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Thomas J Gianfagna - One of the best experts on this subject based on the ideXlab platform.
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chemistry and biological activity of Steroidal glycosides from the lilium genus
2015Co-Authors: John P. Munafo, Thomas J GianfagnaAbstract:Covering: 1989 up to 2014 Plants from the Lilium genus are a rich source of chemical diversity and have been the focus of natural products chemistry research for over twenty years. This manuscript provides a background on the chemistry and nomenclature of Steroidal glycosides, as well as a chronological account of the progress between the years of 1989 up to 2014, with respect to their isolation and characterization from the genus. This review highlights the traditional use of lilies, as both food and medicine, and brings attention to the fact that the genus contains 110 accepted species of which the chemistry and biological activity of the Steroidal glycosides from the majority have not been investigated to date. Thus, making the genus a relatively untapped resource that contains a potential treasure trove of chemical diversity waiting to be discovered.
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Steroidal glycosides from the bulbs of easter lily lilium longiflorum thunb promote dermal fibroblast migration in vitro
2013Co-Authors: Debora Esposito, John P. Munafo, Teresa Lucibello, Manuel E Baldeon, Slavko Komarnytsky, Thomas J GianfagnaAbstract:Abstract Ethnopharmacological relevance Preparations derived from bulbs of various Lilium species have been used to promote the healing of skin abrasions, sores and burns and to aid in healing wounds in Traditional Chinese and Greco-Roman Medicine. Aim of the study To evaluate fractionated Easter lily bulb extracts and their Steroidal glycosides (1–5) for the promotion of dermal fibroblast migration in vitro , a model for the early events in wound healing. Materials and methods An activity-guided screening approach was used by coupling sequential solvent extraction, gel permeation chromatography (GPC), and semi-preparative reverse-phase high performance liquid chromatography (RP-HPLC) with an in vitro dermal fibroblast migration assay. Cytotoxicity was evaluated with methyl thiazole tetrazolium (MTT). To gain insight into the mode of action of the Steroidal glycosides, nitric oxide (NO) production, and expression of genes for transforming growth factor beta-1 (TGF-β) and its receptors were evaluated. Results Fractionated bulb extracts and the two isolated Steroidal glycoalkaloids ( 1 ) and ( 2 ) induced NO production and TGF-β receptor I mRNA expression in fibroblast cell culture. In a cytotoxicity assay, Steroidal glycosides ( 1 ) and ( 3 ) had IC 50 values of 8.2 and 8.7 µM, but the natural acetylation of the C-6″′ hydroxy of the terminal glucose unit in ( 2 ) resulted in a 3-fold decrease in cell cytotoxicity when compared with ( 1 ). Results from the dermal fibroblast migration assay revealed that the Steroidal glycoalkaloids ( 1 ) and ( 2 ), and the furostanol saponin ( 3 ) promoted fibroblast migration from the range of 23.7±5.7 to 37.7±5.1%, as compared with the control. Conclusion Collectively, our data demonstrate that the Steroidal glycosides present in Easter lily bulbs induce, at least in part, the observed dermal fibroblast migration activity of the bulb extracts. This is the first evidence that Steroidal glycosides from Lilium longiflorum may potentially play a role in the wound healing process and may provide a scientific basis for the historical use of lily bulbs for this purpose.
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antifungal activity and fungal metabolism of Steroidal glycosides of easter lily lilium longiflorum thunb by the plant pathogenic fungus botrytis cinerea
2011Co-Authors: John P. Munafo, Thomas J GianfagnaAbstract:Botrytis cinerea Pers. Fr. is a plant pathogenic fungus and the causal organism of blossom blight of Easter lily (Lilium longiflorum Thunb.). Easter lily is a rich source of Steroidal glycosides, compounds which may play a role in the plant–pathogen interaction of Easter lily. Five Steroidal glycosides, including two Steroidal glycoalkaloids and three furostanol saponins, were isolated from L. longiflorum and evaluated for fungal growth inhibition activity against B. cinerea, using an in vitro plate assay. All of the compounds showed fungal growth inhibition activity; however, the natural acetylation of C-6′′′ of the terminal glucose in the Steroidal glycoalkaloid, (22R,25R)-spirosol-5-en-3β-yl O-α-l-rhamnopyranosyl-(1→2)-[6-O-acetyl-β-d-glucopyranosyl-(1→4)]-β-d-glucopyranoside (2), increased antifungal activity by inhibiting the rate of metabolism of the compound by B. cinerea. Acetylation of the glycoalkaloid may be a plant defense response to the evolution of detoxifying mechanisms by the pathogen. Th...
