Cytotoxic Iridoids from the Roots of <i>Patrinia scabra</i>

Li, Ning; Di, Lijun; Gao, Wen-Chao; Wang, Kai‐Jin; Zu, Ling-Bo

doi:10.1021/np300286t

Cited by 41 publications

(29 citation statements)

References 18 publications

(54 reference statements)

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“…The iridomyrmecintype boat form ( 1 B 4 ) of 21 was deduced from the negligible coupling between Hα-1 and H-7a and the coupling constant of 3.8 Hz between Hβ-1 and H-7a, which was consistent with the data in the literature assigned to iridomyrmecin-type analogs [28][29][30][31]. In contrast, Hα-1 and H-7a exhibits a larger coupling constant (11 Hz) in the isoiridomyrmecin-type boat form [28][29][30]32]. Because the carbonyl functionality in the iridomyrmecin-type boat form is folded and located closer to the cyclopentane ring (▶ Fig.…”

Section: Resultssupporting

confidence: 87%

“…Accordingly, 21, which has the same configurations at C-4, C-4a, C7, and C-7a as iridomyrmecin and a consistent optical rotation ( (OH) and 1732 cm −1 (δlactone). Despite the similarities of the IR, MS, and 13 C NMR data of these two compounds, the 1 H NMR spectrum (▶ Table 3 the literature [28][29][30]32]. In accordance with isoiridomyrmecintype analogs, the hydroxymethyl at C-4 was located in the β-pseudo-equatorial position, which was confirmed by the coupling constant of 10.9 Hz between H-4 and H-4a.…”

Section: Resultsmentioning

confidence: 85%

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Cytotoxic and Anti-inflammatory Terpenoids from the Whole Plant of Vaccinium emarginatum

Liang

Huang

et al. 2020

Planta Med

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AbstractTwo new Δ12 ursene-type triterpenoid coumaroyl esters (1 and 2), one new Δ7,15 isopimarane-type diterpenoid glycoside (20), and two new irido-δ-lactone-type iridoids (21 and 22), together with 17 known pentacyclic triterpenoids (3 – 19), were isolated during the phytochemical investigation of a methanol extract of the whole plant of Vaccinium emarginatum. Their structures were determined by detailed analysis of standard spectroscopic data (MS, IR, 1D, and 2D NMR) and comparison with data of known analogs. The isolates were evaluated for their cytotoxicity against the PC-3 and Du145 prostate cancer cell lines (as assessed by an MTT cell proliferation assay), as well as for their anti-inflammatory activity via the inhibition of nitric oxide production in lipopolysaccharide-induced murine macrophage RAW 264.7 cells. Among the isolates, the triterpenoid coumaroyl and feruloyl esters (1, 3, and 4) exhibited strong cytotoxicity against PC-3 prostate cancer cells, with 85.6 – 90.2% inhibition at 10.0 µg/mL. The pomolic acid coumaroyl and feruloyl esters (1 and 3) also showed moderate anti-inflammatory activity against nitric oxide production in lipopolysaccharide-induced RAW 264.7 cells, with 59.2 (± 1.0) and 47.1% (± 0.2) inhibition at 12.5 µg/mL, respectively.

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Section: Resultssupporting

confidence: 87%

Section: Resultsmentioning

confidence: 85%

Cytotoxic and Anti-inflammatory Terpenoids from the Whole Plant of Vaccinium emarginatum

Liang

Huang

et al. 2020

Planta Med

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“…A number of promising new agents are in clinical development based on selective activity against cancer-related molecular targets, including flavopiridol and combretastatin a4 phosphate, while some agents which failed in earlier clinical studies are stimulating renewed interest [33]. Iridoid glycosides and their hydrolysed products which isolated from Scrophularia species have been shown to have cytotoxic and anticancer effects against gastric cancer, Hela Cervix carcinoma cell line, myeloid leukemia K562 and MNK-45 cell lines [34][35][36][37][38]. Natural anticancer and cytotoxic compounds are important in different area of cancer research and determining their possible mechanisms can leads to their proper use in cancer treatment.…”

