A New Dicoumarinyl Ether from the Roots of  Stellera chamaejasme L

Li, Jie; Shen, Quan; Bao, Chen-Hao; Chen, Li-Ting; Li, Xiangrong

doi:10.3390/molecules19021603

Cited by 13 publications

(5 citation statements)

References 13 publications

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“…Its roots are commonly known as ‘Ruixianglang du’ in Chinese, and have been used in China as a traditional Chinese medicine for the treatment of scabies, tinea, stubborn skin ulcers, chronic tracheitis, cancer and tuberculosis (Xu, Qin, Li, & Xu, ; Zhang et al, ; Pan et al, ). Previous phytochemical studies of S. chamaejasme L. have shown that it contains various kinds of chemical components, including diterpene, lignans, coumarins, phenylpropanoid, flavonoids and volatile oil (Li, Shen, Bao, Chen, & Li, ; Yan et al, ; Zhang et al, ). Modern studies have suggested that flavonoids from S. chamaejasme L. are the main components that mostly contribute to the pharmacological efficacy (Liu et al, ; Liu & Zhu, ; Liu, Han, et al, ; Liu, Yang, et al, ), such as anti‐cancer activity (Liu et al, ; Li, Zhang, Pang, ZhengChen, & Gan, ), anti‐fatty liver (Wang, Li, Han, Wang, & Li, ) and anti‐HIV (Asada et al, ).…”

Section: Introductionmentioning

confidence: 99%

A UPLC‐MS/MS method for simultaneous determination of five flavonoids from Stellera chamaejasme L. in rat plasma and its application to a pharmacokinetic study

et al. 2018

Biomedical Chromatography

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Stellera chamaejasme L. has been used as a traditional Chinese medicine for the treatment of scabies, tinea, stubborn skin ulcers, chronic tracheitis, cancer and tuberculosis. A sensitive and selective ultra-high liquid chromatography-tandem mass spectrometry (UPLC-MS/MS) method was developed and validated for the simultaneous determination of five flavonoids (stelleranol, chamaechromone, neochamaejasmin A, chamaejasmine and isochamaejasmin) of S. chamaejasme L. in rat plasma. Chromatographic separation was accomplished on an Agilent Poroshell 120 EC-C column (2.1 × 100 mm, 2.7 μm) with gradient elution at a flow rate of 0.4 mL/min and the total analysis time was 7 min. The analytes were detected using multiple reaction monitoring in positive ionization mode. The samples were prepared by liquid-liquid extraction with ethyl acetate. The UPLC-MS/MS method was validated for specificity, linearity, sensitivity, accuracy and precision, recovery, matrix effect and stability. The validated method exhibited good linearity (r ≥ 0.9956), and the lower limits of quantification ranged from 0.51 to 0.64 ng/mL for five flavonoids. The intra- and inter-day precision were both <10.2%, and the accuracy ranged from -11.79 to 9.21%. This method was successfully applied to a pharmacokinetic study of five flavonoids in rats after oral administration of ethyl acetate extract of S. chamaejasme L.

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Section: Introductionmentioning

confidence: 99%

A UPLC‐MS/MS method for simultaneous determination of five flavonoids from Stellera chamaejasme L. in rat plasma and its application to a pharmacokinetic study

et al. 2018

Biomedical Chromatography

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“…The 35 known analogues ( 14 – 48 ) were identified as umbelliferone ( 14 ), 7-coumarincarboxaldehyde ( 15 ), isoscopoletin ( 16 ), murralonginal ( 17 ), xanthyletin ( 18 ), nordentatin ( 19 ), 1-hydroxybisabola-2,10-dien-4-one ( 20 ), methyl 3- O -feruloylquinate ( 21 ), 2-( p -hydroxyphenyl)ethyl p -coumarate ( 22 ), 4-hydroxy-3-(3-methyl-2-butenyl)cinnamyl alcohol ( 23 ), murpanicin ( 24 ), coumurrayin ( 25 ), sibiricol ( 26 ), osthol ( 27 ), trans -dehydroosthol ( 28 ), gleinadiene ( 29 ), 1′-isovalerylmurrangatin ( 30 ), 2′- O -ethylmurrangatin ( 31 ), osthenon ( 32 ), sibirinol ( 33 ), 5,7-dimethoxy-8-(3-ethoxy-2-hydroxy-3- methylbutyl)coumarin ( 34 ), cis -osthenon ( 35 ), toddalenone ( 36 ), murrangatin ( 37 ), omphalocarpin ( 38 ), auraptenol ( 39 ), (−)-mexoticin ( 40 ), , murracarpin ( 41 ), (−)-murracarpin ( 42 ), minumicrolin ( 43 ), minumicrolin isovalerate ( 44 ), murrangatin isovalerate ( 45 ), isomurralonginol nicotinate ( 46 ), toddalosin ( 47 ), and cladimarin B ( 48 ) by comparison of their observed and reported spectroscopic data.…”

