scholarly journals Semisynthesis of Derivatives of Oleanolic Acid fromSyzygium aromaticumand Their Antinociceptive and Anti-Inflammatory Properties

2016 ◽  
Vol 2016 ◽  
pp. 1-9 ◽  
Author(s):  
Sibusiso Rali ◽  
Opeoluwa O. Oyedeji ◽  
Olukayode O. Aremu ◽  
Adebola O. Oyedeji ◽  
Benedicta N. Nkeh-Chungag
Keyword(s):  
Oleanolic Acid ◽  
Acetyl Derivative ◽  
Syzygium Aromaticum ◽  
Analgesic Effects ◽  
Pentacyclic Triterpenoid ◽  
Ft Ir ◽  
Anti Inflammatory ◽  
Pain Test ◽  
Layer Chromatography ◽  
Derivatives Of

Oleanolic acid is a pentacyclic triterpenoid compound widely found in plants and well known for its medicinal properties. Oleanolic acid (OA) was isolated from the ethyl acetate extract ofSyzygium aromaticumflower buds. Semisynthesis afforded both acetate and ester derivatives. The derived compounds were monitored with thin layer chromatography and confirmed with nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry (MS), Fourier infrared (FT-IR) spectroscopy, and melting point (Mp). All these compounds were evaluated for their analgesic and anti-inflammatory properties at a dose of 40 mg/kg. Significant analgesic and anti-inflammatory effects were noted for all OA-derived compounds. In the formalin-induced pain test, the derivatives showed better analgesic effects compared to their precursor, whereas, in the tale flick test, oleanolic acid proved to be superior in analgesic effects compared to all its derivatives with the exception of the acetyl derivative. Acute inflammatory tests showed that acetyl derivatives possessed better anti-inflammatory activity compared to the other compounds. In conclusion, semisynthesis of oleanolic acid yielded several derivatives with improved solubility and enhanced analgesic and anti-inflammatory properties.

scholarly journals Anti-Cancer Potential of Synthetic Oleanolic Acid Derivatives and Their Conjugates with NSAIDs

Molecules ◽  
2021 ◽  
Vol 26 (16) ◽  
pp. 4957
Author(s):  
Wanda Baer-Dubowska ◽  
Maria Narożna ◽  
Violetta Krajka-Kuźniak
Keyword(s):  
Signaling Pathways ◽  
Oleanolic Acid ◽  
Short Review ◽  
Therapeutic Effects ◽  
Pentacyclic Triterpenoid ◽  
Anti Cancer ◽  
Inflammatory Drugs ◽  
Anti Inflammatory ◽  
Synthetic Derivatives ◽  
Cancer Activity

Naturally occurring pentacyclic triterpenoid oleanolic acid (OA) serves as a good scaffold for additional modifications to achieve synthetic derivatives. Therefore, a large number of triterpenoids have been synthetically modified in order to increase their bioactivity and their protective or therapeutic effects. Moreover, attempts were performed to conjugate synthetic triterpenoids with non-steroidal anti-inflammatory drugs (NSAIDs) or other functional groups. Among hundreds of synthesized triterpenoids, still the most promising is 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid (CDDO), which reached clinical trials level of investigations. The new group of synthetic triterpenoids are OA oximes. The most active among them is 3-hydroxyiminoolean-12-en-28-oic acid morpholide, which additionally improves the anti-cancer activity of standard NSAIDs. While targeting the Nrf2 and NF-κB signaling pathways is the main mechanism of synthetic OA derivatives′ anti-inflammatory and anti-cancer activity, most of these compounds exhibit multifunctional activity, and affect cross-talk within the cellular signaling network. This short review updates the earlier data and describes the new OA derivatives and their conjugates in the context of modification of signaling pathways involved in inflammation and cell survival and subsequently in cancer development.

scholarly journals Anticancer and Anti-Inflammatory Activities of Some New Pyrazolo[3,4-b]pyrazines