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antifungal activity and fungal metabolism of Steroidal glycosides of easter lily lilium longiflorum thunb by the plant pathogenic fungus botrytis cinerea
2011Co-Authors: John P. Munafo, Thomas J GianfagnaAbstract:Botrytis cinerea Pers. Fr. is a plant pathogenic fungus and the causal organism of blossom blight of Easter lily (Lilium longiflorum Thunb.). Easter lily is a rich source of Steroidal glycosides, compounds which may play a role in the plant-pathogen interaction of Easter lily. Five Steroidal glycosides, including two Steroidal glycoalkaloids and three furostanol saponins, were isolated from L. longiflorum and evaluated for fungal growth inhibition activity against B. cinerea, using an in vitro plate assay. All of the compounds showed fungal growth inhibition activity; however, the natural acetylation of C-6''' of the terminal glucose in the Steroidal glycoalkaloid, (22R,25R)-spirosol-5-en-3β-yl O-α-L-rhamnopyranosyl-(1→2)-[6-O-acetyl-β-D-glucopyranosyl-(1→4)]-β-D-glucopyranoside (2), increased antifungal activity by inhibiting the rate of metabolism of the compound by B. cinerea. Acetylation of the glycoalkaloid may be a plant defense response to the evolution of detoxifying mechanisms by the pathogen. The biotransformation of the Steroidal glycoalkaloids by B. cinerea led to the isolation and characterization of several fungal metabolites. The fungal metabolites that were generated in the model system were also identified in Easter lily tissues infected with the fungus by LC-MS. In addition, a Steroidal glycoalkaloid, (22R,25R)-spirosol-5-en-3β-yl O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (6), was identified as both a fungal metabolite of the Steroidal glycoalkaloids and as a natural product in L. longiflorum for the first time.
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quantitative analysis of Steroidal glycosides in different organs of easter lily lilium longiflorum thunb by lc ms ms
2011Co-Authors: John P. Munafo, Thomas J GianfagnaAbstract:The bulbs of the Easter lily (Lilium longiflorum Thunb.) are regularly consumed in Asia as both food and medicine, and the beautiful white flowers are appreciated worldwide as an attractive ornamental. The Easter lily is a rich source of Steroidal glycosides, a group of compounds that may be responsible for some of the traditional medicinal uses of lilies. Since the appearance of recent reports on the role Steroidal glycosides in animal and human health, there is increasing interest in the concentration of these natural products in plant-derived foods. A LC-MS/MS method performed in multiple reaction monitoring (MRM) mode was used for the quantitative analysis of two Steroidal glycoalkaloids and three furostanol saponins, in the different organs of L. longiflorum. The highest concentrations of the total five Steroidal glycosides were 12.02 ± 0.36, 10.09 ± 0.23, and 9.36 ± 0.27 mg/g dry weight in flower buds, lower stems, and leaves, respectively. The highest concentrations of the two Steroidal glycoalkalo...
John P. Munafo - One of the best experts on this subject based on the ideXlab platform.
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chemistry and biological activity of Steroidal glycosides from the lilium genus
2015Co-Authors: John P. Munafo, Thomas J GianfagnaAbstract:Covering: 1989 up to 2014 Plants from the Lilium genus are a rich source of chemical diversity and have been the focus of natural products chemistry research for over twenty years. This manuscript provides a background on the chemistry and nomenclature of Steroidal glycosides, as well as a chronological account of the progress between the years of 1989 up to 2014, with respect to their isolation and characterization from the genus. This review highlights the traditional use of lilies, as both food and medicine, and brings attention to the fact that the genus contains 110 accepted species of which the chemistry and biological activity of the Steroidal glycosides from the majority have not been investigated to date. Thus, making the genus a relatively untapped resource that contains a potential treasure trove of chemical diversity waiting to be discovered.
