Tetrahydroberberine, a pharmacologically active naturally occurring alkaloid

Pingali, Subramanya R. K.; Donahue, James P.; Payton‐Stewart, Florastina

doi:10.1107/s2053229615004076

Cited by 22 publications

(9 citation statements)

References 15 publications

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“…The geometrical characteristics of this structure suggest that the C22-H22BÁ Á ÁO2 i contacts possess a weak hydrogen-bonding characteristic. All of the other close contacts between the H and O atoms of the methoxy groups have C-HÁ Á ÁO angles greater than 100 , which implies that these contacts also possess some hydrogenbonding characteristics (Pingali et al, 2015). However, these contacts are weaker than C22-H22BÁ Á ÁO2 i because a carbonyl O atom is a better hydrogen-bond acceptor than a methoxy O atom.…”

Section: Figurementioning

confidence: 99%

Nobiletin: a citrus flavonoid displaying potent physiological activity

Noguchi

Atsumi

Iwao

et al. 2016

Acta Crystallogr C Struct Chem

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Nobiletin [systematic name: 2-(3,4-dimethoxyphenyl)-5,6,7,8-tetramethoxy-4H-chromen-4-one; C21H22O8] is a flavonoid found in citrus peels, and has been reported to show a wide range of physiological properties, including anti-inflammatory, anticancer and antidementia activities. We have solved the crystal structure of nobiletin, which revealed that the chromene and arene rings of its flavone moiety, as well as the two methoxy groups bound to its arene ring, were coplanar. In contrast, the C atoms of the four methoxy groups bound to the chromene ring are out of the plane, making the molecule conformationally chiral. A comparison of the crystal structures of nobiletin revealed that it could adopt a variety of different conformations through rotation of the covalent bond between the chromene and arene rings, and the orientations of methoxy groups bound to the chromene ring.

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Section: Figurementioning

confidence: 99%

Nobiletin: a citrus flavonoid displaying potent physiological activity

Noguchi

Atsumi

Iwao

et al. 2016

Acta Crystallogr C Struct Chem

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“…Alkaloids and organic acids are two major chemical portions of AEOV. Naturally occurring alkaloids widely isolated from numerous common medicinal plants, have long been known to exert a broad spectrum of pharmacological properties, including anti-endotoxic, antiviral, anticancer, antinociceptive, anti-inflammatory, antimalarial, and antipyretic effects [ 19 , 20 ]. Protocatechuic acid and caffeic acid are the major organic acid constituents isolated from AEOV.…”

Section: Discussionmentioning

confidence: 99%

Hepatoprotective Effect of Aqueous Extract from the Seeds of Orychophragmus violaceus against Liver Injury in Mice and HepG2 Cells

Huo

Liu

Gao

et al. 2017

IJMS

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Orychophragmus violaceus (O. violaceus) is a kind of edible wild herb in north China and its seeds have medical potential, however, the effect of O. violaceus seeds on liver injury and the mechanism of action remains poorly understood. Thus, the purpose of the present study is to investigate the effect of O. violaceus seeds on liver injury and further explore the molecular mechanism of the beneficial effects using aqueous extract from the seeds of O. violaceus (AEOV). Mice were orally administrated with saline, AEOV, and biphenyldicarboxylate for 4 days, and were then injected subcutaneously with 0.1% carbon tetrachloride (CCl4) dissolved in corn oil. Sixteen hours later, mice were sacrificed and blood samples were collected. Then, the serum was separated and used for biochemical assay. Livers were excised and were routinely processed for histological examinations. Enzyme activities and protein levels in liver homogenates were detected using commercial kits or by western blot analysis. Additionally, the hepatoprotective effect of AEOV in vitro was evaluated using epigoitrin, the major alkaloid compound isolated from AEOV. We found that AEOV attenuated liver injury induced by CCl4 as evidenced by decreased levels of alanine aminotransferase (ALT) and aminotransferase (AST) in serum, improvement of liver histopathological changes, and substantial attenuation of oxidative stress and inflammation via regulation of nuclear factor-erythroid 2-related factor-2 (Nrf2) and nuclear factor κB (NFκB) pathways. These effects of AEOV were comparable to that of biphenyldicarboxylate which was commonly used as a hepatoprotective reference. Moreover, pretreatment of HepG2 cells with epigoitrin improved cell viability, decreased lactate dehydrogenase (LDH) and malondialdehyde (MDA) levels, increased superoxide dismutase (SOD) and glutathione peroxidase (GSH-Px) activity, attenuated the NFκB pathway, and elevated the Nrf2 pathway after exposure to H2O2. These results suggest that AEOV could effectively prevent CCl4-induced liver injury in mice via regulating the Nrf2 and NFκB pathways, and reveal the cytoprotective effects of epigoitrin against H2O2-induced oxidative stress in HepG2 cells.

