Limonoids from Aphanamixis polystacha

Mulholland, Dulcie A.; Naidoo, Natasha

doi:10.1016/s0031-9422(99)00157-0

Cited by 37 publications

(36 citation statements)

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“…The action of APE may not only be due to the presence of amooranin and rohitukin alkaloids but may also be due to the presence of complex limonoids like, polystachin, prieurianin, hispidin C, aphanamixin and aphananin [23,24,[59][60][61][62][63][64] whose concerted action may have increased the DNA damage and greater cell kill in the present study.…”

Section: Discussionmentioning

confidence: 88%

“…Certain alkaloids like, amoorastatin and 12-hydroxyamoorastatin, present in the stem bark extract of rohituka have been reported to exhibit cytotoxic and growth inhibitory activities in murine P388 lymphocytic leukaemia cells [22]. Rohituka has been reported to contain certain alkaloids and limonoids [23,24]. Limonoids have been reported to possess anticancer activity in various human cancer cell lines [25].…”

Section: Introductionmentioning

confidence: 99%

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Determination of Antineoplastic Activity of Rohituka, Aphanamixis Polystachya (Wall) RN Parker in Hela Cells: Correlation with Clonogenicity and DNA Damage

Jagetia

Venkatesha

2016

IJCAM

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The antineoplastic activity of chloroform stem bark extract of rohituka, Aphanamixis polystachya (APE) used traditionally to treat spleen and liver tumors was evaluated in cultured HeLa cells by clonogenic and micronucleus assays. Treatment of HeLa cells with 0, 5, 10, 25, 50, 75 or 100µg/ml APE for different times caused a concentration-dependent reduction in the cell survival up to 6 h post-treatment (p<0.005) followed by a non-significant decline in the cells treated with APE for 24 h. Therefore, 6h treatment time was considered as an optimum time for APE exposure and further studies were carried out using this treatment time. Exposure of HeLa cells to different concentrations of APE resulted in a concentration-dependent decline in the cell viability and 100µg/ ml APE resulted in 72% cell death when compared with the non-drug treated control group. These results were further confirmed by clonogenic assay where, APE treatment caused a concentration-dependent decline in the clonogenicity of HeLa cells, and the surviving fraction of cells was reduced to 0.22 after treatment with 100µg/ml APE, the highest concentration screened. The inhibitory concentration (IC50) of APE was found to be 25µg/ml. The APE-induced DNA damage was estimated by micronucleus assay, where the treatment of HeLa cells with various concentrations of APE resulted in a concentration-dependent rise in the frequency of micronuclei in binucleate HeLa cells (MNBNCs) at 20, 30, and 40 h post-treatment. This increase in MNBNCs was significantly higher than the baseline frequency of MNBNCs. APE treatment also increased the frequency of HeLa cells bearing more than one micronucleus (MN) indicating higher degree of DNA damage. The frequency of MNBNC increased with scoring time and a maximum elevation in the MNBNC frequency was observed at 30 h posttreatment. The MNBNC induction and clonogenicity of HeLa cells was inversely related indicating that increased MNBNC formation resulted in a corresponding reduction in the cell survival. The cell proliferation indices (PI) declined with increasing concentration of APE that increased with screening time. Our study demonstrates that APE is able to kill HeLa cells effectively and this cell killing effect of APE may be due its ability to induce DNA damage.

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Section: Discussionmentioning

confidence: 88%

Section: Introductionmentioning

confidence: 99%

Determination of Antineoplastic Activity of Rohituka, Aphanamixis Polystachya (Wall) RN Parker in Hela Cells: Correlation with Clonogenicity and DNA Damage

Jagetia

Venkatesha

2016

IJCAM

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“…The solvent was evaporated in vacuo, and the extracts were combined and concentrated, followed by suspension in water. The water layer was further extracted with CHCl 3 and EtOAc. The CHCl 3 fraction (350 g) was fractionated by column chromatography over D101 porous resin using gradient aqueous ethanol to give five fractions (fractions I-V).…”

Section: Methodsmentioning

confidence: 99%

“…Aphanamixis have led to the isolation of a series of limonoids, [1][2][3][4][5] tirucallane triterpenoids, 6) diterpenoids, 7) sesquiterpenoids, 8) and flavone glycosides. 9) As a part of our continuous interest in the Meliaceae family, [10][11][12] four new tirucallane-type nortriterpenoids, 24,25-epoxy-tirucall-7,20(E)-diene-3,23-dione (1), 24,25,26,27-tetranortirucall-1,7-diene-23(21)-lactone (2), 3a-hydroxy-tirucall-7-ene-20-one (3), and 3-oxo-tirucall-7-ene-3,20-dione (4), along with a known highly complex oxidized limonoid, mombasol (5), 13) were isolated from the EtOH exact of the stem barks of Aphanamixis grandifolia BL., a timer tree mainly distributed in the tropical areas of Asia such as southern China, Malaysia, Indonesia and India.…”