Section: Discussionmentioning

confidence: 99%

Apoptosis and Caspase 3 Pathway Role on Anti-Proliferative Effects of Scrophulariaoxy Sepala Methanolic Extract on Caco-2 Cells

et al. 2017

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Colorectal cancer is one the most important malignancies worldwide and finding new treatment option for this cancer is of high priority. Natural compounds are common source of drugs for treatment of various diseases including cancers. The aim of this study was to investigate the effects of Scrophularia oxysepala extract on Caco-2 cells and explore the possible role of caspase 3 pathway in inducing cell death in this cancer cells in compare with chemotherapy agents of cisplatin and capecitabine. The methanolic extract of Scrophularia oxysepala (SO) was prepared by drench method. The IC50 of extract, cisplatin and capecitabine on Caco-2 cells were determined by MTT assay. The effect of SO extract on caspase 3 expression and inducing apoptosis were determined using TUNEL assay and caspase 3 ELISA methods, respectively. The IC50 of SO extract, cisplatin and capecitabine were 300, 195 and 80 µg/ml, respectively. Analysis for apoptosis revealed that SO methanolic extract increased apoptosis significantly (P<0.001) compared with control group. The effect of high doses of SO extract on apoptosis induction were comparable to cisplatin but significantly were higher than capecitabine. Only high doses of SO methanolic extract showed significant effects (P<0.05) on increasing caspase 3 compared to control group. The methanolic extract of SO showed inhibitory effect on Caco-2 cells and induced apoptosis in a dose-dependent manner comparable to cisplatin and higher than capecitabine 2 commonly used chemotherapeutic agent for various cancers.

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“…Acid hydrolysis was carried out as reported in [25]. Briefly, the sugar residues were obtained by hydrolysis of compounds 1 -7 (2.0 mg) with H 2 SO 4 (2.0 ml, 2 mol/l).…”

Section: Acid Hydrolysis and Determination Of Sugar Compoundsmentioning

confidence: 99%

New Thymoquinol Glycosides and Neuroprotective Dibenzocyclooctane Lignans from the Rattan Stems of Schisandra chinensis

Yang

Guo

et al. 2016

Chemistry & Biodiversity

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Three new lignans (1 - 3), together with four new thymoquinol glycosides (4 - 7), were isolated from 70%-EtOH extract of the rattan stems of Schisandra chinensis. The structures of 1 - 7 were elucidated by detailed spectroscopic analyses, and these new compounds were identified as pinobatol-9-O-β-d-glucopyranoside (1), 1,2,13,14-tetramethoxydibenzocyclooctadiene 3,12-O-β-d-diglucopyranoside (2), 3,7-dihydroxy-1,2,13,14-tetramethoxydibenzocyclooctadiene 12-O-β-d-glucopyranoside (3), thymoquinol 2-O-β-d-apiofuranosyl-(1→6)-β-d-glucopyranoside (4), thymoquinol 2-O-α-d-arabinofuranosyl-(1→6)-β-d-glucopyranoside (5), thymoquinol 5-O-β-d-apiofuranosyl-(1→6)-β-d-glucopyranoside (6), and thymoquinol 5-O-α-d-arabinofuranosyl-(1→6)-β-d-glucopyranoside (7). The neuroprotective activity of 1 - 7 was evaluated on PC12 cells with neurotoxicity induced by amyloid-beta 1 - 42 (Aβ ). Compounds 2 and 3 showed protecting activity against Aβ-induced toxicity in PC12 cells.

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Cytotoxic Iridoids from the Roots of Patrinia scabra

Cited by 41 publications

References 18 publications

Cytotoxic and Anti-inflammatory Terpenoids from the Whole Plant of Vaccinium emarginatum

Cytotoxic and Anti-inflammatory Terpenoids from the Whole Plant of Vaccinium emarginatum

Apoptosis and Caspase 3 Pathway Role on Anti-Proliferative Effects of Scrophulariaoxy Sepala Methanolic Extract on Caco-2 Cells

New Thymoquinol Glycosides and Neuroprotective Dibenzocyclooctane Lignans from the Rattan Stems of Schisandra chinensis

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