Steroidal saponins with induced platelet aggregation activity from the aerial parts of Paris verticillata

Sun, Changli; Ni, Wei; Yan, Hong‐Bin; Liu, Zhenhua; Yang, Lian; Si, Yong-Ai; Hua, Yan; Chen, Chang‐Xiang; He, Li; Zhao, Jinhua; Liu, Haiyang

doi:10.1016/j.steroids.2014.09.008

Cited by 43 publications

(14 citation statements)

References 23 publications

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“…According to the structural features of PPY in related literature and their precursor ions 4 m / z units higher than m / z 899.469, the m / z 903.502 node was elucidated as the C 16 –C 22 and C 22 –C 26 cleavage product of peak 207 , which was tentatively identified as PPY‐52 (peak 166 ). Finally, based on the structural feature of PPY in the relevant literature and the precursors 16 m / z units higher than m / z 903.502, the m / z 919.488 node was determined as a 16‐hydroxyl derivative of PPY‐52 ( PPY‐53 ). In addition, other series of m / z 1079.54 and 1093.585 ions were clustered.…”

Section: Resultsmentioning

confidence: 99%

Structural characterization and discrimination of Paris polyphylla var. yunnanensis by a molecular networking strategy coupled with ultra‐high‐performance liquid chromatography with quadrupole time‐of‐flight mass spectrometry

Wang

Fan

Xiang

et al. 2020

Rapid Comm Mass Spectrometry

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Rationale: Paris polyphylla var. yunnanensis (Franch) Hand Mazz (PPY) is a traditionalChinese medicine with antitumor, antibacterial, hemostatic, and anthelmintic activities. Identification of the chemical composition in PPY is helpful to discover its active ingredients and can be used to establish its quality control protocols.Methods: The composition of PPY was identified using ultra-high-performance liquid chromatography combined with quadrupole time-of-flight mass spectrometry (UHPLC/QTOF-MS/MS) coupled with a molecular networking strategy. First, the UHPLC/QTOF-MS/MS approach was optimized for chemical compound profiling.Then, the MS data were processed using PeakView™ combined with an in-house database to quickly characterize the secondary metabolites. Finally, molecular networking excavated new molecular weights to discover unknown or trace natural products based on the characteristics of each cluster. Results:A total of 222 compounds, including 77 isospirostanols, 2 spirostanols, 19 furostanols, 10 pseudospirostanols, 6 cholesterols, 10 C 21 steroids, 5 insect metamorphosis hormones, 3 plant sterols, 6 five-ring triterpenoids, 4 flavonoids, 8 fatty acids, 2 phenylpropanoids, and 8 other compounds, were characterized in PPY by comparing their main fragmentation characteristics and pathways with the literature data, and 62 of them, 54 steroidals and 8 phenylpropanoids, were discovered or tentatively identified for the first time. Conclusions:This study extended the application of a molecular networking strategy to traditional herbal medicines and developed a molecular networking based screening approach with a significant increase in efficiency for the discovery and identification of trace novel natural products.Yumei Wang and Qian Fan contributed equally to this work as first authors. Paris polyphylla var. yunnanensis (Franch) Hand Mazz (PPY), calledChong Lou, is a well-known, valuable traditional Chinese medicine (TCM) that has been used to treat fractures, hemorrhages, snake bites, and abscess for many years. 1,2 PPY has been used as a main ingredient for the preparation of many TCMs, such as Yunnan Baiyao, Gongxuening capsules, and Jidesheng Sheyao tablets. 3 Phytochemistry studies have indicated that the dried rhizomes of Paris species contain steroidal saponins, triterpenoid saponins, flavonoids, phenylpropanoids, ecdysteroids, phenolic glycosides, and so on. 4-6 The glucosyl groups of steroidal saponins are normally attached to the steroidal aglycones through the hydroxyl groups at the C-3 and/or C-26 positions (and sometimes the C-1, C-21, C-23, and C-24 positions). Four types of steroidal sapogenins 6 (spirostanol, isospirostanol, furostanol, and pseudospirostanol) are considered major aglycones, and typical sugars are arabinose, xylose, apiose, fucose, rhamnose, glucose, and galactose. Comprehensive identification of ingredients in PPY is critical to understanding its biological mechanism and establishing quality control protocols. Because of the complexity of these components, their comprehensive...