Section: Species Of the Genus Aphanamixis (Meliaceae) Are Sources Of mentioning

confidence: 99%

Novel Nortriterpenoids from Aphanamixis grandifolia

Zhang

Wang

Luo

et al. 2011

CHEMICAL & PHARMACEUTICAL BULLETIN

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Species of the genus Aphanamixis (Meliaceae) are sources of various secondary metabolites with interesting diverse chemical structures. Previous chemical investigations onAphanamixis have led to the isolation of a series of limonoids, [1][2][3][4][5] tirucallane triterpenoids, 6) diterpenoids, 7) sesquiterpenoids, 8) and flavone glycosides. 9) As a part of our continuous interest in the Meliaceae family, [10][11][12] four new tirucallane-type nortriterpenoids, 24,25-epoxy-tirucall-7,20(E)-diene-3,23-dione (1), 24,25,26,27-tetranortirucall-1,7-diene-23(21)-lactone (2), 3a-hydroxy-tirucall-7-ene-20-one (3), and 3-oxo-tirucall-7-ene-3,20-dione (4), along with a known highly complex oxidized limonoid, mombasol (5), 13) were isolated from the EtOH exact of the stem barks of Aphanamixis grandifolia BL., a timer tree mainly distributed in the tropical areas of Asia such as southern China, Malaysia, Indonesia and India. 14) In this paper, we describe the isolation and structural elucidation of these compounds. Results and DiscussionCompound 1 was obtained as a white, amorphous powder. Its positive high resolution-electrospray ionization (HR-ESI)-MS showed a quasi-molecular ion at m/z 461. , 24,25-epoxy-tirucall-7,20(E)-diene-3,23-dione (1), 24,25,26,27-tetranortirucall-1,7-diene-23(21)-lactone (2), 3a a-hydroxy-tirucall-7-ene-20-one (3), and 3-oxo-tirucall-7-ene-3,20-dione (4), together with one known compound mombasol (5) were isolated from the stem barks of Aphanamixis grandifolia. Their structures were elucidated on the basis of various spectroscopic analysis including electrospray ionization (ESI)-MS, high resolution (HR)-ESI-MS, IR, 1D-and 2D-NMR techniques (heteronuclear single quantum coherence (HSQC), heteronuclear multiple bond connectivity (HMBC) and rotating frame Overhauser enhancement spectroscopy (ROESY)), and by comparison of their spectral data with those reported. The absolute configuration of compound 1 was determined by circular dichroism (CD) exciton chirality.

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“…polystachya is attributed to certain alkaloids (Harmon et al, 1979), limonoids (Mulholland and Naidoo, 1999), and terpenoids and sterol (Ragasa et al, 2014b) found in its the bark and leaves. Finally, Annona species were found to be cytotoxic against human hepatoma and breast cancer cell lines (Yu, 1999).…”

Section: Int J Biosci 2017mentioning

confidence: 99%

In-vitro Cytotoxicity of Wrightia pubescens (Blanco) Merr., Aphanamixis polystachya (Wall.) Parker, and Platymitra arborea (Blanco) against selected human cancer cell lines

2017

Int. J. Biosci.

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Cancer is the second leading cause of mortality worldwide. Anticancer studies are centered on natural products as these have been found to exhibit properties that activate cell signaling pathways and cell aging and senescence. As such, there is a need for continuing research to explore these natural products especially those that do not only exhibit cytotoxicity but also specificity against cancer cells. This study evaluated the cytotoxic activity of the crude extracts of three Philippine indigenous plants, Wrightia pubescens (Blanco) Merr. Aphanamixis polystachya (Wall.) Parker, and Platymitra arborea (Blanco) against selected human cancer cell lines using 3- (4,5-dimethylthiazol-2-yl)-2-5-diphenyl-2H-tetrazolium bromide (MTT) assay. Extracts were partitioned using hexane and ethyl acetate to determine their active fractions based on their polarity. These active fractions were then tested for their cytotoxicity against human colorectal cancer cell line (HCT116), human adenocarcinoma cell line (A549) and non-cancer Chinese hamster ovary cell line (AA8). Cytotoxic activities of the extracts were found in the ethyl acetate fractions of W. pubescens and P. arborea and hexane fraction of A. polystachya. All active fractions were highly cytotoxic to HCT116 and A549, with A. polystachya exhibiting the highest selectivity against cancer over the non-cancer cells. Results of this study imply that these extracts, especially that of A. polystachya, have a potential use in anti-cancer research due to their selectivity against cancer cell lines.

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Limonoids from Aphanamixis polystacha

Cited by 37 publications

References 10 publications

Determination of Antineoplastic Activity of Rohituka, Aphanamixis Polystachya (Wall) RN Parker in Hela Cells: Correlation with Clonogenicity and DNA Damage

Determination of Antineoplastic Activity of Rohituka, Aphanamixis Polystachya (Wall) RN Parker in Hela Cells: Correlation with Clonogenicity and DNA Damage

Novel Nortriterpenoids from Aphanamixis grandifolia

In-vitro Cytotoxicity of Wrightia pubescens (Blanco) Merr., Aphanamixis polystachya (Wall.) Parker, and Platymitra arborea (Blanco) against selected human cancer cell lines

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