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Biological Properties of Hydroxy Pentacyclic Triterpene Acids (HPTAs)

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Natural Products Chemistry".

Deadline for manuscript submissions: closed (30 June 2023) | Viewed by 8297

Special Issue Editors

1. Laboratory of Health Sciences and Technologies, Higher Institute of Health Sciences, Hassan First University of Settat, Settat, Morocco
2. Biology Department, Faculté des Sciences Ain Chock, Université Hassan II, Immunology and Biodiversity Laboratory, Casablanca, Morocco
Interests: biological properties of medicinal plants and natural products; resistance to anticancer therapies; inflammation and inflammatory diseases

Special Issue Information

Dear Colleagues,

The lack of innovative therapies in human chemotherapy including infectious diseases and cancer is mainly due to the emergence of resistance to the main treatments currently available. This deficit has prompted the scientific community to take an interest in new sources of bioactive compounds. There are many molecules of interest, synthetic or natural, which have been highlighted over the last century, among them secondary metabolites derived from plants, such as hydroxy-pentacyclic triterpene acids (HPTAs), and more particularly ursolic acid (UA), oleanolic acid (OA), and betulinic acid (BA). These molecules, discovered in the context of ethnopharmacological research during the last century, have since been the subject of numerous scientific studies which tend to demonstrate their pleiotropic pharmacological properties—anti-infectious, anticancer, antiproliferative, anti-inflammatory, hepatoprotective—and emphasize their potential interest.

The aim of this Special Issue is to develop an in-depth inventory of the biological properties of hydroxyl pentacyclic triterpene acids (HPTAs) such as antimicrobial (i.e., antibacterial, antiviral or antifungal), anticancer, antiproliferative, anti-inflammatory, hepatoprotective, as well as antioxidant properties/activities. The Special Issue may include original research articles and reviews on the biological properties of HPTAs in order to identify promising natural compounds that could allow us to respond to the urgency of finding new treatments.

Prof. Dr. Raphaël E. Duval
Dr. Youness Limami
Guest Editors

Manuscript Submission Information

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Keywords

  • triterpenes
  • ursolic acid
  • oleanolic acid
  • betulinic acid
  • biological activities
  • anticancer
  • anti-infectives
  • anti-inflammatory

Published Papers (4 papers)

