Heterocycle-fused lupane triterpenoids inhibit <i>Leishmania donovani</i> amastigotes

Haavikko, Raisa; Nasereddin, Abedelmajeed; Sacerdoti‐Sierra, Nina; Kopelyanskiy, Dmitry; Alakurtti, Sami; Tikka, Mari; Jaffe, Charles L.; Yli‐Kauhaluoma, Jari

doi:10.1039/c3md00282a

Cited by 51 publications

(36 citation statements)

References 24 publications

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“…The NMR spectra of 1 are in accordance with data reported in the literature for 3β-E-coumaroylbetulinic acid (1) [17]; 2 for lupeol fatty acid esters [18], 3 for betulonic acid [19], 4 for betulin [20], 5 for betulinic acid [21], 6 for lupeol [16], 7 for lupenone [22], 8 for 3β-E-feruloyllupeol [2], 9 for 3β-Zferuloyllupeol [2], and 10 for chlorophyll a [23].…”

Section: Resultssupporting

confidence: 70%

Triterpenes From Ceriops Decandra (Griff.) W. Theob.

Perez

Shen

Ragasa

2017

Asian J Pharm Clin Res

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Objective: To isolate and identify the chemical constituents of Ceriops decandra. Methods:The chemical constituents of C. decandra (Griff.) W. Theob. were isolated by silica gel chromatography. The structures of the isolated compounds were identified by nuclear magnetic resonance (NMR) spectroscopy.Results: Chemical investigation of the dichloromethane extracts of the leaves of C. decandra has led to the isolation of 3β-E-coumaroylbetulinic acid (1), lupeol fatty acid esters (2), betulonic acid (3), betulin (4), betulinic acid (5), lupeol (6), lupenone (7), and a mixture of 3β-E-feruloyllupeol (8) and 3β-Z-feruloyllupeol (9), and chlorophyll a (10). The structures of 1-10 were identified by comparison of their NMR data with literature data. Conclusion:To the best of our knowledge, this is the first report on the isolation of 1-3 from C. decandra. Literature search revealed that the triterpenes isolated from C. decandra exhibited anticancer properties.

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Section: Resultssupporting

confidence: 70%

Triterpenes From Ceriops Decandra (Griff.) W. Theob.

Perez

Shen

Ragasa

2017

Asian J Pharm Clin Res

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“…27 Preparation of quinoline derivatives was published by Zaprutko. 27 Preparation of quinoline derivatives was published by Zaprutko.…”

Section: Pyridine and Quinolone Derivativesmentioning

confidence: 99%

Pentacyclic triterpenoids with nitrogen- and sulfur-containing heterocycles: synthesis and medicinal significance

et al. 2015

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Triterpenoids are natural compounds with a variety of biological activities and are usually produced by plants as secondary metabolites. In recent decades, scientists focused on the properties of triterpenoids have discovered many activities, such as antitumor, antiviral, antimicrobial, anti-inflammatory and others. Thousands of new triterpenoids with various skeletal modifications have now been synthesized. One of the most important modifications is the formation of a new heterocyclic ring. The simple fact that the vast majority of currently used drugs are heterocyclic compounds has encouraged a lot of researches to synthesize analogous triterpenoid derivatives in order to find new molecules with higher activities and consequently optimize their pharmacological profile. The biological properties of triterpenoid heterocycles are very promising and many of them have been studied, especially as antitumor agents. This review is mainly focused on the synthesis of various types of nitrogen and occasionally sulfur-containing heterocyclic triterpenoids for their potential use as future drugs in medicine and in addition discusses their overall biological activities.

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“…17,18 The derivatives showing at least moderate inhibition (>30%) at 5 lM concentration were selected for cytotoxicity testing on fibroblast and macrophage cell lines, and activity on infected macrophages, respectively. Amphotericin B was used as positive control for activity against infected macrophages.…”

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confidence: 99%

“…Structures and antileishmanial activity of urea, retro-amide and sulfonamide analogs[14][15][16][17][18][19] …”

mentioning

confidence: 99%

Synthesis and biological evaluation of 2-arylbenzimidazoles targeting Leishmania donovani

Keurulainen

Siiskonen

Nasereddin³

et al. 2015

Bioorganic & Medicinal Chemistry Letters

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Heterocycle-fused lupane triterpenoids inhibit Leishmania donovani amastigotes

Abstract: The synthesis of heterocyclic betulin derivatives and their activity against Leishmania donovani are reported.

Cited by 51 publications

References 24 publications

Triterpenes From Ceriops Decandra (Griff.) W. Theob.

Triterpenes From Ceriops Decandra (Griff.) W. Theob.

Pentacyclic triterpenoids with nitrogen- and sulfur-containing heterocycles: synthesis and medicinal significance

Synthesis and biological evaluation of 2-arylbenzimidazoles targeting Leishmania donovani

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