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Triterpene

Triterpenes are a diverse class of natural products composed of six isoprene units, forming a characteristic 30-carbon skeleton that is predominantly found in plants, though also present in fungi, algae, and some animals.^[1] Triterpenoids are their oxygenated or otherwise modified derivatives. These compounds are biosynthesized via the mevalonate (MVA) or methylerythritol 4-phosphate (MEP) pathways, where isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP) condense to form farnesyl pyrophosphate (FPP), which dimerizes into squalene and is then epoxidized to 2,3-oxidosqualene; this intermediate undergoes cyclization catalyzed by oxidosqualene cyclases (OSCs) to yield various skeletons such as protostane, dammarane, lanostane, or lupane.^[2] Structurally, triterpenoids exhibit a wide range of forms, from acyclic to pentacyclic structures, often further modified by oxidation, glycosylation, or acylation to enhance their functionality.^[3] As primary metabolites, triterpenoids play essential roles in plant physiology, including serving as phytosterols that maintain cell membrane fluidity and as brassinosteroids that act as growth-regulating hormones.^[1] In their specialized metabolite capacity, they contribute to ecological interactions by providing defense against herbivores, pathogens, and environmental stresses, such as through antimicrobial saponins or insecticidal cucurbitacins.^[2] Notable examples include β-amyrin (an oleanane-type triterpenoid abundant in many plants), ginsenosides from ginseng (dammarane-type with anti-inflammatory properties), and glycyrrhizin from licorice (a sweet-tasting pentacyclic triterpenoid used in medicine).^[1] Over 20,000 distinct triterpenoid structures have been identified, underscoring their chemical diversity and evolutionary significance across plant taxa like Asteraceae, Cucurbitaceae, and Fabaceae.^[4] Triterpenoids hold substantial biomedical and industrial value due to their pharmacological activities, including anticancer, antiviral, and anti-inflammatory effects, with compounds like celastrol and QS-21 advancing in drug development for cancer therapy and vaccines, respectively.^[1] Their biosynthesis has been extensively studied for metabolic engineering, enabling enhanced production in microbial hosts for sustainable sourcing of high-value products.^[2]

Overview

Definition and Classification

Triterpenes are a class of terpenoids characterized by a molecular formula of C30H48 for their hydrocarbon forms, consisting of six isoprene (C5) units condensed together, distinguishing them from other terpenoids by their specific carbon count and biosynthetic origin from the linear precursor squalene.^[5]^[6] The term "triterpene" derives from the Greek prefix "tri-" combined with "terpene," reflecting their composition as equivalent to three standard terpene units (each C10H16), a nomenclature established to highlight their structural multiplicity relative to monoterpenes (C10).^[7] Within the broader category of terpenoids, triterpenes are classified primarily by their degree of cyclization, ranging from acyclic (linear) forms to highly cyclic structures. Linear triterpenes, such as squalene, represent the uncyclized precursor with an open-chain configuration.^[6] Cyclic triterpenes arise from enzymatic cyclization of 2,3-oxidosqualene and include monocyclic (e.g., achilleol A), bicyclic, and tricyclic variants, while polycyclic types dominate natural occurrences, encompassing tetracyclic skeletons like lanostane (exemplified by lanosterol in animals and cycloartenol in plants) and pentacyclic forms such as hopane (common in prokaryotes).^[6]^[8] Additional polycyclic examples include dammarane (tetracyclic) and lupane, oleanane, and ursane (pentacyclic), each defined by distinct ring fusions and stereochemistry that underpin their biological roles.^[6] Nomenclature for triterpenes follows conventions based on their core carbon skeletons, with trivial names like ursane or oleanane assigned to specific pentacyclic frameworks, supplemented by IUPAC systematic rules for hydrocarbons that prioritize the longest chain or parent ring system with numbered substituents and functional groups.^[6] For instance, ursane-type triterpenes are named as derivatives of the ursane parent hydrocarbon (a pentacyclic structure with specific methyl and ring arrangements), while IUPAC guidelines ensure precise designation of stereoisomers and modifications, such as in lanosterol (systematic name: lanosta-8,24-dien-3β-ol).^[5] This approach allows for standardized identification across diverse natural variants, emphasizing the skeletal integrity over exhaustive substituent listing.^[9]

Historical Discovery

The discovery of triterpenes began in the early 19th century with the isolation of various pentacyclic triterpenoid structures from plant sources. These early isolations relied on basic extraction and crystallization techniques, providing initial insights into the chemical diversity of natural resins and leaves, though full structural elucidation remained elusive for decades due to limited analytical tools. In the 20th century, significant advancements came from Leopold Ruzicka's work in the 1920s, where he determined the structure of squalene, a linear C30 isoprenoid precursor central to triterpene biosynthesis, building on the isoprene rule he formulated to explain terpenoid assembly from isoprene units. Ruzicka's contributions, which earned him the 1939 Nobel Prize in Chemistry, laid the foundation for understanding how triterpenes form through cyclization of squalene derivatives. Later, in the 1950s, John Cornforth and George Popják elucidated the role of lanosterol as a key steroid precursor derived from oxidosqualene cyclization, using isotopic labeling and enzymatic studies to map the biosynthetic pathway in animal and yeast systems.^[10]^[11] A major milestone occurred in the 1960s when Guy Ourisson identified hopanoids as pentacyclic triterpenoids in bacterial membranes, establishing their functional analogy to eukaryotic sterols and providing evidence for evolutionary links between prokaryotic and eukaryotic lipid biosynthesis. Ourisson's isolation of bacteriohopanetetrol and related compounds from bacteria like Methylococcus highlighted the ubiquity of triterpenoids across domains of life. The evolution of analytical techniques further accelerated discoveries, transitioning from classical crystallization methods in the early 20th century to nuclear magnetic resonance (NMR) spectroscopy in the 1950s–1960s for proton assignments, and mass spectrometry (MS) in the 1970s–1980s for precise molecular weight and fragmentation analysis, enabling unambiguous structure elucidation of complex triterpene skeletons.^[12]^[13]

