Cedrelone

Anticancer Agents Med Chem. 2013 Dec;13(10):1645-53.

Effects of limonoid cedrelone on MDA-MB-231 breast tumor cells in vitro.[Pubmed: 23869780]

Cancer is the second leading cause of death, preceded only by cardiovascular diseases, and there is epidemiological evidence that demonstrate this tendency is emerging worldwide.
METHODS AND RESULTS:
Brazil has an extensive vegetal biodiversity with more than 55,000 species listed. Such biodiversity collaborates with the finding of compounds which could be the basis for the design of new anti-tumor drugs, with fewer side effects than the conventional chemotherapy used currently. Cedrelone is a limonoid isolated from Trichilia catigua (Meliaceae) which is a native Brazilian plant. This study demonstrates that Cedrelone inhibits proliferation, adhesion, migration and invasion of breast tumor cells from the line MDA-MB-231. The effects of cell migration and invasion on MDA-MB-231 cell may be explained, at least in part, by the ability of Cedrelone to inhibit MMP activity. We also demonstrate that Cedrelone is able to induce apoptosis in MDA-MB-231 cells.
CONCLUSIONS:
There are only a few works investigating the effect of limonoids in cellular processes closely related to tumor progression such as adhesion, migration and invasion. To the best of our knowledge, this is the first work describing the effects of a limonoid on tumor and non-tumor cell adhesion process.

Photochem Photobiol. 2000 Oct;72(4):464-6.

Photooxidation of cedrelone, a tetranortriterpenoid from Toona ciliata.[Pubmed: 11045715]

METHODS AND RESULTS:
Cedrelone, a tetranortriterpenoid on photolysis by UV light yields a true photooxidation product 3 [14 beta,15beta,22beta,23beta-diepoxy-6-hydroxy-1,5, 20(22)-meliatriene-2,7,21-trione] whose structure is well established by NMR studies and confirmed by X-ray crystallography, along with product 4 [14 beta,15beta-epoxy-6,23-dihydroxy-1,5,20(22)-meliatriene-2,7, 21-trione]. Addition of rose bengal increases the rate of photooxidation whereas DABCO decreases rate of photolysis proving the involvement of singlet oxygen in the photooxygenation.
CONCLUSIONS:
Both the photoproducts exhibited antifeedant activity.

Int. J. Drug Develop.Res.,2012, 4(4):385-92.

Semisynthetic Modification of Cedrelone and its Antimicrobial Activity.[Reference: WebLink]

METHODS AND RESULTS:
Cedrelone was isolated from Toona ciliata heart wood and the compound was modified with various chemical reagents and the resultant product was characterized by IR, 1H NMR, 13C NMR and Mass spectra. The synthesized compounds were screened for antimicrobial activities and the zone of inhibition was ascertained by disc diffusion method. The microorganisms selected for the study was Gram positive organisms such as a) Staphylococcus aureus (ATCC 9144), b) Staphylococcus epidermitis (ATCC 155), c) Bacillus subtilis (ATCC 6633), d) Bacillus cereus (ATCC 11778), e) Micrococcus luteus (ATCC 46789) and Gram negative organisms a) Escherichia coli (ATCC 25922), b) Pseudomonas aeruginosa (ATCC 9027). Fungi organism a) Candida albicans (ATCC 1091), b) Aspergillus niger (ATCC 6275).
CONCLUSIONS:
Cedrelone and its derivatives exerted pronounced inhibitory response against all the species of bacterial organism tested, except E. coli. Bromohydroxy Cedrelone and Michael adduct showed good antifungal activity.

Anticancer Agents Med Chem. 2010 Dec;10(10):769-76.

Evaluation of effect of triterpenes and limonoids on cell growth, cell cycle and apoptosis in human tumor cell line.[Pubmed: 21269253]

METHODS AND RESULTS:
Six triterpenes and eight limonoids were evaluated for their capacity to inhibit the growth of three human tumour cell lines, breast adenocarcinoma (MCF-7), non-small cell lung cancer (NCI-H460) and melanoma (A375-C5). The mechanisms involved in the observed cell growth arrest of the four most potent compounds were carried out by studying their effect in cell cycle profile and programmed cell death.
CONCLUSIONS:
The results showed that one triterpene (odoratol) and two limonoids (gedunin and Cedrelone) caused cell cycle arrest while only the limonoids gedunin and Cedrelone were found to be very potent inducers of apoptosis.

Phytochemistry. 2012 Apr;76:141-9.

Limonoids from the leaves of Toona ciliata var. yunnanensis.[Pubmed: 22277739]

METHODS AND RESULTS:
Twelve limonoids, toonayunnanins A-L (1-12) and eleven known compounds (13-23) were isolated from the leaves of Toona ciliata var. yunnanensis, and their structures were elucidated by means of extensive spectroscopic analyses, particularly 1D and 2D NMR techniques. The inhibitory effects of all the isolated compounds were evaluated on human tumor cell lines, such as HL-60, SMMC-7721, A-549, MCF-7 and SW480.
CONCLUSIONS:
Cedrelone (13) and dysobinin (18) showed significant cytotoxicity, and toonayunnanin B (2) and epoxyazadiradione (14), were found to be slightly cytotoxic against the above cell lines. Furthermore, this study provides valuable information for the chemotaxonomy of T. ciliata varieties.