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Pentacyclic Triterpenoids from the Medicinal Herb, Centella asiatica (L.) Urban
Open accessAbstract
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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“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]
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Citations
Cites
The function of terpene natural products in the natural world
Gershenzon, J., & Dudareva, N. (2007) · Nature Chemical Biology · doi:10.1038/nchembio.2007.5 · Cited by 2,198
Biological activities and distribution of plant saponins
Sparg, S. G., Light, M. E., & van Staden, J. (2004) · Journal of Ethnopharmacology · doi:10.1016/j.jep.2004.05.016 · Cited by 1,469
Herbal Medicines: A Guide for Healthcare Professionals
Newall, C. A., Anderson, L. A., & Phillipson, J. D. (1996) · Medical Entomology and Zoology · Cited by 845
The isoprene rule and the biogenesis of terpenic compounds
Růžička, L. (1953) · Cellular and Molecular Life Sciences · doi:10.1007/bf02167631 · Cited by 746
Fungal Resistance to Plant Antibiotics as a Mechanism of Pathogenesis
Morrissey, J. P., & Osbourn, A. E. (1999) · Microbiology and Molecular Biology Reviews · doi:10.1128/mmbr.63.3.708-724.1999 · Cited by 635
Giri, A., & Narasu, M. L. (2000) · Biotechnology Advances · doi:10.1016/s0734-9750(99)00016-6 · Cited by 579
Chemical, pharmacological and clinical profile of the East Asian medical plant Centella aslatica
Brinkhaus, B., Lindner, M., Schuppan, D., & Hahn, E. G. (2000) · Phytomedicine · doi:10.1016/s0944-7113(00)80065-3 · Cited by 525
Compromised disease resistance in saponin-deficient plants
Papadopoulou, K. Κ., Melton, R. E., Leggett, M., Daniels, M. J., & Osbourn, A. (1999) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.96.22.12923 · Cited by 466
(1980) · Springer eBooks · doi:10.1007/978-3-642-67360-3 · Cited by 450
Biosynthesis of Triterpenoid Saponins in Plants
Haralampidis, K., Trojanowska, M., & Osbourn, A. (2002) · Advances in biochemical engineering, biotechnology · doi:10.1007/3-540-44604-4_2 · Cited by 429
BIOSYNTHESIS AND ACCUMULATION OF STEROLS
Benveniste, P. (2004) · Annual Review of Plant Biology · doi:10.1146/annurev.arplant.55.031903.141616 · Cited by 415
Biosynthetic diversity in plant triterpene cyclization
Phillips, D. R., Rasbery, J. M., Bartel, B., & Matsuda, S. P. T. (2006) · Current Opinion in Plant Biology · doi:10.1016/j.pbi.2006.03.004 · Cited by 393
Production and engineering of terpenoids in plant cell culture
Roberts, S. C. (2007) · Nature Chemical Biology · doi:10.1038/nchembio.2007.8 · Cited by 377
Chemotaxonomy of Flowering Plants
Gibbs, R. D. (1974) · Taxon · doi:10.1002/j.1996-8175.1974.tb04032.x · Cited by 375
Composition and antimicrobial properties of essential oils of four Mediterranean Lamiaceae
Panizzi, L., Flamini, G., Cioni, P. L., & Morelli, I. (1993) · Journal of Ethnopharmacology · doi:10.1016/0378-8741(93)90032-z · Cited by 333
Achnine, L., Huhman, D. V., Farag, M. A., Sumner, L. W., Blount, J. W., & Dixon, R. A. (2005) · The Plant Journal · doi:10.1111/j.1365-313x.2005.02344.x · Cited by 311