Molecules ◽  
2018 ◽  
Vol 23 (10) ◽  
pp. 2657
Author(s):  
Hussein El-Kashef ◽  
Talaat El-Emary ◽  
Pierre Verhaeghe ◽  
Patrice Vanelle ◽  
Maha Samy
Keyword(s):  
Breast Cancer ◽  
Cell Line ◽  
Cancer Cell Line ◽  
Acetyl Derivative ◽  
The Other ◽  
Reference Drug ◽  
Anti Inflammatory ◽  
Sar Study ◽  
Derivatives Of ◽  
Mcf 7

New derivatives of pyrazolo[3,4-b]pyrazines and related heterocycles were synthesized using 5-amino-3-methyl-4-nitroso-1-phenyl-pyrazole (1) as a starting material. The 5-acetyl derivative 15 was shown to be a useful key intermediate for the synthesis of several derivatives of pyrazolopyrazines. Some of the prepared compounds were evaluated for their anti-inflammatory and anti-breast cancer MCF-7 cell line activities. SAR study showed that compounds 15 and 29 exhibited remarkable anti-inflammatory activity, where 15 showed the same activity as that of the reference drug indomethacin. On the other hand, compounds 25i, 25j showed very significant inhibitory activity (p < 0.001) against MCF-7 breast cancer cell line.

A Review on Recent Developments in the Anticancer Potential of Oleanolic acid and its analogs (2017-2020)

2021 ◽  
Vol 21 ◽  
Author(s):  
Nidhi Gupta
Keyword(s):  
Clinical Trials ◽  
Natural Product ◽  
Oleanolic Acid ◽  
Anticancer Agents ◽  
Biological Activities ◽  
Pentacyclic Triterpenoid ◽  
Recent Developments ◽  
Anti Inflammatory ◽  
Pharmaceutical Properties

: Oleanolic acid (OA) is a pentacyclic triterpenoid class of natural product known to possess a broad range of biological activities, specifically, anticancer. Considering the anticancer potential of OA, a large number of analogs have been prepared by several researchers through modifications at C-3, C-12 and C-28 –COOH to develop the potent anticancer agents with improved cytotoxicity and pharmaceutical properties. Some of the synthesized derivatives have been assessed in clinical trials also. This review summarizes the most recent synthetic and biological efforts in the development of oleanolic acid and its analogs during the period 2017-2020. Reports published during this period revealed that both OA and its analogs possess a remarkable potential for the development of effective anticancer agents along with several others such as anti-inflammatory, anti-viral, anti-microbial and anti-diabetic agents.

scholarly journals Interaction of 5′-Guanosine Monophosphate with Organotin(IV) Moieties: Synthesis, Structural Characterization, and Anti-Inflammatory Activity

2012 ◽  
Vol 2012 ◽  
pp. 1-9 ◽  
Author(s):  
Mala Nath ◽  
Hitendra Singh ◽  
George Eng ◽  
Xueqing Song
Keyword(s):  
Structural Characterization ◽  
Spectroscopic Studies ◽  
Guanosine Monophosphate ◽  
Inflammatory Activity ◽  
Albino Rats ◽  
Trigonal Bipyramidal ◽  
Ft Ir ◽  
Anti Inflammatory ◽  
Derivatives Of ◽  
Distorted Trigonal Bipyramidal

