Topoisomerase II inhibitors from the roots of Stellera chamaejasme L.

Liu, Liping; Han, Kun; Chen, Wei; Zhang, Yingying; Tong, Linjiang; Peng, Ting; Xie, Hua; Ding, Jian; Wang, Hongbing

doi:10.1016/j.bmc.2014.05.042

Cited by 32 publications

(16 citation statements)

References 25 publications

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“…Known compounds were identified as daphnane ester 1, 16 excoecariatoxin (2), 17,18 yuanhuacine (5), 19 2′-hydroxy-3′-methoxyflavone (6), 20 2′,3′- dimethoxyflavone (7), 21 6-hydroxy-2′,3′-dimethoxyflavone (8), 22 7,7′-dimethoxy-6,6′-biscoumarin (9), 23 lasiocephalin (10), 23 daphnauranol A (13), 24 and chamaejasmone D (14). 25 (Table 1) were virtually identical to those of yuanhuacine (5). The only difference was in the absence of resonances at δ H 1.30−1.28 and δ C 31.4 and 22.6 (C-8′ and C-9′ in 5) in the spectra of 3.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

hERG Channel Inhibitory Daphnane Diterpenoid Orthoesters and Polycephalones A and B with Unprecedented Skeletons from Gnidia polycephala

Mieri¹,

Du²,

Neuburger³

et al. 2015

J. Nat. Prod.

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The hERG channel is an important antitarget in safety pharmacology. Several drugs have been withdrawn from the market or received severe usage restrictions because of hERG-related cardiotoxicity. In a screening of medicinal plants for hERG channel inhibition using a two-microelectrode voltage clamp assay with Xenopus laevis oocytes, a dichloromethane extract of the roots of Gnidia polycephala reduced the peak tail hERG current by 58.8 ± 13.4% (n = 3) at a concentration of 100 μg/mL. By means of HPLC-based activity profiling daphnane-type diterpenoid orthoesters (DDOs) 1, 4, and 5 were identified as the active compounds [55.4 ± 7.0% (n = 4), 42.5 ± 16.0% (n = 3), and 51.3 ± 9.4% (n = 4), respectively, at 100 μM]. In a detailed phytochemical profiling of the active extract, 16 compounds were isolated and characterized, including two 2-phenylpyranones (15 and 16) with an unprecedented tetrahydro-4H-5,8-epoxypyrano[2,3-d]oxepin-4-one skeleton, two new DDOs (3 and 4), two new guaiane sesquiterpenoids (11 and 12), and 10 known compounds (1, 2, 5-10, 13, and 14). Structure elucidation was achieved by extensive spectroscopic analysis (1D and 2D NMR, HRMS, and electronic circular dichroism), computational methods, and X-ray crystallography.

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Section: ■ Results and Discussionmentioning

confidence: 99%

hERG Channel Inhibitory Daphnane Diterpenoid Orthoesters and Polycephalones A and B with Unprecedented Skeletons from Gnidia polycephala

Mieri¹,

Du²,

Neuburger³

et al. 2015

J. Nat. Prod.

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“…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%

“…. Modern studies have suggested that flavonoids from S. chamaejasme L. are the main components that mostly contribute to the pharmacological efficacy Liu, Han, et al, 2014;Liu, Yang, et al, 2014), such as anti-cancer activity Li, Zhang, Pang, ZhengChen, & Gan, 2014), anti-fatty liver (Wang, Li, Han, Wang, & Li, 2015) and anti-HIV (Asada et al, 2013). effects.…”

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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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“…6 Previous chemical investigations on the roots of this plant have led to the isolation of diverse secondary metabolites, including highly functionalized daphnane diterpenoids, 7–9 tigliane diterpenoids, 10 lignans, 11,12 biflavonoids, 13–16 coumarins, 17,18 and sesquiterpenoids. 11,19 In particular, certain daphnane and tigliane diterpenoids have shown extremely potent anti-HIV activity at low nanomolar concentrations with relatively low cytotoxicity. 7,10 However, these compounds are very difficult to synthesize because of their complex structure.…”

mentioning

confidence: 99%

Stelleralides D–J and Anti-HIV Daphnane Diterpenes from Stellera chamaejasme

Yan

Chen

et al. 2015

J. Nat. Prod.

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Bioassay-guided fractionation of a petroleum ether extract of the roots of Stellera chamaejasme led to the isolation of seven new (stelleralides D–J, 1–7) and 12 known (8–19) daphnane diterpenoids. The structures and relative configurations of 1–7 were established on the basis of extensive spectroscopic analysis, including HRESIMS and comprehensive NMR techniques. All isolates were evaluated for anti-HIV activity in MT4 cells. All compounds tested, except 2, showed anti-HIV activity, and, especially, five 1α-alkyldaphnane diterpenoids (3, 4, 5, 10, and 11) exhibited extremely potent anti-HIV activity, with EC50 values of 0.06–1.1 nM and selectivity index values of more than 10 000.

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Topoisomerase II inhibitors from the roots of Stellera chamaejasme L.

Cited by 32 publications

References 25 publications

hERG Channel Inhibitory Daphnane Diterpenoid Orthoesters and Polycephalones A and B with Unprecedented Skeletons from Gnidia polycephala

hERG Channel Inhibitory Daphnane Diterpenoid Orthoesters and Polycephalones A and B with Unprecedented Skeletons from Gnidia polycephala

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

Stelleralides D–J and Anti-HIV Daphnane Diterpenes from Stellera chamaejasme

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