New pentacyclic triterpene saponins with strong anti-leishmanial activity from the leaves of Maesa balansae

Germonprez, Nils; Puyvelde, Luc Van; Maes, Louis; Tri, Mai Van; Kimpe, Norbert De

doi:10.1016/j.tet.2003.09.042

Cited by 38 publications

(43 citation statements)

References 10 publications

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“…For example, Yoshikawa et al (1994Yoshikawa et al ( , 1997) identified a number of acylated triterpenoid saponins, sitakisosides, in Stephanotis lutchuensis, including some that are acylated with N-methyl anthranilate. Triterpenoid saponins that are acylated with benzoate and that exhibit antileishmanial activity have also been reported from Maesa balansae (Germonprez et al, 2004). Triterpenes have a diverse range of biological activities and are an important source of pharmaceuticals and other commercially valuable compounds (Francis et al, 2002;Sparg et al, 2004;Liby et al, 2007).…”

Section: Discussionmentioning

confidence: 99%

A Serine Carboxypeptidase-Like Acyltransferase Is Required for Synthesis of Antimicrobial Compounds and Disease Resistance in Oats

et al. 2009

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Serine carboxypeptidase-like (SCPL) proteins have recently emerged as a new group of plant acyltransferases. These enzymes share homology with peptidases but lack protease activity and instead are able to acylate natural products. Several SCPL acyltransferases have been characterized to date from dicots, including an enzyme required for the synthesis of glucose polyesters that may contribute to insect resistance in wild tomato (Solanum pennellii) and enzymes required for the synthesis of sinapate esters associated with UV protection in Arabidopsis thaliana. In our earlier genetic analysis, we identified the Saponin-deficient 7 (Sad7) locus as being required for the synthesis of antimicrobial triterpene glycosides (avenacins) and for broad-spectrum disease resistance in diploid oat (Avena strigosa). Here, we report on the cloning of Sad7 and show that this gene encodes a functional SCPL acyltransferase, SCPL1, that is able to catalyze the synthesis of both N-methyl anthraniloyl-and benzoyl-derivatized forms of avenacin. Sad7 forms part of an operon-like gene cluster for avenacin synthesis. Oat SCPL1 (SAD7) is the founder member of a subfamily of monocot-specific SCPL proteins that includes predicted proteins from rice (Oryza sativa) and other grasses with potential roles in secondary metabolism and plant defense.

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Section: Discussionmentioning

confidence: 99%

A Serine Carboxypeptidase-Like Acyltransferase Is Required for Synthesis of Antimicrobial Compounds and Disease Resistance in Oats

et al. 2009

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“…Recently, plant compounds with widely different chemical structures that show antileishmanial activities have been isolated: ancistrolikokine D from Ancistrocladus likoko (8), coronaridine from Peschiera australis (11), 3-heptadecyl-5-metoxyphenol from Oxalis erythrorhiza (15), canthin-6-one and 5-methoxy-canthin-6-one from Zanthoxylum chiloperone (16), maesabalide from Maesa balansae (20), ␥-pirones from Podolepsis hieracioides (28), and 2Ј,6Ј-dihydroxy-4Ј-methoxychalcone from Piper aduncum (41). This demonstrates that medicinal plants hold promise as sources of chemical leads for the development of novel therapeutic agents in the fight against leishmaniasis.…”

Section: Discussionmentioning

confidence: 99%

Antileishmanial Activity of Parthenolide, a Sesquiterpene Lactone Isolated from Tanacetum parthenium

Tiuman

Ueda-Nakamura

Cortez³

et al. 2005

Antimicrob Agents Chemother

183

116

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The in vitro activity of parthenolide against Leishmania amazonensis was investigated. Parthenolide is a sesquiterpene lactone purified from the hydroalcoholic extract of aerial parts of Tanacetum parthenium. This isolated compound was identified through spectral analyses by UV, infrared, 1 H and 13 C nuclear magnetic resonance imaging, DEPT (distortionless enhancement by polarization transfer), COSY (correlated spectroscopy), HMQC (heteronuclear multiple-quantum coherence), and electron spray ionization-mass spectrometry. Parthenolide showed significant activity against the promastigote form of L. amazonensis, with 50% inhibition of cell growth at a concentration of 0.37 g/ml. For the intracellular amastigote form, parthenolide reduced by 50% the survival index of parasites in macrophages when it was used at 0.81 g/ml. The purified compound showed no cytotoxic effects against J774G8 macrophages in culture and did not cause lysis in sheep blood when it was used at higher concentrations that inhibited promastigote forms. Sodium dodecyl sulfate-polyacrylamide gel electrophoresis with gelatin as the substrate showed that the enzymatic activity of the enzyme cysteine protease increased following treatment of the promastigotes with the isolated compound. This finding was correlated with marked morphological changes induced by parthenolide, such as the appearance of structures similar to large lysosomes and intense exocytic activity in the region of the flagellar pocket, as seen by electron microscopy. These results provide new perspectives on the development of novel drugs with leishmanicidal activities obtained from natural products.

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“…In situ acid hydrolysis of 1 afforded D-glucose. According to the molecular rotation formula (Klyne, 1950) (Germonprez, Puyvelde, Maes, Tri, & Kimpe, 2004). According to the molecular rotation calculation, the glucose in 1 should possess the absolute configuration D-form, which is the common form for glucose existing in nature.…”

Section: Resultsmentioning

confidence: 99%

Constituents of Nelumbo nucifera leaves and their antimalarial and antifungal activity

Agnihotri

ElSohly

Khan

et al. 2008

Phytochemistry Letters

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From the leaves of Nelumbo nucifera (an aquatic plant), one new compound, 24(R)-ethylcholest-6-ene-5α-ol-3-O-β-D-glucopyranoside (1), along with 11 known metabolites (2-12), were isolated and identified by spectroscopic methods including 1D-and 2D NMR. Antifungal activity for (R)-roemerine (3) (IC 50 /MIC = 4.5/10 μg/mL against Candida albicans) and antimalarial activity for (R)-roemerine (3) and N-methylasimilobine (5) (IC 50 = 0.2 and 4.8 μg/mL for the D6 clone, respectively, and 0.4 and 4.8 μg/mL for the W2 clone, respectively) was observed. None of the compounds were cytotoxic to Vero cells up to a concentration of 23.8 μg/mL. NMR data for 10-eicosanol (7) and 7,11,15-trimethyl-2-hexadecanone (10) are presented for the first time. An analysis of the structure-activity relationship shows that the substituents in position C-1 and C-2 of aporphine alkaloids are crucial for the antimalarial activity.

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New pentacyclic triterpene saponins with strong anti-leishmanial activity from the leaves of Maesa balansae

Cited by 38 publications

References 10 publications

A Serine Carboxypeptidase-Like Acyltransferase Is Required for Synthesis of Antimicrobial Compounds and Disease Resistance in Oats

A Serine Carboxypeptidase-Like Acyltransferase Is Required for Synthesis of Antimicrobial Compounds and Disease Resistance in Oats

Antileishmanial Activity of Parthenolide, a Sesquiterpene Lactone Isolated from Tanacetum parthenium

Constituents of Nelumbo nucifera leaves and their antimalarial and antifungal activity

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