A Cytotoxic Pennogenin Glycoside from<i>Majanthemum dilatatum</i>

Woo, Eun‐Rhan; Kim, Jong Moon; Kim, Hyoung Ja; Yoon, Seung Hee; Park, Hokoon

doi:10.1055/s-2006-957486

Cited by 10 publications

(3 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Earlier, these substances had been identified in other species of Paris [91011] and other genera/species: Trillium ,[12131415161718] Heloniopsis orientalis ,[1920] Polygonatum kingianum ,[21] Trachycarpus wagnerianus ,[22] Dioscorea ,[2324] Triteleia lactea ,[25] Majanthemum dilatatum ,[26] Ophiopogon japonicus ,[27] Dracaena mannii ,[28] Ypsilandra thibetica . [29] But the six saponins mentioned above have not been isolated at the same time from one species of Paris .…”

Section: Introductionmentioning

confidence: 99%

Isolation and identification of cytotoxic compounds from the rhizomes of Paris quadrifolia L.

et al. 2014

View full text Add to dashboard Cite

Background:Paris quadrifolia L. is a medicinal plant which contains steroidal saponins. The present study reports isolation and structural identification of six pennogenyl saponins obtained from P. quadrifolia rhizomes. The four spirostan saponins were obtained from P. quadrifolia for the first time. The cytotoxic effects of the sub-fractions and six compounds isolated from the plant extract were evaluated on tumour cells.Materials and Methods:Ethanol extract from the rhizomes of P. quadrifolia were partinioned using column chromatography. The saponins were isolated from the obtained sub-fractions by isocratic RP HPLC and their structures were determined by means of 1D and 2D NMR spectroscopy and MALDI TOF MS. The cytotoxic effects of the sub-fractions and the isolated compounds were tested against human promyelocytic leukaemia cells (HL-60), human cervical adenocarcinoma cells (HeLa) and human breast cancer cells (MCF-7) using the [(3-(4,5-dimethylthiazol-2-yl)]-2,5-diphenyltetrazolium bromide (MTT) assay.Results:Six pennogenyl saponins were isolated from P. quadrifolia rhizomes: pennogenin 3-O-β-D-glucopyranoside (1), pennogenin 3-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranoside (2), pennogenin 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (3), pennogenin 3-O-α-L-rhamnopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranoside (4), pennogenin 3-O-α-L-rhamnopyranosyl-(1→4)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside (5), pennogenin 3-O-α-L-rhamnopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→4)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside (6). Pennogenyl saponins 5 and 6 exhibited cytotoxic activity against HL-60, HeLa and MCF-7 tumour cells with IC50 values of 1.0 ± 0.04 μg/ml, 1.8 ± 0.072 μg/ml and 2.4 ± 0.096 μg/ml respectively, and 2.0 ± 0.08 μg/ml, 2.5 ± 0.125 μg/ml and 3.2 ± 0.128 μg/ml respectively.Conclusion:Compounds 1-4 were isolated from this species for the first time.

show abstract

Section: Introductionmentioning

confidence: 99%

Isolation and identification of cytotoxic compounds from the rhizomes of Paris quadrifolia L.

et al. 2014

View full text Add to dashboard Cite

show abstract

“…Therefore, we chose nine typical saponins which showed strong antitumor effect before [2,[4][5][6][7][8][9][10][11][12][13][14][15][16] and some derived saponins for qualitative and quantitative comparison of major saponins in Paris and Trillium.…”

Section: Introductionmentioning

confidence: 99%

Qualitative and quantitative determination of major saponins in Paris and Trillium by HPLC-ELSD and HPLC–MS/MS

Man

Gao

Zhang

et al. 2010

Journal of Chromatography B

View full text Add to dashboard Cite

“…As shown in Table 1, compound 1 showed broad cytotoxicity against several human cancer cell lines using a panel of human cell lines and established protocols (7). Despite the observation that the cytotoxic activity of pennogenin glycosides from Majanthemum dilatatum increased with more monosaccharides attached to the aglycone core pennogenin, parallel with increasing soap activity (8), it was widely accepted that the cytotoxicity of the steroidal glycosides is not just due to their detergent activity but some unique subtle structural features are required for optimal activity (1). It was envisioned that, based on the data available, the cytotoxic activity of steroidal glycosides is very sensitive to their precise functionalization, therefore, more extensive studies are needed before a clear structure-activity relationship can be reached.…”

mentioning

confidence: 99%

Isolation and Characterization of Cytotoxic Saponin Chloromaloside A from Chlorophytum malayense

Qiu¹,

Li²,

Xiong³

et al. 2000

Planta med

View full text Add to dashboard Cite

A cytotoxic steroidal glycoside was isolated from Chlorophytum malayense Ridley and its structure was characterized as a known compound, neohecogenin 3-O-beta-D-glucopyranosyl(1-->2)-[beta-D-xylopyranosyl(1-->3)]-beta-D- glucopyranosyl(1-->4)-beta-D-galactopyranoside (chloromaloside A). The structural identification was performed using 2D-NMR and LC/MS/MS analysis. The previous, erroneously assigned 1H-NMR spectral data were revised whereas the published 13C-NMR spectral assignments were confirmed. This compound showed in vitro cytotoxicity against several human cancer cell lines.

show abstract

A Cytotoxic Pennogenin Glycoside fromMajanthemum dilatatum

Cited by 10 publications

References 0 publications

Isolation and identification of cytotoxic compounds from the rhizomes of Paris quadrifolia L.

Isolation and identification of cytotoxic compounds from the rhizomes of Paris quadrifolia L.

Qualitative and quantitative determination of major saponins in Paris and Trillium by HPLC-ELSD and HPLC–MS/MS

Isolation and Characterization of Cytotoxic Saponin Chloromaloside A from Chlorophytum malayense

Contact Info

Product

Resources

About