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

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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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Crossref · 10.3390/molecules14103922

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Figures

Figure 1 Aglycone skeletons of pentacyclic (A) steroidal spirostane, (B) steroidal furostane and (C) triterpenoid saponins. The R-group is a sugar moity [16]. Tetracyclic terpenes such as lanosterol, sitosterol and cycloartenol can also be derived from oxidosqualene through a different pathway utilizing cycloartenol synthase (CAS1) [19].
Figure 1 Aglycone skeletons of pentacyclic (A) steroidal spirostane, (B) steroidal furostane and (C) triterpenoid saponins. The R-group is a sugar moity [16]. Tetracyclic terpenes such as lanosterol, sitosterol and cycloartenol can also be derived from oxidosqualene through a different pathway utilizing cycloartenol synthase (CAS1) [19].CC BY · PubMed Central
Figure 2 A simplified scheme of triterpenoid biosynthesis in Centella. Farnesyl diphosphate synthase (FPS) isomerizes isopentyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP) to farnesyl diphosphate (FPP), which squalene synthase (SQS) converts to squalene. Squalene epoxidase (SQE) oxidises squalene to 2,3-oxidosqualene. Oxidosqualene cyclase (OSC) enzymes cyclize 2,3-oxidosqualene through cationic intermediates (e.g. dammarenyl cation) to one or more cyclic triterpene skeletons. Other enzymes involved include α/β-amyrin synthases (α/β-AS) which can also form the lupenyl cation but further ring expansion and rearrangements are required before the deprotonation to α/β-amyrin, the precursors of the sapogenins, to generate the products listed in Table 1. Adapted from [19,20].
Figure 2 A simplified scheme of triterpenoid biosynthesis in Centella. Farnesyl diphosphate synthase (FPS) isomerizes isopentyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP) to farnesyl diphosphate (FPP), which squalene synthase (SQS) converts to squalene. Squalene epoxidase (SQE) oxidises squalene to 2,3-oxidosqualene. Oxidosqualene cyclase (OSC) enzymes cyclize 2,3-oxidosqualene through cationic intermediates (e.g. dammarenyl cation) to one or more cyclic triterpene skeletons. Other enzymes involved include α/β-amyrin synthases (α/β-AS) which can also form the lupenyl cation but further ring expansion and rearrangements are required before the deprotonation to α/β-amyrin, the precursors of the sapogenins, to generate the products listed in Table 1. Adapted from [19,20].CC BY · PubMed Central
Figure 3 The model triterpenoid compound from C. asiatica. These triterpenes can occur in the ursane (R6, R7 = methyl) or oleanane (R7, R8 = methyl) types with double bonds occurring at C12-C13, C13-C18 or C20-C21.
Figure 3 The model triterpenoid compound from C. asiatica. These triterpenes can occur in the ursane (R6, R7 = methyl) or oleanane (R7, R8 = methyl) types with double bonds occurring at C12-C13, C13-C18 or C20-C21.CC BY · PubMed Central

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Citations

Cites

Show all 77 references

Research works printed but not linked: 18

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  4. Dutta, 1962, Triterpenoids: Part I. Thankuniside and Thankunic acid – a new triterpene glycoside and acid from Centella asiatica Linn. (Urb.), J. Sci. Ind. Res., B12, 239
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  9. Pinhas, 1967, Sur la constitution chimique de la partie glucidique du madecassoside, Bull. Soc. Chim. Fr., 6, 1888
  10. 1963, New drugs from higher plants recently introduced into therapeutics, Lebanese Pharm., 8, 15
  11. Boely, 1975, Indications of titrated extract of Centella asiaticia in phlebology, Gaz. Med. Fr., 82, 741
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  18. Gaines, 2004, Increasing alkaloid production from Catharanthus roseus suspensions through methyl jasmonate elicitation, Pharm. Eng., 24, 1

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Metadata

Authors
James, J. T., & Dubery, I. A.
Affiliations
University of Johannesburg (ZA)
Corresponding author
Dubery, Ian A.
ORCID
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
Licence
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
  • Physical Sciences › Chemistry › Organic Chemistry › Natural product bioactivities and synthesis
  • Health Sciences › Medicine › Complementary and alternative medicine › Medicinal Plants and Neuroprotection
  • Physical Sciences › Chemistry › Organic Chemistry › 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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