Limonoids from the stem bark of Cedrela odorata

Kipassa, Nsiama Tienabe; Iwagawa, Tetsuo; Okamura, Hiroaki; Doe, Matsumi; Morimoto, Yoshiki; Nakatani, Munehiro

doi:10.1016/j.phytochem.2007.12.015

Cited by 49 publications

(54 citation statements)

References 17 publications

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“…The protona td H = 4.98 ppm (br d, J = 3.5 Hz, H-23) showedH MBC correlations with carbon signals at d C = 110.3 (C-21), 84.1 (C-20), and 54.6 ppm (O-Me), allowing the attribution of one methoxy group at C-23. [11] In particular, proton and carbon atoms of A, D, and furan rings, resonated at almostt he same frequencies as the corresponding signals in 2,w hereas in rings Ba nd C, NMR signals were observed at slightly different positions. Thus, it was concluded that the C-17 side chain is a2 0,22-dihydroxy-21,23-dimethoxy tetrahydrofuran.…”

Section: Resultsmentioning

confidence: 82%

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Identification of Limonol Derivatives as Heat Shock Protein 90 (Hsp90) Inhibitors through a Multidisciplinary Approach

Chini

Malafronte

Vaccaro

et al. 2016

Chemistry A European J

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The identification of inhibitors of Hsp90 is currently a primary goal in the development of more effective drugs for the treatment of various types of multidrug resistant malignancies. In an attempt to identify new small molecules modulating the activity of Hsp90, we screened a small library of tetranortriterpenes. A high-affinity interaction with Hsp90 inducible form was uncovered for eight of these compounds, five of which are described here for the first time. By monitoring the ATPase activity and the citrate synthase thermal induced aggregation, compound 1 (cedrelosin A), 3 (7α-limonylacetate), and 5 (cedrelosin B), containing a limonol moiety, were found to be the most effective in compromising the Hsp90α chaperone activity. Consistent with these findings, the three compounds caused a depletion of c-Raf and pAkt Hsp90 client proteins in HeLa and MCF/7 cell lines. Induced fit docking protocol and molecular dynamics were used to rationalize the structural basis of the biological activity of the limonol derivatives. Taken together, these results point to limonol-derivatives as promising scaffolds for the design of novel Hsp90α inhibitors.

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Section: Resultsmentioning

confidence: 82%

“…The NMR spectroscopic data suggested that 7 was an omilin derivative [11,22] with side chain as pointo fd ifference. The NMR spectroscopic data suggested that 7 was an omilin derivative [11,22] with side chain as pointo fd ifference.…”

Section: Resultsmentioning

confidence: 98%

Identification of Limonol Derivatives as Heat Shock Protein 90 (Hsp90) Inhibitors through a Multidisciplinary Approach

Chini

Malafronte

Vaccaro

et al. 2016

Chemistry A European J

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“…Los anterior sugiere que los individuos que forman al grupo uno pueden llegar a presentar una mejor defensa frente al ataque de H. grandella. Por otro lado, algunas investigaciones reportan que los limonoides son de poco valor en la resistencia al barrenador (Da Silva et al, 1999;De Paula et al, 1997), sin embargo, los limonoides de la familia Meliaceae han sido estudiados por sus propiedades insecticidas, como el estudio de Kipassa et al (2008), quienes hacen referencia a los limonoides de la corteza del tallo de C. odorata y la capacidad anti-alimentaria en Spodoptera littoralis (Lepidoptera: Noctuidae). De esta forma, los individuos del grupo tres resultan interesantes como fuente de limonoides para investigaciones posteriores con respecto a sus propiedades insecticidas.…”

Section: Fig 4 (A) Cromatogramas De Hplc De Extractos Metanólicos Funclassified

“…A pesar de que H. grandella ha sido estudiada (Cornelius & Watt, 2003;Hilje, & Cornelius, 2001;Pérez-Salicrup, & Esquivel, 2008;Soto, Hilje, Mora, & Carballo, 2011), aún no se ha desarrollado un sistema de manejo integrado. Algunos metabolitos secundarios de aceites y extractos de C. odorata han sido evaluados con diferente finalidad, entre ellas, la búsqueda de nuevos limonoides antialimentarios, la implicación ecológica en la atracción de H. grandella, evaluación de las propiedades inhibitorias de crecimiento frente algunos insectos y la investigación de sus propiedades medicinales (Asekun, & Ekundayo, 1999;Da Silva et al, 1999;De Paula et al, 1997;González-Coloma et al, 2012;Maia et al, 2000;Kipassa et al, 2008;Martins et al, 2003;Omar et al, 2003;Silva, Souza, Rogez, Rees, & Larondelle, 2007;Villanueva, Tuten, Haber, & Setzer, 2009). Sin embargo, no se han evaluado las posibles diferencias cuantitativas y cualitativas de diferentes individuos de C. odorata.…”

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Evaluación de fenoles y limonoides en hojas de Cedrela odorata (Meliaceae) de una plantación experimental establecida en Tezonapa Veracruz, México

Mariscal-Lucero

Rosales-Castro

Sánchez-Monsalvo

et al. 2014

RBT

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Cedrela odorata (Meliaceae) is a native timber tree to Tropical America, known for its high-quality wood, unfortunately, plantations of this species are severely attacked by Hypsipyla grandella. The attraction or repellency of this pest is related to secondary metabolites such as phenols and limonoids (triterpenes); therefore, it is important to study these compounds to understand the phytochemical phenomena behind this problem. With this aim, the concentration of total phenols and limonoides was evaluated in C. odorata leaves from a plantation established in Tezonapa Veracruz, Mexico. For this, a total of 66 tree leaves samples, from seven sites, were analyzed. Phenols and limonoids concentration showed significant differences not only among different provenances, but also among individual trees of the same site (Tukey, p≤0.05). Phenols concentration was variable and in the range from 49 to 223mg EAG/g e for total phenols, from 7 to 158mg EC/g e for flavonoids and from 4 to 104mg EC/g e for proanthocyanidins. Limonoids concentration was also variable, ranging between 227 and 748mg EL/g e. A major compound was found by High-Performance Liquid Chromatography with Ultraviolet Diode Array Detection (HPLC-UV-DAD), which corresponded to a flavonol kaempferol glycoside derivative; additionally, a flavanol catechin was also detected at low concentrations. GC–MS allowed the identification of the sesquiterpenoids β-elemene, E-caryophyllene, aromadendrene, α-humulene, γ-cadinene, D-germacrene, bicyclogermacrene, and the poly terpenoids D-α-tocopherol and β-sitosterol. Our results suggest that the evaluation of phenols may play an important role as a selection parameter for improvement and conservation programs, if they are complemented with conventional breeding practices.

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“…3 Basic limonoids contain the 4,4,8-trimethyl-17-furyl steroidal signature-skeleton, and all members of the family of limonoid natural products either contain this structure or are derived from such a precursor with different degrees of oxidation and skeletal rearrangement.…”

Section: Introductionmentioning

confidence: 99%