Triterpenoids from the leaves of Toona ciliata

ArticleinJournal of Asian natural products research 12(6):448-52 · June 2010with9 Reads
DOI: 10.1080/10286020.2010.493329 · Source: PubMed
Abstract
One new limonoid, toonaciliatone A (1), and one new tirucallane-type triterpenoid, toonaciliatine A (4), along with three known compounds, methyl-3beta-acetoxy-1-oxomelic-14(15)-enate (2), perforin A (3), and cholest-14-ene-3,7,24,25-tetrol-21,23-epoxy-21-methoxy-4,4,8-trimethyl-3-(3-methyl-2-butenoate) (5), were isolated from the leaves of Toona ciliata. The structures of the new compounds were established by spectroscopic methods.
    • T. sinensis has also been shown to inhibit steroidogenesis in Leydig cells (Poon, Leu, Hsu, Liu, & Huang, 2005) and improve sperm activity (Wang, Hsu, Hsu, Liao, & Chan, 2005 ). A variety of phytochemical components have been isolated and characterized from T. sinensis leaves, some of these include adenosine, gallic acid, methyl gallic acid, 3-O-b-D-(60-O 0 Galloyl)-glucopyranoside , 4-O-b-D-(60-O 0 Galloyl)-glucopyranoside, methyl gallate, ethyl gallate, kaempferol, kaempferol-3-O-b-glucoside, quercitrin, quercetin-3-O-b-glucoside, rutin, and catechin (Cheng et al., 2009; Li, Mo, & Ning, 2009; Ning et al., 2010 ). Scientists are dedicated to discovering novel drugs that target tumour cells without being toxic to normal cells.
    [Show abstract] [Hide abstract] ABSTRACT: Toona sinensis has been shown to have anti-proliferative effects on several human cancer cell lines. In the present study, we used two clear cell types of renal cell carcinoma (ccRCC) cell lines to study the anti-tumour effect of the T. sinensis leaf extract (TSL-1). TSL-1 was shown to be cytotoxic to ccRCC cells in a concentration- and time-dependent manner. We found that treatment with TSL-1 induced apoptotic characteristics, reactive oxygen species accumulation, and mitochondrial membrane potential reduction in ccRCC cells. Furthermore, treatment with TSL-1 increased the expression of activated caspase-3, -7, -9, and cleaved PARP. TSL-1 also caused cytochrome c release from mitochondria and down-regulation of Bcl-2 and heat shock proteins. We suggest that the TSL-1-induced cytotoxic effects may be due to quercetin, gallic acid, and tannic acid. Taken together, the present study suggests that TSL-1 induces apoptosis in ccRCC cell lines by activating mitochondrial-dependent caspases and inhibiting anti-apoptotic proteins.
    Full-text · Article · Mar 2014
    • H-3 showed correlations with H-2α, H-2β, H 3 -18, and H 2 -19 indicating that it was in the equatorial position in ring A, which adopted a chair conformation , also indicating that H-3 was β-directed. This was supported by its small coupling constants with both H-2α and H-2β (for a H- 3β of this compound class, the coupling constant is normally around 0 to 2.8 Hz, while for a proton in the position of H-3α, the large coupling constant with H-2β is observed at ca. J = 11.5 Hz) [9, 17]. Compounds 5 (C 20 H 32 O 2 ) and 6 (C 20 H 32 O 4 ) were also distinguished to be pimaradiene-type diterpenes by comparing their 1D NMR data (l " Tables 2 and 3) with those of 4. They differed in the numbers and the positions of hydroxy groups in the pimaradiene skeleton, which were corroborated by the HMBC correlations .
    [Show abstract] [Hide abstract] ABSTRACT: Three new limonoids (toonaciliatins N-P, 1-3)and four new pimaradiene-type diterpenoids(toonacilidins A-D, 4-7) were isolated from the leaves and twigs of Toona ciliata Roem. var. yunnanensis.Their structures were elucidated on the basis of spectroscopic methods. Toonacilidin B(5)showed moderate inhibitory activity against H. pylori-SS1 with an MIC of 50 μg/mL.