Biosynthesis

Biosynthetic Pathway

Triterpenes are synthesized via the isoprenoid pathway, starting from the formation of isopentenyl pyrophosphate (IPP) and its isomer dimethylallyl pyrophosphate (DMAPP), which are generated through two alternative routes: the mevalonate (MVA) pathway predominant in animals, fungi, and the cytosol of plants, or the 2-C-methyl-D-erythritol 4-phosphate (MEP) pathway found in bacteria, plastids of plants, and some algae.^[14] These C5 units undergo sequential head-to-tail condensations catalyzed by prenyltransferases: DMAPP combines with one IPP to form geranyl pyrophosphate (GPP, C_{10}), which then reacts with another IPP to yield farnesyl pyrophosphate (FPP, C_{15}).^[14] The MVA pathway involves ATP-dependent phosphorylation steps, including those catalyzed by mevalonate kinase and phosphomevalonate kinase, to activate intermediates for decarboxylation and conversion to IPP.^[14] The committed step in triterpene biosynthesis occurs when two molecules of FPP are dimerized by squalene synthase (also known as farnesyl-diphosphate farnesyltransferase) in a two-stage reaction: first, a stereospecific condensation forms presqualene diphosphate (PSPP), followed by a NADPH-dependent reductive rearrangement to produce the linear hydrocarbon squalene (C_{30}H_{50}).^[15] This process occurs in the endoplasmic reticulum of eukaryotes and requires NADPH as a cofactor for the final reduction, ensuring the release of pyrophosphate and formation of the symmetric squalene backbone.^[15] Squalene is then converted to 2,3-oxidosqualene by squalene epoxidase, a membrane-bound flavin-dependent monooxygenase enzyme that catalyzes the NADPH- and O_{2}-dependent epoxidation at the 2,3-position, introducing an oxygen atom essential for subsequent cyclization.^[16] This step activates the substrate for folding into a chair-boat-chair-boat conformation, priming it for polycyclization. In prokaryotes, an alternative branch bypasses epoxidation, where squalene is directly cyclized by squalene-hopene cyclase to form hopene, a pentacyclic triterpene.^[17] The key cyclization phase is mediated by oxidosqualene cyclases (OSCs), which orchestrate the enzyme-initiated cascade of carbocation rearrangements and ring closures on 2,3-oxidosqualene to generate diverse tetracyclic or pentacyclic skeletons, typically retaining the C_{30}H_{50}O formula as in lanosterol or cycloartenol.^[16] Branching occurs based on organism-specific OSCs: in animals, lanosterol synthase (an OSC) produces lanosterol, a tetracyclic triterpenoid intermediate featuring a lanostane skeleton; in plants, cycloartenol synthase yields cycloartenol, which includes a cyclopropane ring distinguishing the plant pathway.^[14] These cyclizations proceed without additional cofactors beyond the protonation by the enzyme's acidic residues, though the overall pathway's energy demands are met through the prior NADPH reductions and ATP investments in precursor formation.^[14]

Key Enzymes and Regulation

The biosynthesis of triterpenes involves several key enzymes that catalyze committed steps in the pathway from isoprenoid precursors. Squalene synthase (SQS, EC 2.5.1.21) is a pivotal enzyme that condenses two molecules of farnesyl diphosphate (FPP) to form presqualene diphosphate, which is then rearranged and reduced to squalene, marking the first dedicated step toward sterol and triterpene production.^[18] Squalene epoxidase (SQE, EC 1.14.99.7), a flavin-dependent monooxygenase, subsequently oxidizes squalene to 2,3-oxidosqualene, the universal precursor for cyclization reactions, and this step is often rate-limiting in the pathway.^[19] Oxidosqualene cyclases (OSCs), such as lanosterol synthase (EC 5.4.99.7), then catalyze the complex cyclization of 2,3-oxidosqualene to form tetracyclic structures like lanosterol, initiating the diversification of triterpene skeletons.^[20] SQS is a membrane-bound enzyme anchored to the endoplasmic reticulum, featuring two distinct active sites: one for the condensation reaction involving FPP binding via conserved aspartate-rich motifs, and another for the NADPH-dependent reduction of the intermediate.^[21] Crystal structures of human SQS, determined in the early 2000s and refined in subsequent 2010s studies, reveal a dimeric architecture with a central cavity for substrate access and inhibitor binding, highlighting conserved residues critical for catalysis across eukaryotes.^[22] SQE consists of a catalytic domain with a FAD-binding motif and a membrane-interacting region, as elucidated by its 2019 crystal structure, which shows how the enzyme positions squalene for stereospecific epoxidation.^[19] OSCs, typically soluble or peripherally associated with membranes, possess a conserved aspartate-rich DDTA motif that protonates the epoxide to initiate polycyclization, with structural variations among isoforms dictating product specificity.^[20] Regulation of these enzymes occurs at multiple levels to maintain cellular sterol homeostasis. In animals, sterol regulatory element-binding proteins (SREBPs) transcriptionally activate SQS and SQE genes in response to low sterol levels, with nuclear translocation of SREBPs triggered by sterol depletion in the endoplasmic reticulum.^[23] Feedback inhibition by end-products, such as cholesterol, suppresses SQS activity through allosteric mechanisms and reduces upstream flux, while inhibition of SQE or SQS can indirectly elevate HMG-CoA reductase activity via compensatory signaling.^[24] In plants, elicitors like jasmonic acid induce triterpene biosynthesis via jasmonate signaling pathways, upregulating OSCs and SQE through basic helix-loop-helix transcription factors such as TSAR1 and TSAR2, which bind promoter elements to enhance saponin production under stress.^[25] Genetic variations in triterpene pathway enzymes can lead to metabolic disorders. Mutations in the DHCR7 gene, encoding 7-dehydrocholesterol reductase—a downstream enzyme converting 7-dehydrocholesterol to cholesterol in the lanosterol-derived pathway—cause Smith-Lemli-Opitz syndrome, an autosomal recessive condition characterized by cholesterol deficiency, elevated 7-dehydrocholesterol, and developmental abnormalities.^[26] Over 100 such mutations have been identified, often impairing enzyme activity and disrupting sterol balance essential for embryogenesis.^[27]