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Steroidal glycosides from the bulbs of easter lily lilium longiflorum thunb promote dermal fibroblast migration in vitro
2013Co-Authors: Debora Esposito, John P. Munafo, Teresa Lucibello, Manuel E Baldeon, Slavko Komarnytsky, Thomas J GianfagnaAbstract:Abstract Ethnopharmacological relevance Preparations derived from bulbs of various Lilium species have been used to promote the healing of skin abrasions, sores and burns and to aid in healing wounds in Traditional Chinese and Greco-Roman Medicine. Aim of the study To evaluate fractionated Easter lily bulb extracts and their Steroidal glycosides (1–5) for the promotion of dermal fibroblast migration in vitro , a model for the early events in wound healing. Materials and methods An activity-guided screening approach was used by coupling sequential solvent extraction, gel permeation chromatography (GPC), and semi-preparative reverse-phase high performance liquid chromatography (RP-HPLC) with an in vitro dermal fibroblast migration assay. Cytotoxicity was evaluated with methyl thiazole tetrazolium (MTT). To gain insight into the mode of action of the Steroidal glycosides, nitric oxide (NO) production, and expression of genes for transforming growth factor beta-1 (TGF-β) and its receptors were evaluated. Results Fractionated bulb extracts and the two isolated Steroidal glycoalkaloids ( 1 ) and ( 2 ) induced NO production and TGF-β receptor I mRNA expression in fibroblast cell culture. In a cytotoxicity assay, Steroidal glycosides ( 1 ) and ( 3 ) had IC 50 values of 8.2 and 8.7 µM, but the natural acetylation of the C-6″′ hydroxy of the terminal glucose unit in ( 2 ) resulted in a 3-fold decrease in cell cytotoxicity when compared with ( 1 ). Results from the dermal fibroblast migration assay revealed that the Steroidal glycoalkaloids ( 1 ) and ( 2 ), and the furostanol saponin ( 3 ) promoted fibroblast migration from the range of 23.7±5.7 to 37.7±5.1%, as compared with the control. Conclusion Collectively, our data demonstrate that the Steroidal glycosides present in Easter lily bulbs induce, at least in part, the observed dermal fibroblast migration activity of the bulb extracts. This is the first evidence that Steroidal glycosides from Lilium longiflorum may potentially play a role in the wound healing process and may provide a scientific basis for the historical use of lily bulbs for this purpose.
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antifungal activity and fungal metabolism of Steroidal glycosides of easter lily lilium longiflorum thunb by the plant pathogenic fungus botrytis cinerea
2011Co-Authors: John P. Munafo, Thomas J GianfagnaAbstract:Botrytis cinerea Pers. Fr. is a plant pathogenic fungus and the causal organism of blossom blight of Easter lily (Lilium longiflorum Thunb.). Easter lily is a rich source of Steroidal glycosides, compounds which may play a role in the plant–pathogen interaction of Easter lily. Five Steroidal glycosides, including two Steroidal glycoalkaloids and three furostanol saponins, were isolated from L. longiflorum and evaluated for fungal growth inhibition activity against B. cinerea, using an in vitro plate assay. All of the compounds showed fungal growth inhibition activity; however, the natural acetylation of C-6′′′ of the terminal glucose in the Steroidal glycoalkaloid, (22R,25R)-spirosol-5-en-3β-yl O-α-l-rhamnopyranosyl-(1→2)-[6-O-acetyl-β-d-glucopyranosyl-(1→4)]-β-d-glucopyranoside (2), increased antifungal activity by inhibiting the rate of metabolism of the compound by B. cinerea. Acetylation of the glycoalkaloid may be a plant defense response to the evolution of detoxifying mechanisms by the pathogen. Th...
