Cytotoxic phenolic compounds from Chionanthus retusus

Kwak, Jong Hwan; Kang, Min Woo; Roh, Jong Hwa; Choi, Sang Un; Zee, Ok Pyo

doi:10.1007/s12272-009-2203-0

Cited by 66 publications

(28 citation statements)

References 16 publications

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“…1 H–NMR (600 MHz, DMSO‐ d 6 ): δ H 5.87 (1H, brs, H‐1), 7.52 (1H, brs, H‐3), 3.85 (1H, dd, J = 9.1, 4.1 Hz, H‐5), 2.62 (1H, dd, J = 14.5, 4.3 Hz, H‐6a), 2.40 (1H, dd, J = 14.5, 9.3 Hz, H‐6b), 5.97 (1H, q, J = 7.0 Hz, H‐8), 1.64 (3H, dd, J = 7.0, 1.5 Hz, 10‐CH 3 ), 3.64 (3H, s, 11‐OCH 3 ), 6.61(1H, d, J = 1.7 Hz, H‐2′′), 6.47(1H, d, J = 8.0, 1.7 Hz, H‐6′′), 6.63 (1H, d, J = 8.0 Hz, H‐5′′), 2.68 (2H, t, J = 14.4, 7.3 Hz, H‐7′′), 4.07 (2H, m, H‐8′′), 4.65 (1H, d, J = 7.8 Hz, H‐1′), 3.08–3.22 (4H, m, H‐2′‐5′), 3.68 (1H, d, J = 11.6 Hz, H‐6′a), 3.46 (1H, dd, J = 11.6, 6.2 Hz, H‐6′b). These data were in agreement with earlier published data for oleuropein (Kwak, Kang, Roh, Choi, & Zee, ).…”

Section: Resultssupporting

confidence: 93%

An HPLC method for simultaneous quantitative determination of seven secoiridoid glucosides separated from the roots of Ilex pubescens

Zhang

Xiong

Zhao

et al. 2017

Biomedical Chromatography

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A simple and specific high-performance liquid chromatographic method has been developed and validated to simultaneously determine seven secoiridoid glucosides for the first time. Three of them were separated from the ethanolic extract of the roots of Ilex pubescens for the first time, namely nuezhenide A, ligusides B and oleonuezhenide. In quantitative analysis, all of the calibration curves showed good linear regression (r > 0.999) within the tested ranges, and the mean recoveries of three different concentrations ranged from 97.6 to 101.2%. The limit of detection and limit of quantification were <4.18 and 11.63 ng mL , respectively. The relative standard deviation for repeatability and the precision of seven analytes were <3.4 and 1.9%, respectively. The established method was successfully applied to simultaneous determination of seven secoiridoid glucosides in 11 batches of samples collected from different habitats in China.

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Section: Resultssupporting

confidence: 93%

An HPLC method for simultaneous quantitative determination of seven secoiridoid glucosides separated from the roots of Ilex pubescens

Zhang

Xiong

Zhao

et al. 2017

Biomedical Chromatography

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“…They include three monoterpene glucosides, (3S,6R)-cis-linalool-3,7-oxide b-D-glucopyranoside (1) (Jiang et al 2001), 3,7-dimethyl-1-octene-3,6,7-triol-6-O-b-D-glucopyranoside (2) (Manns 1995;Yamamoto et al 2008) and betulabuside B (3) (Kim et al 2008;Park et al 2010), three phenolic acid derivatives, chlorogenic acid butyl ester (4) (Osawa et al 2001), protocatechuic acid (8) (Juliao L de S et al 2010) and ethyl gallate (9) (Picerno et al 2011), two phenylpropanoid glucosides, coniferin (5) (Huang et al 2004) and syringin (6) (Kiem et al 2003) and three flavonoids, yuankanin (7) (Ayers et al 2008 (10) and stenopalustroside A (11) (Liu et al 1999). Moreover, a benzyl alcohol glucoside (12) (Seigler et al 2002), four ionol glucosides, (E)-4-[3 00 -(b-D-glucopyranosyloxy)butylidene]-3,5,5-trimethyl-2-cyclohexen-1-one (13) (Khan et al 2003), 3-oxo-a-ionol-9-O-b-D-glucopyranoside (14) (De Tommasi et al 1992;Sueyoshi et al 2006), blumenol C-glucoside (15) (Matsunami et al 2010) and vomifoliol-9-O-b-D-glucopyranoside (16) (De Tommasi et al 1992;Sueyoshi et al 2006), three lignans, phyllyrin (17) (Masataka & Masao 1991;Kwak et al 2009), syringaresinol-4-O-b-D-glucopyranoside (18) (Gohari et al 2011;Jung et al 2004) and lariciresinol-4 00 -O-b-D-glucopyranoside (19) (Tanahashi et al 1995;Shoeb et al 2004) and a biscoumarin giraldoid A (20) (Li et al 2005) were found. Several isolated compounds (1 -4 and 9 -17) are new for the family Thymelaeaceae, and compounds 5 -8 and 18-20 are isolated for the first time from the genus Thymelaea.…”