Natural Occurrence

In Plants and Fungi

Triterpenes are highly prevalent in the plant kingdom, with over 100 distinct carbon skeletons identified across more than 50 families, including prominent examples in Asteraceae and Fabaceae, where they contribute to structural diversity and secondary metabolism.^[28]^[29] They are also found in algae, such as the green alga Botryococcus braunii, which can accumulate triterpene hydrocarbons comprising up to 30% of its dry biomass.^[30] In particular, betulin, a lupane-type triterpene, accumulates abundantly in birch bark (Betula spp.), comprising up to 30% of the dry weight in the outer bark layer, serving as a key reservoir for these compounds.^[31] In fungi, triterpenes manifest through sterol biosynthesis pathways, with ergosterol—derived from the triterpene precursor squalene—being a dominant component in yeasts such as Saccharomyces cerevisiae, essential for cellular membrane function.^[32] Additionally, hopanoids, pentacyclic triterpenoids analogous to sterols, occur in certain fungi, including fission yeasts like Schizosaccharomyces japonicus, where they enhance membrane rigidity and stability in collaboration with ergosterol.^[33] These compounds are also noted in mycorrhizal fungi, supporting membrane integrity under environmental stress. Biodiversity hotspots, particularly tropical flora in regions like the Americas and Africa, represent rich sources due to high species diversity and elevated triterpene accumulation, facilitating targeted collection from resinous trees.^[34]

In Animals and Microorganisms

In animals, triterpenes manifest primarily as sterols derived from the tetracyclic triterpenoid lanosterol, which serves as a key biosynthetic intermediate in vertebrates. Cholesterol, a C27 sterol ultimately derived from lanosterol through demethylation and other modifications, is an essential component of eukaryotic cell membranes, typically comprising 20-40 mol% of plasma membrane lipids to maintain fluidity and integrity.^[35]^[36]^[37] In microorganisms, triterpenoid-like compounds known as bacteriohopanepolyols (BHPs) play analogous roles to sterols in stabilizing bacterial membranes. These pentacyclic structures, such as bacteriohopanetetrol, are produced by diverse bacteria and can constitute up to 20% of membrane lipids, as observed in species like Zymomonas mobilis, where they modulate fluidity and stress resistance.^[38]^[39]^[40] Evolutionarily, hopanoids represent prokaryotic precursors or analogs to eukaryotic sterols, facilitating membrane ordering in oxygen-poor environments; fossilized hopane biomarkers in 2.7 billion-year-old Australian rocks provide evidence of their ancient prevalence in microbial communities.^[41]^[42]

Biological Roles

Structural and Metabolic Functions

Triterpenes, particularly sterols, are essential for maintaining cellular membrane architecture in diverse organisms. In animal cells, cholesterol embeds within phospholipid bilayers, ordering the acyl chains of phospholipids to modulate membrane fluidity and reduce permeability. This interaction broadens the temperature range over which membranes remain in a liquid-ordered state, preventing gel-phase transitions that could impair function. Similarly, in plants, phytosterols like β-sitosterol and stigmasterol perform comparable roles, stabilizing membranes by promoting ordered packing and influencing phase behavior.^[43]^[44]^[45] In bacteria, hopanoids—pentacyclic triterpenoids—function as sterol analogs to support membrane integrity under environmental stresses. These molecules rigidify bacterial membranes, decreasing passive ion diffusion and enhancing resilience to desiccation and osmotic fluctuations. For instance, in Rhodopseudomonas palustris, hopanoid mutants exhibit compromised membrane stability during low-pH or desiccation challenges, underscoring their role in osmoregulation and overall envelope homeostasis.^[38]^[46]^[47] Beyond structural support, triterpenes act as key metabolic intermediates in eukaryotic pathways. Lanosterol, an early triterpenoid precursor, is cyclized from squalene in the mevalonate pathway and undergoes demethylation and desaturation to yield cholesterol. This cholesterol then serves as a substrate for synthesizing vitamin D via photochemical conversion in skin and bile acids through hepatic oxidation, facilitating nutrient absorption and metabolic regulation.^[48]^[49]^[50] Deficiencies in these triterpenes reveal their quantitative impacts on cellular processes. Cholesterol depletion, often induced experimentally with methyl-β-cyclodextrin, disrupts lipid raft formation—cholesterol-enriched domains that organize signaling proteins—with studies showing reduction in raft-associated proteins like GPI-anchored enzymes. This leads to impaired signal transduction, such as diminished receptor clustering in pathways like Fas-mediated apoptosis, highlighting triterpenes' critical role in membrane-mediated metabolism.^[51]^[52]^[53]

Defensive and Signaling Roles

Triterpenes, particularly saponins, play crucial roles in plant defense against herbivores by acting as antifeedants that deter insect feeding and disrupt cellular integrity. In ginseng (Panax ginseng), ginsenosides, a class of triterpenoid saponins, exhibit potent antifeedant activity against pests such as the small white butterfly (Pieris rapae), reducing larval feeding and oviposition through interference with gustatory receptors and digestive processes. These compounds permeabilize insect cell membranes, leading to leakage of cellular contents and eventual lysis, thereby enhancing plant survival against herbivory.^[54]^[55]^[56] In plant-pathogen interactions, triterpenoids serve as signaling molecules that trigger defensive responses, including localized cell death to restrict pathogen spread. For instance, phytolaccagenin, a triterpenoid aglycone derived from Phytolacca species, contributes to antifungal defense by inhibiting the growth of pathogenic fungi such as Candida species through disruption of fungal membrane function.^[57]^[58] Triterpenes also function as allelochemicals, mediating interplant competition by inhibiting the growth of neighboring species. Ursolic acid, a pentacyclic triterpenoid abundant in plants like Alstonia scholaris, leaches into the soil and suppresses weed seed germination and seedling development, as demonstrated in bioassays against species such as Bidens pilosa. This allelopathic effect alters soil microbial activity and nutrient availability, favoring the producer plant in competitive environments.^[59]^[60] Brassinosteroids, a class of triterpenoid hormones, play key signaling roles in plant growth and development, regulating processes such as cell elongation, division, and differentiation, as well as responses to environmental stresses like drought and temperature extremes.^[1] In microorganisms, hopanoids—bacterial triterpenoids analogous to sterols—modulate community behaviors through membrane stabilization that supports quorum sensing and biofilm architecture. In species like Rhodopseudomonas palustris, hopanoids promote surface attachment and extracellular matrix production, essential for biofilm initiation and maturation, while influencing density-dependent signaling to coordinate collective responses such as virulence factor expression. Deficiency in hopanoid biosynthesis impairs biofilm integrity and quorum sensing-regulated processes, highlighting their role in bacterial adaptation and persistence.^[61]^[62]