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antifungal activity and fungal metabolism of Steroidal glycosides of easter lily lilium longiflorum thunb by the plant pathogenic fungus botrytis cinerea
2011Co-Authors: John P. Munafo, Thomas J GianfagnaAbstract:Botrytis cinerea Pers. Fr. is a plant pathogenic fungus and the causal organism of blossom blight of Easter lily (Lilium longiflorum Thunb.). Easter lily is a rich source of Steroidal glycosides, compounds which may play a role in the plant-pathogen interaction of Easter lily. Five Steroidal glycosides, including two Steroidal glycoalkaloids and three furostanol saponins, were isolated from L. longiflorum and evaluated for fungal growth inhibition activity against B. cinerea, using an in vitro plate assay. All of the compounds showed fungal growth inhibition activity; however, the natural acetylation of C-6''' of the terminal glucose in the Steroidal glycoalkaloid, (22R,25R)-spirosol-5-en-3β-yl O-α-L-rhamnopyranosyl-(1→2)-[6-O-acetyl-β-D-glucopyranosyl-(1→4)]-β-D-glucopyranoside (2), increased antifungal activity by inhibiting the rate of metabolism of the compound by B. cinerea. Acetylation of the glycoalkaloid may be a plant defense response to the evolution of detoxifying mechanisms by the pathogen. The biotransformation of the Steroidal glycoalkaloids by B. cinerea led to the isolation and characterization of several fungal metabolites. The fungal metabolites that were generated in the model system were also identified in Easter lily tissues infected with the fungus by LC-MS. In addition, a Steroidal glycoalkaloid, (22R,25R)-spirosol-5-en-3β-yl O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (6), was identified as both a fungal metabolite of the Steroidal glycoalkaloids and as a natural product in L. longiflorum for the first time.
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quantitative analysis of Steroidal glycosides in different organs of easter lily lilium longiflorum thunb by lc ms ms
2011Co-Authors: John P. Munafo, Thomas J GianfagnaAbstract:The bulbs of the Easter lily (Lilium longiflorum Thunb.) are regularly consumed in Asia as both food and medicine, and the beautiful white flowers are appreciated worldwide as an attractive ornamental. The Easter lily is a rich source of Steroidal glycosides, a group of compounds that may be responsible for some of the traditional medicinal uses of lilies. Since the appearance of recent reports on the role Steroidal glycosides in animal and human health, there is increasing interest in the concentration of these natural products in plant-derived foods. A LC-MS/MS method performed in multiple reaction monitoring (MRM) mode was used for the quantitative analysis of two Steroidal glycoalkaloids and three furostanol saponins, in the different organs of L. longiflorum. The highest concentrations of the total five Steroidal glycosides were 12.02 ± 0.36, 10.09 ± 0.23, and 9.36 ± 0.27 mg/g dry weight in flower buds, lower stems, and leaves, respectively. The highest concentrations of the two Steroidal glycoalkalo...
Sonia Piacente - One of the best experts on this subject based on the ideXlab platform.
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determination of Steroidal glycosides in yucca gloriosa flowers by lc ms ms
2010Co-Authors: Paola Montoro, A V Skhirtladze, Angela Perrone, Mariam Benidze, Ether Kemertelidze, Sonia PiacenteAbstract:An high-performance liquid chromatography (HPLC) coupled with tandem mass spectrometry (MS/MS) method, was developed for the quantitative analysis of the Steroidal glycosides occurring in Yucca gloriosa flowers. The HPLC experiments were performed by means of an octadecyl-modified reversed-phase C-18 column and a binary mobile phase system under gradient elution conditions. The fragmentation patterns of Steroidal saponins were analyzed by ESI-MS(n) in positive ion mode and a specific multiple reaction monitoring MS/MS detection was developed for their quantitative determination. The described method provides high sensitivity and specificity for quantitative determination of the Steroidal glycosides in Y. gloriosa flowers. Quantification was performed against an external calibration line obtained using each pure Steroidal glycoside. Short- and long-term repeatabilities of the methods were better than 3 and 6%, respectively. The method was validated according to EMEA guidelines and applied to real samples.
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Steroidal glycosides from the leaves of ruscus colchicus isolation and structural elucidation based on a preliminary liquid chromatography electrospray ionization tandem mass spectrometry profiling
2009Co-Authors: Angela Perrone, Cosimo Pizza, A V Skhirtladze, Ether Kemertelidze, Tamara Muzashvili, Assunta Napolitano, Sonia PiacenteAbstract:Abstract An HPLC–ESIMS n method, based on high-performance liquid chromatography coupled to electrospray positive ionisation multistage ion trap mass spectrometry, has been used as an effective tool to rapidly identify and guide the isolation of target saponins from the ethanol extract of the leaves of Ruscus colchicus Y. Yeo. Twenty-two Steroidal glycosides, including seventeen furostanol, four spirostanol and one cholestane glycosides, were online identified. Subsequently, compounds were isolated and their structures were established by the extensive use of 1D- and 2D-NMR experiments. The structures identified by MS were fully consistent with those elucidated by NMR data. Sixteen Steroidal glycosides, including thirteen furostanol, two spirostanol and one cholestane glycosides, were identified along with four known furostanol and two spirostanol glycosides. The saponin profile shows that the furostanol glycosides are the main constituents of R. colchicus extract, unlike the other Ruscus species, for which the spirostanol derivatives generally are reported as the major compounds. Moreover, for the first time a cholestane glycoside has been isolated from R. colchicus .
