A lignan from Schizandra chinensis

doi:10.1016/0031-9422(88)83143-1

Phytochemistry

Volume 27, Issue 2, 1988, Pages 569-573

https://doi.org/10.1016/0031-9422(88)83143-1 Get rights and content

Abstract

A new dibenzocyclooctadiene lignan, isoschizandrin was isolated from the fruits of Schizandra chinensis. The structure was elucidated on the basis of the spectral analysis and chemical correlation with schizandrin and (+)− deoxyschizandrin. In experiments using rats, schizandrin and its derivatives, including isoschizandrin, showed inhibitory effects on stress-induced gastric ulceration (p.o.).

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Schisandra chinensis: A comprehensive review on its phytochemicals and biological activities
2021, Arabian Journal of Chemistry
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Different ester groups, such as, angeloyl, tigloyl, acetyl, and benzoyl may exist at the C-6 of the octatomic ring, and ester group linkage are usually β-configuration (Wang et al., 2021). Compounds 112–143 possess a R-biphenyl configuration (Choi et al., 2006; Hu et al., 2014; Ikeya et al., 1978, 1988a,a,b,e; Kim et al., 2015; Kochetkov et al., 1961, 1962a,b; Li et al., 2017; Liu et al., 2020; Nakajima et al., 1983; Pel et al., 2017; Sovová et al., 2007; Taguchi and Ikeya, 1977; Xue et al., 2015), and compounds 144–182 possess a S-biphenyl configuration (Taguchi et al., 1977; Ikeya et al., 1979b, 1979c, 1979d, 1980, 1982a, 1982b; Piao et al., 2005; Šmejkal et al., 2010; Hu et al., 2014; Zhu et al., 2015; Kim et al., 2015; Xue et al., 2015; Yang et al., 2016; Pel et al., 2017; Choi et al., 2006, 2020). Among them, schisandrosides A (1 2 5), B (1 2 4), C(1 7 1) and D (1 7 2) represent the first example of a dibenzocyclooctadiene lignan glycoside (Kim et al., 2015).
Schisandra chinensis (Turcz.) Baill is a climbing plant widely distributed in the northeastern part of China, Korea, and Japan, and used in traditional Chinese herb as a tonic, antitussive, and sedative agent. This review focuses on the phytochemicals, biological activities and analytical methods, in order to promote further studies on the plant. 202 chemical compounds have been isolated and identified from this plant, and the most important are dibenzocyclooctadiene lignans and triterpenoids. The isolated compounds of S. chinensis were shown to possess anti-cancer, anti-oxidant, neuroprotective, hepatoprotective, anti-inflammatory activities and so on. Further studies should be carried on this plant in order to disclose many more active principles and mechanisms of active components.
Structural characterization of birch lignin isolated from a pressurized hot water extraction and mild alkali pulped biorefinery process
2018, Industrial Crops and Products
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Based on the chemical shift of the CH3 it most probably originated from a methoxy group. While the 13C NMR chemical shift of methoxy group in lignin moieties are typically at 56 ppm some uncommon structures, such as the 4-OMe from 5-substituted veratryl units and the 5-OMe from 6-substituted lignans, have been known to have a slightly higher chemical shift (Ikeya et al., 1988). The higher shift of the methoxy group seems to occur when it has substituents on both of its neighboring aromatic carbons.
In this work we have characterized a mild soda pulped birch (betula pendula) lignin after a novel pressurized hot water extraction pilot process. In the process hemicelluloses are first isolated from woods chips with hot water at oxygen-starved conditions, followed by mild alkali pulping at oxygen-starved conditions to remove lignin from the cellulose. Lignin was precipitated, washed and fractionated from the black liquor and characterized by quantitative ¹³C NMR, ¹³C DEPT experiments, ³¹P NMR, 2D HSQC, FTIR, size exclusion chromatography (SEC), elemental analysis, pyrolysis-gas chromatography-mass spectrometry (py-GC–MS), methoxyl group quantification and residual carbohydrate analysis after methanolysis. The structure was compared to a MWL of birch obtained from the same wood chips and the differences were an increase in phenolic hydroxyl groups, carboxylic groups, polydispersity index, and reduction of aliphatic hydroxyl groups. The process resulted in β-O-4 cleavage and condensation of the structure. This lignin is therefore suitable to be used in its polymeric form, rather than for degradation of the structure to small building blocks.
Dibenzocyclooctadiene lignans from Schisandra chinensis and their inhibitory activity on NO production in lipopolysaccharide-activated microglia cells
2014, Phytochemistry
