108-73-6Relevant articles and documents
Molecular cloning, expression, and characterization of acyltransferase from Pseudomonas protegens
Schmidt, Nina G.,??d?o-Dobrowolska, Anna,Ruppert, Valerie,H?flehner, Christian,Wiltschi, Birgit,Kroutil, Wolfgang
, p. 6057 - 6068 (2018)
The formation of C-C bonds by using CoA independent acyltransferases may have significant impact for novel methods for biotechnology. We report the identification of Pseudomonas strains with CoA-independent acyltransferase activity as well as the heterolo
Molecular and catalytic properties of monoacetylphloroglucinol acetyltransferase from pseudomonas sp. YGJ3
Hayashi, Asuka,Saitou, Hiroki,Mori, Tomomi,Matano, Ikue,Sugisaki, Hiroyuki,Maruyama, Kiyofumi
, p. 559 - 566 (2012)
Monoacetylphloroglucinol (MAPG) acetyltransferase, catalyzing the conversion of MAPG to 2,4-diacetylphloroglucinol (DAPG), was purified from Pseudomonas sp. YGJ3 grown without Cl-. Cl- and pyoluteorin repressed expression of the enzyme. SDS-polyacrylamide gel electrophoresis showed that the purified enzyme (Mr = 330 kDa) was composed of three subunits of 17, 38, and 43 kDa, and protein sequencing identified these as PhlB, PhlA, and PhlC respectively. The enzyme catalyzed the reversible disproportionation of 2 moles of MAPG to phloroglucinol (PG) and DAPG. The equilibrium constant K (=[DAPG][PG]/[MAPG]2) was estimated to be about 1.0 at 25°C. A KpnI 20-kb DNA fragment was cloned from the genomic DNA of strain YGJ3, and a 12,598-bp long DNA region containing the phl gene cluster phlACBDEFGHI was sequenced. PCR cloning and expression of the phl genes in Escherichia coli confirmed that expression of phlACB genes produced MAPG ATase.
Biosynthesis of phloroglucinol
Achkar, Jihane,Xian, Mo,Zhao, Huimin,Frost
, p. 5332 - 5333 (2005)
Substantial concentrations of phloroglucinol were synthesized by Pseudomonas fluorescens Pf-5 expressing the plasmid-localized phlACBDE gene cluster responsible for biosynthesis of 2,4-diacetylphloroglucinol. Expression in Escherichia coli of a single gene in this cluster, P. fluorescens Pf-5 phlD, led to extracellular accumulation of phloroglucinol. Purification of PhlD to homogeneity afforded an enzyme that catalyzed the conversion of malonyl-CoA into phloroglucinol with Km = 5.6 μM and kcat = 10 min-1. Acetylase and deacetylase activities were observed with the catalyzed interconversions of phloroglucinol, 2-acetylphloroglucinol, and 2,4-diacetylphloroglucinol when phlACB was expressed in E. coli. Beyond the mechanistic implications attendant with the identification of an enzyme that catalyzes the conversion of malonyl-CoA into phloroglucinol, PhlD provides the basis for environmentally benign syntheses of phloroglucinol and resorcinol from glucose. Copyright
A FLAVONE GLYCOSIDE FROM THE STEM OF IXORA ARBOREA
Chauhan, J. S.,Kumar, Santosh,Chaturvedi, Rajesh
, p. 2404 - 2405 (1984)
A new flavone glycoside isolated from the stem of Ixora arborea has been characterized as chrysin 5-O-β-D-xylopyranoside on the basis of spectral data, colour reactions and degradation studies.Key Word Index - Ixora arborea; Rubiaceae; stem; chrysin 5-O-β-D-xylopyranoside
Identification of the products of oxidation of quercetin by air oxygen at ambient temperature
Zenkevich, Igor G.,Eshchenko, Anna Yu.,Makarova, Svetlana V.,Vitenberg, Alexander G.,Dobryakov, Yuri G.,Utsal, Viktor A.