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Steroidal glycosides from the seeds of hyoscyamus niger l
2008Co-Authors: Irina Lunga, Carla Bassarello, Pavel Kintia, Stepan Shvets, Sonia Piacente, Cosimo PizzaAbstract:The investigation of the Steroidal glycosides of the seeds of Hyoscyamus niger L. led to the isolation of two new spirostane saponins (2, 6) together with seven known glycosides with either furosta...
Angela Perrone - One of the best experts on this subject based on the ideXlab platform.
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determination of Steroidal glycosides in yucca gloriosa flowers by lc ms ms
2010Co-Authors: Paola Montoro, A V Skhirtladze, Angela Perrone, Mariam Benidze, Ether Kemertelidze, Sonia PiacenteAbstract:An high-performance liquid chromatography (HPLC) coupled with tandem mass spectrometry (MS/MS) method, was developed for the quantitative analysis of the Steroidal glycosides occurring in Yucca gloriosa flowers. The HPLC experiments were performed by means of an octadecyl-modified reversed-phase C-18 column and a binary mobile phase system under gradient elution conditions. The fragmentation patterns of Steroidal saponins were analyzed by ESI-MS(n) in positive ion mode and a specific multiple reaction monitoring MS/MS detection was developed for their quantitative determination. The described method provides high sensitivity and specificity for quantitative determination of the Steroidal glycosides in Y. gloriosa flowers. Quantification was performed against an external calibration line obtained using each pure Steroidal glycoside. Short- and long-term repeatabilities of the methods were better than 3 and 6%, respectively. The method was validated according to EMEA guidelines and applied to real samples.
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Steroidal glycosides from the leaves of ruscus colchicus isolation and structural elucidation based on a preliminary liquid chromatography electrospray ionization tandem mass spectrometry profiling
2009Co-Authors: Angela Perrone, Cosimo Pizza, A V Skhirtladze, Ether Kemertelidze, Tamara Muzashvili, Assunta Napolitano, Sonia PiacenteAbstract:Abstract An HPLC–ESIMS n method, based on high-performance liquid chromatography coupled to electrospray positive ionisation multistage ion trap mass spectrometry, has been used as an effective tool to rapidly identify and guide the isolation of target saponins from the ethanol extract of the leaves of Ruscus colchicus Y. Yeo. Twenty-two Steroidal glycosides, including seventeen furostanol, four spirostanol and one cholestane glycosides, were online identified. Subsequently, compounds were isolated and their structures were established by the extensive use of 1D- and 2D-NMR experiments. The structures identified by MS were fully consistent with those elucidated by NMR data. Sixteen Steroidal glycosides, including thirteen furostanol, two spirostanol and one cholestane glycosides, were identified along with four known furostanol and two spirostanol glycosides. The saponin profile shows that the furostanol glycosides are the main constituents of R. colchicus extract, unlike the other Ruscus species, for which the spirostanol derivatives generally are reported as the major compounds. Moreover, for the first time a cholestane glycoside has been isolated from R. colchicus .
Yue-hu Pei - One of the best experts on this subject based on the ideXlab platform.
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Structure determination of two new C21 Steroidal glycosides from Cynanchum komarovii
2017Co-Authors: Dan Zhao, Gang Chen, Ming-xu Tang, Yu-bo Wang, Shao-fei Chen, Hai-feng Wang, Yue-hu PeiAbstract:Two new 13,14:14,15-disecopregnane-type C21 Steroidal glycosides, namely komarosides R (1) and S (2), along with four known compounds (3–6), were obtained from the 95% ethanol extract of the whole herbs of Cynanchum komarovii Al.Iljinski (Asclepiadaceae). The structures of new compounds were elucidated on the basis of 1D, 2D NMR spectroscopic data and acid hydrolysis. Compounds 1 and 2 showed potent inhibitory activities against human leukemia cell line (HL-60) with IC50 values being 6.2 and 17.6 μM, respectively, compared to the positive control 5-fluorouracil (6.4 μM).
