A New Phenolic Glycoside from Chamaecyparis obtusa var. breviramea f. crippsii

Zhang, Yumei; Xu, Jian; Xiao, Lin; Zeng, Guang‐Zhi; Sun, Zhang‐Hua; Tan, Ning‐Hua

doi:10.3390/molecules18011255

Cited by 7 publications

(5 citation statements)

References 21 publications

(17 reference statements)

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“…The methanol extract (6.5 g) yielded taxifolin ( 1 ) [ 8 ], astragalin ( 2 ) [ 9 ], isorhamnetin 3- O -β- d -glucoside ( 3 ) [ 10 ], (−)-catechin ( 4 ) [ 11 ], benzoate glucoside ( 5 ) [ 12 ], benzyl-β- d -glucoside ( 6 ) [ 13 ], benzyl-β- d -rutinoside ( 7 ) [ 14 ], 2-methoxy-phenyl-β- d -glucoside ( 8 ) [ 15 ], 3,4-dimethoxyphenyl-β- d -glucoside ( 9 ) [ 16 ], raspberry ketone ( 10 ) [ 17 ], p-anisic acid ( 11 ) [ 18 ], 4-hydroxybenzoic acid 4- O -β- d -glucoside ( 12 ) [ 19 ], p-coumaric acid ( 13 , 6.0 mg) and its glucoside ( 14 ) [ 20 , 21 ], trans -vaginoside ( 15 ) [ 22 ] and abscisic alcohol glucoside ( 16 ) [ 23 ]. The methanol:water (5:1) extract afforded kaempferol-3- O -β-rutinoside ( 17 ) [ 24 ], kaempferide-3- O -β-rutinoside ( 18 ) [ 25 ], tiliroside ( 19 ) [ 26 ], and syringetin 3- O -β- d -glucoside ( 20 ) [ 27 ] ( Figure 1 ).…”

Section: Resultsmentioning

confidence: 99%

The Occurrence of Flavonoids and Related Compounds in Cedrus brevifolia A. Henry ex Elwes & A. Henry Needles. Inhibitory Potencies on Lipoxygenase, Linoleic Acid Lipid Peroxidation and Antioxidant Activity

Douros

Hadjipavlou‐Litina

Νικολάου

et al. 2017

Plants

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The phytochemical analysis of the polar extracts of Cedrus brevifolia needles yielded 20 compounds, namely from the methanol extract we isolated three flavonoids (1–3), one hydrolysable tannin (4), eleven phenolic derivatives (5–15) and one apocarotenoid (16), while from the methanol: water (5:1) extract we isolated four flavonoids (17–20). Chemical structures of all isolated compounds were determined by 1D, 2D-NMR (1 Dimension, 2 Dimensions Nuclear Magnetic Resonance) and UV-Vis (Ultraviolet-Visible) spectroscopy. Furthermore, the antioxidant potentials and the anti-inflammatory activities of both crude extracts and isolates were evaluated through DPPH radical scavenging capability, linoleic acid lipid peroxidation inhibition, and soybean LOX inhibition assays. This is the first report on the chemical profile of C. brevifolia needles. Catechin was the main compound derived from the methanol extract. According to our results, 4-O-β-d-glucopyranyl trans-p-coumaric acid and taxifolin were the most active ingredients.

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Section: Resultsmentioning

confidence: 99%

The Occurrence of Flavonoids and Related Compounds in Cedrus brevifolia A. Henry ex Elwes & A. Henry Needles. Inhibitory Potencies on Lipoxygenase, Linoleic Acid Lipid Peroxidation and Antioxidant Activity

Douros

Hadjipavlou‐Litina

Νικολάου

et al. 2017

Plants

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“…Moreover, various chemical components isolated from the latter species have exhibited cytotoxic effects towards various cell lines. In particular, quercetin demonstrated activity against BGC-823, Hela, and A549 cell lines [14], while 13-epi-toruolsol showed efficacy against BGC-823 and Hela, and 3-epitriptobenzene B displayed activity against BGC-823, Hela, and A549 cancer cell lines [57].…”

Section: Discussionmentioning

confidence: 99%

“…Recently, species of the family Cupressaceae are considered as a valuable source for various bioactive natural products including EOs [7][8][9][10][11][12]. Various studies have explored the cytotoxic properties of EOs from different species in this family, revealing their potential as effective drugs for treating cancer [12][13][14][15][16][17][18][19]. Chamaecyparis lawsoniana (A. Murray) Parl.…”