Section: Resultsmentioning

confidence: 99%

Anti-Inflammatory Prenylated Phenylpropenols and Coumarin Derivatives from Murraya exotica

et al. 2018

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Three new prenylated phenylpropenols, exotiacetals A-C (1-3), 10 new coumarin derivatives, exotimarins A-I (4-13), and 35 known analogues (14-48) were isolated from the roots of Murraya exotica. The absolute configurations of the new compounds were assigned via comparison of their specific rotations, single-crystal X-ray diffraction data, Mosher's method, the ECD exciton coupling method, comparison of experimental and calculated ECD data, and the ECD data of the in situ formed transition metal complexes. Compounds 1-3, which possess an unprecedented hexahydro-1H-isochromen-1-ol system, are presumably biosynthesized from two prenylated p-coumaryl alcohol moieties via Diels-Alder [4+2] cycloaddition and cyclic hemiacetal formation reactions. Compounds 1, 28, 33, and 35 demonstrated inhibition against LPS-induced NO production in BV-2 microglial cells with IC values of 8.6 ± 0.3, 11.8 ± 0.9, 15.5 ± 0.9, and 16.9 ± 1.0 μM, respectively.

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“…This was determined as the HMBC spectrum showed that H-2' and H-6'(δ H 7.11) correlated with C-2 (δ C 81.8), H-2"' and H-6"' (δ H 6.92) correlated with C-2" (δ C 83.5), and H-2""' and H-6""' (δ H 7.01) correlated with C-2"" (δ C 82.8) (Figure 2 Compounds 2-10 (Figure 1) were identified using different spectroscopic techniques and by comparing the resulting data with the data published in the literature. The compounds were identified as daphnoretin methyl ether (2) [27], rutamontine (3) [28], neodaphnoretin (4) [29], acetyl daphnoretin (5) [30], edgeworthin (6) [27], genkwanin (7) [31,32], trans-tiliroside (8) [33], p-Hydroxybenzoic acid (9) [34] and β-sitosterol glucoside (10) [35].…”

Section: Identification Of Compounds 1-10mentioning

confidence: 99%

New Antiproliferative Triflavanone from Thymelaea hirsuta—Isolation, Structure Elucidation and Molecular Docking Studies

et al. 2021

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In this study isolates from Thymelaea hirsuta, a wild plant from the Sinai Peninsula of Egypt, were identified and their selective cytotoxicity levels were evaluated. Phytochemical examination of the ethyl acetate (EtOAc) fraction of the methanolic (MeOH) extract of the plant led to the isolation of a new triflavanone compound (1), in addition to the isolation of nine previously reported compounds. These included five dicoumarinyl ethers found in Thymelaea: daphnoretin methyl ether (2), rutamontine (3), neodaphnoretin (4), acetyldaphnoretin (5), and edgeworthin (6); two flavonoids: genkwanin (7) and trans-tiliroside (8); p-hydroxy benzoic acid (9) and β sitosterol glucoside (10). Eight of the isolated compounds were tested for in vitro cytotoxicity against Vero and HepG2 cell lines using a sulforhodamine-B (SRB) assay. Compounds 1, 2 and 5 exhibited remarkable cytotoxic activities against HepG2 cells, with IC50 values of 8.6, 12.3 and 9.4 μM, respectively, yet these compounds exhibited non-toxic activities against the Vero cells. Additionally, compound 1 further exhibited promising cytotoxic activity against both MCF-7 and HCT-116 cells, with IC50 values of 4.26 and 9.6 μM, respectively. Compound 1 significantly stimulated apoptotic breast cancer cell death, resulting in a 14.97-fold increase and arresting 40.57% of the cell population at the Pre-G1 stage of the cell cycle. Finally, its apoptosis-inducing activity was further validated through activation of BAX and caspase-9, and inhibition of BCL2 levels. In silico molecular docking experiments revealed a good binding mode profile of the isolates towards Ras activation/pathway mitogen-activated protein kinase (Ras/MAPK); a common molecular pathway in the development and progression of liver tumors.

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A New Dicoumarinyl Ether from the Roots of Stellera chamaejasme L

Cited by 13 publications

References 13 publications

A UPLC‐MS/MS method for simultaneous determination of five flavonoids from Stellera chamaejasme L. in rat plasma and its application to a pharmacokinetic study

A UPLC‐MS/MS method for simultaneous determination of five flavonoids from Stellera chamaejasme L. in rat plasma and its application to a pharmacokinetic study

Anti-Inflammatory Prenylated Phenylpropenols and Coumarin Derivatives from Murraya exotica

New Antiproliferative Triflavanone from Thymelaea hirsuta—Isolation, Structure Elucidation and Molecular Docking Studies

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