Pentacyclic Triterpenoids from the Medicinal Herb, Centella asiatica (L.) Urban

James, Jacinda T.; Dubery, Ian A.

doi:10.3390/molecules14103922

Cited by 399Natural product bioactivities and synthesisMedicinal Plants and NeuroprotectionPhytochemical Studies and Bioactivities

Pentacyclic Triterpenoids from the Medicinal Herb, Centella asiatica (L.) Urban

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James, Jacinda T., Dubery, Ian A.·2009·Molecules

DOI 10.3390/molecules14103922PMC PMC6255425

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Abstract

Centella asiatica accumulates large quantities of pentacyclic triterpenoid saponins, collectively known as centelloids. These terpenoids include asiaticoside, centelloside, madecassoside, brahmoside, brahminoside, thankuniside, sceffoleoside, centellose, asiatic-, brahmic-, centellic- and madecassic acids. The triterpene saponins are common secondary plant metabolites and are synthesized via the isoprenoid pathway to produce a hydrophobic triterpenoid structure (aglycone) containing a hydrophilic sugar chain (glycone). The biological activity of saponins has been attributed to these characteristics. In planta, the Centella triterpenoids can be regarded as phytoanticipins due to their antimicrobial activities and protective role against attempted pathogen infections. Preparations of C. asiatica are used in traditional and alternative medicine due to the wide spectrum of pharmacological activities associated with these secondary metabolites. Here, the biosynthesis of the centelloid triterpenoids is reviewed; the range of metabolites found in C. asiatica, together with their known biological activities and the chemotype variation in the production of these metabolites due to growth conditions are summarized. These plant-derived pharmacologically active compounds have complex structures, making chemical synthesis an economically uncompetitive option. Production of secondary metabolites by cultured cells provides a particularly important benefit to manipulate and improve the production of desired compounds; thus biotechnological approaches to increase the concentrations of the metabolites are discussed.

