Cardenolides from <i>Saussurea stella</i> with Cytotoxicity toward Cancer Cells

Wang, Tian Min; Hojo, Toshinari; Ran, Fu Xiang; Wang, Ru Feng; Wang, Rui Qing; Chen, Hubiao; Cui, Jing; Shang, Ming; Cai, Shao Qing

doi:10.1021/np070150o

Cited by 35 publications

(15 citation statements)

References 21 publications

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“…The structures of the two known cardiac glycosides 4 and 5 isolated from the stem bark of S. asper in the present study were determined by comparison of their spectroscopic data (Tables 1 and 2 and Table S1, Supporting Information) with literature data for (+)-3- O-β - d -fucopyranosylperiplogenin ( 4 ) 18 and (+)-strebloside ( 5 ), 5 respectively. The (3 S , 5 S , 8 R , 9 S , 10 R , 13 R , 14 S , 17 R , 1' R , 2' R , 3' S , 4' R , 5' R ) and (3 S , 5 S , 8 R , 9 S , 10 S , 13 R , 14 S , 17 R , 1' R , 2' R , 3' S , 4' S , 5' R ) absolute configurations were evident for 4 and 5 , respectively, from their ECD and 2D NOESY NMR spectra, which were consistent with those of 1 (Figures 1 and 3 and Figures S15 and S16, Supporting Information).…”

Section: Resultsmentioning

confidence: 99%

Cardiac Glycoside Constituents of Streblus asper with Potential Antineoplastic Activity

et al. 2016

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Three new (1–3) and two known (4 and 5) cytotoxic cardiac glycosides were isolated and characterized from a medicinal plant, Streblus asper, collected in Vietnam, with six new and one known derivatives (5a–5g) synthesized from (+)-strebloside (5). A preliminary structure-activity relationship study indicated that the C-19 formyl and C-5 and C-14 hydroxy groups and C-3 sugar unit play important roles in the mediation of the cytotoxicity of (+)-strebloside (5) against HT-29 human colon cancer cells. When evaluated in NCr nu/nu mice implanted intraperitoneally with hollow fibers facilitated with either MDA-MB-231 human breast or OVCAR3 human ovarian cancer cells, (+)-strebloside (5) showed significant cell growth inhibitory activity in both cases, in the dose range 5–30 mg/kg.

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Section: Resultsmentioning

confidence: 99%

Cardiac Glycoside Constituents of Streblus asper with Potential Antineoplastic Activity

et al. 2016

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“…[56] In addition, convallatoxin, also found in Antiaris toxicaria (Moraceae) trunk bark, [25] demonstrated cytotoxic activity against a human epidermal keratinocyte cell lines (HaCaT) in vitro, a psoriasis-related model cell lines, and exhibited antipsoriatic activities in two mouse models of psoriasis in vivo, highlighting the potential of convallatoxin as a novel therapeutic strategy for the treatment of psoriasis. [57] Moreover, convallatoxin has also shown cytotoxic activity against human gastric cancer cells, [58] human hepatoma cells [58] and neuroblastoma stem cells. [25] The presence of artocarpin and convallatoxin in the hydroethanolic extract from B. gaudichaudii may be related to the cytotoxic activity observed.…”

Section: Cytotoxic Assaymentioning

confidence: 99%

Chemical Characterization, Antioxidant and Cytotoxic Activities of the Edible Fruits of Brosimun gaudichaudii Trécul, a Native Plant of the Cerrado Biome

Engelbrecht

Ribeiro

Yoshida

et al. 2021

Chemistry & Biodiversity

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In Brazil, there is a large diversity of species of small edible fruits that are considered sources of nutrients and functional properties. They present a high innovation domain for the pharmaceutical, cosmetic and food industries due to their health-promoting properties. Edible fruits from Brosimum gaudichaudii (Moraceae) are widely consumed and used in folk medicine and in feed by the population of the Brazilian Cerrado. Nevertheless, detailed information on the chemical fingerprint, antiradical activity and safety aspects of these fruits is still unknown. Thus, the aim of this work was to investigate the bioactive compounds of hydroethanolic extracts of fruits from Brosimum gaudichaudii using high-performance liquid chromatography combined with mass spectrometry using electrospray ionization (HPLC ESI-MS). Eighteen different compounds, including flavonoids, coumarins, arylbenzofurans, terpenoids, stilbenes, xanthones and esters, were detected. Moreover, the study indicated that the hydroethanolic extract of fruits from B. gaudichaudii presented low scavenging activity against 2,2-diphenyl-1-picrylhydrazyl radicals (IC 50 > 800 μg mL À 1 ) and was cytotoxic (IC 50 < 30 μg mL À 1 ) in Chinese hamster ovary cells (CHOÀ K1) by an in vitro assay. This is the first report of the chemical profile, antioxidant activity and cytotoxic properties of the hydroethanolic extract of fruits from B. gaudichaudii.

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“…Protocatechuic acid, 1, 5-dicaffeoylquinic acid, quercitroside, diosmetin 3-O-glucoside, kaempferol 3-O-rhamnoside, acacetin 7-O-glucoside, arctiin, quercetin and apigenin were isolated from Saussurea stella Maxim., a plant of same genus as S. involucrata [16]. The purity of these chemical standards was determined to be more than 98% by normalization of the peak areas detected by LC-DAD.…”

Section: Reagents and Chemicalsmentioning

confidence: 99%

Identification and Determination of the Major Constituents in the Traditional Uighur Medicinal Plant Saussurea involucrata by LC-DAD-MS

Chen

Zhao

et al. 2009

Chroma

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A high-performance liquid chromatography (LC) coupled with diode array detector (DAD) and electrospray ionization mass spectrometry (ESI-MS) method was developed for the simultaneous analysis of the major constituents in Saussurea involucrata (SI). A comprehensive validation of the developed method was conducted, and the unique properties of the present method were confirmed by analyzing eleven SI samples. Seventeen compounds including phenolic acids, flavonoids, and lignanoids were identified by online ESI-MS and by comparison with known data in the literature and standard compounds; of these, eight were simultaneously quantified by LC-DAD. All linear regressions were acquired with R 2 > 0.99, and the limits of detection ranged from 0.85 to 3.03 ng. Repeatability was evaluated by intra-and inter-day assays; the relative standard deviation (RSD) value was within 4.95%. Recovery studies for the quantified compounds were found to be within the range 95.20-102.32% with RSD less than 2.18%. Overall, the present hyphenation procedure is highly efficient and reliable, and hence suitable for qualitative and quantitative analysis of a large number of samples.

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Cardenolides from Saussurea stella with Cytotoxicity toward Cancer Cells

Cited by 35 publications

References 21 publications

Cardiac Glycoside Constituents of Streblus asper with Potential Antineoplastic Activity

Cardiac Glycoside Constituents of Streblus asper with Potential Antineoplastic Activity

Chemical Characterization, Antioxidant and Cytotoxic Activities of the Edible Fruits of Brosimun gaudichaudii Trécul, a Native Plant of the Cerrado Biome

Identification and Determination of the Major Constituents in the Traditional Uighur Medicinal Plant Saussurea involucrata by LC-DAD-MS

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