, p. 654 - 672 (2007)
Oxidation of quercetin by air oxygen takes place in water and aqueous ethanol solutions under mild conditions, namely in moderately-basic media (pH ～ 8-10) at ambient temperature and in the absence of any radical initiators, without enzymatic catalysis or irradiation of the reaction media by light. The principal reaction products are typical of other oxidative degradation processes of quercetin, namely 3,4-dihydroxy-benzoic (protocatechuic) and 2,4,6-trihydroxybenzoic (phloroglucinic) acids, as well as the decarboxylation product of the latter - 1,3,5-trihydroxybenzene (phloroglucinol). In accordance with the literature data, this process involves the cleavage of the γ-pyrone fragment (ring C) of the quercetin molecule by oxygen, with primary formation of 4,6-dihydroxy-2-(3,4-dihydroxybenzoyloxy)benzoic acid (depside). However under such mild conditions the accepted mechanism of this reaction (oxidative decarbonylation with formation of carbon monoxide, CO) should be reconsidered as preferably an oxidative decarboxylation with formation of carbon dioxide, CO2. Direct head-space analysis of the gaseous components formed during quercetin oxidation in aqueous solution at ambient temperature indicates that the ratio of carbon dioxide/carbon monoxide in the gas phase after acidification of the reaction media is ca. 96:4 %. Oxidation under these mild conditions is typical for other flavonols having OH groups at C3 (e.g., kaempferol), but it is completely suppressed if this hydroxyl group is substituted by a glycoside fragment (as in rutin), or a methyl substituent. An alternative oxidation mechanism involving the direct cleavage of the C2-C3 bond in the diketo-tautomer of quercetin is proposed.
Flavonoid oligosides from georgian astragalus falcatus
Alaniya,Kavtaradze,Skhirtladze,Sutiashvili
, p. 377 - 381 (2011)
New flavonoid oligosides were isolated from leaves and flowers of Astragalus falcatus Lam. It was found on the basis of chemical transformations, UV, IR, PMR, 13C NMR, HMBC, HSQC, 1D-TOCSY, and mass spectral properties that falcoside C had the structure quercetin 3-O-[β-D- glucopyranosyl(1→3)-α-Lrhamnopyranosyl( 1→6)]-β-D- galactopyranoside 7-O-β-D-glucopyranoside; falcoside D, isorhamnetin 3-O-[β-D-xylopyranosyl(1→3)-α-L-rhamnopyranosyl(1→6)] -β-D-galactopyranoside 7-O-α-Lrhamnopyranoside.
A NEW FLAVONOL GLYCOSIDE FROM Azara microphylla
Sagareishvili, T. G.,Alaniya, M. D.,Kemertelidze, E. P.
, p. 275 - 278 (1983)
The leaves of Azara microphylla Hook., introduced into the Sukhami Botanical Garden of the Academy of Sciences of the Georgian SSR, have yielded a new glycoside, which has been called azamicroside and its structure has been established as myricetin 3-O-L-dirhamnoside.
Synthesis method of high-purity phloroglucinol compound
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, (2021/06/09)
The invention discloses a one-step chemical catalytic synthesis method of high-purity phloroglucinol by taking 3,5-dichlorophenol as a starting material and taking strong base and a catalyst as auxiliary materials. Through the method, the phloroglucinol compound with high molar yield, high purity and low cost can be effectively synthesized.
Preparation method of phloroglucinol
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Paragraph 0049-0080, (2021/10/27)
The invention discloses a preparation method of phloroglucinol, the preparation method comprises the following steps: reacting 1, 3, 5-trimethoxybenzene serving as a raw material with boron trihalide to obtain a phloroglucinol crude product, removing boric acid through post-treatment, and purifying the product through refining, so that the reaction time is short, the reaction condition is mild, and the product purity is higher and the purification is convenient due to few side reactions, and good industrial production prospects are realized.
Preparation process of medicinal high-purity phloroglucinol
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Paragraph 0006; 0016-0019, (2021/09/26)
The invention belongs to the technical field of medicine production, and particularly relates to a synthesis process of phloroglucinol, which comprises the following steps: reacting 1, 3, 5-trimethoxybenzene with boron trifluoride, quenching by using a mixed solution of methanol and dichloromethane after the reaction is completed, and purifying by filtering, leaching, pulping and the like to obtain the high-purity phloroglucinol (HPLC: 99.95%). According to the invention, the problem of violent heat release of the reaction system in a short time is solved, and the reaction energy consumption is reduced. The method has the advantages of mild reaction conditions, convenience of operation, convenience of post-treatment, good impurity removal effect and high product purity, and is suitable for industrial production.