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Centella triterpenoids can be considered as phytoanticipins against wide range of bacterial, fungal and parasitic agents due to antimicrobial activities, selective cytotoxicity and protective function against pathogenic infections.
“The Centella triterpenoids can be considered as phytoanticipins against a wide range of bacterial, fungal and parasitic agents due to their antimicrobial activities, selective cytotoxicity and protective function against pathogenic infections.”
From Therapeutic Properties and Pharmacological Activities of Asiaticoside and Madecassoside: A Review (2023) · cites this paper as [3]
The Biological Activities section attributes antimicrobial activity and a likely role in plant disease resistance to Centella triterpenoids, supporting the phytoanticipin characterization. It does not establish activity against a wide range of bacterial, fungal and parasitic agents or selective cytotoxicity as reasons for that characterization. (LLM, conf=0.84)
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De novo sequencing and assembly of Centella asiatica leaf transcriptome for mapping of structural, functional and regulatory genes with special reference to secondary metabolism
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Centella asiaticaExtract Improves Behavioral Deficits in a Mouse Model of Alzheimer's Disease: Investigation of a Possible Mechanism of Action
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Madecassic acid, the contributor to the anti-colitis effect of madecassoside, enhances the shift of Th17 toward Treg cells via the PPARγ/AMPK/ACC1 pathway
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Comparative Studies on Different Extraction Methods of Centella asiatica and Extracts Bioactive Compounds Effects on Antimicrobial Activities
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A Review on Medicinal Properties of Centella Asiatica
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Identification of Major Active Ingredients Responsible for Burn Wound Healing ofCentella asiaticaHerbs
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Centella asiatica (Gotu kola) as a neuroprotectant and its potential role in healthy ageing
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Caffeoylquinic Acids in Centella asiatica Protect against Amyloid-β Toxicity
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Toona sinensis: a comprehensive review on its traditional usages, phytochemisty, pharmacology and toxicology
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Cardiovascular Protective Effects of Centella asiatica and Its Triterpenes: A Review
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Pharmacological Effects of Centella asiatica on Skin Diseases: Evidence and Possible Mechanisms
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Centella asiatica: Secondary metabolites, biological activities and biomass sources
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Chemical structures, production and enzymatic transformations of sapogenins and saponins from Centella asiatica (L.) Urban
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Anti-Planktonic and Anti-Biofilm Properties of Pentacyclic Triterpenes—Asiatic Acid and Ursolic Acid as Promising Antibacterial Future Pharmaceuticals
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A new ursane-type triterpenoid glycoside from Centella asiatica leaves modulates the production of nitric oxide and secretion of TNF-α in activated RAW 264.7 cells
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Centella asiatica extract protects against amyloid β1–40-induced neurotoxicity in neuronal cells by activating the antioxidative defence system
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Unveiling Nature's potential: Promising natural compounds in Parkinson's disease management
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Metabolomic Analysis of Methyl Jasmonate-Induced Triterpenoid Production in the Medicinal Herb Centella asiatica (L.) Urban
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Influence of triterpenoids present in apple peel on inflammatory gene expression associated with inflammatory bowel disease (IBD)
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Centella asiatica alleviates psoriasis through JAK/STAT3-mediated inflammation: An in vitro and in vivo study
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Novel triterpenoids isolated from hawthorn berries functioned as antioxidant and antiproliferative activities
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Phytochemical screening and antibacterial activity of leaf and callus extracts of Centella asiatica
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Pharmacokinetics of a Standardized Extract of Centella asiatica ECa 233 in Rats
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Ecologically relevant UV-B dose combined with high PAR intensity distinctly affect plant growth and accumulation of secondary metabolites in leaves of Centella asiatica L. Urban
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Discrimination of Three Pegaga (Centella) Varieties and Determination of Growth-Lighting Effects on Metabolites Content Based on the Chemometry of 1H Nuclear Magnetic Resonance Spectroscopy
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Characterization of the Asiatic Acid Glucosyltransferase, UGT73AH1, Involved in Asiaticoside Biosynthesis in Centella asiatica (L.) Urban
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Enhanced biosynthesis of triterpenoids in Centella asiatica hairy root culture by precursor feeding and elicitation
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Triterpenoids principle of Wedelia calendulacea attenuated diethynitrosamine-induced hepatocellular carcinoma via down-regulating oxidative stress, inflammation and pathology via NF-kB pathway
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Asiatic acid induces endoplasmic reticulum stress and apoptotic death in glioblastoma multiforme cells both in vitro and in vivo
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Total Triterpenes, Polyphenols, Flavonoids, and Antioxidant Activity of Bioactive Phytochemicals of Centella asiatica by Different Extraction Techniques
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Biotechnological production of centellosides in cell cultures of Centella asiatica (L) Urban
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Centelloside accumulation in leaves of Centella asiatica is determined by resource partitioning between primary and secondary metabolism while influenced by supply levels of either nitrogen, phosphorus or potassium
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Ethno-Herbal-Medico in Wound Repair: An Incisive Review
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Synthesis and Anti‐HCV Entry Activity Studies of β‐Cyclodextrin–Pentacyclic Triterpene Conjugates
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Bioactive Compounds and Bioactivities of Centella asiatica (L.) Urban Prepared by Different Drying Methods and Conditions
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Peroxisome proliferator-activated receptor gamma and its natural agonists in the treatment of kidney diseases
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Asiaticoside Induces Type I Collagen Synthesis and Osteogenic Differentiation in Human Periodontal Ligament Cells
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Evaluation of the topical spray containing Centella asiatica extract and its efficacy on excision wounds in rats
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A Novel Multifunctional C-23 Oxidase, CYP714E19, is Involved in Asiaticoside Biosynthesis