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Two new 14, 15-secopregnane-type Steroidal glycosides from the roots of Cynanchum limprichtii
2017Co-Authors: Jia-chuan Liu, Gang Chen, Dan Zhao, Shao-fei Chen, Hai-feng Wang, Yue-hu PeiAbstract:Two new Steroidal glycosides 1 and 2, along with three known ones (3–5), were isolated from the 95% ethanol extract of the roots of Cynanchum limprichtii Schltr. The structure of the new compounds was elucidated as 3-O-α-L-diginopyranosyl-(1→4)-β-D-digitoxopyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-thevetopyranosyl-14, 16:15, 20:18, 20-triepoxy-14, 15-secopregn-4, 6, 8 (14)-triene (1) and 3-O-α-L-cymaropyranosyl-(1→4)-β-D-digitoxopyranosyl- (1→4)-β-D-3-demethyl-2-deoxythevetopyranosyl-14, 16: 15, 20: 8, 20-triepoxy-14, 15-secopregn-5, 8 (14)-diene (2) on the basis of spectroscopic analysis together with acidic hydrolysis. All compounds showed cytotoxic activity against the human cancer cell line HL60, with IC50 values of 55.36, 65.41, 17.88, 17.68 and 33.5 μM, respectively. While, only compound 3 showed cytotoxicity against the Caco-2 cell line, with an IC50 value of 67.47 μM.
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c21 Steroidal glycosides from the roots of cynanchum paniculatum
2016Co-Authors: Dan Zhao, Gang Chen, Shao-fei Chen, Hai-feng Wang, Baomin Feng, Xianan Sang, Yue-hu PeiAbstract:As a part of our continuing research for bioactive constituents from Cynanchum plants, four new C21 Steroidal glycosides, cynapanoside D-G (1-4), together with six known compounds (5-10) were isolated from the roots of Cynanchum paniculatum (Bge.) Kitag. Their structures were elucidated on the basis of 1D- and 2D-NMR spectroscopic data as well as HR-ESI-MS analysis. Compound 8 exhibited potent inhibitory activities against HL-60, HT-29, PC-3 and MCF-7 cell lines with IC50 values of 8.3, 7.5, 34.3 and 19.4μM, respectively and compounds 1-4 and 9 displayed moderate cytotoxicity against the four cell lines. The in vitro antioxidant activities of compounds 1-4, 8 and 9 were assayed by DPPH radical scavenging activity. Antibacterial and antifungal activities of compounds 1-4, 8 and 9 were also tested.
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Steroidal glycosides with anti tumor activity from the roots of cynanchum wallichii wight
2010Co-Authors: Gang Chen, Qihui Zhang, Yue-hu PeiAbstract:Two new Steroidal glycosides characterized with 2,6-dideoxypyranoses as component sugars have been isolated from roots of Cynanchum wallichii Wight. Their structure elucidation and cytotoxic activities against HL-60 and PC-3 cells are reported.
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c21 Steroidal glycosides from cynanchum wallichii wight
2009Co-Authors: Gang Chen, Yue-hu PeiAbstract:Three new C21 Steroidal glycosides, characterized with rostratamine and qinyangshengenin as aglycone moiety and 2,6-dideoxy-pyranoses as component sugars, have been isolated from the roots of Cynanchum wallichii Wight. The structures of the three new C21 Steroidal glycosides were elucidated as rostratamine-3-O-β-d-oleandropyranosyl-(1 → 4)-β-d-cymaropyranosyl-(1 → 4)-β-d-cymaropyranoside, qinyangshengenin-3-O-β-d-cymaropyranosyl-(1 → 4)-β-d-digitoxo-pyranoside, and qinyangshengenin-3-O-β-d-oleandropyranosyl-(1 → 4)-β-d-cymaropyranosyl-(1 → 4)-β-d-digitoxopyranoside.