Four dibenzocyclooctadiene lignans, schisanchinins A–D, and 10 known compounds were isolated from the EtOAc extract of fruits of Schisandra chinensis (Turcz.) Baill. Structures of compounds 1–4 were elucidated using a combination of spectroscopic techniques, including MS, UV and IR, NMR (¹H NMR, ¹³C NMR, HMQC, HMBC). The stereochemistry of the chiral centers and the biphenyl configuration were determined using NOESY, as well as analysis of CD spectra. In vitro activity assays showed that 11 of the 14 compounds exhibited inhibitory activity on lipopolysaccharide (LPS)-induced NO release in primary murine BV2 microglia cells.
Compounds from Kadsura angustifolia with anti-HIV activity
2011, Bioorganic and Medicinal Chemistry Letters
Four new cycloartane triterpenoids, angustific acid A (1), angustific acid B (2), angustifodilactone A (3) and angustifodilactone B (4) were isolated from the branches of Kadsura angustifolia together with six known compounds, micranoic acid B (5), nigranoic acid (6), schisandrin (7), schisantherin D (8), interiotherin B (9), schisantherin B (10). Their structures were established on the basis of extensive spectroscopic data analyses and comparison with spectroscopic data reported. Compound 1, characterized by the presence of a C-16/C-17, C-20/C-21 conjugated diene and a C-1/C-7 ester bridge formed in rings A and B, provided a novel structural skeleton for 3,4-secocycloartane triterpenoid derivatives. In addition, the anti-HIV activities of these compounds were determined in infected C8166 cells, and it was found that angustific acid A (1) exhibited the most potent anti-HIV activity with an EC₅₀ value of 6.1 μg/mL and a therapeutic index of more than 32.8.
Simultaneous determination of nine lignans using pressurized liquid extraction and HPLC-DAD in the fruits of Schisandra chinensis
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The pressurized liquid extraction and HPLC-DAD was developed for extraction and determination of bioactive lignans in Schisandra chinensis. The efficient PLE conditions employed methanol as extraction solvent, 125 °C of extraction temperature, 5 min of static extraction time and only one cycle. A rapid HPLC-DAD method was described for simultaneous determination of nine lignans, including schisandrol A, gomisin J, schisandrol B, tigloylgomisin H, angeloylgomisin H, schisandrin A, γ-schisandrin, gomisin N and schisandrin C. The extraction efficiency of PLE was observed to be comparable with reflux and sonication. In addition, the contents of nine lignans in S. chinensis from different regions were analysed by PLE and HPLC-DAD method.
Chemical constituents from the fruits of Schisandra sphenanthera and their cytotoxicity activity
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Citation Excerpt :
Consequently, the structure of compound 1 was determined as erythro-4-(3,4-dimethoxyphenyl)-4-hydroxy-3-methlbutan-2-yl-3,4-dimethoxybenzoate. The known compounds, phydroxy benzaldehyde (2) (Kim et al., 2003), vanillin (3) (Pouységu et al., 2010), coniferaldehyde (4) (Carpinella et al., 2003), arisantetralone A, C (5 6) (Cheng et al., 2009), schizandrin (7) (Ikeya et al., 1988b), gomisin S (8) (Ikeya et al., 1988a), gomisin D (9) (Ikeya et al., 1976), 3′,4′-dimethoxybenzoic acid (3′′,4′′-dimethoxyphenyl)-2-methyl-3-oxobutyl ester (10) (Li et al., 2013), schisanlactone C (11) (Liu and Huang, 1984), lancifodilactone L (12) (Xiao et al., 2006a), 20-hydroxymicrandilactone D (13) (Xiao et al., 2010a), schirubridilactone E (14) (Xiao et al., 2010b), henridilactone A (15) (Li et al., 2004) and micrandilactone F (16) (Li et al., 2005) were identified by comparison of their NMR and MS data with those reported in the literature. All the isolated compounds were tested for their cytotoxicity in Hela, HepG2 and HCT-116 cells (Table 1S).
Schisandra sphenanthera Rehder & E.H. Wilson, Schisandraceae, is well known as a type of traditional medicine for the treatment of hepatitis, diarrhea and insomnia in Asia. It was also reported to have antiviral and anti-HIV activities. Using various chromatographic resins and isolation techniques, a new lignan (1), erythro-4-(3,4-dimethoxyphenyl)-4-hydroxy-3-methylbutan-2yl-3,4-dimethoxybenzoate, along with fifteen known compounds, were isolated from fruits of S. sphenanthera. The structures of the compounds were identified by extensive spectroscopic and spectrometric methods including 1D and 2D NMR and MS data. All the isolated compounds were evaluated for their cytotoxicity activity against Hela, HepG2 and HCT-116 cells. Among them, compound schisanlactone C showed significant cytotoxicity activity.

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: Part 14 of the series 'The Constituents of Schizandra chinensis Baill'; for Part 13 see ref. [1].

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A lignan from Schizandra chinensis

Abstract

Jpn J. Pharmacol.

Yakugaku Zasshi

Chem. Pharm. Bull.