Secondary metabolism of hairy root cultures in bioreactors
Kim, Y., Wyslouzil, B. E., & Weathers, P. J. (2002) · In Vitro Cellular & Developmental Biology - Plant · doi:10.1079/ivp2001243 · Cited by 290
Degenhardt, J., Gershenzon, J., Baldwin, I. T., & Keßler, A. (2003) · Current Opinion in Biotechnology · doi:10.1016/s0958-1669(03)00025-9 · Cited by 287
Babu, T. D., Kuttan, G., & Padikkala, J. (1995) · Journal of Ethnopharmacology · doi:10.1016/0378-8741(95)01284-k · Cited by 217
Determination of biologically active constituents in Centella asiatica
Inamdar, P. K., Yeole, R. D., Ghogare, A. B., & SOUZA, N. J. D. (1996) · Journal of Chromatography A · doi:10.1016/0021-9673(96)00237-3 · Cited by 197
Liu, J., & Henkel, T. O. (2002) · Current Medicinal Chemistry · doi:10.2174/0929867023369709 · Cited by 157
Hayashi, H., Huang, P., & Inoue, K. (2003) · Plant and Cell Physiology · doi:10.1093/pcp/pcg054 · Cited by 149
Kim, O.-T., Bang, K.-H., Shin, Y.-S., Lee, M. J., Jung, S., Hyun, D.-Y., Kim, Y., Seong, N.-S., Cha, S.-W., & Hwang, B. (2007) · Plant Cell Reports · doi:10.1007/s00299-007-0400-1 · Cited by 147
Chemical components of Centella asiatica and their bioactivities
Zheng, C. (2007) · Journal of Chinese Integrative Medicine · doi:10.3736/jcim20070324 · Cited by 146
Secondary product formation in plant tissue cultures
COLLIN, H. A. (2001) · Plant Growth Regulation · doi:10.1023/a:1013374417961 · Cited by 140
Matsuda, H., Morikawa, T., Ueda, H. R., & Yoshikawa, M. (2001) · Chemical and Pharmaceutical Bulletin · doi:10.1248/cpb.49.1368 · Cited by 133
Kim, O. T., Kim, M. Y., Hong, M. H., Ahn, J.-H., & Hwang, B. (2004) · Plant Cell Reports · doi:10.1007/s00299-004-0826-7 · Cited by 126
Pharmacognosy, Phytochemistry, Medicinal Plants (2nd ed.)
Kennedy, J. F., & Thorley, M. (2000) · Carbohydrate Polymers · doi:10.1016/s0144-8617(99)00211-8 · Cited by 125
In vitro keratinocyte antiproliferant effect of Centella asiatica extract and triterpenoid saponins
Sampson, J., Raman, A., Karlsen, G., Navsaria, H. A., & Leigh, I. M. (2001) · Phytomedicine · doi:10.1078/0944-7113-00032 · Cited by 125
Mangas, S., Bonfill, M., Osuna, L., Moyano, E., Tortoriello, J., Cusido, R. M., Piñol, M. T., & Palazón, J. (2006) · Phytochemistry · doi:10.1016/j.phytochem.2006.06.025 · Cited by 125
Oyedeji, A. O., & Afolayan, A. J. (2005) · Pharmaceutical Biology · doi:10.1080/13880200590928843 · Cited by 118
Randriamampionona, D., Diallo, B., Rakotoniriana, E. F., Rabemanantsoa, C., Cheuk, K., Corbisier, A.-M., Mahillon, J., Ratsimamanga, S., & Jaziri, M. E. (2007) · Fitoterapia · doi:10.1016/j.fitote.2007.03.016 · Cited by 112
A reinvestigation of the triterpenes of Centella asiatica
Singh, B., & Rastogi, R. P. (1969) · Phytochemistry · doi:10.1016/s0031-9422(00)85884-7 · Cited by 107
Production of asiaticoside and madecassoside in Centella asiatica in vitro and in vivo
Aziz, Z. A., Davey, M. R., Power, J. B., Anthony, P., Smith, R. M., & Lowe, K. C. (2007) · Biologia Plantarum · doi:10.1007/s10535-007-0008-x · Cited by 97