Section: Introductionmentioning

confidence: 99%

Chamaecyparis lawsoniana Leaf Essential Oil as a Potential Anticancer Agent: Experimental and Computational Studies

Fikry

Orfali

Elbaramawi

et al. 2023

Plants

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Cancer remains one of the leading causes of death worldwide, affected by several factors including oxidative stress; and although conventional synthetic medicines have been used to treat cancer, they often result in various side effects. Consequently, there is a growing need for newer, safer and more effective alternatives, such as natural plant products. Essential oils (EOs) are one such alternative, offering a wide range of bioactivities, including antibacterial, antiviral, antioxidant, and anticancer properties. Accordingly, the objective of the present study was to investigate the chemical composition, as well as the antioxidant and anticancer properties of the leaf essential oil of Chamaecyparis lawsoniana (CLLEO) belonging to the Cupressaceae family. Totally, 59 constituents were identified by gas chromatography-mass spectrometry (GC-MS) analysis. cis-Abienol, trans-ferruginol, α-cadinol, δ-muurolene and α-pinene were the major components. The in vitro cytotoxicity study against human breast (MCF-7), colon (HCT-116), lung (A-549), hepatocellular (HepG-2) carcinoma cells using MTT assay indicated a promising cytotoxic activity against all the tested cancer cells, particularly HepG-2, with significant selectivity indices. CLLEO exhibited weak antioxidant activity according to the DPPH, ABTS and FRAP assays. In silico docking of these constituents against the epidermal growth factor receptor (EGFR), the myeloid cell leukemia-1 (Mcl-1) and caspase-8 using Molecular Operating Environment (MOE) software demonstrated good binding affinities of the components with the active site of these targets. These findings suggested using CLLEO, or its individual components, as a potentially viable therapeutic option for managing cancerous conditions.

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“…[10,11] Chamaecyparis obtusa is a species of cupressaceae that is native to central Japan and is distributed mostly in Korea, Japan, North America, Taiwan, and the north eastern parts of China. [12,13] The leaves containing cellulose can be hydrolyzed for the production of monosaccharides. To make full use of C. obtusa leaves, some flavonoids in C. obtusa leaves, such as myricetin, quercitrin, and amentoflavone ( Figure 1), are extracted first.…”

Section: Introductionmentioning

confidence: 99%

Effects of β-glucanase-Immobilized Silica on Hydrolysis of Polysaccharides in Chamaecyparis obtusa Residues

Lee

Tang

Zhang

et al. 2014

Journal of Liquid Chromatography & Related Technologies

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Enzymatic hydrolysis, which is one of the steps in the production of bioethanol, is a major process in the degradation of polysaccharides. Enzyme-immobilized technology has been developed because enzymes can be contaminated easily and are difficult to reuse. In this study, b-glucanase was immobilized on silica, and the effects of the enzyme-silica size, time, temperature, and amount of enzyme-silica on the hydrolysis of polysaccharides in the Chamaecyparis obtusa residue were studied. The enzyme-silica size, time range, temperature, and amount of enzyme-silica studied ranged from 10 to 63 mm, 2 to 12 hr, 25 to 45 C, and 0.05 to 0.25 g, respectively. The optimal enzyme-silica size, time range, temperature, and amount of b-glucanase immobilized on enzyme-silica for the hydrolysis of polysaccharides were found to be 10-25 mm silica, 10 hr, 40 C, and 0.15 g, respectively. The enzyme could not be used at temperatures higher than 40 C due to denaturation. Under the optimal conditions, the glucose yield was 12.77 mg=mL.

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A New Phenolic Glycoside from Chamaecyparis obtusa var. breviramea f. crippsii

Cited by 7 publications

References 21 publications

The Occurrence of Flavonoids and Related Compounds in Cedrus brevifolia A. Henry ex Elwes & A. Henry Needles. Inhibitory Potencies on Lipoxygenase, Linoleic Acid Lipid Peroxidation and Antioxidant Activity

The Occurrence of Flavonoids and Related Compounds in Cedrus brevifolia A. Henry ex Elwes & A. Henry Needles. Inhibitory Potencies on Lipoxygenase, Linoleic Acid Lipid Peroxidation and Antioxidant Activity

Chamaecyparis lawsoniana Leaf Essential Oil as a Potential Anticancer Agent: Experimental and Computational Studies

Effects of β-glucanase-Immobilized Silica on Hydrolysis of Polysaccharides in Chamaecyparis obtusa Residues

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