Derivatives

Triterpenoids

Triterpenoids are oxygenated derivatives of triterpenes, characterized by the incorporation of functional groups such as hydroxyl (-OH), carbonyl (C=O), and carboxyl (-COOH) at various positions on the parent hydrocarbon skeleton. These modifications enhance the chemical reactivity and biological functionality of the molecules compared to their non-oxidized precursors.^[63] The formation of triterpenoids typically occurs through post-cyclization oxidative processes mediated by cytochrome P450-dependent monooxygenases (P450s), which introduce oxygen atoms at specific carbon sites, often leading to the production of carboxylic acids. For instance, oleanolic acid (C₃₀H₄₈O₃), a pentacyclic triterpenoid, arises from the sequential oxidation of β-amyrin, primarily at the C-28 position, catalyzed by enzymes like CYP716A subfamily members. This biosynthetic step follows the initial cyclization of 2,3-oxidosqualene and contributes to the structural diversification observed in nature.^[64]^[65] Over 20,000 triterpenoid structures have been identified, reflecting immense diversity driven by variations in oxidation patterns across different skeletal frameworks.^[66] They are commonly classified based on these oxidation motifs and the underlying carbon skeleton, such as the lupane-type triterpenoids featuring a 3β-hydroxyl group, as seen in compounds like betulin. This classification highlights how site-specific oxidations generate distinct subclasses with tailored properties.^[67] Compared to parent triterpene hydrocarbons, triterpenoids exhibit increased polarity due to their oxygen-containing functional groups, which alters their stability and solubility profiles. While hydrocarbons are highly non-polar and primarily soluble in non-polar solvents, triterpenoids demonstrate improved solubility in polar organic solvents like alcohols (e.g., ethanol), facilitating their extraction and biological interactions without compromising lipophilicity.^[68]^[69]

Steroids and Saponins

Steroids represent a subclass of triterpenoid derivatives characterized by a tetracyclic gonane nucleus, consisting of three six-membered rings and one five-membered ring, often with methyl groups at C10 and C13, and variable side chains at C17.^[70] These compounds are classified by carbon content into various types, such as C18 (e.g., estrane-based estrogens), C19 (e.g., androstane-based androgens lacking a side chain beyond C17), C21 (e.g., pregnane-based progestogens and corticosteroids with an additional two-carbon extension at C17), and C27 (e.g., sterols).^[70] A prototypical example is cholesterol, a C27 sterol with the molecular formula C27H46O, featuring a hydroxyl group at C3 and a double bond between C5 and C6, derived biosynthetically from the triterpenoid lanosterol through sequential modifications.^[71] Steroids often function as aglycones in essential hormones, such as cortisol (a C21 glucocorticoid), which regulates metabolism and immune response without sugar attachments.^[72] In contrast, saponins are glycosylated triterpenoids where a hydrophobic aglycone—typically based on oleanane, ursane, or lupane skeletons—is covalently linked to one or more hydrophilic sugar moieties, conferring an amphiphilic character.^[63] This structure enables saponins to act as natural surfactants, producing stable foams upon agitation, a property exploited in traditional uses like soap substitutes.^[63] A representative example is ginsenoside Rb1 from Panax ginseng, featuring a dammarane-type aglycone with glucose and arabinose sugars attached at multiple positions, enhancing water solubility and bioactivity. Saponins exhibit hemolytic activity by interacting with cholesterol in cell membranes, forming pores that disrupt integrity, which contributes to their role as plant defense compounds against herbivores and pathogens.^[73] Key differences between steroids and saponins lie in their glycosylation status and functional roles: steroids remain as non-glycosylated aglycones critical for animal hormone signaling, exemplified by cortisol's mediation of stress responses, whereas saponins are predominantly glycosides serving defensive purposes in plants with potent hemolytic effects.^[63] Biosynthetically, steroids arise via demethylation shortcuts from lanosterol, where cytochrome P450 enzymes like CYP51 remove methyl groups at C4 and C14 in a multi-step process to yield streamlined structures like cholesterol.^[72] In saponins, the pathway diverges toward glycosylation, with UDP-glycosyltransferases adding sugar chains to the triterpene aglycone, which modifies solubility and toxicity without extensive demethylation.^[63]

Applications and Research

Pharmacological Uses

Triterpenes exhibit significant pharmacological potential in various therapeutic areas, particularly due to their anti-inflammatory, anticancer, antiviral, and hepatoprotective properties. Boswellic acids, pentacyclic triterpenes derived from the resin of Boswellia serrata (frankincense), act as potent inhibitors of 5-lipoxygenase (5-LOX), a key enzyme in leukotriene biosynthesis, with acetyl-11-keto-β-boswellic acid demonstrating an IC50 of 1.5 μM in cell-free assays.^[74] This inhibition reduces pro-inflammatory mediators, contributing to their efficacy in managing chronic inflammatory conditions such as osteoarthritis. Clinical trials, including randomized double-blind studies, have shown that boswellic acid extracts (e.g., 5-Loxin® at 100-250 mg/day) improve pain, stiffness, and physical function in osteoarthritis patients, with benefits observed after 90 days of treatment and a favorable safety profile compared to placebo.^[75] In oncology, ginsenosides, triterpene saponins from Panax ginseng, promote apoptosis in cancer cells by modulating the Bcl-2 family proteins, increasing the pro-apoptotic Bax/Bcl-2 ratio and activating caspase pathways.^[76] For instance, ginsenoside Rh2 induces mitochondrial membrane depolarization and cell cycle arrest in breast cancer cell lines like MDA-MB-231, enhancing tumor cell death without significant toxicity to normal cells.^[77] Although primarily supported by preclinical data, phase II clinical trials of ginseng extracts (containing ginsenosides) have explored their role in breast cancer, such as evaluating biomarker changes in tumors with gelatin-encapsulated American ginseng root (1000-2000 mg/day), demonstrating potential immunomodulatory effects and reduced cancer-related fatigue in survivors.^[78]^[79] Antiviral applications of triterpenes are exemplified by betulinic acid derivatives, which target viral maturation processes. Bevirimat, a semisynthetic betulinic acid analog, functions as an HIV-1 maturation inhibitor by blocking the cleavage of the Gag-SP1-NC junction, preventing the formation of infectious virions with EC50 values in the low nanomolar range against wild-type HIV-1.^[80] The U.S. FDA granted fast-track designation to bevirimat in 2004 for HIV treatment, leading to phase II clinical trials in the 2000s that confirmed its antiviral activity in treatment-experienced patients, though development was later discontinued due to variability in patient responses.^[81] Glycyrrhizin, a triterpenoid glycoside from Glycyrrhiza glabra (licorice root), has been investigated for chronic hepatitis C virus (HCV) infection, where intravenous administration (up to 240 mg thrice weekly) significantly lowers serum alanine aminotransferase (ALT) levels by 20-50% during treatment, reflecting reduced liver inflammation without altering HCV-RNA titers.^[82] Meta-analyses of randomized controlled trials confirm this ALT reduction (mean decrease of 15.63 U/L) with oral or intravenous doses of 100-240 mg/day over 4-26 weeks, supporting its adjunctive use in HCV management.^[83] However, prolonged use at doses exceeding 100 mg/day can lead to side effects such as hypertension and hypokalemia due to cortisol-like mineralocorticoid activity, necessitating monitoring in patients with cardiovascular risk.^[84]