Reaction(s) of 5′-guanosine monophosphate (5′GMP) with di- and triorganotin(IV) chloride(s) led to formation of organotin(IV) derivatives of general formulae, [R2Sn(5′-GMP)·H2O]n and [(R′3Sn)2(5′-GMP)·H2O]n, where R = Me, n-Bu, and Ph; R′ = Me, i-Pr, n-Bu, and Ph; (5′-GMP)2− = 5′-guanosine monophosphate. An attempt has been made to prove the structures of the resulting derivatives on the basis of FT-IR, multinuclear 1H, 13C, and 119Sn NMR and 119Sn Mössbauer spectroscopic studies. These investigations suggest that both di- and triorganotin(IV)-5′-guanosine monophosphates are polymeric in which (5′-GMP)2− is bonded through phosphate group resulting in a distorted trigonal bipyramidal geometry around tin. The ribose conformation in all of the derivatives is C3′-endo, except diphenyltin(IV) and tri-i-propyltin(IV) derivatives where it is C2′-endo. All of the studied derivatives exhibited mild-to-moderate anti-inflammatory activity (~15.64–20.63% inhibition) at 40 mg kg−1 dose and LD50 values > 400 mg kg−1 in albino rats.

Synthesis and anti-inflammatory activity of saponin derivatives of δ-oleanolic acid

2021 ◽  
Vol 209 ◽  
pp. 112932
Author(s):  
Liu Liu ◽  
Haobin Li ◽  
Kaiwen Hu ◽  
Qinglong Xu ◽  
Xiaoan Wen ◽  
...  
Keyword(s):  
Oleanolic Acid ◽  
Inflammatory Activity ◽  
Anti Inflammatory ◽  
Derivatives Of

scholarly journals Anti-dengue activity of super critical extract and isolated oleanolic acid of Leucas cephalotes using in vitro and in silico approach

2021 ◽  
Vol 21 (1) ◽  
Author(s):  
Sulochana Kaushik ◽  
Lalit Dar ◽  
Samander Kaushik ◽  
Jaya Parkash Yadav
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Oleanolic Acid ◽  
Plant Extract ◽  
In Silico ◽  
Rt Pcr ◽  
Ft Ir ◽  
Isolated Compound ◽  
Layer Chromatography

Abstract Backgrounds Leucas cephalotes is a common ethnomedicinal plant widely used by traditional healers for the treatment of Malaria and other types of fever. Oleanolic acid and its derivatives have been reported for various types of pharmacological activities, such as anti-inflammatory, antioxidant, anticancer, hepatoprotective, anti-HIV and anti-HCV activity. Methods L.cephalotes plant extracts were prepared by supercritical fluid extraction (SFE) method and oleanolic acid was isolated by preparatory thin-layer chromatography. The compound was identified and characterize by using ultraviolet-visible spectroscopy (UV-VIS), Fourier transform infra-Red spectroscopy (FT-IR) and high-performance thin-layer chromatography (HPTLC). The structure of the compound was elucidated by proton nuclear magnetic resonance (1HNMR) and carbon nuclear magnetic resonance (1CNMR) and the purity checked by differential scanning calorimetry (DSC). The MTT assay was used to determine the toxicity of plant extract and oleanolic acid using a microplate reader at 595 nm. The anti-dengue activity of plant extract and oleanolic acid was tested in vitro and in silico using real-time RT-PCR. Results The optimum yield of the extract was obtained at 40 °C temperature and 15Mpa pressure. The maximum non-toxic dose (MNTD) of plant extract and oleanolic acid were found as 46.87 μg/ml and 93.75 μg/ml, respectively in C6/36 cell lines. UV spectrophotometer curve of the isolated compound was overlapped with standard oleanolic acid at 232 nm. Superimposed FT-IR structure of the isolated compound was indicated the same spectra at 3433, 2939, 2871, 1690, 1500,1463, 1387, 1250, 1209, 1137 and 656 position as per marker compound. HPTLC analysis showed the retention factor of L. cephalotes extract was 0.19 + 0.06 as similar to the standard oleanolic acid chromatogram. The NMR structure of the isolated compound was identified as similar to the marker oleanolic acid structure. DSC analysis revealed the purity of isolated oleanolic acid was 98.27% with a melting point of 311.16 °C. Real-time RT PCR results revealed that L. cephalotes supercritical extract and isolated oleanolic acid showed 100 and 99.17% inhibition against the dengue − 2 virus when treated with MNTD value of plant extract (46.87 μg/ml) and the test compound (93.75 μg/ml), respectively. The molecular study demonstrated the binding energy of oleanolic acid with NS1and NS5 (non-structural protein) were − 9.42 & -8.32Kcal/mol, respectively. Conclusions The SFE extract L. cephalotes and its active compound, oleanolic acid inhibiting the activity of dengue-2 serotype in the in vitro and in silico assays. Thus, the L.cephalotes plant could be an excellent source for drug design for the treatment of dengue infection.