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Research

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19 pages, 1130 KiB  
Article
Antibiofilm and Anti-Quorum Sensing Potential of Cycloartane-Type Triterpene Acids from Cameroonian Grassland Propolis: Phenolic Profile and Antioxidant Activity of Crude Extract
by Alfred Ngenge Tamfu, Ozgur Ceylan, Geta Cârâc, Emmanuel Talla and Rodica Mihaela Dinica
Molecules 2022, 27(15), 4872; https://doi.org/10.3390/molecules27154872 - 29 Jul 2022
Cited by 21 | Viewed by 2153
Abstract
Propolis is very popular for its beneficial health properties, such as antimicrobial activity and antioxidant effects. It is one of the most long-serving traditional medicines to mankind due to its interesting chemical diversity and therapeutic properties. The detailed chemical information of propolis samples [...] Read more.
Propolis is very popular for its beneficial health properties, such as antimicrobial activity and antioxidant effects. It is one of the most long-serving traditional medicines to mankind due to its interesting chemical diversity and therapeutic properties. The detailed chemical information of propolis samples is very necessary to guarantee its safety and for it to be accepted into health care systems. The phenolic profile of the hydroethanolic extract was determined using HPLC-DAD, and the antioxidant was evaluated using five complementary methods. Triterpenoids were isolated using column chromatography and characterized using 1H NMR and 13C NMR. The effects of the extract and the isolated compounds on quorum sensing mediated processes and biofilm formation in bacteria were evaluated. Protocatechic acid (40.76 ± 0.82 µg/g), 4-hydroxybenzoic acid (24.04 ± 0.21 µg/g), vanillic acid (29.90 ± 1.05 µg/g), quercetin (43.53 ± 1.10 µg/g), and luteolin (4.44 ± 0.48 µg/g) were identified and quantified. The extract showed good antioxidant activity in the DPPH, ABTS•+, CUPRAC, and metal chelating assays, and this antioxidant effect was confirmed by cyclic voltammetry. 27-Hydroxymangiferonic acid (1), Ambolic acid (2), and Mangiferonic acid (3) were isolated from anti-quorum sensing activity at MIC, and it was indicated that the most active sample was the extract with inhibition diameter zone of 18.0 ± 1.0 mm, while compounds 1, 2, and 3 had inhibition zones of 12.0 ± 0.5 mm, 9.0 ± 1.0 mm, and 12.3 ± 1.0 mm, respectively. The samples inhibited the P. aeruginosa PA01 swarming motility at the three tested concentrations (50, 75, and 100 μg/mL) in a dose-dependent manner. The propolis extract was able to inhibit biofilm formation by S. aureus, E. coli, P. aeruginosa, C. albicans, and C. tropicalis at MIC concentration. Compound 1 proved biofilm inhibition on S. aureus, L. monocytogenes, E. faecalis, E. coli, and C. tropicalis at MIC and MIC/2; compound 2 inhibited the formation of biofilm at MIC on S. aureus, E. faecalis, E. coli, S. typhi, C. albicans, and C. tropicalis; and compound 3 inhibited biofilm formation on E. faecalis, E. coli, C. albicans, and C. tropicalis and further biofilm inhibition on E. coli at MIC/4 and MIC/8. The studied propolis sample showed important amounts of cycloartane-type triterpene acids, and this indicates that there can be significant intra-regional variation probably due to specific flora within the vicinity. The results indicate that propolis and its compounds can reduce virulence factors of pathogenic bacteria. Full article
(This article belongs to the Special Issue Biological Properties of Hydroxy Pentacyclic Triterpene Acids (HPTAs))
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12 pages, 4042 KiB  
Article
Bioactive Evaluation of Ursane-Type Pentacyclic Triterpenoids: β-Boswellic Acid Interferes with the Glycosylation and Transport of Intercellular Adhesion Molecule-1 in Human Lung Adenocarcinoma A549 Cells
by Kaori Nakano, Saki Sasaki and Takao Kataoka
Molecules 2022, 27(10), 3073; https://doi.org/10.3390/molecules27103073 - 11 May 2022
Cited by 2 | Viewed by 1530
Abstract
Ursane-type pentacyclic triterpenoids exert various biological effects, including anticancer and anti-inflammatory activities. We previously reported that ursolic acid, corosolic acid, and asiatic acid interfered with the intracellular trafficking and glycosylation of intercellular adhesion molecule-1 (ICAM-1) in human lung adenocarcinoma A549 cells stimulated with [...] Read more.
Ursane-type pentacyclic triterpenoids exert various biological effects, including anticancer and anti-inflammatory activities. We previously reported that ursolic acid, corosolic acid, and asiatic acid interfered with the intracellular trafficking and glycosylation of intercellular adhesion molecule-1 (ICAM-1) in human lung adenocarcinoma A549 cells stimulated with the pro-inflammatory cytokine interleukin-1α. However, the structure–activity relationship of ursane-type pentacyclic triterpenoids remains unclear. In the present study, the biological activities of seven ursane-type pentacyclic triterpenoids (β-boswellic acid, uvaol, madecassic acid, 3-O-acetyl-11-keto-β-boswellic acid, ursolic acid, corosolic acid, and asiatic acid) were investigated. We revealed that the inhibitory activities of ursane-type pentacyclic triterpenoids on the cell surface expression and glycosylation of ICAM-1 and α-glucosidase activity were influenced by the number of hydroxy groups and/or the presence and position of a carboxyl group. We also showed that β-boswellic acid interfered with ICAM-1 glycosylation in a different manner from other ursane-type pentacyclic triterpenoids. Full article
(This article belongs to the Special Issue Biological Properties of Hydroxy Pentacyclic Triterpene Acids (HPTAs))
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Review