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Advances and emerging research trends for modulation of centelloside biosynthesis in Centella asiatica (L.) Urban- A review
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Pharmacokinetics and Pharmacodynamics of Key Components of a Standardized Centella asiatica Product in Cognitively Impaired Older Adults: A Phase 1, Double-Blind, Randomized Clinical Trial
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Comparison of the Antiaging and Protective Properties of Plants from the Apiaceae Family
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Ethnobotany, Phytochemistry and Pharmacological Features of Centella asiatica: A Comprehensive Review
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Comparative pharmacokinetics between madecassoside and asiaticoside presented in a standardised extract ofCentella asiatica, ECa 233 and their respective pure compound given separately in rats
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Integration of mass spectral fingerprinting analysis with precursor ion (MS1) quantification for the characterisation of botanical extracts: application to extracts of Centella asiatica (L.) Urban
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Critical Evaluation of Ayurvedic Plants for Stimulating Intrinsic Antioxidant Response
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Dynamics of flavonol accumulation in leaf tissues under different UV-B regimes in Centella asiatica (Apiaceae)
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Dermal targeting ofCentella asiaticaextract using hyaluronic acid surface modified niosomes
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Decreasing α-synuclein aggregation by methanolic extract of Centella asiatica in zebrafish Parkinson's model
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Neuroprotective Effect of Terpenoids Recovered from Olive Oil By-Products
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Nerve Protective Effect of Asiaticoside against Ischemia-Hypoxia in Cultured Rat Cortex Neurons
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Phytoremediation of Aluminum and Iron from Industrial Wastewater Using Ipomoea aquatica and Centella asiatica
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Development of Hairy Root Cultures for Biomass and Triterpenoid Production in Centella asiatica
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Centella asiatica extracts modulate hydrogen peroxide-induced senescence in human dermal fibroblasts
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Synthesis of Novel Heterocyclic Ring‐Fused 18β‐Glycyrrhetinic Acid Derivatives with Antitumor and Antimetastatic Activity
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Therapeutic Potential of Different Natural Products for the Treatment of Alzheimer’s Disease
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Herbal Therapeutics for Alzheimer's Disease: Ancient Indian Medicine System from the Modern Viewpoint
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Preclinical safety assessment of standardized extract of Centella asiatica (L.) urban leaves
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Stellera chamaejasme and its constituents induce cutaneous wound healing and anti-inflammatory activities
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Asiaticoside induces osteogenic differentiation of human periodontal ligament cells through the Wnt pathway
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Metabolic gene expression and centelloside production in elicited Centella asiatica hairy root cultures
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Comparison of the Antioxidant Potency of Four Triterpenes of Centella asiatica against Oxidative Stress
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In VitroAntimicrobial Activity of Spices and Medicinal Herbs against Selected Microbes Associated with Juices
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Low temperature and water dehydration increase the levels of asiaticoside and madecassoside in Centella asiatica (L.) Urban
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Antiproliferative, Cell-Cycle Dysregulation Effects of Novel Asiatic Acid Derivatives on Human Non-small Cell Lung Cancer Cells
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Combining In Silico and In Vitro Studies to Evaluate the Acetylcholinesterase Inhibitory Profile of Different Accessions and the Biomarker Triterpenes of Centella asiatica
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Pharmacological effects of pentacyclic triterpenoids isolated from Centella asiatica
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Centella asiatica: Advances in Extraction Technologies, Phytochemistry, and Therapeutic Applications
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Extraction and Mass Spectrometric Characterization of Terpenes Recovered from Olive Leaves Using a New Adsorbent-Assisted Supercritical CO2 Process
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Titrated extract of Centella asiatica provides a UVB protective effect by altering microRNA expression profiles in human dermal fibroblasts
An, I., An, S., Kang, S., Choe, T., Lee, S. N., Jang, H. H., & Bae, S. (2012) · International Journal of Molecular Medicine · doi:10.3892/ijmm.2012.1117 · Cited by 32 · see citing works
Complete Comparison Display (CCD) evaluation of ethanol extracts of Centella asiatica and Withania somnifera shows that they can non-synergistically ameliorate biochemical and behavioural damages in MPTP induced Parkinson's model of mice
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Molecular, chemical and biological stability of plants derived from artificial seeds of Centella asiatica (L.) Urban—An industrially important medicinal herb
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Authors: James, J. T., & Dubery, I. A.
Affiliations: University of Johannesburg (ZA)
Corresponding author: Dubery, Ian A.
ORCID: James, Jacinda T.
Dubery, Ian A.
Venue: Molecules
Publisher: MDPI AG
Published: 2009-10-09
Volume: 14
Issue: 10
Pages: 3922-3941
ISSN: 1420-3049 (ISSN-L)
DOI: 10.3390/molecules14103922
PMC: PMC6255425
OpenAlex: W2124211842
Cited by: 399
References: 77
Citations by year: 2026: 24 · 2025: 44 · 2024: 30 · 2023: 34 · 2022: 29 · 2021: 38 · 2020: 25 · 2019: 26 · 2018: 21 · 2017: 26 · 2016: 23 · 2015: 15 · 2014: 19 · 2013: 20 · 2012: 13
FWCI: 0.64
Type: journal article
Language: en
Open access: gold
doi.org
Licence: cc-by
creativecommons.org/licenses/by/3.0/ (vor)
Locations: Molecules (publishedVersion, cc-by)
Europe PMC (PubMed Central) (publishedVersion, other-oa)
PubMed Central (publishedVersion, cc-by)
PubMed (publishedVersion)
DOAJ (DOAJ: Directory of Open Access Journals) (submittedVersion)
Topics: Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Natural product bioactivities and synthesis
Health Sciences › Medicine › Complementary and alternative medicine › Medicinal Plants and Neuroprotection
Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Phytochemical Studies and Bioactivities
Keywords: Centella asiatica, pentacyclic triterpenes, triterpenoid saponins, asiaticoside, madecassoside, triterpenoid biosynthesis, isoprenoid pathway, antimicrobial activity, phytoanticipins, secondary metabolites, cell culture production, biotechnological production, traditional medicine
MeSH terms: Humans, Plants, Medicinal, Saponins, Triterpenes, Centella

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Pentacyclic Triterpenoids from the Medicinal Herb, Centella asiatica (L.) Urban

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