Cited by 651Natural product bioactivities and synthesisPhytochemical Studies and BioactivitiesPharmacological Effects of Natural Compounds

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Triterpenoids and rexinoids as multifunctional agents for the prevention and treatment of cancer

Liby, Karen T., Yore, Mark M., Sporn, Michael B.·2007·Nature Reviews Cancer

DOI 10.1038/nrc2129

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Abstract

Synthetic oleanane triterpenoids and rexinoids are two new classes of multifunctional drugs. They are neither conventional cytotoxic agents, nor are they monofunctional drugs that uniquely target single steps in signal transduction pathways. Synthetic oleanane triterpenoids have profound effects on inflammation and the redox state of cells and tissues, as well as being potent anti-proliferative and pro-apoptotic agents. Rexinoids are ligands for the nuclear receptor transcription factors known as retinoid X receptors. Both classes of agents can prevent and treat cancer in experimental animals. These drugs have unique molecular and cellular mechanisms of action and might prove to be synergistic with standard anti-cancer treatments.

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“The homo-triterpenoid bardoxolone methyl (RTA402; methyl (4aS,6aR,6bS,8aR,12aR,14aR,14bS)-11-isocyano2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,7,8,8a,14a,14bdecahydropicene-4a-carboxylate) contains an a,b-unsaturated carbonyl unit (Liby et al., 2007) and is in clinical development for the treatment of diabet…”
Background
Microbial Transformation of Triterpenoids
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p38 MAPK Signaling Mediates Mitochondrial Apoptosis in Cancer Cells Induced by Oleanolic Acid
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Synthesis of new potential anticancer agents based on 4-thiazolidinone and oleanane scaffolds
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“, 2000a, b), antiviral (6) (Cichewicz and Kouzi, 2004), antibacterial and anticancer (7) activities (Honda et al., 2000a; Liby et al., 2007; Liu 2005; Couch et al., 2005) (Fig.”
Background
Targeted Therapeutic Remodeling of the Tumor Microenvironment Improves an HER-2 DNA Vaccine and Prevents Recurrence in a Murine Breast Cancer Model
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“Synthetic triterpenoids are a class of multifunctional inhi - bitors shown to suppress solid tumor growth through inacti - vation of STATs ( 11 ) .”
Influential
Benefits of Black Cohosh (Cimicifuga racemosa) for Women Health: An Up-Close and In-Depth Review
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“Triterpenes and saponins have been shown to possess a range of biological actions such as anti-inflammatory and anti-cancer effects, and can promote or induce apoptosis [24,28].”
Background
Activation of AMPK by Bitter Melon Triterpenoids Involves CaMKKβ
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“Alternatively, as BMTs are structurally similar to bile acids [44], they could agonise the bile acid receptor TGR5, another G-protein coupled receptor which has antidiabetic properties, though this has not been linked to CaMKKb or AMPK activities [45].”
Background
Bismuth triflate-catalyzed Wagner-Meerwein rearrangement in terpenes. Application to the synthesis of the 18α-oleanane core and A-neo-18α-oleanene compounds from lupanes
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Corosolic Acid Induces Non-Apoptotic Cell Death through Generation of Lipid Reactive Oxygen Species Production in Human Renal Carcinoma Caki Cells
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“Corosolic acid is a pentacyclic triterpenoid discovered in traditional Asian medical herbs such as Lagerstroemia speciose [8,9].”
Background
Oleanane triterpenoid CDDO-Me induces apoptosis in multidrug resistant osteosarcoma cells through inhibition of Stat3 pathway
Ryu, K., Susa, M., Choy, E., Cao, Y., Hornicek, F. J., Mankin, H. J., & Duan, Z. (2010) · BMC Cancer · doi:10.1186/1471-2407-10-187 · Cited by 61
“The results are consistent with a series of studies showing that CDDO-related compounds are not monofunctional drugs that strictly target single steps in signal transduction pathways [32,40,48].”
Influential
Non-enzymatic post-translational protein modifications and proteostasis network deregulation in carcinogenesis
Trougakos, I. P., Sesti, F., Tsakiri, E. N., & Gorgoulis, V. G. (2013) · Journal of Proteomics · doi:10.1016/j.jprot.2013.02.024 · Cited by 63
Triterpenoid Dihydro-CDDO-Trifluoroethyl Amide Protects against Maladaptive Cardiac Remodeling and Dysfunction in Mice: A Critical Role of Nrf2
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“Derivatives of oleanolic acid are relatively non-toxic and cytoprotective, and have emerged as attractive drug candidates for the treatment of various diseases [27].”
Background
Dietary Phytochemicals in Neuroimmunoaging: A New Therapeutic Possibility for Humans?
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“…share common properties and play an important role to activate the phase II detoxifying and antioxidant enzymes like HO-1, glutathione peroxidase (GSH-Px), and glutathione-S-transferase (GST) by targeting the common transcription factor Nrf2 (Liby et al., 2007; Tosetti et al., 2009).”
Background
Shuganning injection, a traditional Chinese patent medicine, induces ferroptosis and suppresses tumor growth in triple-negative breast cancer cells
Du, J., Wang, L., Huang, X., Zhang, N., Long, Z., Yang, Y. Q., Zhong, F., Zheng, B., Lan, W., Lin, W., et al. (2021) · Phytomedicine · doi:10.1016/j.phymed.2021.153551 · Cited by 61
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Corosolic acid isolated from Eriobotrya japonica leaves reduces glucose level in human hepatocellular carcinoma cells, zebrafish and rats
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Chemoprevention of Colon Carcinogenesis by Oleanolic Acid and Its Analog in Male F344 Rats and Modulation of COX-2 and Apoptosis in Human Colon HT-29 Cancer Cells
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“Past studies have reported the anti-inflammatory, anti-tumor promoting properties of the several natural triterpenes like ONA, ursolic acid, lupeol and glycyrrhetinic acid (36,37).”
Background
Developing Phytocompounds from Medicinal Plants as Immunomodulators
Wen, C.-C., Chen, H., & Yang, N. (2012) · Advances in botanical research · doi:10.1016/b978-0-12-394591-4.00004-0 · Cited by 67
“There are more than 20,000 naturally occurring triterpenoids which have cyclic structures (Ajikumar et al., 2008; Liby et al., 2007) .”
