The Beckmann Rearrangement Applied to Ursolic Acid with Antimalarial Activity in Medicinal Chemistry Studies

Dalla-Vechia, Luciana; Dassonville‐Klimpt, Alexandra; Grellier, Philippe; Sonnet, Pascal; Gosmann, Grace; Gnoatto, Simone Cristina Baggio

doi:10.2174/157017812800221708

Cited by 10 publications

(8 citation statements)

References 7 publications

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“…Substances were detected by 10% H 2 SO 4 with subsequent heating to 100-120 • C for 2-3 min. Betulonic aldehyde [24], compounds 1 [20], 3 [21], ursonic acid and 4 [22], 11 [23] were obtained according to the methods described previously.…”

Section: General Methods and Physical Measurementsmentioning

confidence: 99%

“…The following p-TsOH catalyzed rearrangement of compound 1 resulted in azepanoallobetulin 2 with a yield of 86%. Reduction of lupane A-azepanono-C28-nitryl 3 [21] and 2-cyano-3,4-seco-ursolic acid 4 [22] with LiAlH 4 under reflux in tetrahydrofurane led to methylenamino-derivatives 5 and 6. Betulin and C28-hydroxy-triterpenoids 1 or 6 were converted to corresponding aldehydes and were reacted with spermidine in MeOH under reflux to obtain aldimines 7-9 in yields of 65-72%.…”

Section: Chemistrymentioning

confidence: 99%

“…A mixture of compound 3 [21] (225 mg, 0.5 mmol) or compound 4 [22] (226 mg, 0.5 mmol) and LiAlH 4 (230 mg, 0.65 mmol) in dry THF (20 mL) was refluxed for 3 h and then poured into a 5% HCl solution (100 mL). The crude product was extracted with CHCl 3 (3 × 40 mL), and then the organic layer was washed with H 2 O, dried over CaCl 2 and evaporated under reduced pressure.…”

Section: Synthesis Of 5 Andmentioning

confidence: 99%

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A-Ring-Modified Triterpenoids and Their Spermidine–Aldimines with Strong Antibacterial Activity

Казакова

Brunel

Khusnutdinova

et al. 2019

Molbank

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Synthesis of A-ring-modified lupane, oleanane and ursane type triterpenoid conjugates with spermidine through an aldimine linkage or diethylentriamine via an amide bond is described. These derivatives were evaluated for their in vitro antimicrobial properties against human pathogens. Except for derivatives 1 and 7, all compounds have moderate to weak minimum inhibitory concentrations (MICs) against Gram-positive Staphylococcus aureus bacteria, with MICs varying from 3.125 to 200 µM. Compound 11 is efficient against Escherichia coli and Pseudomonas aeruginosa, with MICs of 25 and 50 µM, respectively, while all other derivatives do not possess important antimicrobial activities against these Gram-negative bacteria.

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Section: General Methods and Physical Measurementsmentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

Section: Synthesis Of 5 Andmentioning

confidence: 99%

See 1 more Smart Citation

A-Ring-Modified Triterpenoids and Their Spermidine–Aldimines with Strong Antibacterial Activity

Казакова

Brunel

Khusnutdinova

et al. 2019

Molbank

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“…Moreover, UNA was shown to exert an in vitro suppressive effect in Trichomonas vaginalis, which is responsible for trichomoniasis, a sexually transmitted disease (55% inhibition at a dose of 100 µM) [68]. In addition, UNA showed an antimalarial effect against a chloroquine-resistant strain of Plasmodium falciparum in a micromolar dosage (IC 50 = 41 µM), which was slightly more active than the effect from ULA (IC 50 = 53 µM) [69]. It is noteworthy that UNA exhibited suppressive effects in different types of parasitic protozoa, exhibiting IC 50 values with micromolar concentrations.…”

Section: Antiprotozoan Effectsmentioning

confidence: 99%

Therapeutic Potential of Ursonic Acid: Comparison with Ursolic Acid

Son

Lee

2020

Biomolecules

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Plants have been used as drugs to treat human disease for centuries. Ursonic acid (UNA) is a naturally occurring pentacyclic triterpenoid extracted from certain medicinal herbs such as Ziziphus jujuba. Since the pharmacological effects and associated mechanisms of UNA are not well-known, in this work, we attempt to introduce the therapeutic potential of UNA with a comparison to ursolic acid (ULA), a well-known secondary metabolite, for beneficial effects. UNA has a keto group at the C-3 position, which may provide a critical difference for the varied biological activities between UNA and ULA. Several studies previously showed that UNA exerts pharmaceutical effects similar to, or stronger than, ULA, with UNA significantly decreasing the survival and proliferation of various types of cancer cells. UNA has potential to exert inhibitory effects in parasitic protozoa that cause several tropical diseases. UNA also exerts other potential effects, including antihyperglycemic, anti-inflammatory, antiviral, and antioxidant activities. Of note, a recent study highlighted the suppressive potential of UNA against severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2). Molecular modifications of UNA may enhance bioavailability, which is crucial for in vivo and clinical studies. In conclusion, UNA has promising potential to be developed in anticancer and antiprotozoan pharmaceuticals. In-depth investigations may increase the possibility of UNA being developed as a novel reagent for chemotherapy.

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“…In 2006 two independent research teams led by van Baren [197] and Cimanga [200] discovered that triterpenes (including UA) were responsible for the anti-malarial activity of extracts from Satureja parvifolia and Morinda lucida . Innocente et al [198] and Della-Veccia et al [199] developed UA derivatives and evaluated them by their anti-Plasmodium activity. Despite using different modification methods both teams acquired compounds with very high anti-malarial properties.…”

Section: Anti-microbial Properties Of Ursolic Acidmentioning

confidence: 99%

Ursolic Acid—A Pentacyclic Triterpenoid with a Wide Spectrum of Pharmacological Activities

2015

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Ursolic acid (UA) is a natural terpene compound exhibiting many pharmaceutical properties. In this review the current state of knowledge about the health-promoting properties of this widespread, biologically active compound, as well as information about its occurrence and biosynthesis are presented. Particular attention has been paid to the application of ursolic acid as an anti-cancer agent; it is worth noticing that clinical tests suggesting the possibility of practical use of UA have already been conducted. Amongst other pharmacological properties of UA one can mention protective effect on lungs, kidneys, liver and brain, anti-inflammatory properties, anabolic effects on skeletal muscles and the ability to suppress bone density loss leading to osteoporosis. Ursolic acid also exhibits anti-microbial features against numerous strains of bacteria, HIV and HCV viruses and Plasmodium protozoa causing malaria.

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The Beckmann Rearrangement Applied to Ursolic Acid with Antimalarial Activity in Medicinal Chemistry Studies

Cited by 10 publications

References 7 publications

A-Ring-Modified Triterpenoids and Their Spermidine–Aldimines with Strong Antibacterial Activity

A-Ring-Modified Triterpenoids and Their Spermidine–Aldimines with Strong Antibacterial Activity

Therapeutic Potential of Ursonic Acid: Comparison with Ursolic Acid

Ursolic Acid—A Pentacyclic Triterpenoid with a Wide Spectrum of Pharmacological Activities

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