    Full-text · Article · Apr 2011
  • [Show abstract] [Hide abstract] ABSTRACT: The genus Toona belongs to family Meliaceae is a group of traditionally important medicinal plants. Toona is commonly known as toon, the leaves, barks and roots of toon is commonly used as herbal medicine and also as timber. Extensive research works have been carried out on chemical constituents and biological activities of the genus Toona. In this review, we summarize previous and current information regarding chemical constituents and biological activities of the genus Toona and provide new insights for future study in this discipline. This study shows that Toona species posses several biological activities mainly due to the presence of coumarins, flavonoids, phytosterol, phenols, tenins, alkaloids, triterpenes and anthraquinons.
    Full-text · Article · Jan 2011
  • [Show abstract] [Hide abstract] ABSTRACT: Some of the important naturally occurring limonoids from Meliaceae discovered in the last six decades, from 1942 to June 30, 2010, and their various bioactivities, are discussed. The cedrelone-class limonoids are characterized as the 5,6-enol-7-one derivatives and Burke et al. presented the chemical correlation of anthothecol with hirtin. Under mildly acid conditions, the first stage of the ring-opening of havanensin gives a 15-hydroxy-14- carbonium ion, which then either undergoes Wagner-Meerwein rearrangement or loses a proton to give a 15-ketone enolate and involves participation of the oxygenated function at C-7. The photooxidation of salannin and nimbin by UV light in the presence of oxygen led to more polar unstable intermediates that rearranged on silica gel to two final products in which the furan ring had been oxidized to isomeric hydroxybutenolides.
    Full-text · Article · Sep 2011
  • [Show abstract] [Hide abstract] ABSTRACT: Five new tetranortriterpenoids, toonaciliatones B–F (1–5, resp.), together with four known compounds, dihydrocedrelone (6), cedrelone (7), 6α-acetoxyazadirone (8), and 6α-acetoxy-14β,15β-epoxyazadirone (9), were isolated from the seeds of Toona ciliata. Their structures were elucidated by spectroscopic methods, including 1D- and 2D-NMR spectroscopy.
    Article · Feb 2012
  • [Show abstract] [Hide abstract] ABSTRACT: Background In the present study, the different solvent extracts viz., petroleum ether, chloroform, ethyl acetate and methanol of the medicinal plant Toona ciliata (leaf and flower) were evaluated for phytochemical analysis, antimicrobial and antioxidant activities. Methods A qualitative phytochemical study was conducted to know the presence or absence of phytoconstituents in the test extracts. Antibacterial and antifungal activities were determined using disc diffusion assay against human and phytopathogens. MIC was carried out using Micro-broth dilution method for pathogenic bacteria and fungi. Radical scavenging activity was also studied using DPPH and ABTS method. Results The study revealed the presence of carbohydrates, proteins, phytosterols, flavonoids, glycosides, tannins and phenolic compounds. Ethyl acetate and methanol extracts showed moderate activity against test phytopathogenic bacteria compared to tetracycline. Moderate activity was found against Proteus mirabilis and least activity against Klebsiella pneumoniae, Salmonella typhi and Staphylococcus aureus with ethyl acetate and methanol extracts. Ethyl acetate and methanol extracts of Toona ciliata exhibited lowest MIC varied from 10-2.5 mgml-1 against test human pathogenic and phytopathogenic bacteria Significant antifungal activity against Microsporum canis was observed in methanol extract with an MIC of 1.25 mgml-1 compared to miconozole. All the test extracts showed significant DPPH and ABTS radical scavenging activity in comparison with BHT. Conclusions The present study concludes that the plant Toona ciliata could be exploited for the isolation of bioactive compounds which could be a potential source for antimicrobials and antioxidants.
    Full-text · Article · Dec 2013
Show more