2086-83-1Relevant articles and documents
(S)-TETRAHYDROPROTOBERINE OXIDASE THE FINAL ENZYME IN PROTOBERBERINE BIOSYNTHESIS
Amann, M.,Nagakura, N.,Zenk, M. H.
, p. 953 - 954 (1984)
A new flavin enzyme has been discovered which in the presence of oxygen catalyzes the oxidation of (S)-tetrahydroprotoberberines to protoberberines via the intermediate 7,14-dehydroberberinium.
Facile synthesis of tetrahydroprotoberberine and protoberberine alkaloids from protopines and study on their antibacterial activities
Cheng, Pi,Wang, Bin,Liu, Xiubin,Liu, Wei,Kang, Weisong,Zhou, Jie,Zeng, Jianguo
, p. 413 - 419 (2014)
A series of isoquinoline alkaloids including tetrahydroprotoberberines, N-methyl tetrahydroprotoberberines and protoberberines were facile synthesised with protopines as the starting material. All compounds were evaluated for their antibacterial activities against four pathogenic bacteria Escherichia coli, Staphyloccocus aureus, Staphylococcus gallinarum and Salmonella choleraesuis. Experimental results indicated that protoberberines were the most active compounds to the target bacteria among the tested alkaloids. It was suggested that planar molecule with high aromatisation level (e.g. coptisine 5 and berberine 6) or a positive charge of the molecules (e.g. N-methyl tetrahydroprotoberberines 11 and 12) had a positive influence on the antibacterial effects.
Method for synthesizing benzophenanthridine and protoberberine alkaloids through modular diversity regulation and control
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, (2021/05/29)
The invention discloses a method for synthesizing benzophenanthridine and protoberberine alkaloids through modular diversity regulation and control. The method comprises the following steps: improving a substituent group of a high-iodine salt leaving group, generating pyridine alkyne under the action of relatively mild potassium tert-butoxide, and carrying out [4 + 2] cycloaddition reaction on the pyridine alkyne and diene to obtain polysubstituted isoquinoline ring precursor compounds. Ring opening and aromatization of the isoquinoline ring precursor are realized by developing a novel iridium-catalyzed cross-coupling method, polysubstituted isoquinoline ring compounds with connecting capacity are efficiently synthesized, and then the polysubstituted isoquinoline ring compounds are coupled with a high-activity polysubstituted cyclic boric acid to obtain 3-aryl isoquinoline high-grade intermediates. Through application of two different chemical principles, regulation and control of the 3-aryl isoquinoline high-grade intermediates are realized, and benzophenanthridine and protoberberine alkaloids are modularly, diversely and efficiently synthesized.
A General, Concise Strategy that Enables Collective Total Syntheses of over 50 Protoberberine and Five Aporhoeadane Alkaloids within Four to Eight Steps
Zhou, Shiqiang,Tong, Rongbiao
, p. 7084 - 7089 (2016/05/19)
A concise, catalytic, and general strategy that allowed efficient total syntheses of 22 natural 13-methylprotoberberines within four steps for each molecule is reported. This synthesis represents the most efficient and shortest route to date, featuring three catalytic processes: CuI-catalyzed redox-A3 reaction, Pd-catalyzed reductive carbocyclization, and PtO2-catalyzed hydrogenation. Importantly, this new strategy to the tetracyclic framework has also been applied to the collective concise syntheses of >30 natural protoberberines (without 13-methyl group) and five aporhoeadane alkaloids.
Berberine derivatives and their use
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Paragraph 0024; 0025; 0026; 0028, (2019/02/02)
The invention provides a compound shown in the formula (I) or a salt thereof and use of the compound and the salt, and R is C10-C18 alkyl or benzyl. The growth inhibition, growth inhibition, and invasion inhibition of the compound and the salt on malignant glioma cells are surprisingly better than that of a berberine derivative and berberine self. In addition, the compounds can be well positioned to mitochondria, so that the compounds can be used as a mitochondrial targeting drug delivery system.
