A Review of Natural and Modified Betulinic, Ursolic and Echinocystic Acid Derivatives as Potential Antitumor and Anti-HIV Agents

Baglin, Isabelle; Mitaine-Offer, Anne Claire; Nour, Mohammed; Tan, Kimny; Cavé, Christian; Lacaille‐Dubois, Marie‐Aleth

doi:10.2174/1389557033487917

Cited by 94 publications

(57 citation statements)

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“…OA, UA and their derivatives efficiently inhibit the development of several viruses including HIV. The mechanism of their antiviral activity is already partially resolved, which should permit the therapeutic use of these compounds in the near future [16][17][18][19][20].…”

Section: Introductionmentioning

confidence: 99%

Antibacterial activity of oleanolic and ursolic acids and their derivatives

et al. 2010

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Bacterial resistance to antibiotics is increasing at an alarming rate and many commonly used antibiotics are no longer effective.Thus, there is considerable interest in investigating novel antibacterial compounds, such as the plant-derived pentacyclic triterpenoids, including oleanolic acid (OA), ursolic acid (UA) and their derivatives. These compounds can be isolated from many medicinal and crop plants and their antibacterial, antiviral, antiulcer and anti-inflammatory effects are well documented. OA and UA are active against many bacterial species, particularly Gram-positive species, including mycobacteria. They inhibit bacterial growth and survival, and the spectrum of minimal inhibitory concentration (MIC) values is very broad. In addition, OA, UA and their derivatives display potent antimutagenic activity. Studies to identify the cellular targets and molecular mechanisms of OA and UA action were initiated a few years ago and it has already been demonstrated that both acids influence bacterial gene expression, the formation and maintenance of biofilms, cell autolysis and peptidoglycan turnover. Before these compounds can be used clinically as antimicrobial agents, further extensive studies are required to determine their cytotoxicity and the optimum mode of their application.

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Section: Introductionmentioning

confidence: 99%

Antibacterial activity of oleanolic and ursolic acids and their derivatives

et al. 2010

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“…This class of natural products and their derivatives have been reported to have interesting biological activities, such as anti-HIV, 6,7) antiplasmodial 8,9) and cytotoxic activities. 10,11) Previous investigations have shown that triterpenes also exhibit moderate to high in vitro antimycobacterial activity against M. tuberculosis. [12][13][14] It was reported 12) that betulinic acid (1) was more active than its C-3 epimer, epi-betulinic acid.…”

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Antimycobacterial Activity of Cinnamate-Based Esters of the Triterpenes Betulinic, Oleanolic and Ursolic Acids

et al. 2008

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Betulinic acid, oleanolic acid and ursolic acid have been modified at the C-3 position to cinnamate-based esters and in vitro antimycobacterial activity against Mycobacterium tuberculosis H 37 Ra has been determined. The results indicated that modification of the parent structures of betulinic acid, oleanolic acid and ursolic acid to the p-coumarate and, in the case of the latter two triterpenes, the ferulate ester analogues resulted in high antimycobacterial activity. Structure-activity relationships within the lupane, oleanane and ursane analogues and between these triterpenes are discussed.

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“…A major breakthrough occurred 2 years later, when betulinic acid, dihydrobetulinic acid, and platanic acid were shown to be potent and moderately selective HIV inhibitors and that, among various betulinic acid derivatives esterified at C3, the hemisuccinate retained similar potency (Fujioka et al 1994). This led to the development of the extremely potent 3-O-(3 0 ,3 0 -dimethylsuccinyl)betulinic acid, which inhibited HIV replication with EC 50 \ 0.35 nM and a selectivity index of 20,000 (Hashimoto et al 1997) (Bevirimat,, and which is now in Phase II clinical studies: Two important reviews published just before the period we are covering are those of Sun et al (2003) and Baglin et al (2003), the latter concentrating on triterpenoids and more specifically betulinic, ursolic and echinocystic acid derivatives. A short paper on the HIV-1 antiviral activity of betulinic acid derivatives is one by Aiken and Chen (2005).…”

Section: Introductionmentioning

confidence: 99%

Anti-HIV activity of natural triterpenoids and hemisynthetic derivatives 2004–2009

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Asencio²

2010

Phytochem Rev

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The continued advance of HIV-AIDS makes the development of relatively inexpensive, freely accessible, and mechanistically more diverse antiviral therapies an urgent need. Natural products are, directly or indirectly, an important potential source of compounds meeting these conditions. A review of the recent literature indicates that some hemisynthetic triterpenoid derivatives, particularly belonging to the lupane, oleanane and ursane series, may be nearing a stage where they can be used to complement existing therapeutic approaches. On the other hand, although some natural derivatives of tetracyclic terpenoid families have revealed many novel structures and some promise as anti-HIV substances, their chemical modification to improve their potency and selectivity remains practically untouched. While ongoing work with the more 'classical' pentacyclic triterpenoids will continue to be a fertile field for HIV-AIDS drug discovery, the other structural groups offer unprecedented opportunities for the development of additional substances with useful properties and for the discovery of novel targets for antiviral therapy.

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A Review of Natural and Modified Betulinic, Ursolic and Echinocystic Acid Derivatives as Potential Antitumor and Anti-HIV Agents

Cited by 94 publications

References 0 publications

Antibacterial activity of oleanolic and ursolic acids and their derivatives

Antibacterial activity of oleanolic and ursolic acids and their derivatives

Antimycobacterial Activity of Cinnamate-Based Esters of the Triterpenes Betulinic, Oleanolic and Ursolic Acids

Anti-HIV activity of natural triterpenoids and hemisynthetic derivatives 2004–2009

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