Enzymatic biotransformation of terpenes as bioactive agents
Sultana, N., & Saify, Z. S. (2012) · Journal of Enzyme Inhibition and Medicinal Chemistry · doi:10.3109/14756366.2012.727411 · Cited by 58
“Hydroxylation was found to be the most common reaction in sesquiterpenes pyrethrosin (5), plectranthone (6)(62), costunolide (8)(38,63) and partheniol (7) (Scheme 1) afforded mainly their hydroxylated derivatives with various fungal strains.”
Background
Mechanism of HMGB1 release inhibition from RAW264.7 cells by oleanolic acid in Prunus mume Sieb. et Zucc.
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Oncogenic potential of truncated RXRα during colitis-associated colorectal tumorigenesis by promoting IL-6-STAT3 signaling
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Adaptation of the master antioxidant response connects metabolism, lifespan and feather development pathways in birds
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Panda, S. S., Thangaraju, M., & Lokeshwar, B. L. (2022) · Molecules · doi:10.3390/molecules27248981 · Cited by 59
“These are a large and structurally diverse group of NPs having about 200 distinct skeletons, and more than 20,000 triterpenoids are isolated and identified from nature [14,15].”
Background
CDDO-Methyl Ester Delays Breast Cancer Development in Brca1-Mutated Mice
Kim, E., Deng, C., Sporn, M. B., Royce, D. B., Risingsong, R., Williams, C. R., & Liby, K. T. (2011) · Cancer Prevention Research · doi:10.1158/1940-6207.capr-11-0359 · Cited by 57
“Rather, the pentacyclic scaffold of CDDOMe, together with the exocyclic methyl groups of this triterpenoid, provide a highly stereospecific platform for interaction with unique cysteine residues on target proteins (20, 30, 31).”
BackgroundSelf-citation
Triterpenoids CDDO-Methyl Ester or CDDO-Ethyl Amide and Rexinoids LG100268 or NRX194204 for Prevention and Treatment of Lung Cancer in Mice
Liby, K. T., Risingsong, R., Royce, D. B., Williams, C. R., Ma, T., Yore, M. M., & Sporn, M. B. (2009) · Cancer Prevention Research · doi:10.1158/1940-6207.capr-09-0085 · Cited by 57
“Although it has not yet been used in clinical trials, LG 100268 has been widely used in many experimental studies and has produced excellent preclinical results in rodents for more than 10 years (7).”
BackgroundMethodInfluentialSelf-citation
Betulin and betulinic acid in cancer research
Hordyjewska, A., Ostapiuk, A., & Horecka, A. (2018) · Journal of Pre-Clinical and Clinical Research · doi:10.26444/jpccr/92743 · Cited by 57
“Therefore, triterpenoids form approximately 50% of the total known amount of terpenes [2, 4].”
Background
The synthetic oleanane triterpenoid, CDDO-methyl ester, is a potent antiangiogenic agent
Vannini, N., Lorusso, G., Cammarota, R., Barberis, M. C. P., Noonan, D. M., Sporn, M. B., & Albini, A. (2007) · Molecular Cancer Therapeutics · doi:10.1158/1535-7163.mct-07-0451 · Cited by 56
“oleanolic acid have been synthesized recently (8), and two of them, 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid (CDDO) and its methyl ester (CDDO-Me), are now on”
BackgroundSelf-citation
Anti-cancer and Anti-angiogenic Properties of Various Natural Pentacyclic Tri-terpenoids and Some of their Chemical Derivatives
Rufino‐Palomares, E. E., Pérez‐Jiménez, A., Reyes‐Zurita, F. J., Garcı́a-Salguero, L., Mokhtari, K., Herrera-Merchan, A., Medina, P. P., Peragón, J., & Lupiáñez, J. A. (2015) · Current Organic Chemistry · doi:10.2174/1385272819666150119225952 · Cited by 56
Multifunctional pentacyclic triterpenoids as adjuvants in cancer chemotherapy: a review
Kamble, S. M., Goyal, S. N., & Patil, C. R. (2014) · RSC Advances · doi:10.1039/c4ra02784a · Cited by 56
Design, synthesis and biological evaluation of novel l-ascorbic acid-conjugated pentacyclic triterpene derivatives as potential influenza virus entry inhibitors
Wang, H., Xu, R., Shi, Y., Si, L., Jiao, P., Fan, Z., Xu, H., Wu, X., Zhou, X., Yu, F., et al. (2016) · European Journal of Medicinal Chemistry · doi:10.1016/j.ejmech.2016.01.005 · Cited by 55
Current Evidence on the Anticancer Potential of Chios Mastic Gum
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“Both synthetic and naturally occurring triterpenoid analogues have been evaluated for their anticancer activity ( 57 – 61 ).”
Citral Is Renoprotective for Focal Segmental Glomerulosclerosis by Inhibiting Oxidative Stress and Apoptosis and Activating Nrf2 Pathway in Mice
Yang, S., Hua, K., Lin, Y., Chen, A., Chang, J., Chao, L. K., Ho, C., & Ka, S. (2013) · PLoS ONE · doi:10.1371/journal.pone.0074871 · Cited by 55
“However, recently studies using a highly selective Nrf2 agonist bardoxolone suggest that bardoxolone actually worsened proteinuria [57,58], although bardoxolone and related synthetic triterpenoid analogs have been shown to have beneficial effects on prevention and therapy of tissue injury mediated by inflammatory and…”
Background
Cancer Chemopreventive Activity of Maslinic Acid: Suppression of COX-2 Expression and Inhibition of NF- κ B and AP-1 Activation in Raji Cells
Yap, W. H., Yew, W. T., Hong, P., Soo, K. K., Hoon, L., Chieng, Y., & Mooi, L. (2010) · Planta Medica · doi:10.1055/s-0030-1250203 · Cited by 54
Synthesis and cytotoxic activity of novel A-ring cleaved ursolic acid derivatives in human non-small cell lung cancer cells
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Current status and future prospects of molecular hybrids with thiazolidinedione (TZD) scaffold in anticancer drug discovery
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Synthesis and Pro‐Apoptotic Activity of Novel Glycyrrhetinic Acid Derivatives
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Synthesis and Anti‐HCV Entry Activity Studies of β‐Cyclodextrin–Pentacyclic Triterpene Conjugates
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A library of 1,2,3-triazole-substituted oleanolic acid derivatives as anticancer agents: design, synthesis, and biological evaluation
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Anticancer Effects of Seaweed-Derived Bioactive Compounds
Lee, H., Selvaraj, B., & Lee, J. W. (2021) · Applied Sciences · doi:10.3390/app112311261 · Cited by 57
A Novel Acetylenic Tricyclic bis-(Cyano Enone) Potently Induces Phase 2 Cytoprotective Pathways and Blocks Liver Carcinogenesis Induced by Aflatoxin
Liby, K. T., Yore, M. M., Roebuck, B. D., Baumgartner, K. J., Honda, T., Sundararajan, C., Yoshizawa, H., Gribble, G. W., Williams, C. R., Risingsong, R., et al. (2008) · Cancer Research · doi:10.1158/0008-5472.can-08-1123 · Cited by 52
Self-citation

