Cytotoxic activities of chemical constituents from rhizomes of Anemarrhena asphodeloides and their analogues

Guo, Jing; Xu, Cheng-Hui; Xue, Rui; Jiang, Weixin; Wu, Bin; Huang, Chenggang

doi:10.1007/s12272-014-0431-4

Cited by 16 publications

(5 citation statements)

References 14 publications

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“…Norathyriol for reference (purity >98%, HPLC) and dosing (purity >95%, HPLC) was prepared through deglycosylation of mangiferin and identified by MS and NMR. 31 β-glucuronidase (type H-2, Helix pomatia, > 85000 units/ mL), sulfatase (type H-1, Helix pomatia, > 53570 units/g), and HPLC-grade formic acid were products of Sigma-Aldrich (St. Louis, MO). Deionized water was purified by a Milli-Q system (Millipore Corporation, Milford, MA).…”

Section: ■ Introductionmentioning

confidence: 99%

Absorption, Metabolism, and Pharmacokinetics Profiles of Norathyriol, an Aglycone of Mangiferin, in Rats by HPLC-MS/MS

Cheng

Shi

et al. 2018

J. Agric. Food Chem.

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Norathyriol, an aglycone of mangiferin, is a bioactive tetrahydroxyxanthone present in mangosteen and many medicinal plants. However, the biological fate of norathyriol in vivo remains unclear. In this study, the absorption and metabolism of norathyriol in rats were evaluated through HPLC-MS/MS. Results showed that norathyriol was well absorbed, as indicated by its absolute bioavailability of 30.4%. Besides, a total of 21 metabolites of norathyriol were identified in rats, including methylated, glucuronidated, sulfated and glycosylated conjugates, which suggested norathyriol underwent extensive phase II metabolism. Among those metabolites, 15 metabolites were also identified in hepatocytes incubated with norathyriol, indicating the presence of hepatic metabolism. Furthermore, glucuronide and sulfate conjugates, rather than their parent compound, were found to be the main forms existing in vivo after administration of norathyriol, as implicated by the great increase of exposure of norathyriol determined after hydrolysis with β-glucuronidase and sulfatase. The information obtained from this study contributes to better understanding of the pharmacological mechanism of norathyriol.

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Section: ■ Introductionmentioning

confidence: 99%

Absorption, Metabolism, and Pharmacokinetics Profiles of Norathyriol, an Aglycone of Mangiferin, in Rats by HPLC-MS/MS

Cheng

Shi

et al. 2018

J. Agric. Food Chem.

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“…Furthermore, comparing physical and spectroscopic data with those reported in the literature, the chemical structures of the known compounds (Figure 1) were determined as 26- O - β -D-glucopyranosyl-(25 R )-5 α -furostan-20(22)-en-3 β ,26-diol (2) [22] , pseudoprotodioscin (3) [23] , 26- O - β -D-glucopyranosyl-(25 R )-5 α -furostan-20(22)-en-3 β ,26-diol-3- O -{ β -D-xylopyranosyl-(1→2)-[ β -D-xylopyranosyl-(1→3)]- β -D-glucopyranosyl-(1→4)-[ α -L-rhamnopyranosyl-(1→2)]- β -D-galactopyranoside}(4) [24] , 26- O - β -D-glucopyranosyl-(25 R )-5 α -furost-20(22)-en-2 α , 3 β ,26-triol-3- O - β -D-glucopyranosyl-(1→2)-[ β -D-xylopyranosyl-(1→3)]- β -D-glucopyranosyl-(1→4)- β -D-galactopyranoside (5) [25] , 26- O - β -D-glucopyranosyl-(25 R )-5 β -furostan-20(22)-en-3 β , 26-diol-3- O - β -D-glucopyranosyl (1→2)-[ β -D-xylopyranosyl (1→3)]- β -D-glucopyranosyl (1→4)- β -D-galactopyranoside (6) [26] , protodioscin (7) [27] , (25 R )-26- O - β -D-glucopyranosyl-5 α -furostan-3 β ,22 α , 26-triol-3- O -{ β -D-xylopyranosyl-(1→2)-[ β -D-xylopyranosyl-(1→3)]- β -D-glucopyranosyl-(1→4)-[ α -L-rhamnopyranosyl-(1→2)]- β -D-galactopyranoside} (8) [28] , tibllin (9) [29] , (25 R )-5 α -spirostan-2 α , 3 β -diol-3- O - β -D-glucopyranosyl-(1→2)-[ β -D-xylopyranosyl-(1→3)]- β -D-glucopyranosyl-(1→4)- β -D-galactopyranoside (10) [30] , hecogenin-3- O - β -D-glucopyranosyl (1→2)-[ β -D-xylopyranosyl (1→3)]- β -D-glucopyranosyl (1→4)- β -D-galactopyranoside (11) [25] , gitogenin (12) [31] , (25 R )-spirostan-4-en-24 β -hydroxy-3, 12-dione (13) [32] , (25 R )-spirostan-4-en-3, 12-dione (14) [32] , and terrestrinin A (15) [33] .…”

Section: Resultsmentioning

confidence: 99%

Steroidal saponins with anti-inflammatory activity from Tribulus terrestris L.