Industrial and Emerging Applications

Triterpenes and their derivatives find diverse industrial applications beyond pharmaceuticals, leveraging their unique chemical properties for commercial products. Betulin, a pentacyclic triterpene extracted primarily from birch bark using methods such as organic solvent extraction or microwave-assisted techniques, is incorporated into cosmetic formulations for its protective effects against ultraviolet (UV) radiation and oxidative stress.^[31] These extracts, yielding up to 18% betulin, enhance skin barrier function and provide antioxidant benefits in creams and lotions.^[85] Similarly, squalene, a linear triterpene historically sourced from shark liver oil, serves as a key ingredient in lubricants due to its high stability and low volatility, as well as in vaccine adjuvants like MF59 for emulsion stability.^[86] Traditional shark-derived squalene has been largely replaced by plant-based alternatives to address sustainability concerns, maintaining its role in industrial emulsions.^[87] In food processing and agriculture, triterpene saponins demonstrate utility as natural surfactants and biopesticides. Saponins extracted from quinoa residues exhibit strong detergent and emulsifying properties, offering a sustainable alternative to synthetic cleaners in grain processing; studies show these compounds achieve comparable foaming and cleaning efficacy while being biodegradable.^[88] In pest control, neem-derived triterpenoids, particularly azadirachtin, act as effective insect growth regulators and antifeedants, disrupting insect development without broad environmental harm; commercial formulations like Nimbecidine apply these at rates of 1 liter per acre for crops such as cotton against whiteflies.^[89]^[90] Emerging applications harness biotechnological innovations to scale triterpene production. Metabolic engineering of yeast, such as Saccharomyces cerevisiae, enables de novo biosynthesis of steroid precursors like campesterol at yields exceeding 900 mg/L through pathway optimization and enzyme overexpression, with CRISPR-Cas9 facilitating precise genome edits for enhanced flux.^[91]^[92] Nanotechnology exploits triterpenoids' amphiphilic nature for self-assembling nanostructures, such as betulinic acid nanoparticles, which improve delivery in industrial formulations like coatings or emulsifiers.^[93] Sustainability efforts in the 2020s emphasize plant cell cultures as biofactories; for instance, engineered Nicotiana tabacum cells produce triterpenoid precursors at scalable levels (up to 573 μg/g dry weight), reducing reliance on wild harvesting and minimizing ecological impact through controlled, solvent-free systems.^[94] These advances support green extraction techniques, such as supercritical CO2 for betulin, promoting eco-friendly industrial scaling.^[95]

