Dibenzo[a,c]cyclooctadiene lignans of the genus Schisandra: importance, isolation and determination

Opletal, Lubomı́r; Sovová, Helena; Bártlová, Milena

doi:10.1016/j.jchromb.2004.07.040

Cited by 77 publications

(17 citation statements)

References 59 publications

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“…These compounds have been reported to have antioxidant and anti-proliferation properties [29], [30]. Deoxyschizandrin, Syringin, taxifoliol, parthenolide and gramine have been shown to have a wide range of biological activates including anti-viral, anti-inflammatory and anti-cancer properties [31]–[38]. These natural products have been long used in traditional Chinese medicine.…”

Section: Discussionmentioning

confidence: 99%

Identification of Adiponectin Receptor Agonist Utilizing a Fluorescence Polarization Based High Throughput Assay

et al. 2013

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Adiponectin, the adipose-derived hormone, plays an important role in the suppression of metabolic disorders that can result in type 2 diabetes, obesity, and atherosclerosis. It has been shown that up-regulation of adiponectin or adiponectin receptor has a number of therapeutic benefits. Given that it is hard to convert the full size adiponectin protein into a viable drug, adiponectin receptor agonists could be designed or identified using high-throughput screening. Here, we report on the development of a two-step screening process to identify adiponectin agonists. First step, we developed a high throughput screening assay based on fluorescence polarization to identify adiponectin ligands. The fluorescence polarization assay reported here could be adapted to screening against larger small molecular compound libraries. A natural product library containing 10,000 compounds was screened and 9 hits were selected for validation. These compounds have been taken for the second-step in vitro tests to confirm their agonistic activity. The most active adiponectin receptor 1 agonists are matairesinol, arctiin, (-)-arctigenin and gramine. The most active adiponectin receptor 2 agonists are parthenolide, taxifoliol, deoxyschizandrin, and syringin. These compounds may be useful drug candidates for hypoadiponectin related diseases.

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Section: Discussionmentioning

confidence: 99%

Identification of Adiponectin Receptor Agonist Utilizing a Fluorescence Polarization Based High Throughput Assay

et al. 2013

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“…The Schisandra fruits are characterized by a rich, still not fully known, chemical composition. The most important constituents are lignans (Umezawa 2003;Opletal et al 2004). There are different classifications of these compounds.…”

Section: Classification Of Lignans In the Plant Kingdommentioning

confidence: 99%

“…Schisandra chinensis fruit extracts are used in medicine because of their valuable biological properties: hepatoprotective, adaptogenic and ergogenic, anti-cancer, anti-inflammatory, antiulcer, antioxidative and detoxifying (Szopa et al 2017a). These activities are mainly driven by dibenzocyclooctadiene lignans, which are called, even in the professional scientific literature, 'Schisandra chinensis lignans' due to their complex, and at the same time unique, structure (they are present mainly in the fruit, from 7.2 to 19.2% DW) (Opletal et al 2004;World Health Organization 2007;Szopa et al 2017a) (Table 1). The main source of this raw material in Europe and America are imports from Southeast Asia, primarily from China.…”

Section: Introductionmentioning

confidence: 99%

Phytochemical studies and biological activity of three Chinese Schisandra species (Schisandra sphenanthera, Schisandra henryi and Schisandra rubriflora): current findings and future applications

Szopa

Barnaś

2018

Phytochem Rev

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Schisandra chinensis (Chinese magnolia vine) is the best-known representative of the genus Schisandra, widely used in the official East-Asian, North American and European medicine. The article recalls the healing value of this species and, above all, presents the current state of knowledge on the chemical composition and biological activity of three other species of the Schisandra genus: Schisandra sphenanthera, Schisandra henryi and Schisandra rubriflora. In addition to dibenzocyclooctadiene lignans (the so-called 'Schisandra chinensis lignans'), they also contain other groups of lignans (e.g. 4aryltetralin, aryltetralone, tetrahydrofuran and butane-type lignans) as the main compounds responsible for biological activity. The lignans are accompanied by other groups of compounds, including triterpenoids and nortriterpenoids. A review of biological studies, e.g. of empirically confirmed hepatoprotective, cytotoxic and anti-HIV-1 activities, proves that these species have a high therapeutic potential and may constitute a new East-Asian proposition for European medicine. The article also draws attention to the possibility of using the biosynthetic potential of the biomass from in vitro cultures of the described species and biotechnological solutions as an alternative to plant raw materials.

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“…[2] These cyclooctanoid species include many terpenoids, as well as several lignans and pigments. [3,4] Target molecules containing eight-membered heterocycles have attracted extensive synthetic interest in recent years due to their presence in a large number of naturally occurring molecules, such as balasubramide (1), [5] serotobenine (2; Figure 1), [6] the lundurine class of molecules, [7] and 7-aza-(-)steganacin. [8] Eight-membered heterocycles are also found in many biologically active compounds.…”

Section: Introductionmentioning

confidence: 99%

Diastereoselective Synthesis of Isoindole‐Fused Diazacyclooctaindenones from Spirochromenes through Domino Reactions with Aliphatic 1,2‐Diamines

Pathak¹,

Pramanik²

2013

Eur J Org Chem

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A diastereoselective synthesis of isoindole‐fused diazacyclooctaindenone derivatives has been accomplished through tandem ring‐opening and ring‐closing of spirochromene derivatives triggered by different aliphatic 1,2‐diamines. When ethanolic solutions of spirochromenes are refluxed with different aliphatic 1,2‐diamines such as 1,2‐ethylenediamine, (±)‐1,2‐propylenediamine and (±)‐trans‐1,2‐cyclohexanediamine, the isoindole‐fused eight‐membered heterocycles are formed in moderate to high yields within 5–15 min.

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Dibenzo[a,c]cyclooctadiene lignans of the genus Schisandra: importance, isolation and determination

Cited by 77 publications

References 59 publications

Identification of Adiponectin Receptor Agonist Utilizing a Fluorescence Polarization Based High Throughput Assay

Identification of Adiponectin Receptor Agonist Utilizing a Fluorescence Polarization Based High Throughput Assay

Phytochemical studies and biological activity of three Chinese Schisandra species (Schisandra sphenanthera, Schisandra henryi and Schisandra rubriflora): current findings and future applications

Diastereoselective Synthesis of Isoindole‐Fused Diazacyclooctaindenones from Spirochromenes through Domino Reactions with Aliphatic 1,2‐Diamines

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Dibenzo[a,c]cyclooctadiene lignans of the genus Schisandra: importance, isolation and determination

Cited by 77 publications

References 59 publications

Identification of Adiponectin Receptor Agonist Utilizing a Fluorescence Polarization Based High Throughput Assay

Identification of Adiponectin Receptor Agonist Utilizing a Fluorescence Polarization Based High Throughput Assay

Phytochemical studies and biological activity of three Chinese Schisandra species (Schisandra sphenanthera, Schisandra henryi and Schisandra rubriflora): current findings and future applications

Diastereoselective Synthesis of Isoindole‐Fused Diazacyclooctaindenones from Spiro­chromenes through Domino Reactions with Aliphatic 1,2‐Diamines

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Diastereoselective Synthesis of Isoindole‐Fused Diazacyclooctaindenones from Spirochromenes through Domino Reactions with Aliphatic 1,2‐Diamines