N-arylmethylideneaminophthalimide: Design, Synthesis and Evaluation as Analgesic and Anti-inflammatory Agents

2019 ◽  
Vol 19 (8) ◽  
pp. 679-687 ◽  
Author(s):  
Nasimossadat Banarouei ◽  
Asghar Davood ◽  
Hamed Shafaroodi ◽  
Ghazaleh Saeedi ◽  
Abbas Shafiee
Keyword(s):  
Room Temperature ◽  
Antiinflammatory Activity ◽  
Chemical Characterization ◽  
Design Synthesis ◽  
Reference Drug ◽  
Anti Inflammatory ◽  
Pain Test ◽  
Derivatives Of

Background and Objective: N-aryl derivatives of phthalimide and 4-nitro phthalimide have demonstrated cyclooxygenase inhibitory activity. Also, they possess excellent analgesic and antiinflammatory activity. In this work, a new series of N-arylmethylideneamino derivatives of phthalimide and 4-nitro phthalimide were designed and synthesized. Methods: The designed compounds were synthesized by condensation of the appropriate aldehyde and N-aminophthalimide in ethanol at room temperature at PH around 3. Their analgesic and antiinflammatory activity were evaluated by acetic acid-induced pain test and carrageenan-induced paw edema test in mice and rats, respectively. Results and Conclusion:: The details of the synthesis and chemical characterization of the analogs are described. In vivo screening showed compounds 3a, 3b, 3f and 3h were the most potent analgesic compounds. In addition, compounds 3a, 3c, 3d, 3e and 3j indicated comparable anti-inflammatory activity to indomethacin as a reference drug.

Evaluation of Anti-inflammatory and Analgesic Effects of Synthesized Derivatives of Ibuprofen

2014 ◽  
Vol 85 (5) ◽  
pp. 623-632 ◽  
Author(s):  
Jingjie Wang ◽  
Dongyan Dai ◽  
Qianqian Qiu ◽  
Xin Deng ◽  
Haiyan Lin ◽  
...  
Keyword(s):  
Analgesic Effects ◽  
Anti Inflammatory ◽  
Derivatives Of

scholarly journals Synthesis, Characterization and Preliminary Anti-inflammatory Evaluation of New Fenoprofen Hydrazone Derivatives

2020 ◽  
Vol 29 (2) ◽  
pp. 239-244
Author(s):  
Hayder M. Abdulhamza ◽  
Muthanna S. Farhan
Keyword(s):  
Ir Spectroscopy ◽  
Egg White ◽  
Inflammatory Activity ◽  
Paw Edema ◽  
Ft Ir ◽  
Anti Inflammatory ◽  
Multistep Reaction ◽  
Derivatives Of ◽  
Ft Ir Spectroscopy ◽  
Inflammatory Effect

New hydrazone derivatives of Fenoprofen were synthesized and evaluated for their anti-inflammatory activity by means of egg white induced paw edema method. All the synthesized target compounds were characterized by FT-IR spectroscopy, 1HNMR analysis and by measure of their physical properties. The synthesis of the target compounds(H1-H4) was accomplished by multistep reaction procedures. The synthesized target compounds were show activity in reducing paw edema thickness and their anti-inflammatory effect was comparable to that of the standard (Fenoprofen) except for compound H3 which show anti-inflammatory activity higher than Fenoprofen.

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