Total Synthesis of (−)-Corilagin

Yamada, Hidetoshi; Nagao, Kohei; Dokei, Kazutoyo; Kasai, Yusuke; Michihata, Naoki

doi:10.1021/ja803111z

Cited by 86 publications

(96 citation statements)

References 23 publications

(23 reference statements)

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“…Although corilagin can be synthesized by chemicals, the actual output for synthesis is limited [11]. Thereby some novel techniques were used to purify corilagin from plants [45].…”

Section: Discussionmentioning

confidence: 99%

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Anti-inflammatory and anti-oxidative effects of corilagin in a rat model of acute cholestasis

Jin

Cheng

Tao³

et al. 2013

BMC Gastroenterol

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BackgroundNowadays, treatments for cholestasis remain largely nonspecific and often ineffective. Recent studies showed that inflammatory injuries and oxidative stress occur in the liver with cholestasis. In this study, we would use corilagin to treat the animal model of acute cholestasis in order to define the activity to interfere with inflammation-related and oxidative stress pathway in cholestatic pathogenesis.MethodsRats were administrated with alpha-naphthylisothiocyanate to establish model of cholestasis and divided into corilagin, ursodeoxycholic acid, dexamethasone, model and normal groups with treatment of related agent. At 24h, 48h and 72h time points after administration, living condition, serum markers of liver damage, pathological changes of hepatic tissue, nuclear factor (NF)-kappaB, myeloperoxidase (MPO), malondialdehyde (MDA), superoxide dismutase (SOD) and nitric oxide (NO) were examined and observed.ResultsCompared to model group, corilagin had remarkable effect on living condition, pathological manifestation of liver tissue, total bilirubin, direct bilirubin, (P<0.01), but no effect on alanine aminotransferase (ALT) and aspartate aminotransferase (AST). With corilagin intervention, levels of MPO, MDA and translocation of NF-κB were notably decreased, and levels of SOD and NO were markedly increased (P<0.05 or P<0.01).ConclusionsIt is shown that corilagin is a potential component to relieve cholestasis through inflammation-related and oxidation-related pathway.

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“…Although corilagin can be synthesized by chemicals, the actual output for synthesis is limited [11]. Thereby some novel techniques were used to purify corilagin from plants [45].…”

Section: Discussionmentioning

confidence: 99%

“…Corilagin, a member of the tannin family with its molecular formula C 27 H 22 O 18 [11], has been discovered in many medicinal plants such as Phyllanthus speices etc. [12].…”

Section: Introductionmentioning

confidence: 99%

Anti-inflammatory and anti-oxidative effects of corilagin in a rat model of acute cholestasis

Jin

Cheng

Tao³

et al. 2013

BMC Gastroenterol

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“…For the exhaustive synthesis of ellagitannins, one of the most fundamental tasks is the formation of the chiral HHDP group, a C-C digallate, which has been achieved through several procedures [15][16][17][18] . The second and most impactful task would be the establishment of a methodology for synthesizing C-O digallates because their structure is the primary cause of structural diversity in this family.…”

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confidence: 99%

A unified strategy for the synthesis of highly oxygenated diaryl ethers featured in ellagitannins

et al. 2014

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Ellagitannins are a family of polyphenols containing more than 1,000 natural products. Nearly 40% of these compounds contain a highly oxygenated diaryl ether that is one of the most critical elements to their structural diversity. Here, we report a unified strategy for the synthesis of highly oxygenated diaryl ethers featured in ellagitannins. The strategy involves oxa-Michael addition of phenols to an orthoquinone building block, with subsequent elimination and reductive aromatization. The design of the building block-a halogenated orthoquinone monoketal of gallal-reduces the usual instability of orthoquinone and controls addition/elimination. Reductive aromatization is achieved with perfect chemoselectivity in the presence of other reducible functional groups. This strategy enables the synthesis of different diaryl ethers. The first total synthesis of a natural ellagitannin bearing a diaryl ethers is performed to demonstrate that the strategy increases the number of synthetically available ellagitannins.

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“…(8), and its molecular formula is C 27H2 P l8 (9). Literature shows that corilagin has multifunctions such as hepatoprotective, antioxidative, anti-inflammatory effects.…”

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confidence: 99%

Activity of Corilagin on Post-Parasiticide Liver Fibrosis in Schistosomiasis Animal Model

Huang

Zhang

Jin

et al. 2013

Int J Immunopathol Pharmacol

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The first two authors contributed equally to this study This study investigates the effects and possible molecular mechanisms of corilagin extraction on prevention of Schistosoma japonicum ova-induced granulomas and liver fibrosis. As a result, under a light microscope, when compared to a model group, the corilagin group showed smaller granulomas, less liver cell denaturation and less inOammatory cell infiltration, and the connective tissues were significantly decreased. By Masson staining, the liver sections from the corilagin group showed less collagen distributed around granulomas, decreased liver fibrosis in the portal tracts and less formed interlobular tissue. The expression of hydroxyproline, IL-13 in liver and GATA3 in spleen in the model group was significantly higher than that in the normal group (P<0.05 or 0.01), while the level of hydroxyproline, IL-13 and GATA3 in the corilagin group were significantly lower than that in the model group (P<0.05). In conclusion, corilagin extraction can decrease the level of Th2-associated profibrotic cytokine IL-13, and down-regulate the transcription of GATA3 mRNA in spleen cells, which alleviate the hepatic fibrosis caused by egg granuloma in Schistosoma japonicum infection.Schistosomiasis is a chronic, sometimes fatal, disease with serious symptoms including liver fibrosis, ascites and splenomegaly. The main pathogen is the helminth parasite Schistosoma and the adult

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Total Synthesis of (−)-Corilagin

Cited by 86 publications

References 23 publications

Anti-inflammatory and anti-oxidative effects of corilagin in a rat model of acute cholestasis

Anti-inflammatory and anti-oxidative effects of corilagin in a rat model of acute cholestasis

A unified strategy for the synthesis of highly oxygenated diaryl ethers featured in ellagitannins

Activity of Corilagin on Post-Parasiticide Liver Fibrosis in Schistosomiasis Animal Model

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