Constituents of Leaves of Phellodendron japonicum MAXIM. and Their Antioxidant Activity

Chiu, C. J.; Chiu, Chao‐Chen; Niwa, Masayuki; Kitanaka, Susumu; Damu, Amooru G.; Lee, E-Jian; Wu, Tong

doi:10.1248/cpb.53.1118

Cited by 21 publications

(9 citation statements)

References 27 publications

(16 reference statements)

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“…431 New flavanone glycosides are listed in Table 5, which contains information on 23 compounds (502-524). 128,138,139,233,406,[432][433][434][435][436][437][438][439][440] The majority are mono-or disaccharides O-linked at C-7, C-4 0 or both, these being typical patterns of flavanone glycosylation. Less common is glycosylation at 6-OH, as illustrated by the 6-Ob-glucopyranoside of carthamidin (511) isolated from EtOH extracts of the flowers of Carthamus tinctorius (Asteraceae) using high-speed counter-current chromatography.…”

Section: Flavanonesmentioning

confidence: 99%

“…A constituent of the leaves of Eupatorium micranthum (Asteraceae), it co-occurs with its enantiomer, micranthoside, which has the (2R,3R)-configuration.456 Two new glycosides of 8-prenylaromadendrin have been described from species of Phellodendron in the Rutaceae. Phellodensin G (544) is a 7,4 0 -di-O-b-glucopyranoside from the leaves of P. chinense, 457 whereas 545 was obtained from leaves of P. japonicum (Japanese corktree) 233. As an acetyl derivative of phellamurin (8-prenylaromadendrin 7-O-b-glucopyranoside), it is a rare example of an acylated dihydroflavonol glycoside.…”

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confidence: 99%

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Flavonoids and their glycosides, including anthocyanins

2008

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This review describes more than 600 new examples of naturally occurring flavonoids found either as aglycones or glycosides, comprising flavones, flavonols, chalcones, dihydrochalcones, aurones, flavanones, dihydroflavonols, anthocyanidins and anthocyanins. The main topics addressed are source, identification, biological activity, biosynthesis, synthesis, and ecological or chemosystematic significance, and 514 references are cited.

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Section: Flavanonesmentioning

confidence: 99%

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confidence: 99%

Flavonoids and their glycosides, including anthocyanins

2008

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“…The association of cytotoxicity against cancer cell lines and chemical composition showed a clear relationship, since up to 20 compounds were found to be responsible for the cytotoxicity against cancer cell lines of Selaginella species. Only a few of them have been already reported for their cytotoxicity against cancer cell lines, these being hexahydroxybiflavone [52], selaginellin O [33] and P [30], methyl cinnamate [53], seladoeflavone E [20], sinensioside A [54], oleic acid [55,56], chalcone [57], and phellodensin F [58].…”

Section: Discussionmentioning

confidence: 99%

Comparison of Chemical Composition and Biological Activities of Eight Selaginella Species

et al. 2020

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Selaginella P. Beauv. is a group of vascular plants in the family Selaginellaceae Willk., found worldwide and numbering more than 700 species, with some used as foods and medicines. The aim of this paper was to compare methanolic (MeOH) and dichloromethane (DCM) extracts of eight Selaginella species on the basis of their composition and biological activities. Six of these Selaginella species are underinvestigated. Using ultra-high performance liquid chromatography–high-resolution mass spectrometry (UHPLC–HRMS) analysis, we identified a total of 193 compounds among the tested Selaginella species, with flavonoids predominating. MeOH extracts recovered more constituents that were detected, including selaginellins, the occurrence of which is only typical for this plant genus. Of all the tested species, Selaginellaapoda contained the highest number of identified selaginellins. The majority of the compounds were identified in S. apoda, the fewest compounds in Selaginellacupressina. All the tested species demonstrated antioxidant activity using oxygen radical absorption capacity (ORAC) assay, which showed that MeOH extracts had higher antioxidant capacity, with the half maximal effective concentration (EC50) ranging from 12 ± 1 (Selaginellamyosuroides) to 124 ± 2 (Selaginellacupressina) mg/L. The antioxidant capacity was presumed to be correlated with the content of flavonoids, (neo)lignans, and selaginellins. Inhibition of acetylcholinesterase (AChE) was mostly discerned in DCM extracts and was only exhibited in S. myosuroides, S. cupressina, Selaginellabiformis, and S. apoda extracts with the half maximal inhibitory concentration (IC50) in the range of 19 ± 3 to 62 ± 1 mg/L. Substantial cytotoxicity against cancer cell lines was demonstrated by the MeOH extract of S. apoda, where the ratio of the IC50 HEK (human embryonic kidney) to IC50 HepG2 (hepatocellular carcinoma) was 7.9 ± 0.2. MeOH extracts inhibited the production of nitrate oxide and cytokines in a dose-dependent manner. Notably, S. biformis halved the production of NO, tumor necrosis factor (TNF)-α, and interleukin (IL)-6 at the following concentrations: 105 ± 9, 11 ± 1, and 10 ± 1 mg/L, respectively. Our data confirmed that extracts from Selaginella species exhibited cytotoxicity against cancer cell lines and AChE inhibition. The activity observed in S. apoda was the most promising and is worth further exploration.

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“…The free radical scavenging activity of compounds 1 , 4 , 5 , 7 , 8 , 11−18 , and 20 was measured with DPPH • using the method of Chiu et al . [ 15 ]. Briefly, 0.1 mM solution of DPPH • in ethanol was prepared, and sample (20 μL) was added.…”

Section: Methodsmentioning

confidence: 99%

Chemical Constituents and Biological Studies of the Leaves of Grevillea robusta

Chuang

Chan

et al. 2011

Molecules

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Three new compounds: Graviquinone (1), cis-3-hydroxy-5-pentadecylcyclohexanone (2), and methyl 5-ethoxy-2-hydroxycinnamate (3), and thirty-eight known compounds were isolated and identified from the leaves of Grevillea robusta. The structures of these compounds were determined by spectroscopic and chemical transformation methods. Graviquinone (1) showed the strongest cytotoxicity against MCF-7, NCI-H460, and SF-268 cell lines. Methyl 2,5-dihydroxycinnamate (4), graviphane (13), and dehydrograviphane (14) exhibited very potent DPPH scavenging activity compared with α-tocopherol. Methyl 2,5-dihydroxycinnamate (4) and bis-norstriatol (17) demonstrated strong inhibition of L-DOPA oxidation by mushroom tyrosinase compared with kojic acid.

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Constituents of Leaves of Phellodendron japonicum MAXIM. and Their Antioxidant Activity

Cited by 21 publications

References 27 publications

Flavonoids and their glycosides, including anthocyanins

Flavonoids and their glycosides, including anthocyanins

Comparison of Chemical Composition and Biological Activities of Eight Selaginella Species

Chemical Constituents and Biological Studies of the Leaves of Grevillea robusta

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