Triterpenoid Saponins from the Roots of Clematis argentilucida and Their Cytotoxic Activity

Zhao, Ming; Ma, Ning; Qiu, Feng; Hai, Wenli; Tang, Hai‐Feng; Zhang, Yan; Wen, Aidong

doi:10.1055/s-0034-1382838

Cited by 18 publications

(6 citation statements)

References 17 publications

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“…This result indicates that the spatial configuration of a terminal a-L-rhamnopyranosyl residue is favorable to the a-glucosidase inhibitory activity. In previous reports, the monodesmosidic saponin 7 exhibited cytotoxic activity against human tumor HL-60, HepG-2, and SGC-7901 cell lines [41], and compound 8 upregulated PPARg transcriptional activity in a dose-dependent manner in HepG2 cells [42]. However, their a-amylase and a-glucosidase inhibitory effects have not been reported.…”

Section: Biological Evaluationsmentioning

confidence: 90%

Synthesis and Evaluation of a Series of Oleanolic Acid Saponins as α‐Glucosidase and α‐Amylase Inhibitors

Guo

et al. 2015

Archiv der Pharmazie

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Sixteen naturally occurring oleanolic acid saponins and their derivatives were synthesized in an efficient and practical strategy, and their inhibitory activities against α-glucosidase and α-amylase were evaluated in vitro. Among all the compounds, 28-O-monoglucoside 8 exhibited remarkably potent inhibitory activity against α-glucosidase with an IC50 value of 87.3 µM, which was fivefold stronger than that of the antidiabetic acarbose. Based on the preliminary structure-activity relationships, for 28-O-monoglucosides, the presence of a terminal α-l-rhamnopyranosyl residue enhanced the α-glucosidase and α-amylase inhibitory activities. Furthermore, for 3,28-O-bidesmosides, sugar-substituted moieties attached to the C-3 and C-28 positions of the oleanolic acid scaffold are helpful to increase the inhibitory activities against α-amylase and α-glucosidase.

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Section: Biological Evaluationsmentioning

confidence: 90%

Synthesis and Evaluation of a Series of Oleanolic Acid Saponins as α‐Glucosidase and α‐Amylase Inhibitors

Guo

et al. 2015

Archiv der Pharmazie

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“…Several saponins have exhibited potent cytotoxic [33], antiproliferative [34], antifungal [35], anti-inflammatory [36], and antiviral activity [37], which indicates a significant potential for drug development. One particulary promising property of spirostan saponins is their anticancer activity.…”

Section: Discussionmentioning

confidence: 99%

Apoptotic and autophagic cell death induced by glucolaxogenin in cervical cancer cells

Sánchez-Sánchez

Escobar²,

Sandoval‐Ramírez

et al. 2015

Apoptosis

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The antiproliferative and cytotoxic activity of glucolaxogenin and its ability to induce apoptosis and autophagy in cervical cancer cells are reported. We ascertained that glucolaxogenin exerts an inhibitory effect on the proliferation of HeLa, CaSki and ViBo cells in a dose-dependent manner. Analysis of DNA distribution in the cell-cycle phase of tumor cells treated with glucolaxogenin suggests that the anti-proliferative activity of this steroid is not always dependent on the cell cycle. Cytotoxic activity was evaluated by detection of the lactate dehydrogenase enzyme in supernatants from tumor cell cultures treated with the steroid. Glucolaxogenin exhibited null cytotoxic activity. With respect to the apoptotic activity, the generation of apoptotic bodies, the presence of active caspase-3 and annexin-V, as well as the DNA fragmentation observed in all tumor lines after treatment with glucolaxogenin suggests that this compound does indeed induce cell death by apoptosis. Also, a significantly increased presence of the LC3-II, LC3 and Lamp-1 proteins was evidenced with the ultrastructural existence of autophagic vacuoles in cells treated with this steroidal glycoside, indicating that glucolaxogenin also induces autophagic cell death. It is important to note that this compound showed no cytotoxic effect and did not affect the proliferative capacity of mononuclear cells obtained from normal human peripheral blood activated by phytohaemagglutinin. Thus, glucolaxogenin is a compound with anti-proliferative properties that induces programmed cell death in cancer cell lines, though it is selective with respect to normal lymphocytic cells. These findings indicate that this glycoside could have a selective action on tumor cells and, therefore, be worthy of consideration as a therapeutic candidate with anti-tumor potential.

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“…The aglycones of Clematis pentacyclic triterpene saponins mainly belong to oleanolic type (A), olean-3β, 28-diol type (B), hederagenin type (C) or hederagenin-11, 13-dien type (D), where types A and C are predominant [ 1 , 7 ]. Many Clematis saponins have cytotoxic activity against human glioblastoma [ 14 ], hepatoma [ 15 ], cervical cancer [ 16 ], leukemia [ 15 , 17 ], gastric cancer [ 15 , 17 ], colon cancer [ 18 ], and prostate cancer [ 19 ]. However, the mechanistic study is scarce.…”

Section: Cell Death Pathwaysmentioning

confidence: 99%

Anticancer Chemodiversity of Ranunculaceae Medicinal Plants: Molecular Mechanisms and Functions

Hao

Shen³

et al. 2016

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The buttercup family, Ranunculaceae, comprising more than 2,200 species in at least 62 genera, mostly herbs, has long been used in folk medicine and worldwide ethnomedicine since the beginning of human civilization. Various medicinal phytometabolites have been found in Ranunculaceae plants, many of which, such as alkaloids, terpenoids, saponins, and polysaccharides, have shown anti-cancer activities in vitro and in vivo. Most concerns have been raised for two epiphany molecules, the monoterpene thymoquinone and the isoquinoline alkaloid berberine. At least 17 genera have been enriched with anti-cancer phytometabolites. Some Ranunculaceae phytometabolites induce the cell cycle arrest and apoptosis of cancer cells or enhance immune activities, while others inhibit the proliferation, invasion, angiogenesis, and metastasis, or reverse the multi-drug resistance of cancer cells thereby regulating all known hallmarks of cancer. These phytometabolites could exert their anti-cancer activities via multiple signaling pathways. In addition, absorption, distribution, metabolism, and excretion/toxicity properties and structure/activity relationships of some phytometabolites have been revealed assisting in the early drug discovery and development pipelines. However, a comprehensive review of the molecular mechanisms and functions of Ranunculaceae anti-cancer phytometabolites is lacking. Here, we summarize the recent progress of the anti-cancer chemo- and pharmacological diversity of Ranunculaceae medicinal plants, focusing on the emerging molecular machineries and functions of anti-cancer phytometabolites. Gene expression profiling and relevant omics platforms (e.g. genomics, transcriptomics, proteomics, and metabolomics) could reveal differential effects of phytometabolites on the phenotypically heterogeneous cancer cells.

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Triterpenoid Saponins from the Roots of Clematis argentilucida and Their Cytotoxic Activity

Cited by 18 publications

References 17 publications

Synthesis and Evaluation of a Series of Oleanolic Acid Saponins as α‐Glucosidase and α‐Amylase Inhibitors

Synthesis and Evaluation of a Series of Oleanolic Acid Saponins as α‐Glucosidase and α‐Amylase Inhibitors

Apoptotic and autophagic cell death induced by glucolaxogenin in cervical cancer cells

Anticancer Chemodiversity of Ranunculaceae Medicinal Plants: Molecular Mechanisms and Functions

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