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Triterpenoids are natural products that modulate reactive oxygen species (ROS), which regulate cell survival and function, and can induce cell death.
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Bismuth triflate-catalyzed Wagner-Meerwein rearrangement in ...
The use of bismuth(III) salts as catalysts for the Wagner-Meerwein rearrangement of lupane derivatives with expansion of ring E and formation of an additional ...Missing: triterpenes | Show results with:triterpenes
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Wagner-meerwein rearrangements in acacic acid lactone and some ...
Sapogenins of acacia concinna DC—IV: Wagner-meerwein rearrangements in acacic acid lactone and some selected triterpenes ; A.S.R. Anjaneyulu ; M.Narayana Rao
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Triterpenes of Poria obliqua - ScienceDirect.com
The second, named obliquol, C30H50O2, was shown to have two hydroxyl groups and two double bonds, one of which is inert to hydrogenation. Spectral data ...
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Stereoselective Epoxidation of Triterpenic Allylic Alcohols and ... - NIH
Jan 5, 2023 · The epoxidation process of semi-synthetic triterpenoids 2-methyl-3-oxo-19β,28-epoxy- 18α-olean-1-ene, and its allylic alcohol derivatives were examined.
[27]
Crystal Structures of a Multifunctional Triterpene/Flavonoid ...
The known or predicted glycosylation sites are labeled with numbers: quercetin (3, 5, 7, 3′, and 4′), medicagenic acid (3 or 28), and hederagenin (3 or 28).
[28]
Enantioselective total synthesis of oleanolic acid, erythrodiol, .beta.
The application of the shapiro reaction to the stereoselective synthesis of E-trisubstituted olefins for cation-olefin cyclization by three component ...
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Development of a gas chromatography–mass spectrometry (GC–MS ...
Aug 20, 2025 · A sensitive GC–MS method was developed for the characterization and quantification of 20 triterpenic acid derivatives. •. The method allows for ...2. Material And Method · 2.3. Gc--Ms Analysis · 3. Results And Discussion
[30]
Optimization, Validation and Application of HPLC-PDA Methods for ...
Mar 16, 2021 · This research aimed at developing and validating HPLC-PDA methods for the determination and screening of triterpenoids in extracts of lingonberry leaves, ...2.2. Validation Of Methods · 3. Materials And Methods · 3.6. Chromatographic...
[31]
Isolation and Chromatographic Analysis of Bioactive Triterpenoids ...
The structures of the isolated compounds were elucidated by spectroscopic (NMR) and chromatographic (GC-MS) techniques as well as literature data comparisons.
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Biosynthesis of Cholesterol and Other Sterols | Chemical Reviews
Sep 8, 2011 · However, primary sequences of lanosterol synthase were discovered recently in three different laboratories from dicotyledonous plant species ...
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Production of Squalene in Bacillus subtilis by Squalene Synthase ...
Squalene is a linear triterpene formed via the MVA or MEP biosynthetic pathway and is widely distributed in bacteria, fungi, algae, plants, and animals.<|control11|><|separator|>
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Oxidosqualene cyclases involved in the biosynthesis of triterpenoids ...
May 15, 2020 · Model of triterpenoid biosynthesis in Quercus suber cork tissue. From squalene epoxide (in center), the Q. suber lupeol synthase QsOSC1 (salmon) ...
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A Case Study in Biomimetic Total Synthesis: Polyolefin ...
Squalene−hopene cyclase has been found to be more substrate-permissive, accepting squalene, (3R)-oxidosqualene, (3S)-oxidosqualene, and even 2,3- ...
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Biosynthesis of Squalene from Farnesyl Diphosphate in Bacteria
Apr 20, 2015 · Squalene synthase (SQS) is a bifunctional enzyme that catalyzes the condensation of two mols. of farnesyl diphosphate (FPP) to give presqualene ...
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Structure and inhibition mechanism of the catalytic domain of human ...
Jan 9, 2019 · Squalene epoxidase (SQLE), also known as squalene monooxygenase, catalyzes the stereospecific conversion of squalene to 2,3(S)-oxidosqualene ...
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Research Advances in Oxidosqualene Cyclase in Plants - MDPI
Aug 30, 2022 · Oxidosqualene cyclase (OSC) can catalyze the cyclization of 2,3-oxidosqualene to sterols and triterpenes with different skeletons [7,8]. It is a ...
[39]
Functional characterization of squalene synthase ... - PubMed Central
Squalene synthase (SQS) and squalene epoxidase (SQE) catalyze key steps in the biosynthesis of cyclic terpenoids, but neither enzyme has yet been characterized ...
[40]
Crystal structure of human squalene synthase. A key enzyme in ...
Sep 29, 2000 · We have determined, for the first time, the crystal structures of recombinant human squalene synthase complexed with several different ...
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Sterol regulatory element binding protein-dependent regulation of ...
We found that inhibition of SREBP function induced ER-stress when the supply of exogenous lipids was reduced. SREBP inhibition blocked Akt-dependent protein ...Ablation Of Srebp1 And... · Ablation Of Srebp Function... · Srebp Function Is Required...
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Inhibition of squalene synthase and squalene epoxidase in tobacco ...
Inhibition of either SQS or squalene epoxidase was found to trigger a severalfold increase in enzyme activity of 3-hydroxy-3-methylglutaryl coenzyme A reductase ...
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The bHLH Transcription Factors TSAR1 and TSAR2 Regulate ...
Here, we report on two homologous jasmonate-inducible transcription factors of the basic helix-loop-helix family, TRITERPENE SAPONIN BIOSYNTHESIS ACTIVATING ...
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Smith-Lemli-Opitz Syndrome Is Caused by Mutations in the 7 ...
Our data demonstrate that Smith-Lemli-Opitz syndrome is caused by mutations in the gene coding for 7-dehydrocholesterol reductase.Missing: mutation | Show results with:mutation
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Mutational spectrum of Smith-Lemli-Opitz syndrome - PubMed
Nov 15, 2012 · SLOS is caused by mutations in the DHCR7 gene, which encodes 7-dehydrocholesterol reductase, the enzyme that catalyzes the final step in ...
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Triterpenoid Biosynthesis and Engineering in Plants - Frontiers
The molecular diversity of OSCs enables more than 100 skeletal variations of triterpenoids in plants (Xu et al., 2004). Until now, some dozens of OSC genes from ...Abstract · Introduction · Triterpenoid Biosynthesis · Bioengineering of Plant...
[47]
Chemotaxonomic investigation of plant terpenoids with an ...
Apr 4, 2022 · Asteraceae plants produce the most terpenoid skeletons, in which sesquiterpenoids are dominant. (a) The number of skeletons in the top 30 ...
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Methods of Betulin Extraction from Birch Bark - PMC - NIH
Jun 5, 2022 · The amount of betulin can be up to 20–30% (or even almost 45%) [23] of the dry mass of the outer bark, depending on the species of birch ( ...
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Regulation of Ergosterol Biosynthesis in Saccharomyces cerevisiae
Jul 15, 2020 · Ergosterol, which is structurally analogous to cholesterol, has been used as a precursor of vitamin D2 and steroid hormone drugs.
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Horizontal acquisition of prokaryotic hopanoid biosynthesis ... - Nature
Apr 7, 2025 · Taken together, our results suggest that ergosterol and hopanoids collaborate to support membrane properties in S. japonicus in a variety of ...
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Effect of Ursolic Acid from Epicuticular Waxes of Jacaranda ...
Effect of Ursolic Acid from Epicuticular Waxes of Jacaranda decurrens on ... Screening of Uruguayan plants for deterrent activity against insects.Missing: cuticular herbivores
