavor of various plants and serving as precursors for other essential compounds. They are also notable for their wide array of biological activities, including anti-inflammatory, antimicrobial, and anticancer properties.
Taxol: Taxol, also known as paclitaxel, is a chemotherapeutic agent derived from the bark of the Pacific yew tree (Taxus brevifolia) that is primarily used to treat various cancers, including breast and ovarian cancer. It works by stabilizing microtubules and preventing their depolymerization during cell division, thereby disrupting the normal function of the mitotic spindle.
Triterpenes: Triterpenes are a class of chemical compounds composed of six isoprene units, resulting in a structure that typically consists of 30 carbon atoms. These compounds are known for their diverse biological activities and are found in a variety of plants, playing significant roles in medicinal chemistry and pharmacology due to their therapeutic potential.