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16 pages, 3840 KiB  
Review
Ursolic Acid’s Alluring Journey: One Triterpenoid vs. Cancer Hallmarks
by Youness Limami, Aline Pinon, Hicham Wahnou, Mounia Oudghiri, Bertrand Liagre, Alain Simon and Raphaël Emmanuel Duval
Molecules 2023, 28(23), 7897; https://doi.org/10.3390/molecules28237897 - 01 Dec 2023
Cited by 2 | Viewed by 1273
Abstract
Cancer is a multifactorial disease characterized by various hallmarks, including uncontrolled cell growth, evasion of apoptosis, sustained angiogenesis, tissue invasion, and metastasis, among others. Traditional cancer therapies often target specific hallmarks, leading to limited efficacy and the development of resistance. Thus, there is [...] Read more.
Cancer is a multifactorial disease characterized by various hallmarks, including uncontrolled cell growth, evasion of apoptosis, sustained angiogenesis, tissue invasion, and metastasis, among others. Traditional cancer therapies often target specific hallmarks, leading to limited efficacy and the development of resistance. Thus, there is a growing need for alternative strategies that can address multiple hallmarks concomitantly. Ursolic acid (UA), a naturally occurring pentacyclic triterpenoid, has recently emerged as a promising candidate for multitargeted cancer therapy. This review aims to summarize the current knowledge on the anticancer properties of UA, focusing on its ability to modulate various cancer hallmarks. The literature reveals that UA exhibits potent anticancer effects through diverse mechanisms, including the inhibition of cell proliferation, induction of apoptosis, suppression of angiogenesis, inhibition of metastasis, and modulation of the tumor microenvironment. Additionally, UA has demonstrated promising activity against different cancer types (e.g., breast, lung, prostate, colon, and liver) by targeting various cancer hallmarks. This review discusses the molecular targets and signaling pathways involved in the anticancer effects of UA. Notably, UA has been found to modulate key signaling pathways, such as PI3K/Akt, MAPK/ERK, NF-κB, and Wnt/β-catenin, which play crucial roles in cancer development and progression. Moreover, the ability of UA to destroy cancer cells through various mechanisms (e.g., apoptosis, autophagy, inhibiting cell growth, dysregulating cancer cell metabolism, etc.) contributes to its multitargeted effects on cancer hallmarks. Despite promising anticancer effects, this review acknowledges hurdles related to UA’s low bioavailability, emphasizing the need for enhanced therapeutic strategies. Full article
(This article belongs to the Special Issue Biological Properties of Hydroxy Pentacyclic Triterpene Acids (HPTAs))
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16 pages, 1161 KiB  
Review
Multifunctional Roles of Betulinic Acid in Cancer Chemoprevention: Spotlight on JAK/STAT, VEGF, EGF/EGFR, TRAIL/TRAIL-R, AKT/mTOR and Non-Coding RNAs in the Inhibition of Carcinogenesis and Metastasis
by Ammad Ahmad Farooqi, Assiya Turgambayeva, Gulnara Tashenova, Aigul Tulebayeva, Aigul Bazarbayeva, Gulnara Kapanova and Symbat Abzaliyeva
Molecules 2023, 28(1), 67; https://doi.org/10.3390/molecules28010067 - 21 Dec 2022
Cited by 4 | Viewed by 2281
Abstract
The pursual of novel anticancer molecules from natural sources has gained worthwhile appreciation, and a significant fraction of conceptual knowledge has revolutionized our understanding about heterogeneous nature of cancer. Betulinic acid has fascinated interdisciplinary researchers due to its tremendous pharmacological properties. Ground-breaking discoveries [...] Read more.
The pursual of novel anticancer molecules from natural sources has gained worthwhile appreciation, and a significant fraction of conceptual knowledge has revolutionized our understanding about heterogeneous nature of cancer. Betulinic acid has fascinated interdisciplinary researchers due to its tremendous pharmacological properties. Ground-breaking discoveries have unraveled previously unprecedented empirical proof-of-concept about momentous chemopreventive role of betulinic acid against carcinogenesis and metastasis. Deregulation of cell signaling pathways has been reported to play a linchpin role in cancer progression and colonization of metastatically competent cancer cells to the distant organs for the development of secondary tumors. Importantly, betulinic acid has demonstrated unique properties to mechanistically modulate oncogenic transduction cascades. In this mini-review, we have attempted to provide a sophisticated compendium of regulatory role of betulinic acid in cancer chemoprevention. We have partitioned this multi-component review into different sections in which we summarized landmark research-works which highlighted betulinic acid mediated regulation of JAK/STAT, VEGF, EGF/EGFR, TRAIL/TRAIL-R, AKT/mTOR and ubiquitination pathways in the inhibition of cancer. In parallel, betulinic acid mediated regulation of signaling cascades and non-coding RNAs will be critically analyzed in cell culture and animal model studies. Better comprehension of the pharmaceutical features of betulinic acid and mapping of the existing knowledge gaps will be valuable in the translatability of preclinical studies into rationally designed clinical trials. Full article
(This article belongs to the Special Issue Biological Properties of Hydroxy Pentacyclic Triterpene Acids (HPTAs))
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