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“…[1,2] Amongt hese polyheterocycles,b erberine (BB, Figure1)a nd its derivatives are of considerable interestb ecause they possess severalt herapeutic properties. [3][4][5][6][7] Berberine is an isoquinoline alkaloid extracted fromr hizomes and roots of several species of plants, such as Coptis (Coptis chinensis and Coptis japonica), Hydrastis and Berberis (Berberis vulgaris and Berberis croatica). These plants have long been used in traditional Chinese, Ayurvedic and Native Americanm edicine for the treatment of different maladies.…”

Section: Introductionmentioning

confidence: 99%

“…[6] Te trahydroberberine (THB, Figure 1), the fully reduced form of BB, is an aturallyo ccurring alkaloid mainly extracted from Corydalisa mbigua known to have significant pharmacological properties that differ from that of the parentB B. [7] In fact, THB shows little antiproliferative activity towards everall ines of cells, but instead it is effective as an antioxidant [8a] and aC a 2 + channel blocker. [8b] Additionally,T HB has also been observed to block ATP-sensitive K + ion channels involved in the pathogenesis of Parkinson's disease, [8c] indicating an important neuroprotectiverole.…”

Section: Introductionmentioning

confidence: 99%

“…Fragment A can be correlatedt ot he azo-ene system of 1,2-diaza-1,3-dienes (DDs), that have represented the main field of our research for the past several years. [11] The fragment B can be related to the di-hydro-pyridine D,w hichi sp art of the structure of 7,8-dihydroberberine (7,, the partially reduced form of BB ( Figure 1, Scheme 1). In fact, 7,8-DHB contains an enamine moiety that could reactwith the azo-enesystem of DDs, as shown in previous reports.…”

Section: Introductionmentioning

confidence: 99%

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Heteroring‐Annulated Pyrrolino‐Tetrahydroberberine Analogues

et al. 2017

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Af acile method for the synthesis of pyrrolino-tetrahydroberberine derivatives startingf rom 1,2-diaza-1,3dienes and dihydroberberines is reported. The synthesis is ac ascade reactioni nvolving aM ichael-typea ddition of the enaminem oiety of dihydroberberine to an azo-enes ystem, followed by nitrogen cyclization on the resulting iminium ion.[a] G.Supporting information and the ORCID identification number(s) for the author(s) of this article can be found under http://dx.Figure 2. Pyrrolo[2,3-b]pyridine core of chaetominines and kapakahines and of isoschizogaminea nd isoschizogaline. Scheme1.Retrosynthetic analysis of pyrrolo[2,3-b]pyridine systems.Scheme2.Synthesis of 7,8-dihydroberberine 2 [14] and of 8-acetonyl-7,8-dihydroberberine 3, [15] starting from commercial berberinechloride 1.Scheme3.Proposed mechanism for the synthesis of fused pyrrolino-THBderivative 6e.2 96 3 72[a] Isolated yields of fused pyrrolino-tetrahydroberberine derivatives 6.[ b] All of the reactionstook placewithin 0.25 h.

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Tetrahydroberberine, a pharmacologically active naturally occurring alkaloid

Cited by 22 publications

References 15 publications

Nobiletin: a citrus flavonoid displaying potent physiological activity

Nobiletin: a citrus flavonoid displaying potent physiological activity

Hepatoprotective Effect of Aqueous Extract from the Seeds of Orychophragmus violaceus against Liver Injury in Mice and HepG2 Cells

Heteroring‐Annulated Pyrrolino‐Tetrahydroberberine Analogues

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