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A review of the fernane-type triterpenoids as anti-fungal drugs - PMC
Aug 21, 2024 · This review reported the discovery of enfumafungin and ibrexafungerp, their anti-fungal mechanism, summed up 63 fernane-type triterpenoids from natural ...
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Dec 15, 2015 · Isolation of triterpene-rich extracts from outer birch bark by hot ... first half of the 19th century (Hünefeld, 1836), researchers ...
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Post-Cyclization Skeletal Rearrangements in Plant Triterpenoid ...
Feb 23, 2023 · Triterpenoids are cyclized from oxidized squalene precursors by oxidosqualene cyclases, creating more than 100 different cyclical triterpene ...
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Cholesterol (or other higher sterols such as ergosterol and phytosterols) is universally present in large amounts (20-40 mol%) in eukaryotic plasma ...Missing: percentage | Show results with:percentage
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Lanosterol - an overview | ScienceDirect Topics
Lanosterol is defined as a triterpenoid alcohol that is converted into cholesterol in animals, involving the loss of three methyl groups and structural ...
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Steroidal Triterpenes of Cholesterol Synthesis - PMC - NIH
Apr 4, 2013 · This article reviews all hitherto known structures of post-squalene steroidal triterpenes of cholesterol synthesis, their biological roles and the enzymes ...
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Cholesterol Synthesis - an overview | ScienceDirect Topics
Cholesterol synthesis takes place in all cell types. However, the liver represents the main site for de novo cholesterol synthesis contributing to approximately ...<|control11|><|separator|>
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Cholesterol synthesis in the liver, kidneys and brain after injection of ...
Therefore, cholesterol synthesis seemed to happen at a faster rate than the other lipid syntheses in liver and kidneys, where the rate of linoleic acid ...Missing: vertebrates | Show results with:vertebrates
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Hopanoids Play a Role in Membrane Integrity and pH Homeostasis ...
Lack of hopanoids results in increased membrane permeability. Because hopanoids have been shown to localize to the inner and outer membranes of some ...
[61]
Hopanoids as functional analogues of cholesterol in bacterial ... - NIH
Using lipid thin-layer chromatography (TLC), we found that the major hopanoid diplopterol and its methylated derivative comprised roughly 19 mol% of the total ...
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Analysis of Intact Hopanoids and Other Lipids from the Bacterium ...
Hopanoids and other lipids were extracted from Zymomonas mobilis and quantitatively analyzed by highperformance liquid chromatography.
[63]
Functional convergence of hopanoids and sterols in membrane ...
We show that diplopterol, the simplest bacterial hopanoid, has similar properties and that hopanoids are bacterial “sterol surrogates” with the ability to order ...
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The origin of modern terrestrial life - PMC - PubMed Central - NIH
The older biomarker record regards the presence of hopanes, lipids that today are distinctive of cyanobacteria, in 2.7 Ga old rocks from Australia (Brocks et al ...Primitive Atmosphere And... · The Fossil Record · Heterotrophic Versus...
[65]
Sterols and membrane dynamics - PMC - PubMed Central - NIH
It is shown that all sterols share a common property: the ability to regulate dynamics in order to maintain membranes in a microfluid state.Sterols And Membrane... · Sterols And The ``raft''... · Sterols In Complex ``live''...Missing: triterpenes | Show results with:triterpenes<|control11|><|separator|>
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Sterols in plant biology – Advances in studying membrane dynamics
May 29, 2025 · Among these lipids, sterols regulate membrane fluidity and thus, protein functions. However, plant sterols are diverse in structure and ...
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Phytosterols, phytostanols, and their conjugates in foods
Phytosterols (plant sterols) are triterpenes that are important structural components of plant membranes, and free phytosterols serve to stabilize phospholipid ...
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Covalently linked hopanoid-lipid A improves outer-membrane ...
Oct 30, 2014 · Hopanoids are thought to stabilize membranes, control fluidity and permeability and bolster the integrity of bacterial cell envelope.Missing: percentage | Show results with:percentage<|control11|><|separator|>
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The role of hopanoids in fortifying rhizobia against a changing climate
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Biochemistry, Cholesterol - StatPearls - NCBI Bookshelf - NIH
Cholesterol is a structural component of cell membranes and serves as a building block for synthesizing various steroid hormones, vitamin D, and bile acids.
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Structural enzymology of cholesterol biosynthesis and storage - PMC
Apr 7, 2022 · It also serves as a precursor molecule for the biosynthesis of steroid hormones, bile acids, vitamin D, and a signaling transducer of the ...
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Bile Acid and Cholesterol Metabolism in Atherosclerotic ...
Dec 30, 2020 · Cholesterol is a precursor to steroid hormones, vitamin D, and bile acids. ... The alternative bile acid synthesis pathway is initiated by ...
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Cholesterol, lipid rafts, and disease - PMC - PubMed Central - NIH
Most importantly, it has been shown that cholesterol depletion inhibits β-cleavage and Aβ formation in neurons and other cells, while at the same time promoting ...
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Role of Cholesterol and Lipid Rafts in Cancer Signaling
As a consequence, depletion of membrane cholesterol by leading to disruption of lipid rafts strongly impaired Fas/CD95 death signaling (Gajate and Mollinedo, ...
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Lipid rafts: novel therapeutic targets for metabolic ...
Apr 17, 2025 · Cholesterol depletion, a common approach for disrupting lipid rafts, attenuates receptor-mediated signaling pathways, underscoring the ...<|control11|><|separator|>
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Antifeedant and oviposition-deterring activity of total ginsenosides ...
Our results are consistent with those from previous studies that triterpenoid saponins are repellent or deterrent to some insect herbivores (Gao et al., 2011, ...
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Ginsenosides and Biotic Stress Responses of Ginseng - PMC - NIH
Mar 1, 2023 · Ginsenosides may provide a defense against insects and other animals. The major insect pests of ginseng are cutworms (Noctuidae spp.), thrips ( ...
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Saponins, the Unexplored Secondary Metabolites in Plant Defense
Mar 10, 2025 · At the cellular level, saponins alter the permeability of the plasma membrane in insects, resulting in the lysis of the host cell. Due to their ...
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Antifungal activity of saponin-rich extracts of Phytolacca dioica and ...
A saponin-rich extract of Phytolacca dioica L. berries, its acid hydrolysate, and its major aglycone, phytolaccagenin, were assayed for antifungal activity ...Missing: defense | Show results with:defense
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The antifungal activity and mechanisms of action of quantified ...
Sapogenin phytolaccagenin is considered one of the most essential bioactive components of Phytolacca radix. It can be found in many Phytolacca species, such as ...
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The role of pentacyclic triterpenoids in the allelopathic effects of ...
4 Jan 2014 · In the field, ursolic acid accumulated abundantly in the soil in A. scholaris forests, and suppressed weed growth during summer and winter. Our ...