Schaneberg, B. T., Mikell, Bedіr, E., & Khan, I. A. (2003) · PubMed · Cited by 87
Zhang, H., Shibuya, M., Yokota, S., & Ebizuka, Y. (2003) · Biological and Pharmaceutical Bulletin · doi:10.1248/bpb.26.642 · Cited by 84
Rajkumar, S., & JEBANESAN, A. (2007) · PubMed · Cited by 82
Bonfill, M., Mangas, S., Cusido, R. M., Osuna, L., Piñol, M. T., & Palazón, J. (2005) · Biomedical Chromatography · doi:10.1002/bmc.564 · Cited by 76
Pointel, J. P., Boccalon, H., Cloarec, M., Ledevehat, C., & Joubert, M. (1987) · Angiology · doi:10.1177/000331978703800106 · Cited by 71
Immunomodulatory Activity of Boswellic Acids (Pentacyclic Triterpene Acids) fromBoswellia serrata
Sharma, M., Kaul, A., Khajuria, A., Singh, S. K., & Singh, G. B. (1996) · Phytotherapy Research · doi:10.1002/(sici)1099-1573(199603)10:2 · Cited by 67
The Formation of Sugar Chains in Triterpenoid Saponins and Glycoalkaloids
Kalinowska, M., Zimowski, J., Pączkowski, C., & Wojciechowski, Z. A. (2005) · Phytochemistry Reviews · doi:10.1007/s11101-005-1422-3 · Cited by 60
Chemotaxonomy of Flowering Plants
Gibbs, R. D. (1974) · McGill-Queen's University Press eBooks · doi:10.1515/9780773592889 · Cited by 59
Mono- and sesquiterpenoids from Hydrocotyle and Centella species
Asakawa, Y., Matsuda, R., & TAKEMOTO, T. (1982) · Phytochemistry · doi:10.1016/0031-9422(82)85264-3 · Cited by 58
Kim, O.-T., Kim, M. Y., Huh, S. M., Bai, D. G., Ahn, J. C., & Hwang, B. (2005) · Plant Cell Reports · doi:10.1007/s00299-005-0927-y · Cited by 52
James, J. T., Meyer, R., & Dubery, I. A. (2008) · Plant Cell Tissue and Organ Culture (PCTOC) · doi:10.1007/s11240-008-9391-z · Cited by 51
Self-citationYoshikawa, M., Matsuda, H., Morikawa, T., & Ueda, H. R. (2001) · Heterocycles · doi:10.3987/com-01-9259 · Cited by 51
Biocatalyzed Generation of Molecular Diversity: Selective Modification of the Saponin Asiaticoside
Monti, D., Candido, A., Silva, M. M., Vladimír Křen, A., Riva, S., & Danieli, B. (2005) · Advanced Synthesis & Catalysis · doi:10.1002/adsc.200505047 · Cited by 44
Reverse-phase high performance liquid chromatography of asiaticoside in Centella asiatica
Verma, R. K., Bhartariya, K. G., Gupta, M. M., & Kumar, S. (1999) · Phytochemical Analysis · doi:10.1002/(sici)1099-1565(199907/08)10:4 · Cited by 43
A Novel Triterpene from Centella asiatica
Yu, Q.-L., Duan, H., Takaishi, Y., & Gao, W. (2006) · Molecules · doi:10.3390/11090661 · Cited by 40
Correlation between genomicdiversity and asiaticoside content in Centella asiatica (L.) Urban.
Das, A. (1991) · Botanical studies · Cited by 39
Jenner, H. L., Townsend, B., & Osbourn, A. (2004) · Planta · doi:10.1007/s00425-004-1434-z · Cited by 33
Clinical applications of Centella asiatica (L.) Urb.
Kartnig, T. (1988) · Europe PMC (PubMed Central) · Cited by 33
New Triterpenoid Glycosides fromCentella asiatica
Jiang, Z., Zhang, X., Zhou, J., & Chen, J. (2005) · Helvetica Chimica Acta · doi:10.1002/hlca.200590011 · Cited by 32
A taxonomic evaluation of fruit structure in the family Apiaceae.