Section: Resultsmentioning

confidence: 99%

Chemical composition and antioxidant activity of a polar extract ofThymelaea microphyllaCoss. et Dur.

Kerbab

Mekhelfi

Zaiter

et al. 2014

Natural Product Research

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Thymelaea microphylla Coss. et Dur. (Thymelaeaceae) is a rare medicinal plant endemic to Algeria. In order to continue our studies on this species, herein we report the isolation and characterisation of 20 compounds from a hydroalcoholic extract (EtOH-H2O 7:3) of the aerial parts. They include monoterpene glucosides (1-3), phenolic acid derivatives (4, 8 and 9), phenylpropanoid glucosides (5 and 6), flavonoids (7, 10 and 11), a benzyl alcohol glucoside (12), ionol glucosides (13-16), lignans (17-19) and a bis-coumarin (20). All the structures were elucidated by spectroscopic methods including 1D and 2D NMR experiments, as well as ESI-MS analysis. Moreover, the extract of T. microphylla showed a significant and concentration-dependent free radical-scavenging activity in vitro, correlated to the presence of phenolic and chlorogenic acid derivatives (8, 9 and 4).

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“…The canthin-6-one alkaloids have antifungal activity [50, 51] and are cytotoxic against P-388 leukemia [52], MCF-7 breast, and A-549 lung cancer lines [53]. We also identified the coumarin scopoletin, an anti-radical scavenging compound with anti-inflammatory activity [54-56]. We found it to be the most cytotoxic compound against MCF-7 and SK-BR-3 cells.…”

Section: Discussionmentioning

confidence: 99%

Induction of murine embryonic stem cell differentiation by medicinal plant extracts

Reynertson

Charlson

Gudas

2011

Experimental Cell Research

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Epidemiological evidence indicates that diets high in fruits and vegetables provide a measure of cancer chemoprevention due to phytochemical constituents. Natural products are a rich source of cancer chemotherapy drugs, and primarily target rapidly-cycling tumor cells. Increasing evidence indicates that many cancers contain small populations of resistant, stem-like cells that have the capacity to regenerate tumors following chemotherapy and radiation, and have been linked to the initiation of metastases. Our goal is to discover natural product-based clinical or dietary interventions that selectively target cancer stem cells, inducing differentiation. We adapted an alkaline phosphatase (AP) stain to assay plant extracts for the capacity to induce differentiation in embryonic stem (ES) cells. AP is a characteristic marker of undifferentiated ES cells, and this represents a novel approach to screening medicinal plant extracts. Following a survey of approximately 100 fractions obtained from twelve species of ethnomedically utilized plants, we found fractions from three species that induced differentiation, decreasing AP and transcript levels of pluripotency markers (Nanog, Oct-4, Rex-1). These fractions affected proliferation of murine ES, and human embryonal, prostate, and breast carcinoma cells in a dose-dependent manner. Several phytochemical constituents were isolated; the antioxidant phytochemicals ellagic acid and gallic acid were shown to affect viability of cultured breast carcinoma cells.

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Cytotoxic phenolic compounds from Chionanthus retusus

Cited by 66 publications

References 16 publications

An HPLC method for simultaneous quantitative determination of seven secoiridoid glucosides separated from the roots of Ilex pubescens

An HPLC method for simultaneous quantitative determination of seven secoiridoid glucosides separated from the roots of Ilex pubescens

Chemical composition and antioxidant activity of a polar extract ofThymelaea microphyllaCoss. et Dur.

Induction of murine embryonic stem cell differentiation by medicinal plant extracts

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