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Ursolic Acid and Its Derivatives as Bioactive Agents - PMC
29 Jul 2019 · Allelochemicals can cause inhibition of photosynthesis, decreases in ... Oleanolic acid and ursolic acid inhibit peptidoglycan biosynthesis in ...
[83]
Extended hopanoid lipids promote bacterial motility, surface ...
Sep 21, 2018 · Hopanoids are steroid-like bacterial lipids that enhance membrane rigidity and promote bacterial growth under diverse stresses.
[84]
Hopanoid Production Is Required for Low-pH Tolerance ...
Because hopanoids are hypothesized to act as membrane stabilizers, it is possible that lack of hopanoid production would result in membrane damage. Transmission ...
[85]
Metabolic and functional diversity of saponins, biosynthetic ...
The triterpene aglycones are then modified, mainly oxidized, by a series of cytochrome P450-dependent monooxygenases (P450s). ... The widespread presence of ...
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The ancient CYP716 family is a major contributor to the ... - Nature
Feb 6, 2017 · Enzymes belonging to the cytochrome P450 family have an essential role in creating the immense structural diversity of triterpenoids across ...
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Cytochrome P450 CYP716A254 catalyzes the formation of oleanolic ...
Jan 1, 2018 · The biosynthesis of oleanolic acid involves cyclization of 2,3-oxidosqualene to the oleanane-type triterpenoid skeleton, followed by a series of ...Missing: post- | Show results with:post-
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Evolution of Structural Diversity of Triterpenoids - Frontiers
Triterpenoids are cyclized from oxidized squalene precursors by oxidosqualene cyclases, creating more than 100 different cyclical triterpene scaffolds.<|separator|>
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Terpenes and terpenoids as main bioactive compounds of essential ...
Terpenes and terpenoids are the main bioactive compounds of essential oils (EOs). EOs and their major constituents confer several biological activities.
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[PDF] Triterpenoids and Saponins - CABI Digital Library
According to convention, the rings of triterpenes are labelled A–D (or E if present) and the carbons are numbered as shown on the diagram. Page 2. 96. The ...<|separator|>
[91]
Gonane - an overview | ScienceDirect Topics
Androstane is a C19 steroid with two methyl groups. Pregnane is a C21 steroid with methyl and ethyl groups.
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Cholesterol | C27H46O | CID 5997 - PubChem - NIH
Cholesterol is a cholestanoid consisting of cholestane having a double bond at the 5,6-position as well as a 3beta-hydroxy group.
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Sterol 14α-Demethylase Cytochrome P450 (CYP51), a P450 in all ...
CYP51, or Sterol 14α-Demethylase, is a P450 enzyme that catalyzes the removal of a 14α-methyl group from sterol precursors in sterol biosynthesis.
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https://pubmed.ncbi.nlm.nih.gov/24141692/
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Boswellic acids: novel, specific, nonredox inhibitors of 5-lipoxygenase
Among the BAs, acetyl-11-keto-beta-BA induced the most pronounced inhibition of 5-lipoxygenase (5-LO) product formation with an IC50 of 1.5 microM. In contrast ...Missing: μM | Show results with:μM
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Comparative Efficacy and Tolerability of 5-Loxin® and Aflapin ... - NIH
Nov 1, 2010 · Although a significant number of clinical study reports support the anti-inflammatory and anti-arthritic properties of Boswellia extract-, no ...Missing: IC50 | Show results with:IC50
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Ginsenoside Rg3 Induces Apoptosis of Human Breast Cancer (MDA ...
Rg3 treatment resulted in an increase in the ratio of proapoptotic Bax to antiapoptotic Bcl-2, depolarization of the mitochondria membrane potential and the ...
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Ginsenoside Rh2 Induces Bcl-2 Family Proteins-Mediated Apoptosis ...
Aug 5, 2025 · This study was undertaken to gain insights into the molecular mechanisms of ginsenoside Rh2 (Rh2)-induced cell death in human breast cancer cell ...
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Study Details | NCT00631852 | A Phase II Biomarker Trial of Gelatin ...
This study was designed to explore the changes brought about by gelatin encapsulated extract of American Ginseng Root (LEAG) in breast cancer tumors and ...
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https://academic.oup.com/jnci/article/105/16/1230/942502
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Discovery and Development of Natural Product-Derived ...
Feb 26, 2010 · It was a potent inhibitor of primary HIV-1 isolates in vitro, retained activity against virus isolates resistant to NRTIs, NNRTIs, and PIs, and ...<|control11|><|separator|>
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[PDF] Bevirimat
Aug 13, 2023 · Bevirimat, which was granted fast track designation by the FDA in 2004, is presently in phase II clinical evaluation (25). Preclinical ...
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Intravenous glycyrrhizin for the treatment of chronic hepatitis C
Glycyrrhizin up to 240 mg, thrice weekly, lowers serum ALT during treatment, but has no effect on HCV-RNA levels ... No major side-effects were noted.Missing: hypertension | Show results with:hypertension
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A systematic review and meta‐analysis of RCTs - Wiley Online Library
Jul 30, 2024 · Licorice significantly reduced alanine aminotransferase (ALT) by 15.63 U/L (95% CI: −25.08, −6.18; p = 0.001) and aspartate aminotransferase ( ...
[105]
Licorice: Overview, Uses, Side Effects, Precautions, Interactions ...
Mar 24, 2023 · Eating licorice 5 grams or more daily for several weeks can cause severe side effects including heart attack. People who have heart disease, ...
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https://doi.org/10.3390/molecules27113621
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Squalene Squalane | Shark Angels
Finally, squalene has some limited industrial uses as well, serving as a basis for lubricants and cleaning agents. Cosmetic uses for squalene. Shark-based ...
[108]
From Sharks to Yeasts: Squalene in the Development of Vaccine ...
It is currently used for numerous vaccine and drug delivery emulsions due to its stability-enhancing properties and biocompatibility. Squalene-based vaccine ...Missing: betulin lubricants
[109]
Exploring Their Surfactant, Emulsifying, and Detergent Properties
Oct 18, 2024 · This study explores saponins extracted from quinoa (Chenopodium quinoa) residues as a sustainable alternative.
[110]
Feeding Deterrence and Toxicity of Neem Triterpenoids
The neem tree, Azadirachta indica, produces a plethora of triterpenoids. One of these is azadirachtin, a complex compound with powerful insecticidal proper.
[111]
Traditional to modern perspectives on Neem (Azadirachta indica)
Sep 1, 2025 · Neem derived pesticides such as Nimbecidine or Achook @ 1.0 litre per acre have been found effective and economical in controlling whitefly ...
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Yeast as a promising heterologous host for steroid bioproduction
Jul 13, 2020 · In this mini-review, we summarize the recent engineering efforts of using yeast to synthesize various steroids, and discuss the structural ...
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https://doi.org/10.1007/s00253-019-10076-x
[114]
Self‐assembly of Renewable Nano‐sized Triterpenoids - Bag - 2017
Feb 14, 2017 · We have discussed the self-assembly properties of the individual triterpenoids like betulinic acid, betulin, oleanolic acid, glycyrrhetinic acid ...
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https://www.cell.com/plant-communications/fulltext/S2590-3462(21
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Green Techniques for Extracting Triterpenoids from Cannabis Roots
Jul 18, 2024 · Pressurized extraction technologies, classified as green extraction, avoid harmful organic solvents and are increasingly favored for extracting ...