Liu, M. R. (2008) · Cited by 30
PAN, J., Kai, G., YUAN, C., ZHOU, B., Jin, R., & YUAN, Y. (2007) · Chinese Journal of Chromatography · doi:10.1016/s1872-2059(07)60009-1 · Cited by 28
Gershenzon, J., & Kreis, W. (1999) · MPG.PuRe (Max Planck Society) · Cited by 28
A new triterpene and a saponin from Centella asiatica
Yu, Q. L., Duan, H. Q., Gao, W. Y., & Takaishi, Y. (2007) · Chinese Chemical Letters · doi:10.1016/j.cclet.2006.11.033 · Cited by 28
High performance thin layer chromatography of asiaticoside in Centella asiatica
Gupta, A. P., Gupta, M. M., & Kumar, S. (1999) · Zenodo (CERN European Organization for Nuclear Research) · doi:10.5281/zenodo.5852496 · Cited by 27
Ayyanar, M., & Savarimuthu Ignacimuthu, S. J. (2008) · Iranian journal of pharmacology & therapeutics · Cited by 26
Induction of triterpene biosynthesis by elicitors in suspension cultures of Tabernaemontana species
van der Heijden, R., Verheij, E. R., Schripsema, J., Svendsen, A. B., Verpoorte, R., & Harkes, P. A. A. (1988) · Plant Cell Reports · doi:10.1007/bf00272977 · Cited by 26
Shukla, Y. N., Srivastava, R., Tripathi, A. K., & Prajapati, V. (2000) · Pharmaceutical Biology · doi:10.1076/1388-0209(200009)3841-aft262 · Cited by 25
Mathur, S., Verma, R. K., Gupta, M. M., Ram, M. K., Sharma, M. C., & Sushil Kumar, K. (2000) · The Journal of Horticultural Science and Biotechnology · doi:10.1080/14620316.2000.11511284 · Cited by 23
Montecchio, G. P., Samaden, A., Carbone, S., Vigotti, M., Siragusa, S., & Piovella, F. (1991) · PubMed · Cited by 21
Compartmentalization of Plant Secondary Metabolism
Samanani, N., & Facchini, P. J. (2006) · Recent advances in phytochemistry · doi:10.1016/s0079-9920(06)80037-7 · Cited by 20
Étude comparative deCentella asiaticad'origine malgache et d'origine indienne
Rouillard-Guellec, F., Robin, J.-R., Rakoto‐Ratsimamanga, A., Ratsimamanga, S., & Rasaoanaivo, P. (1997) · Acta Botanica Gallica · doi:10.1080/12538078.1997.10515791 · Cited by 20
Production of Triterpene Glycosides from Whole Plant Cultures of Centella asiatica (L.) Urban
Kim, O.-T. (2002) · Journal of Plant Biotechnology · doi:10.5010/jpb.2002.29.4.281 · Cited by 12
Bouhouche, N., Solet, J.-M., Simon-Ramiasa, A., Bonaly, J., & Cosson, L. (1998) · Phytochemistry · doi:10.1016/s0031-9422(97)00676-6 · Cited by 9
The biosynthesis of secondary metabolites
(2007) · Tutorial chemistry texts · doi:10.1039/9781847551535-00105 · Cited by 8
Centella asiatica (L.) Urban in perspective: an evaluative account
Labadie, R. P., & Silva, K. T. D. D. (1987) · BRILL eBooks · doi:10.1163/9789004646582_013 · Cited by 3
Moyano, E., Bonfill, M., Mangas, S., Cusido, R. M., Piñol, M. T., & Palazón, J. (2007) · Journal of Biotechnology · doi:10.1016/j.jbiotec.2007.07.074 · Cited by 2
[EXPERIENCES WITH MADECASSOL IN THE TREATMENT OF ULCERATIVE SKIN CHANGES].
Wolfram, S. (1965) · PubMed · Cited by 2
On Some Species of Centella – II
Adamson, R. S. (1949) · Journal of South African Botany · doi:10.5962/p.388448 · Cited by 1
Flagged first, then by citations
5 of the 77 references couldn’t be matched to a known paper.
Research works printed but not linked: 18
- Devon, T.K., and Scott, A.I. (1972). Handbook of Natural Occurring Compounds, Academic Press.
- Bell, E.A., and Charlwood, B.V. (1980). Encyclopedia of Plant Physiology, Springer Verlag.