Characterization of a flavoprotein oxidase from opium poppy catalyzing the final steps in sanguinarine and papaverine biosynthesis
Hagel, Jillian M.,Beaudoin, Guillaume A. W.,Fossati, Elena,Ekins, Andrew,Martin, Vincent J. J.,Facchini, Peter J.
, p. 42972 - 42983 (2013/03/13)
Benzylisoquinoline alkaloids are a diverse class of plant specialized metabolites that includes the analgesic morphine, the antimicrobials sanguinarine and berberine, and the vasodilator papaverine. The two-electron oxidation of dihydrosanguinarine catalyzed by dihydrobenzophenanthridine oxidase (DBOX) is the final step in sanguinarine biosynthesis. The formation of the fully conjugated ring system in sanguinarine is similar to the four-electron oxidations of (S)-canadine to berberine and (S)-tetrahydropapaverine to papaverine. We report the isolation and functional characterization of an opium poppy (Papaver somniferum) cDNA encoding DBOX, a flavoprotein oxidase with homology to ( S)-tetrahydroprotoberberine oxidase and the berberine bridge enzyme. A query of translated opium poppy stem transcriptome databases using berberine bridge enzyme yielded several candidate genes, including an (S)-tetrahydroprotoberberine oxidase-like sequence selected for heterologous expression in Pichia pastoris. The recombinant enzyme preferentially catalyzed the oxidation of dihydrosanguinarine to sanguinarine but also converted (RS)-tetrahydropapaverine to papaverine and several protoberberine alkaloids to oxidized forms, including (RS)-canadine to berberine. The Km values of 201 and 146 μM for dihydrosanguinarine and the protoberberine alkaloid (S)-scoulerine, respectively, suggested high concentrations of these substrates in the plant. Virus-induced gene silencing to reduce DBOX transcript levels resulted in a corresponding reduction in sanguinarine, dihydrosanguinarine, and papaverine accumulation in opium poppy roots in support of DBOX as a multifunctional oxidative enzyme in BIA metabolism.
Activation of iodosobenzene by catalytic tetrabutylammonium iodide and its application in the oxidation of some isoquinoline alkaloids
Huang, Wei-Jan,Singh, Om V.,Chen, Chung-Hsiung,Chiou, Sheng-You,Lee, Shoei-Sheng
, p. 1069 - 1078 (2007/10/03)
Oxidation of N-methyltetrahydroisoquinolines with iodosylbenzene in the presence of a catalytic amount of tetrabutylammonium iodide in various solvents afforded N-methyl-2H-3,4-dihydroisoquinol-1-ones in almost quantitative yields. The application of this finding to the oxidation of other isoquinolines, including tetrahydroisoquinolines, lycorine diacetate, and benzyltetrahydroisoquinolines, also afforded the corresponding lactams in good yields, however, accompanied by a few minor byproducts. Under similar conditions, tetrahydroberberine gave a rearranged compound, berberal, as the major product, accompanied by 8-oxoberberine and berberine.
The Polonovski-Potier reaction of berbine N-oxides. Synthesis of 8-hydroxymethyl and 8-methylberbines
Suau, Rafael,Nájera, Francisco,Rico, Rodrigo
, p. 9713 - 9723 (2007/10/03)
The Polonovski-Potier reaction of trans and cis berbines N-oxides was studied. The 8-cyano derivative obtained from trans N-oxides were used to synthesize 8-hydroxymethyl and 8-methyl berbines. This procedure was applied to the stereocontroled synthesis of (8R, 14S)-(-)-8-methylcanadine from (14S)-(-)-canadine. (C) 2000 Elsevier Science Ltd.
A TOTAL SYNTHESIS OF (+/-)-CORYDAINE FROM COPTISINE
Hanaoka, Miyoji,Ashimori, Atsuyuki,Yasuda, Shingo
, p. 2263 - 2264 (2007/10/02)
Regioselective protection of C8-hydroxy of the spiro-diol (6b) derived from coptisine (1b), followed by oxidation of C13-hydroxy afforded the keto-oxazolidine (8b) which was treated with sodium cyanoborohydride to provide (+/-)-corydaine (5b) in an excellent yield.