Yang

Oppong

et al. 2022

Acupuncture and Herbal Medicine

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Objective: Tribulus terrestris L. (T. terrestris) is a highly valuable traditional Chinese medicine used to treat stroke, inflammation, pulmonary fibrosis, liver cancer, and urolithiasis. To identify the basic substance responsible for the anti-inflammatory effect of TST (total saponins of Tribulus), its chemical composition was systematically studied, and its effect of inhibiting nitric oxide generation and the expression of related inflammatory factors were determined.Methods: To separate chemical constituents from T. terrestris by column chromatography. Spectroscopic methods, including 1D and 2D nuclear magnetic resonance spectroscopy (NMR) and mass spectrometry (MS) techniques, were used to elucidate the isolated compounds. The anti-inflammatory activities of TST and several compounds were evaluated in vitro.Results: Fifteen steroidal saponins, including 9 furostanol steroidal saponins (1, 2, 3, 4, 5, 6, 7, 8, and 15) and 6 isospirostanol steroidal saponins (9, 10, 11, 12, 13, and 14), were isolated from T. terrestris. TST significantly decreased the expression of tumor necrosis factor-a (TNF-a) and interleukin-6 (IL-6) in RAW 264.7 cells stimulated by lipopolysaccharides. Compounds 13 and 15 evidently reduced TNF-a expression. Compounds 6, 10, 12, 13, and 15 markedly reduced IL-6 expression. Conclusions: Compounds 1 was a novel furostanol steroidal saponin, named 26-O-b-D-glucopyranosyl-(25R)-5afurostan-12-carbonyl-20(22)-en-3b, 26-diol-3-O-{b-D-xylopyranosyl-(1→2)-[b-D-xylopyranosyl-(1→3)]-b-D-glucopyranosyl-(1→4)-[a-L-rhamnopyranosyl-(1→2)]-b-D-galactopyranoside}. Compounds 2 was isolated from the family Zygophyllaceae for the first time, and 5 and 6 were isolated from the Tribulus genus. TST and compounds 6, 10, 12, 13, and 15 exerts antiinflammatory activity.

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“…Similar results were confirmed in reports by Okubo et al, Beit-Yannai et al, Dai et al (furospirostane < furostane < spirostane saponin). In addition, structures containing two or more sugar chains at the C-3 position (especially the additional rhamnose units), ,, and the 25( R / S )-configuration (25 R > 25 S : A549, Caski, HepG2, and MCF-7; , 25 S > 25 R : BEL-7402, HT-29, Hela, MDA-MB-468, BT549, and SW620 cell lines , ) were considered important for cytotoxicity. Moreover, the aforementioned factors also influenced anti-inflammatory, − antiatherosclerotic, antidiabetic, and antiosteosarcoma activities.…”

Section: Furostane Saponinsmentioning

confidence: 99%

Characterization of Seven New Steroidal Saponins from Korean Oat Cultivars by UPLC-QTOF-MS and UPLC-MS/MS

Kwon,

Lee,

Kim

et al. 2024

ACS Omega

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Oat saponins are composed of triterpenoid and steroidal saponins, and their potential biological activities, such as antibacterial, antifungicidal, osteogenic, and anticancer activities, have been reported. In this study, qualitative and quantitative analyses of oat saponins were conducted by using UPLC-QToF-MS and UPLC-Triple Q-MS/MS. A total of 22 saponins were analyzed in seven Korean oat cultivars. Among them, 7 saponins were identified as new compounds in this source, which were tentatively confirmed as nuatigenin-type saponins with 26-O-diglucoside and 3-Omalonylglucoside forms and (25S)-furost-5-en-3β,22,26-triol-type saponins. In addition, the total content of these saponins ranged from 70.61 to 141.38 mg/100 g dry weight, and it was affected by the type of oat cultivar and the presence or absence of hulling. These detailed profiles will be suggested as fundamental data for breeding superior oat cultivars, evaluating of related products, and various industries.

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Cytotoxic activities of chemical constituents from rhizomes of Anemarrhena asphodeloides and their analogues

Cited by 16 publications

References 14 publications

Absorption, Metabolism, and Pharmacokinetics Profiles of Norathyriol, an Aglycone of Mangiferin, in Rats by HPLC-MS/MS

Absorption, Metabolism, and Pharmacokinetics Profiles of Norathyriol, an Aglycone of Mangiferin, in Rats by HPLC-MS/MS

Steroidal saponins with anti-inflammatory activity from Tribulus terrestris L.

Characterization of Seven New Steroidal Saponins from Korean Oat Cultivars by UPLC-QTOF-MS and UPLC-MS/MS

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