- Rastogi, 1963, Chemical examination of Centella asiatica Linn. II. Brahmoside and brahminoside, Indian J. Chem., 1, 267
- 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
- Bhattacharyya, 1956, Constituents of Centella asiatica Part II. Structure of the terpene acids, J. Indian Chem. Soc., 33, 630
- Rao, 1970, Variation in the chemical composition of Indian samples of Centella asiatica, Curr. Sci., 38, 77
- Dutta, 1968, Isothankunic acid–A new triterpene acid from Centella asiatica (URB), Bull. Nat. Inst. Sci. India, 37, 178
- Castellani, 1981, The Centella asiatica, Bull. Chim. Farm., 120, 570
- Pinhas, 1967, Sur la constitution chimique de la partie glucidique du madecassoside, Bull. Soc. Chim. Fr., 6, 1888
- 1963, New drugs from higher plants recently introduced into therapeutics, Lebanese Pharm., 8, 15
- Boely, 1975, Indications of titrated extract of Centella asiaticia in phlebology, Gaz. Med. Fr., 82, 741
- Wolfram, 1965, Erfahrungen mit Maddecasol bei der behandling ulzererõserser Hautverãnderungen, Wien. Med. Wschr., 115, 439
- Cristoni, 1998, Management of local adiposity with botanicals, Chimica Oggi/Chemistry Today, 16, 11
- Lucia, 1997, Phamacological and toxicological studies on Centella asiatica, Fitotherapia, LXVIII, 413
- Jatisatienr, C., and Tragoolpua, K. (4,, January June). Effect of the extract from eight species of medicinal plants on growth of selected plant pathogenic molds and dermatophyte. International Symposium on Breeding Research on Medicinal and Aromatic Plants, Quedlingberg, Germany.
- Srivastava, 1997, Antibacterial activity of Centella asiatica, Fitotherapia, 68, 466
- Ullah, 2009, Antimicrobial, cytotoxic and antioxidant activity of Centella asiatica, Eur. J. Sci. Res., 30, 260
- Gaines, 2004, Increasing alkaloid production from Catharanthus roseus suspensions through methyl jasmonate elicitation, Pharm. Eng., 24, 1
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Therapeutic and Medicinal Uses of Terpenes
Cox-Georgian, D., Ramadoss, N., Dona, C., & Basu, C. (2019) · Springer eBooks · doi:10.1007/978-3-030-31269-5_15 · Cited by 466
Centella asiatica: Phytochemistry and mechanisms of neuroprotection and cognitive enhancement
Gray, N. E., Alcazar Magana, A., Lak, P., Wright, K. M., Quinn, J., Stevens, J. F., Maier, C. S., & Soumyanath, A. (2018) · Phytochemistry Reviews · doi:10.1007/s11101-017-9528-y · Cited by 299
Triterpene Composition and Bioactivities of Centella asiatica
Hashim, P., Sidek, H., Helan, M. H. M., Sabery, A., Palanisamy, U. D., & Ilham, M. (2011) · Molecules · doi:10.3390/molecules16021310 · Cited by 266
Triterpenoid-biosynthetic UDP-glycosyltransferases from plants
Rahimi, S., Kim, J., Mijakovic̀, I., Jung, K., Choi, G., Kim, S., & Kim, Y. (2019) · Biotechnology Advances · doi:10.1016/j.biotechadv.2019.04.016 · Cited by 234
Centella asiatica in Dermatology: An Overview
Bylka, W., Znajdek-Awiżeń, P., Studzińska-Sroka, E., Dańczak‐Pazdrowska, A., & Brzezińska, M. (2014) · Phytotherapy Research · doi:10.1002/ptr.5110 · Cited by 231
Metadata
- Authors
- James, J. T., & Dubery, I. A.
- Affiliations
- University of Johannesburg (ZA)
- Corresponding author
- Dubery, Ian A.
- Venue
- Molecules
- Publisher
- MDPI AG
- Published
- 2009-10-09
- Volume
- 14
- Issue
- 10
- Pages
- 3922-3941
- ISSN
- 1420-3049 (ISSN-L)
- 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
- 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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