Authors: Liby, K. T., Yore, M. M., & Sporn, M. B.
Affiliations: Dartmouth College (US)
Corresponding author: Sporn, Michael B.
ORCID: Liby, Karen T.
Venue: Nature Reviews Cancer
Publisher: Springer Science and Business Media LLC
Published: 2007-04-19
Volume: 7
Issue: 5
Pages: 357-369
ISSN: 1474-175X (ISSN-L)
1474-1768
DOI: 10.1038/nrc2129
OpenAlex: W2000178617
Cited by: 637
References: 175
Citations by year: 2026: 9 · 2025: 13 · 2024: 23 · 2023: 30 · 2022: 32 · 2021: 23 · 2020: 28 · 2019: 27 · 2018: 15 · 2017: 35 · 2016: 36 · 2015: 44 · 2014: 47 · 2013: 43 · 2012: 48
FWCI: 3.46
Type: journal article
Language: en
Open access: closed
Licence: www.springer.com/tdm (tdm)
Locations: Nature reviews. Cancer (publishedVersion)
PubMed (publishedVersion)
Topics: Physical Sciences › Chemistry › Organic Chemistry › Natural product bioactivities and synthesis
Physical Sciences › Chemistry › Organic Chemistry › Phytochemical Studies and Bioactivities
Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Pharmacology › Pharmacological Effects of Natural Compounds
Keywords: oleanane triterpenoids, rexinoids, cancer prevention, cancer therapy, retinoid X receptor, antiproliferative agents, apoptosis, inflammation, redox state, multi-target drugs, drug synergy
MeSH terms: Animals, Anti-Inflammatory Agents, Antineoplastic Agents, Dose-Response Relationship, Drug, Humans, Neoplasms, Oleanolic Acid, Anticarcinogenic Agents, Retinoid X Receptors, Mice

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Triterpenoids and rexinoids as multifunctional agents for the prevention and treatment of cancer

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