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Section: Resultsmentioning

confidence: 99%

Structural characterization and discrimination of Paris polyphylla var. yunnanensis by a molecular networking strategy coupled with ultra‐high‐performance liquid chromatography with quadrupole time‐of‐flight mass spectrometry

Wang

Fan

Xiang

et al. 2020

Rapid Comm Mass Spectrometry

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“…Its main bioactive components are four kinds of saponins: Paris saponins I, II, VI, and VII [38,39]. The saponins in Paris saponins have many pharmacological properties, such as anti-tumor [40,41], hemostatic [42], anti-bacterial [43], anti-inflammatory [44], angiogenesis-inhibitory [45] and immune-regulatory [46] effects. However, in recent years, some studies have reported the in vivo hepatotoxicity of Paris saponins [3,4,5,6,7].…”

Section: Discussionmentioning

confidence: 99%

Hepatocellular Toxicity of Paris Saponins I, II, VI and VII on Two Kinds of Hepatocytes-HL-7702 and HepaRG Cells, and the Underlying Mechanisms

Wang

Liu

Sun

et al. 2019

Cells

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Rhizoma paridis is a popularly-used Chinese medicine in clinics, based on the pharmacodynamic properties of its saponin components. The four main saponins in Rhizoma paridis are designated saponins I, II, VI, and VII. At present, much attention is focused on the anticancer effect of Rhizoma paridis which is manifested in its cytotoxicity to various cancer cells. The purpose of this study was to investigate the hepatocellular toxicities of the four saponins in Rhizoma paridis and the relative intensities of their cytotoxic effects. It was found that the four saponins were cytotoxic to two types of hepatocytes-HL-7702 and HepaRG cells. The cytotoxicities of the four saponins to the two cell models were compared. One of the most cytotoxic saponins was Rhizoma paridis saponin I (PSI). This was used to determine the mechanism of hepatocellular toxicity. Results from MTT assays demonstrated that the four saponins induced apoptosis of the two hepatocyte models in a dose-dependent and time-dependent manner. In addition, fluorescent 4′,6-diamidino-2-phenylindole (DAPI) staining was used to observe the morphological changes of HepaRG cells after saponin administration. Further, as the concentration increased, PSI-induced lactate dehydrogenase (LDH) release from HepaRG cells increased gradually. In addition, PSI enhanced the levels of reactive oxygen species (ROS) and blocked the S and G2 phases of the cell cycle in HepaRG cells. A western blot indicated that PSI upregulated the protein expression levels of p53, p21, and Fas. Furthermore, the PSI-induced changes in the p53 protein increased the Bax/bcl-2 ratio, resulting in enhancement of the release of mitochondrial cytochrome c, activation of caspases-3, -8, and -9, poly-ADP ribose polymerase (PARP), and ultimately apoptosis. Increased Fas protein activated caspase-8, which led to the activation of caspase-3 and its downstream PARP protein, resulting in cell apoptosis. These results indicate that PSI induced apoptosis in HepaRG cells through activation of ROS and death receptor pathways. The results obtained in this study suggest that the hepatocellular toxicity of saponins in Rhizoma paridis should be considered during the clinical application of this drug. In addition, they provide a reference for future anti-cancer studies on Rhizoma paridis.

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“…1 ; Table 1 ), named chonglouosides SL-1–SL-20 ( 1 – 20 ) [ 25 – 27 ], polyphyllosides III ( 21 ) and IV ( 22 ) [ 28 ], as well as two new steroidal sapogenins, named 27-hydroxylpennogenin ( 23 ) and 27,23 β -dihydroxylpennogenin ( 24 ) [ 29 ]. In addition, three new pennogenin saponins ( 25 – 27 ) [ 30 , 31 ], three new spirostanol saponins ( 28 – 30 ) and one new cholestane saponin ( 31 ) [ 32 ], and two new highly oxygenated spirostanol saponins ( 32 and 33 ) [ 33 ] were isolated from P. axialis (rhizomes), P. verticillata (aerial parts), and P. polyphylla var. stenophylla (rhizomes), respectively (Fig.…”

Section: Steroidal Sapogenins and Saponinsmentioning

confidence: 99%

Untiring Researches for Alternative Resources of Rhizoma Paridis

Qin

Chen

et al. 2018

Nat. Prod. Bioprospect.

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Rhizoma Paridis (RP, 重楼), a traditional Chinese medicine, is the rhizoma of Paris polyphylla var. yunnanensis (PPY) or P. polyphylla var. chinensis which are widely used as important raw materials for several Chinese patent drugs. However, the wild resources of these herbs have become less and less due to their slow-growing characteristics and previously excessive excavation. This review covers untiring investigations on alternative resources of RP by our research group over the past decades, including non-medicinal parts of PPY as well as other plants of Liliaceae and Liliflorae families. The arial parts of PPY and the whole plants of Trillium kamtschaticum might be alternative resources for RP based on the fact that they shared the same or similar saponins and bioactivities.

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Steroidal saponins with induced platelet aggregation activity from the aerial parts of Paris verticillata

Cited by 43 publications

References 23 publications

Structural characterization and discrimination of Paris polyphylla var. yunnanensis by a molecular networking strategy coupled with ultra‐high‐performance liquid chromatography with quadrupole time‐of‐flight mass spectrometry

Structural characterization and discrimination of Paris polyphylla var. yunnanensis by a molecular networking strategy coupled with ultra‐high‐performance liquid chromatography with quadrupole time‐of‐flight mass spectrometry

Hepatocellular Toxicity of Paris Saponins I, II, VI and VII on Two Kinds of Hepatocytes-HL-7702 and HepaRG Cells, and the Underlying Mechanisms

Untiring Researches for Alternative Resources of Rhizoma Paridis

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